Interaction capacity of 2, 10, 16, 24-tetrakis(benzhydryloxy) Zn(II) phthalocyanine complex with DNA

Interaction capacity of 2, 10, 16, 24-tetrakis(benzhydryloxy) Zn(II) phthalocyanine complex with DNA | Research Square window.SnipcartSettings = { analytics: { enabled: false } }; (function() { var accessVector = localStorage.getItem('access_vector') || ''; window.dataLayer = window.dataLayer || []; if (accessVector) { window.dataLayer.push({ user: { profile: { profileInfo: { snid: accessVector } } } }); } })(); (function(w,d,s,l,i){w[l]=w[l]||[];w[l].push({'gtm.start':new Date().getTime(),event:'gtm.js'});var f=d.getElementsByTagName(s)[0],j=d.createElement(s),dl=l!='dataLayer'?'&l='+l:'';j.async=true;j.src='https://www.googletagmanager.com/gtm.js?id='+i+dl;f.parentNode.insertBefore(j,f);})(window,document,'script','dataLayer','GTM-K279D39R'); Browse Preprints In Review Journals COVID-19 Preprints AJE Video Bytes Research Tools Research Promotion AJE Professional Editing AJE Rubriq About Preprint Platform In Review Editorial Policies Our Team Advisory Board Help Center Sign In Submit a Preprint Cite Share Download PDF Research Article Interaction capacity of 2, 10, 16, 24-tetrakis(benzhydryloxy) Zn(II) phthalocyanine complex with DNA Ali Arslantaş, Mehmet Salih Ağırtaş This is a preprint; it has not been peer reviewed by a journal. https://doi.org/ 10.21203/rs.3.rs-4448560/v1 This work is licensed under a CC BY 4.0 License Status: Posted Version 1 posted You are reading this latest preprint version Abstract The mechanism of interaction of peripheral tetra-substituted zinc (II) phthalocyanine complex with DNA was evaluated by various procedures in the present study. The DNA interaction capacity of 2, 10, 16, 24-tetrakis (benzhydryloxy) zinc (II) phthalocyanine complex was probed together with the electronic absorption spectra, fluorescence spectra, electrophoresis, thermal denaturation and study of viscosity. DNA binding constant (Kb) and changes in the thermal melting profile of DNA by addition of ZnPc compound revealed that the complex has the capability to attach to CT-DNA by an intercalative binding mechanism. The binding constant K b that is a crucial parameter for getting information on the binding mechanism, it was estimated to be 1.392 10 6 M − 1 owing to the electronic absorption analysis and else prominent instrument is fluorescence spectroscopy to clear up the interaction capacity of ZnPc with the DNA. Fluorescence spectrophotometric data provide the evidence that the compound can reacts with DNA thru an intercalative coupling formation pathway. By the outcomes of electrophoresis assays, the declines in the intensity of CT-DNA bands demonstrated that the ZnPc complex interacts with DNA. Further, the data of viscosity measurements demonstrated that the reaction of ZnPc with DNA is most likely via the intercalative binding pathway. All these experimental data revealed that the ZnPc compound interacts with DNA and the compound may be appropriate drugs for the treating cancer due to its DNA interaction activity. Phthalocyanine Zinc complex DNA UV/Vis Thermal denaturation Figures Figure 1 Figure 2 Figure 3 Figure 4 Figure 5 Figure 6 Introduction Phthalocyanines and derivatives of these compounds are extremely valuable molecules and for this fact, large-scale studies on phthalocyanines have been under way for several decades. Up to now, the derivatives of metal complex of phthalocyanines have had a number of potential applications in the field of materials science, among them In the sectors of chemical sensors, liquid crystals, films and sensitisers for the photodynamic treatment of cancer in the human body [ 1 – 6 ]. They are also recognized for their high conductivity properties, as in optical compounds for nonlinear optics [ 7 , 8 ]. Over time additional undiscovered functions of such molecules will be invented. The more new features of these kinds of molecules are uncovered, the many researchers in this field will drawn to the further captivating characteristics of phthalocyanines [ 9 ]. Strong absorption, emission, photochemical stability, effectiveness in the manufacture of singlet oxygen and ROS, low cytotoxicity in the dark, high flexibility in targeted conformational tuning have enhanced the appeal of phthalocyanines as specific reactants [ 10 , 11 ]. DNA represents the storehouse of all genetic knowledge, it serves an enormous role in antitumor drug synthesis by contributing data on cellular activities. Understanding the effectiveness and mechanism of drug bonding to DNA can aid us in assessing the magnitude of tumor inhibition in cancer treatment [ 12 ]. Metal phthalocyanine macromolecules can react with DNA molecules because of their sheet form. Furthermore, Phthalocyanine compounds may be readily modified concerning the nucleic acid target site. Such as the spectral properties of these compounds may be regulated by way of preferential incorporation of metal atom [ 12 ]. In a general way, these compounds can coordinate with various elements, but the interaction of phthalocyanine componds with diamagnetic metals has been much searched for its interesting characteristic [ 13 ]. Wide range of publications have highlighted theimportance of phthalocyanine metal complexes, which has been quaternised with both aromatic and heteroaromatic units and has demonstrated potential biological effects [ 12 ]. The primary target of this work was to commentate the interactivity of compound under investigation along with DNA as a prospective photosensitiser. Within the scope of the present study, 2, 10, 16, 24-tetrakis(benzhydryloxy)phthalocyaninato)zinc(II) (ZnPc ) was produced from 4-(benzhydryloxy)phthalonitrile compound [ 14 ]. The DNA bonding behavior of the Zn(II) phthalocyanine complex has been probed by several different techniques such as spectrophotometric, thermal denaturation, viscosity and gel eletrophoresis assays to explore its potency as a prospective anticancer drug. Experimental section Materials and instrumentation Chemicals, reactants and solvents are all commercially available for use without further refining. CT-DNA was acquired from Sigma-Aldrich, Inc. All solutions of the DNA used were made up in the buffer consisting of NaOH at a pH of 7.04 and then stored in a freezer at 4 o C. UV/Visible absorption spectra and thermal denaturation testing were accomplished utilizing a Cary Absorption Spectrophotometer and fluorescence data was gathered utilizing a Perkin Elmer Emission Spectrophotometer. Agarose gel electrophoresis analysis was run on the Scientific Owl Electrophoresis machine at pH 7.04 at 25 o C. Viscosity data for this study were collected with the aid of a Ostwald Viscometer. Preparation of 4-(benzhydryloxy)phthalonitrile compound In the published literature, the mechanism of the preparation of 4-(benzhydryloxy)phthalonitrile was reported [ 14 ]. The route of preparation of the tetrakis(benzhydryloxy-phthalocyaninato) Zn (II) complex (ZnPc) Tetrakis(benzhydryloxyphthalocyaninato) Zn (II) was generated by the route reported in the published literature [ 14 ]. Results and discussion Producing of tetrakis(benzhydryloxy) Zn(II) phthalocyanine complex The structural formula of 2,10,16,24-tetrakis(benzhydryloxy) Zn(II) phthalocyanine complex beneath examination is illustrated in Fig. 1 . The tetra-replaced ZnPc was made by a process of cyclotetramerisation of 4-(benzhydryloxy) phthalonitrile by a reflux procudure beneath N 2 . The product was completely analysed employing electronic spectra, mass spectroscopy and FT-IR approaches. The data had been in agreement to the prospective molecular conformation. Details of synthesizing and characterisation had been previously appeared in the literature [ 14 ]. Interactivity study of ZnPc by DNA The ZnPc had titrated via CT-DNA at 25 o C at pH 7.04 using UV/Vis absorption titration. DNA sample was disassembled in the buffer medium. The absorbance of the DNA main sample was tested and it was observed that the sample did not consist of adequate protein [ 15 ]. The ZnPc stock sample was obtained in the solvent DMF. The sample was later diluted to the intended amount using the buffer, pH 7.04. electronic spectra titrations had conducted by gradually input quantities of the DNA to a specified amount (25 µM) of ZnPc. Absorption spectra were collected after each adding. The Wolfe-Schimer equation [ 12 ] was utilised to compute the bonding coefficient (K b ) for the complex. The absorbance of ZnPc reduced and became saturated above 25 µM DNA concentration as the input of the DNA increased. The interacting of the complex along with DNA manufectured the hypochromism of two main peaks at around 347 and 679 nm, related a moderate red shift for each peak. ZnPc displayed hypochromism for spectra with bands around 347 and 679 nm, respectively, as can be seen in Fig. 2 . Hypochromism, which correlates with mild bathochromic shear, is typically due to the intercalative binding mechanism consisting of packing interacting between aromatic compounds and DNA [ 16 ]. An intercalating binding mode with CT DNA is likely to be present in the largely planar central part of ZnPc with its conjugated cyclic structure. The binding constant, K b , was identified to have a value of 1.392 10 6 M − 1 . Fluorescence study of ZnPc complex Since emission titration is one of the most extensive and highly delicate approaches in DNA interaction investigations and generate more knowledge about the intercalative binding mechanism of chemical complexes, this technique has been used to analyse drug-DNA interactions. Fluorescence testing is a procedure based on fluorescence spectra variation when a molecule attaches to DNA. A chemical compound attaches to the biologycal compound using intercalative regions of DNA bases. Hence, fluorescence efficiency can be greatly rised when compounds link to DNA molecule. The attachment of tested chemical to intercalative regions upon DNA can be tracted viaa decline in fluorescence spectrum with increasing concentration of the complex [ 17 ]. As illustrated in Fig. 3 , in lack of DNA, ZnPc complex radiated powerful fluorescence spectrum, with the maximum peak occurring at around 508 nm. Just as seen in Fig. 3 , when CT-DNA was added, it was observed that the emission intensities were gradually dropped. The obtained results suggested that ZnPc complex links to DNA via an intercalative interaction process. Viscosity Analyses for ZnPc complex The mechanism of interaction between ZnPc compound and DNA was analysed by viscosity assay. The measurement of DNA viscosity can supply essential evidence for the DNA binding pathway because this technique is length-sensitive modification of the DNA. It is also recognised as the least unspecific and extremely tender test for the DNA binding pathway [ 18 , 19 ]. In principle, When a complex enters DNA, the DNA helix prolongs as base pairs are torn apart to accommodate the bound ligand, leading to enhanced DNA viscosity. Namely, the compound that interacts with DNA through an intercalation can lower the effective length of DNA by kinking the strand, and viscosity may diminish accordingly [ 20 ]. In one more, the modes of electrostatic and groove binding have little influence on DNA viscosity. Figure 4 indicates the variation in viscosity of CT-DNA when ZnPc is added. There is a regular increase in the viscosity of the DNA solution as the concentration of ZnPc is increased. These data indicate that the ZnPc complex is able to penetrate among the bases of DNA. Studies upon thermal denaturation Thermal behaviour of the DNA in existence of the ZnPc complex can provide an idea about the conformational change as the temperature increases. The melting point (T m ) of the DNA sample is commonly referred to as the temperature where half of the overall base pairs are produced. are no longer bound. It is a frequently used a device for scrutiny the inetraction of transition metal compounds to the nucleic acid. As a basic rule, the melting temperature of DNA goes up when metal complexes attach to DNA by intercalating, since intercalating the chemical agent between DNA bases leads to a stabilisation of the base stacking and consequently to an elevating of T m of backbone DNA. Melting plots of DNA lacking and containing the ZnPc complex were Illustrated in Fig. 5 . T m of the DNA found as a 65.3 o C in the absent of the ZnPc complex. When a certain amount of ZnPc complex was added to the medium, it was observed that T m of CT-DNA increased. The T m of 74.7 o C was determined for the thermal denaturation of DNA in existence of ZnPc. The significant rise in DNA Tm associated with the ZnPc complex is also compared to that reported for intercalators [ 21 – 23 ]. Gel electrophoresis The interacting of ZnPc compound by CT-DNA was characterised via agarose gel electrophoresis. The bands were imaged and photographed under a UV light source. The binding capacity was evaluated by the intensity of band of the DNA. By analysing the impact of different amounts of ZnPc compound upon CT-DNA, the interacting capacity of the synthesized compound to DNA was probed by gel electrophoresis. The findings are illustrated in Fig. 6 , which indicates that the intensity of DNA bands detected for the compound after attaching to CT-DNA was reduced when compared to the free CT-DNA band. The reduced intensity of the bands detected after binding ZnPc to CT-DNA is attributed to the distortion of the DNA double helix. Earlier reported studies demonstrated that DNA distortion may have been caused basically by backbone disintegration owing to nucleophilic targeting of basic residues [ 24 , 17 ]. It was stated that the bands intensity displayed by ethidium bromide intercalated into DNA base pairs in hand electrophoresis relate the quantity of molecule but also on the DNA length [ 25 , 26 ]. Consequently, the decline in intensity of the bands of CT-DNA on interacting with ZnPc complex may be caused by interference of the complex with the stacked bases inside the helix and with surface interaction at the more active nucleophilic regions of DNA [ 27 – 30 ]. Conclusion Of great interest for medical research is the mechanism of the linking of phthalocyanine compounds to CT-DNA. This study is concerned with the interaction of 2,10,16,24-tetrakis(benzhydryloxy) Zn(II) phthalocyanine compound with CT-DNA. The interaction of ZnPc via CT-DNA was evaluated by absorption titration, emission titration, viscosity, thermal denaturation and electrophoresis experiments and the complex demonstrates strong binding capability. The computed binding potency of ZnPc to CT-DNA points to an intercalative interaction.. The results that were obtained from emission titration also confirmed the binding of the ZnPc complex to DNA. The variation in the T m of DNA after interaction of ZnPc also favours an intercalative interaction. In addition to the above studies, the findings from viscosity and gel electrophoresis also confirmed the interaction of ZnPc with CT-DNA. As a result, the complex displays a powerful binding capability to DNA, which highlights the promoting features of the 2,10,16,24-tetrakis(benzhydryloxy) Zn(II) phthalocyanine complex as a potential anticancer substance. Declarations Conflict of interest statement All authors declare no conflict of interest. Author Contribution AA: supervises the experiments, planned, performed the experiments, sample preparation, data collection, analysis, interpretation of the results, and writing the manuscript. MSA: supervises the experiments, sample preparation, synthesis of compounds and helps with sample characterization of the complexes. Acknowledgements This research was supported by Karabük University. References C.C. Leznoff, A.B.P. Lever, Phthalocyanines: Properties and applications; (VCH New York, NY, USA. 1993) M. Hanack, M. Lang, Adv. Mater. 6, 819 (1994) https://doi.org/10.1002/adma.19940061103 N.B. McKeown, (Phthalocyanine materials: synthesis, structure, and function. (Cambridge, U.K.; New York: Cambridge University Press1998); pp. 193. S.V. Kudrevich, M.G. Galpern, J.E. Van Lier, Synth. 8, 779 (1994) https://doi.org/10.1055/s-1994-25571 F. Mitzel, S. Fitzgerald, A. Beeby, R. Faust, Chem. Commun. 24, 2596 (2001) https://doi.org/10.1039/B109742N A. Baran, S. Çol, E. Karakılıç, F. 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Agirtas, Chemistryselect 3(11), 3155 (2018) https://doi.org/10.1002/slct.201800572 Additional Declarations No competing interests reported. Cite Share Download PDF Status: Posted Version 1 posted You are reading this latest preprint version Research Square lets you share your work early, gain feedback from the community, and start making changes to your manuscript prior to peer review in a journal. As a division of Research Square Company, we’re committed to making research communication faster, fairer, and more useful. We do this by developing innovative software and high quality services for the global research community. Our growing team is made up of researchers and industry professionals working together to solve the most critical problems facing scientific publishing. Also discoverable on Platform About Our Team In Review Editorial Policies Advisory Board Help Center Resources Author Services Accessibility API Access RSS feed Manage Cookie Preferences © Research Square 2026 | ISSN 2693-5015 (online) Privacy Policy Terms of Service Do Not Sell My Personal Information {"props":{"pageProps":{"initialData":{"identity":"rs-4448560","acceptedTermsAndConditions":true,"allowDirectSubmit":true,"archivedVersions":[],"articleType":"Research Article","associatedPublications":[],"authors":[{"id":308070428,"identity":"5f965f1a-1f53-4850-9339-fc1e144363e0","order_by":0,"name":"Ali Arslantaş","email":"data:image/png;base64,iVBORw0KGgoAAAANSUhEUgAAAZAAAAAyAQMAAABI0h/eAAAABlBMVEX///8AAABVwtN+AAAACXBIWXMAAA7EAAAOxAGVKw4bAAAAxklEQVRIiWNgGAWjYNCCHzVyIOrAA6J1MPYcMwZrSSDeFjbmxAYQTZQW/tnHHz78wcOWPj/s8EOgLXZyug0EtEicyzE2kLCQyd14O80AqCXZ2OwAIWvO8LBJGPCw5W6cnQDSciBxGyEt8mfYn0kksDGnG85O/0CcFoMzDGYSB9iYE+Slc4i0xfAMj7FhY88xww3SOQUHEgyI8IvcGXZgiP2okZefnb75w4cKOznC3oe7EKzSgFjlICDfQIrqUTAKRsEoGFEAAKGnQyZvSL+YAAAAAElFTkSuQmCC","orcid":"","institution":"İzmir Bakırçay University, İzmir,","correspondingAuthor":true,"prefix":"","firstName":"Ali","middleName":"","lastName":"Arslantaş","suffix":""},{"id":308070431,"identity":"422d6d05-231a-4181-89c1-fe237caf3675","order_by":1,"name":"Mehmet Salih Ağırtaş","email":"","orcid":"","institution":"Van Yüzüncü Yıl University, Van","correspondingAuthor":false,"prefix":"","firstName":"Mehmet","middleName":"Salih","lastName":"Ağırtaş","suffix":""}],"badges":[],"createdAt":"2024-05-20 10:43:24","currentVersionCode":1,"declarations":"","doi":"10.21203/rs.3.rs-4448560/v1","doiUrl":"https://doi.org/10.21203/rs.3.rs-4448560/v1","draftVersion":[],"editorialEvents":[],"editorialNote":"","failedWorkflow":false,"files":[{"id":57520989,"identity":"9750f014-97b0-4735-925d-a0f8bc576cf9","added_by":"auto","created_at":"2024-05-31 21:48:01","extension":"png","order_by":1,"title":"Figure 1","display":"","copyAsset":false,"role":"figure","size":32901,"visible":true,"origin":"","legend":"\u003cp\u003eThe structural formula of ZnPc complex.\u003c/p\u003e","description":"","filename":"floatimage1.png","url":"https://assets-eu.researchsquare.com/files/rs-4448560/v1/d1f0cd6ffccd8e28f47b5ade.png"},{"id":57520988,"identity":"8b19d0dc-a792-46df-8767-10e87a7e1412","added_by":"auto","created_at":"2024-05-31 21:48:01","extension":"png","order_by":2,"title":"Figure 2","display":"","copyAsset":false,"role":"figure","size":72811,"visible":true,"origin":"","legend":"\u003cp\u003eElectronic titration of ZnPc (25 µM) at growing quantities of CT-DNA (0-15 µM at pH 7.04). Arrows indicate the decrease in absorbance peaks as the amount of DNA increases.\u003c/p\u003e","description":"","filename":"floatimage2.png","url":"https://assets-eu.researchsquare.com/files/rs-4448560/v1/e55879b8db697c79f2a44041.png"},{"id":57520987,"identity":"66119ac2-f4e9-46bc-a31f-8fda373b0482","added_by":"auto","created_at":"2024-05-31 21:48:01","extension":"png","order_by":3,"title":"Figure 3","display":"","copyAsset":false,"role":"figure","size":59504,"visible":true,"origin":"","legend":"\u003cp\u003eThe fluorescence spectra of interaction of \u0026nbsp;ZnPc with DNA. Arrow represents variations in the intensity with increasing amounts of DNA.\u003c/p\u003e","description":"","filename":"floatimage3.png","url":"https://assets-eu.researchsquare.com/files/rs-4448560/v1/64bb2c600b179151bafdc739.png"},{"id":57521234,"identity":"b1ca4354-2d49-4268-b585-e3b86a5644dd","added_by":"auto","created_at":"2024-05-31 21:56:01","extension":"png","order_by":4,"title":"Figure 4","display":"","copyAsset":false,"role":"figure","size":37384,"visible":true,"origin":"","legend":"\u003cp\u003eThe impact of growing quantity of ZnPc upon the relative viscosity of DNA.\u003c/p\u003e","description":"","filename":"floatimage4.png","url":"https://assets-eu.researchsquare.com/files/rs-4448560/v1/e2dc32a89f84a8e8e2e50ea4.png"},{"id":57520992,"identity":"5f950b4b-94d5-4371-87be-c97cdd6a3542","added_by":"auto","created_at":"2024-05-31 21:48:01","extension":"png","order_by":5,"title":"Figure 5","display":"","copyAsset":false,"role":"figure","size":24712,"visible":true,"origin":"","legend":"\u003cp\u003eT\u003csub\u003em\u003c/sub\u003e of CT-DNA in the lack and in the presence of a ZnPc complex.\u003c/p\u003e","description":"","filename":"floatimage5.png","url":"https://assets-eu.researchsquare.com/files/rs-4448560/v1/0120775175019a7024367c71.png"},{"id":57520991,"identity":"6aebda12-81b0-4752-96c1-7d0c75c49e0f","added_by":"auto","created_at":"2024-05-31 21:48:01","extension":"png","order_by":6,"title":"Figure 6","display":"","copyAsset":false,"role":"figure","size":43063,"visible":true,"origin":"","legend":"\u003cp\u003eThe interaction study of ZnPc with CT-DNA using \u0026nbsp;agarose gel electrophores method. Lane C: blank CT-DNA. Lanes 1-3: 15 µM CT-DNA + (10, 15, 20 µM) ZnPc.\u003c/p\u003e","description":"","filename":"floatimage6.png","url":"https://assets-eu.researchsquare.com/files/rs-4448560/v1/0636c43ac7e2d4988dc85ac6.png"},{"id":57761475,"identity":"e5dbcd5a-1304-4a46-8729-d611971d5b1b","added_by":"auto","created_at":"2024-06-05 09:38:25","extension":"pdf","order_by":0,"title":"","display":"","copyAsset":false,"role":"manuscript-pdf","size":554620,"visible":true,"origin":"","legend":"","description":"","filename":"manuscript.pdf","url":"https://assets-eu.researchsquare.com/files/rs-4448560/v1/45f8e24f-0f90-4b95-be6f-a711acb3c42c.pdf"}],"financialInterests":"No competing interests reported.","formattedTitle":"Interaction capacity of 2, 10, 16, 24-tetrakis(benzhydryloxy) Zn(II) phthalocyanine complex with DNA","fulltext":[{"header":"Introduction","content":"\u003cp\u003ePhthalocyanines and derivatives of these compounds are extremely valuable molecules and for this fact, large-scale studies on phthalocyanines have been under way for several decades. Up to now, the derivatives of metal complex of phthalocyanines have had a number of potential applications in the field of materials science, among them In the sectors of chemical sensors, liquid crystals, films and sensitisers for the photodynamic treatment of cancer in the human body [\u003cspan additionalcitationids=\"CR2 CR3 CR4 CR5\" citationid=\"CR1\" class=\"CitationRef\"\u003e1\u003c/span\u003e\u0026ndash;\u003cspan citationid=\"CR6\" class=\"CitationRef\"\u003e6\u003c/span\u003e]. They are also recognized for their high conductivity properties, as in optical compounds for nonlinear optics [\u003cspan citationid=\"CR7\" class=\"CitationRef\"\u003e7\u003c/span\u003e, \u003cspan citationid=\"CR8\" class=\"CitationRef\"\u003e8\u003c/span\u003e]. Over time additional undiscovered functions of such molecules will be invented. The more new features of these kinds of molecules are uncovered, the many researchers in this field will drawn to the further captivating characteristics of phthalocyanines [\u003cspan citationid=\"CR9\" class=\"CitationRef\"\u003e9\u003c/span\u003e]. Strong absorption, emission, photochemical stability, effectiveness in the manufacture of singlet oxygen and ROS, low cytotoxicity in the dark, high flexibility in targeted conformational tuning have enhanced the appeal of phthalocyanines as specific reactants [\u003cspan citationid=\"CR10\" class=\"CitationRef\"\u003e10\u003c/span\u003e, \u003cspan citationid=\"CR11\" class=\"CitationRef\"\u003e11\u003c/span\u003e].\u003c/p\u003e \u003cp\u003eDNA represents the storehouse of all genetic knowledge, it serves an enormous role in antitumor drug synthesis by contributing data on cellular activities. Understanding the effectiveness and mechanism of drug bonding to DNA can aid us in assessing the magnitude of tumor inhibition in cancer treatment [\u003cspan citationid=\"CR12\" class=\"CitationRef\"\u003e12\u003c/span\u003e]. Metal phthalocyanine macromolecules can react with DNA molecules because of their sheet form. Furthermore, Phthalocyanine compounds may be readily modified concerning the nucleic acid target site. Such as the spectral properties of these compounds may be regulated by way of preferential incorporation of metal atom [\u003cspan citationid=\"CR12\" class=\"CitationRef\"\u003e12\u003c/span\u003e]. In a general way, these compounds can coordinate with various elements, but the interaction of phthalocyanine componds with diamagnetic metals has been much searched for its interesting characteristic [\u003cspan citationid=\"CR13\" class=\"CitationRef\"\u003e13\u003c/span\u003e]. Wide range of publications have highlighted theimportance of phthalocyanine metal complexes, which has been quaternised with both aromatic and heteroaromatic units and has demonstrated potential biological effects [\u003cspan citationid=\"CR12\" class=\"CitationRef\"\u003e12\u003c/span\u003e].\u003c/p\u003e \u003cp\u003eThe primary target of this work was to commentate the interactivity of compound under investigation along with DNA as a prospective photosensitiser. Within the scope of the present study, 2, 10, 16, 24-tetrakis(benzhydryloxy)phthalocyaninato)zinc(II) (ZnPc\u003cb\u003e)\u003c/b\u003e was produced from 4-(benzhydryloxy)phthalonitrile compound [\u003cspan citationid=\"CR14\" class=\"CitationRef\"\u003e14\u003c/span\u003e]. The DNA bonding behavior of the Zn(II) phthalocyanine complex has been probed by several different techniques such as spectrophotometric, thermal denaturation, viscosity and gel eletrophoresis assays to explore its potency as a prospective anticancer drug.\u003c/p\u003e"},{"header":"Experimental section","content":"\u003cdiv id=\"Sec3\" class=\"Section2\"\u003e \u003ch2\u003eMaterials and instrumentation\u003c/h2\u003e \u003cp\u003eChemicals, reactants and solvents are all commercially available for use without further refining. CT-DNA was acquired from Sigma-Aldrich, Inc. All solutions of the DNA used were made up in the buffer consisting of NaOH at a pH of 7.04 and then stored in a freezer at 4\u003csup\u003eo\u003c/sup\u003eC. UV/Visible absorption spectra and thermal denaturation testing were accomplished utilizing a Cary Absorption Spectrophotometer and fluorescence data was gathered utilizing a Perkin Elmer Emission Spectrophotometer. Agarose gel electrophoresis analysis was run on the Scientific Owl Electrophoresis machine at pH 7.04 at 25 \u003csup\u003eo\u003c/sup\u003eC. Viscosity data for this study were collected with the aid of a Ostwald Viscometer.\u003c/p\u003e \u003c/div\u003e \u003cdiv id=\"Sec4\" class=\"Section2\"\u003e \u003ch2\u003ePreparation of 4-(benzhydryloxy)phthalonitrile compound\u003c/h2\u003e \u003cp\u003eIn the published literature, the mechanism of the preparation of 4-(benzhydryloxy)phthalonitrile was reported [\u003cspan citationid=\"CR14\" class=\"CitationRef\"\u003e14\u003c/span\u003e].\u003c/p\u003e \u003c/div\u003e \u003cdiv id=\"Sec5\" class=\"Section2\"\u003e \u003ch2\u003eThe route of preparation of the tetrakis(benzhydryloxy-phthalocyaninato) Zn (II) complex (ZnPc)\u003c/h2\u003e \u003cp\u003eTetrakis(benzhydryloxyphthalocyaninato) Zn (II) was generated by the route reported in the published literature [\u003cspan citationid=\"CR14\" class=\"CitationRef\"\u003e14\u003c/span\u003e].\u003c/p\u003e \u003c/div\u003e"},{"header":"Results and discussion","content":"\u003cdiv id=\"Sec7\" class=\"Section2\"\u003e \u003ch2\u003eProducing of tetrakis(benzhydryloxy) Zn(II) phthalocyanine complex\u003c/h2\u003e \u003cp\u003eThe structural formula of 2,10,16,24-tetrakis(benzhydryloxy) Zn(II) phthalocyanine complex beneath examination is illustrated in Fig.\u0026nbsp;\u003cspan refid=\"Fig1\" class=\"InternalRef\"\u003e1\u003c/span\u003e. The tetra-replaced ZnPc was made by a process of cyclotetramerisation of 4-(benzhydryloxy) phthalonitrile by a reflux procudure beneath N\u003csub\u003e2\u003c/sub\u003e. The product was completely analysed employing electronic spectra, mass spectroscopy and FT-IR approaches. The data had been in agreement to the prospective molecular conformation. Details of synthesizing and characterisation had been previously appeared in the literature [\u003cspan citationid=\"CR14\" class=\"CitationRef\"\u003e14\u003c/span\u003e].\u003c/p\u003e \u003cp\u003e \u003c/p\u003e \u003c/div\u003e \u003cdiv id=\"Sec8\" class=\"Section2\"\u003e \u003ch2\u003eInteractivity study of ZnPc by DNA\u003c/h2\u003e \u003cp\u003eThe ZnPc had titrated via CT-DNA at 25\u003csup\u003eo\u003c/sup\u003eC at pH 7.04 using UV/Vis absorption titration. DNA sample was disassembled in the buffer medium. The absorbance of the DNA main sample was tested and it was observed that the sample did not consist of adequate protein [\u003cspan citationid=\"CR15\" class=\"CitationRef\"\u003e15\u003c/span\u003e]. The ZnPc stock sample was obtained in the solvent DMF. The sample was later diluted to the intended amount using the buffer, pH 7.04. electronic spectra titrations had conducted by gradually input quantities of the DNA to a specified amount (25 \u0026micro;M) of ZnPc. Absorption spectra were collected after each adding. The Wolfe-Schimer equation [\u003cspan citationid=\"CR12\" class=\"CitationRef\"\u003e12\u003c/span\u003e] was utilised to compute the bonding coefficient (K\u003csub\u003eb\u003c/sub\u003e) for the complex.\u003c/p\u003e \u003cp\u003eThe absorbance of ZnPc reduced and became saturated above 25 \u0026micro;M DNA concentration as the input of the DNA increased. The interacting of the complex along with DNA manufectured the hypochromism of two main peaks at around 347 and 679 nm, related a moderate red shift for each peak. ZnPc displayed hypochromism for spectra with bands around 347 and 679 nm, respectively, as can be seen in Fig.\u0026nbsp;\u003cspan refid=\"Fig2\" class=\"InternalRef\"\u003e2\u003c/span\u003e. Hypochromism, which correlates with mild bathochromic shear, is typically due to the intercalative binding mechanism consisting of packing interacting between aromatic compounds and DNA [\u003cspan citationid=\"CR16\" class=\"CitationRef\"\u003e16\u003c/span\u003e]. An intercalating binding mode with CT DNA is likely to be present in the largely planar central part of ZnPc with its conjugated cyclic structure. The binding constant, K\u003csub\u003eb\u003c/sub\u003e, was identified to have a value of 1.392 10\u003csup\u003e6\u003c/sup\u003e M\u003csup\u003e\u0026minus;\u0026thinsp;1\u003c/sup\u003e.\u003c/p\u003e \u003cp\u003e \u003c/p\u003e \u003c/div\u003e \u003cdiv id=\"Sec9\" class=\"Section2\"\u003e \u003ch2\u003eFluorescence study of ZnPc complex\u003c/h2\u003e \u003cp\u003eSince emission titration is one of the most extensive and highly delicate approaches in DNA interaction investigations and generate more knowledge about the intercalative binding mechanism of chemical complexes, this technique has been used to analyse drug-DNA interactions. Fluorescence testing is a procedure based on fluorescence spectra variation when a molecule attaches to DNA. A chemical compound attaches to the biologycal compound using intercalative regions of DNA bases. Hence, fluorescence efficiency can be greatly rised when compounds link to DNA molecule. The attachment of tested chemical to intercalative regions upon DNA can be tracted viaa decline in fluorescence spectrum with increasing concentration of the complex [\u003cspan citationid=\"CR17\" class=\"CitationRef\"\u003e17\u003c/span\u003e].\u003c/p\u003e \u003cp\u003eAs illustrated in Fig.\u0026nbsp;\u003cspan refid=\"Fig3\" class=\"InternalRef\"\u003e3\u003c/span\u003e, in lack of DNA, ZnPc complex radiated powerful fluorescence spectrum, with the maximum peak occurring at around 508 nm. Just as seen in Fig.\u0026nbsp;\u003cspan refid=\"Fig3\" class=\"InternalRef\"\u003e3\u003c/span\u003e, when CT-DNA was added, it was observed that the emission intensities were gradually dropped. The obtained results suggested that ZnPc complex links to DNA via an intercalative interaction process.\u003c/p\u003e \u003cp\u003e \u003c/p\u003e \u003cdiv id=\"Sec10\" class=\"Section3\"\u003e \u003ch2\u003eViscosity Analyses for ZnPc complex\u003c/h2\u003e \u003cp\u003eThe mechanism of interaction between ZnPc compound and DNA was analysed by viscosity assay. The measurement of DNA viscosity can supply essential evidence for the DNA binding pathway because this technique is length-sensitive modification of the DNA. It is also recognised as the least unspecific and extremely tender test for the DNA binding pathway [\u003cspan citationid=\"CR18\" class=\"CitationRef\"\u003e18\u003c/span\u003e, \u003cspan citationid=\"CR19\" class=\"CitationRef\"\u003e19\u003c/span\u003e]. In principle, When a complex enters DNA, the DNA helix prolongs as base pairs are torn apart to accommodate the bound ligand, leading to enhanced DNA viscosity. Namely, the compound that interacts with DNA through an intercalation can lower the effective length of DNA by kinking the strand, and viscosity may diminish accordingly [\u003cspan citationid=\"CR20\" class=\"CitationRef\"\u003e20\u003c/span\u003e]. In one more, the modes of electrostatic and groove binding have little influence on DNA viscosity. Figure\u0026nbsp;\u003cspan refid=\"Fig4\" class=\"InternalRef\"\u003e4\u003c/span\u003e indicates the variation in viscosity of CT-DNA when ZnPc is added.\u003c/p\u003e \u003cp\u003e \u003c/p\u003e \u003cp\u003eThere is a regular increase in the viscosity of the DNA solution as the concentration of ZnPc is increased. These data indicate that the ZnPc complex is able to penetrate among the bases of DNA.\u003c/p\u003e \u003c/div\u003e \u003c/div\u003e \u003cdiv id=\"Sec11\" class=\"Section2\"\u003e \u003ch2\u003eStudies upon thermal denaturation\u003c/h2\u003e \u003cp\u003eThermal behaviour of the DNA in existence of the ZnPc complex can provide an idea about the conformational change as the temperature increases. The melting point (T\u003csub\u003em\u003c/sub\u003e) of the DNA sample is commonly referred to as the temperature where half of the overall base pairs are produced. are no longer bound. It is a frequently used a device for scrutiny the inetraction of transition metal compounds to the nucleic acid. As a basic rule, the melting temperature of DNA goes up when metal complexes attach to DNA by intercalating, since intercalating the chemical agent between DNA bases leads to a stabilisation of the base stacking and consequently to an elevating of T\u003csub\u003em\u003c/sub\u003e of backbone DNA.\u003c/p\u003e \u003cp\u003e \u003c/p\u003e \u003cp\u003eMelting plots of DNA lacking and containing the ZnPc complex were Illustrated in Fig.\u0026nbsp;\u003cspan refid=\"Fig5\" class=\"InternalRef\"\u003e5\u003c/span\u003e. T\u003csub\u003em\u003c/sub\u003e of the DNA found as a 65.3 \u003csup\u003eo\u003c/sup\u003eC in the absent of the ZnPc complex. When a certain amount of ZnPc complex was added to the medium, it was observed that T\u003csub\u003em\u003c/sub\u003e of CT-DNA increased. The T\u003csub\u003em\u003c/sub\u003e of 74.7 \u003csup\u003eo\u003c/sup\u003eC was determined for the thermal denaturation of DNA in existence of ZnPc. The significant rise in DNA Tm associated with the ZnPc complex is also compared to that reported for intercalators [\u003cspan additionalcitationids=\"CR22\" citationid=\"CR21\" class=\"CitationRef\"\u003e21\u003c/span\u003e\u0026ndash;\u003cspan citationid=\"CR23\" class=\"CitationRef\"\u003e23\u003c/span\u003e].\u003c/p\u003e \u003c/div\u003e \u003cdiv id=\"Sec12\" class=\"Section2\"\u003e \u003ch2\u003eGel electrophoresis\u003c/h2\u003e \u003cp\u003eThe interacting of ZnPc compound by CT-DNA was characterised via agarose gel electrophoresis. The bands were imaged and photographed under a UV light source. The binding capacity was evaluated by the intensity of band of the DNA.\u003c/p\u003e \u003cp\u003e \u003c/p\u003e \u003cp\u003eBy analysing the impact of different amounts of ZnPc compound upon CT-DNA, the interacting capacity of the synthesized compound to DNA was probed by gel electrophoresis. The findings are illustrated in Fig.\u0026nbsp;\u003cspan refid=\"Fig6\" class=\"InternalRef\"\u003e6\u003c/span\u003e, which indicates that the intensity of DNA bands detected for the compound after attaching to CT-DNA was reduced when compared to the free CT-DNA band. The reduced intensity of the bands detected after binding ZnPc to CT-DNA is attributed to the distortion of the DNA double helix. Earlier reported studies demonstrated that DNA distortion may have been caused basically by backbone disintegration owing to nucleophilic targeting of basic residues [\u003cspan citationid=\"CR24\" class=\"CitationRef\"\u003e24\u003c/span\u003e, \u003cspan citationid=\"CR17\" class=\"CitationRef\"\u003e17\u003c/span\u003e]. It was stated that the bands intensity displayed by ethidium bromide intercalated into DNA base pairs in hand electrophoresis relate the quantity of molecule but also on the DNA length [\u003cspan citationid=\"CR25\" class=\"CitationRef\"\u003e25\u003c/span\u003e, \u003cspan citationid=\"CR26\" class=\"CitationRef\"\u003e26\u003c/span\u003e]. Consequently, the decline in intensity of the bands of CT-DNA on interacting with ZnPc complex may be caused by interference of the complex with the stacked bases inside the helix and with surface interaction at the more active nucleophilic regions of DNA [\u003cspan additionalcitationids=\"CR28 CR29\" citationid=\"CR27\" class=\"CitationRef\"\u003e27\u003c/span\u003e\u0026ndash;\u003cspan citationid=\"CR30\" class=\"CitationRef\"\u003e30\u003c/span\u003e].\u003c/p\u003e \u003c/div\u003e"},{"header":"Conclusion","content":"\u003cp\u003eOf great interest for medical research is the mechanism of the linking of phthalocyanine compounds to CT-DNA. This study is concerned with the interaction of 2,10,16,24-tetrakis(benzhydryloxy) Zn(II) phthalocyanine compound with CT-DNA. The interaction of ZnPc via CT-DNA was evaluated by absorption titration, emission titration, viscosity, thermal denaturation and electrophoresis experiments and the complex demonstrates strong binding capability. The computed binding potency of ZnPc to CT-DNA points to an intercalative interaction.. The results that were obtained from emission titration also confirmed the binding of the ZnPc complex to DNA. The variation in the T\u003csub\u003em\u003c/sub\u003e of DNA after interaction of ZnPc also favours an intercalative interaction. In addition to the above studies, the findings from viscosity and gel electrophoresis also confirmed the interaction of ZnPc with CT-DNA. As a result, the complex displays a powerful binding capability to DNA, which highlights the promoting features of the 2,10,16,24-tetrakis(benzhydryloxy) Zn(II) phthalocyanine complex as a potential anticancer substance.\u003c/p\u003e"},{"header":"Declarations","content":"\u003cp\u003e \u003ch2\u003eConflict of interest statement\u003c/h2\u003e \u003cp\u003eAll authors declare no conflict of interest.\u003c/p\u003e \u003c/p\u003e\u003ch2\u003eAuthor Contribution\u003c/h2\u003e\u003cp\u003eAA: supervises the experiments, planned, performed the experiments, sample preparation, data collection, analysis, interpretation of the results, and writing the manuscript. MSA: supervises the experiments, sample preparation, synthesis of compounds and helps with sample characterization of the complexes.\u003c/p\u003e\u003ch2\u003eAcknowledgements\u003c/h2\u003e \u003cp\u003eThis research was supported by Karab\u0026uuml;k University.\u003c/p\u003e"},{"header":"References","content":"\u003col\u003e\u003cli\u003e\u003cspan\u003eC.C. Leznoff, A.B.P. Lever, Phthalocyanines: Properties and applications; (VCH New York, NY, USA. 1993)\u003c/span\u003e\u003c/li\u003e \u003cli\u003e\u003cspan\u003eM. Hanack, M. Lang, Adv. Mater. 6, 819 (1994) \u003cspan class=\"ExternalRef\"\u003e\u003cspan class=\"RefSource\"\u003ehttps://doi.org/10.1002/adma.19940061103\u003c/span\u003e\u003cspan address=\"10.1002/adma.19940061103\" targettype=\"DOI\" class=\"RefTarget\"\u003e\u003c/span\u003e\u003c/span\u003e\u003c/span\u003e\u003c/li\u003e \u003cli\u003e\u003cspan\u003eN.B. McKeown, (Phthalocyanine materials: synthesis, structure, and function. 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Agirtas, Chemistryselect 3(11), 3155 (2018) \u003cspan class=\"ExternalRef\"\u003e\u003cspan class=\"RefSource\"\u003ehttps://doi.org/10.1002/slct.201800572\u003c/span\u003e\u003cspan address=\"10.1002/slct.201800572\" targettype=\"DOI\" class=\"RefTarget\"\u003e\u003c/span\u003e\u003c/span\u003e\u003c/span\u003e\u003c/li\u003e\u003c/ol\u003e"}],"fulltextSource":"","fullText":"","funders":[],"hasAdminPriorityOnWorkflow":false,"hasManuscriptDocX":true,"hasOptedInToPreprint":true,"hasPassedJournalQc":"","hasAnyPriority":false,"hideJournal":true,"highlight":"","institution":"","isAcceptedByJournal":false,"isAuthorSuppliedPdf":false,"isDeskRejected":"","isHiddenFromSearch":false,"isInQc":false,"isInWorkflow":false,"isPdf":false,"isPdfUpToDate":true,"isWithdrawnOrRetracted":false,"journal":{"display":true,"email":"[email protected]","identity":"researchsquare","isNatureJournal":false,"hasQc":true,"allowDirectSubmit":true,"externalIdentity":"","sideBox":"","snPcode":"","submissionUrl":"/submission","title":"Research Square","twitterHandle":"researchsquare","acdcEnabled":true,"dfaEnabled":false,"editorialSystem":"","reportingPortfolio":"","inReviewEnabled":false,"inReviewRevisionsEnabled":true},"keywords":"Phthalocyanine, Zinc complex, DNA, UV/Vis, Thermal denaturation","lastPublishedDoi":"10.21203/rs.3.rs-4448560/v1","lastPublishedDoiUrl":"https://doi.org/10.21203/rs.3.rs-4448560/v1","license":{"name":"CC BY 4.0","url":"https://creativecommons.org/licenses/by/4.0/"},"manuscriptAbstract":"\u003cp\u003eThe mechanism of interaction of peripheral tetra-substituted zinc (II) phthalocyanine complex with DNA was evaluated by various procedures in the present study. The DNA interaction capacity of 2, 10, 16, 24-tetrakis (benzhydryloxy) zinc (II) phthalocyanine complex was probed together with the electronic absorption spectra, fluorescence spectra, electrophoresis, thermal denaturation and study of viscosity. DNA binding constant (Kb) and changes in the thermal melting profile of DNA by addition of ZnPc compound revealed that the complex has the capability to attach to CT-DNA by an intercalative binding mechanism. The binding constant K\u003csub\u003eb\u003c/sub\u003e that is a crucial parameter for getting information on the binding mechanism, it was estimated to be 1.392 10\u003csup\u003e6\u003c/sup\u003e M\u003csup\u003e\u0026minus;\u0026thinsp;1\u003c/sup\u003e owing to the electronic absorption analysis and else prominent instrument is fluorescence spectroscopy to clear up the interaction capacity of ZnPc with the DNA. Fluorescence spectrophotometric data provide the evidence that the compound can reacts with DNA thru an intercalative coupling formation pathway. By the outcomes of electrophoresis assays, the declines in the intensity of CT-DNA bands demonstrated that the ZnPc complex interacts with DNA. Further, the data of viscosity measurements demonstrated that the reaction of ZnPc with DNA is most likely via the intercalative binding pathway. All these experimental data revealed that the ZnPc compound interacts with DNA and the compound may be appropriate drugs for the treating cancer due to its DNA interaction activity.\u003c/p\u003e","manuscriptTitle":"Interaction capacity of 2, 10, 16, 24-tetrakis(benzhydryloxy) Zn(II) phthalocyanine complex with DNA","msid":"","msnumber":"","nonDraftVersions":[{"code":1,"date":"2024-05-31 21:47:56","doi":"10.21203/rs.3.rs-4448560/v1","editorialEvents":[{"type":"communityComments","content":0}],"status":"published","journal":{"display":true,"email":"[email protected]","identity":"researchsquare","isNatureJournal":false,"hasQc":true,"allowDirectSubmit":true,"externalIdentity":"","sideBox":"","snPcode":"","submissionUrl":"/submission","title":"Research Square","twitterHandle":"researchsquare","acdcEnabled":true,"dfaEnabled":false,"editorialSystem":"","reportingPortfolio":"","inReviewEnabled":false,"inReviewRevisionsEnabled":true}}],"origin":"","ownerIdentity":"8da2b3f6-1d80-4c8c-aac8-dc3870800190","owner":[],"postedDate":"May 31st, 2024","published":true,"recentEditorialEvents":[],"rejectedJournal":[],"revision":"","amendment":"","status":"posted","subjectAreas":[],"tags":[],"updatedAt":"2024-06-05T09:30:18+00:00","versionOfRecord":[],"versionCreatedAt":"2024-05-31 21:47:56","video":"","vorDoi":"","vorDoiUrl":"","workflowStages":[]},"version":"v1","identity":"rs-4448560","journalConfig":"researchsquare"},"__N_SSP":true},"page":"/article/[identity]/[[...version]]","query":{"redirect":"/article/rs-4448560","identity":"rs-4448560","version":["v1"]},"buildId":"8U1c8b4HqxoKbykW_rLl7","isFallback":false,"isExperimentalCompile":false,"dynamicIds":[84888],"gssp":true,"scriptLoader":[]}