{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,5,11]],"date-time":"2026-05-11T01:00:17Z","timestamp":1778461217957,"version":"3.51.4"},"reference-count":97,"publisher":"MDPI AG","issue":"3","license":[{"start":{"date-parts":[[2023,1,17]],"date-time":"2023-01-17T00:00:00Z","timestamp":1673913600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["IJMS"],"abstract":"<jats:p>A set of arylazo sulfones, known to undergo N\u2013S bond cleavage upon light exposure, has been synthesized, and their activity in the dark and upon irradiation towards DNA has been investigated. Their interaction with calf-thymus DNA has been examined, and the significant affinity observed (most probably due to DNA intercalation) was analyzed by means of molecular docking \u201cin silico\u201d calculations that pointed out polar contacts, mainly via the sulfonyl moiety. Incubation with plasmid pBluescript KS II revealed DNA cleavage that has been studied over time and concentration. UV-A irradiation considerably improved DNA damage for most of the compounds, whereas under visible light the effect was slightly lower. Moving to in vitro experiments, irradiation was found to slightly enhance the death of the cells in the majority of the compounds. Naphthylazosulfone 1 showed photo-disruptive effect under UV-A irradiation (IC50 ~13 \u03bc\u039c) followed by derivatives 14 and 17 (IC50 ~100 \u03bc\u039c). Those compounds were irradiated in the presence of two non-cancer cell lines and were found equally toxic only upon irradiation and not in the dark. The temporal and spatial control of light, therefore, might provide a chance for these novel scaffolds to be useful for the development of phototoxic pharmaceuticals.<\/jats:p>","DOI":"10.3390\/ijms24031834","type":"journal-article","created":{"date-parts":[[2023,1,18]],"date-time":"2023-01-18T01:57:57Z","timestamp":1674007077000},"page":"1834","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":11,"title":["Effect of Arylazo Sulfones on DNA: Binding, Cleavage, Photocleavage, Molecular Docking Studies and Interaction with A375 Melanoma and Non-Cancer Cells"],"prefix":"10.3390","volume":"24","author":[{"given":"Chrysoula","family":"Mikra","sequence":"first","affiliation":[{"name":"Laboratory of Organic Chemistry, Faculty of Chemistry, Aristotle University of Thessaloniki, 54124 Thessaloniki, Greece"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9980-7773","authenticated-orcid":false,"given":"Achilleas","family":"Mitrakas","sequence":"additional","affiliation":[{"name":"Laboratory of Cellular Biology and Cell Cycle, Molecular Biology and Genetics Department, Democritus University of Thrace, University Campus, Dragana, 68100 Alexandroupolis, Greece"},{"name":"Department of Radiotherapy and Oncology, Democritus University of Thrace, University General Hospital of Alexandroupolis, 68100 Alexandroupolis, Greece"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Virginia","family":"Ghizzani","sequence":"additional","affiliation":[{"name":"PhotoGreen Lab, Department of Chemistry, University of Pavia, V. Le Taramelli 12, 27100 Pavia, Italy"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Katerina R.","family":"Katsani","sequence":"additional","affiliation":[{"name":"Laboratory of Biochemistry and Molecular Virology, Molecular Biology and Genetics Department, Democritus University of Thrace, Dragana, 68100 Alexandroupolis, Greece"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Maria","family":"Koffa","sequence":"additional","affiliation":[{"name":"Laboratory of Cellular Biology and Cell Cycle, Molecular Biology and Genetics Department, Democritus University of Thrace, University Campus, Dragana, 68100 Alexandroupolis, Greece"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Michael","family":"Koukourakis","sequence":"additional","affiliation":[{"name":"Department of Radiotherapy and Oncology, Democritus University of Thrace, University General Hospital of Alexandroupolis, 68100 Alexandroupolis, Greece"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5879-7265","authenticated-orcid":false,"given":"George","family":"Psomas","sequence":"additional","affiliation":[{"name":"Laboratory of Inorganic Chemistry, Faculty of Chemistry, Aristotle University of Thessaloniki, 54124 Thessaloniki, Greece"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5313-5692","authenticated-orcid":false,"given":"Stefano","family":"Protti","sequence":"additional","affiliation":[{"name":"PhotoGreen Lab, Department of Chemistry, University of Pavia, V. 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Chem."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"336","DOI":"10.1016\/j.bcp.2018.07.030","article-title":"Challenging transcription by DNA-binding antitumor drugs","volume":"155","author":"Portugal","year":"2018","journal-title":"Biochem. Pharmacol."},{"key":"ref_3","first-page":"212","article-title":"Chemistry and biology of DNA-binding small molecules","volume":"102","author":"Paul","year":"2012","journal-title":"Curr. Sci."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1016\/j.jphotobiol.2013.03.013","article-title":"Drug-DNA interactions and their study by UV-Visible, fluorescence spectroscopies and cyclic voltametry","volume":"124","author":"Sirajuddin","year":"2013","journal-title":"J. Photochem. Photobiol. B Biol."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"4499","DOI":"10.1016\/j.bmcl.2008.07.052","article-title":"Metal-free artificial nucleases based on simple oxime and hydroxylamine scaffolds","volume":"18","author":"Fernandes","year":"2008","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"864","DOI":"10.1016\/j.ejmech.2018.03.042","article-title":"Synthesis and evaluation of novel coumarin-oxime ethers as potential anti-tubercular agents: Their DNA cleavage ability and BSA interaction study","volume":"150","author":"Reddy","year":"2018","journal-title":"Eur. J. Med. Chem."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"103885","DOI":"10.1016\/j.bioorg.2020.103885","article-title":"Antibacterial activities and DNA-cleavage properties of novel fluorescent imidazo-phenanthroline derivatives","volume":"100","author":"Arslan","year":"2020","journal-title":"Bioorg. Chem."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"105851","DOI":"10.1016\/j.bioorg.2022.105851","article-title":"1H-imidazo[4,5-f][1,10]phenanthroline carbohydrate conjugates: Synthesis, DNA interactions and cytotoxic activity","volume":"125","author":"Gratal","year":"2022","journal-title":"Bioorg. Chem."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"619","DOI":"10.1080\/15257770.2021.1922700","article-title":"Synthesis, characterization and molecular docking studies of new indol(1H-3-yl)pyrimidine derivatives: Insights into their role in DNA interaction","volume":"40","author":"Bhat","year":"2021","journal-title":"Nucleosides Nucleotides Nucleic Acids"},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"103476","DOI":"10.1016\/j.bioorg.2019.103476","article-title":"Derivatives of pyridine and thiazole hybrid: Synthesis, DFT, biological evaluation via antimicrobial and DNA cleavage activity","volume":"95","author":"Kozak","year":"2020","journal-title":"Bioorg. Chem."},{"key":"ref_11","first-page":"292","article-title":"Naphthoquinone-thiazole hybrids bearing adamantane: Synthesis, antimicrobial, DNA cleavage, antioxidant activity, acid dissociation constant, and drug-likeness","volume":"25","author":"Sari","year":"2021","journal-title":"J. Res. Pharm."},{"key":"ref_12","first-page":"1772","article-title":"Schiff base clubbed benzothiazole: Synthesis, potent antimicrobial and MCF-7 anticancer activity, DNA cleavage and computational study","volume":"38","author":"Mishra","year":"2020","journal-title":"J. Biomol. Struct. Dyn."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"96","DOI":"10.1016\/j.molstruc.2019.06.062","article-title":"BSA interaction and DNA cleavage studies of anti-bacterial benzothiazol-2-yl-malonaldehyde","volume":"1196","author":"Katrahalli","year":"2019","journal-title":"J. Mol. Struct."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"128453","DOI":"10.1016\/j.bmcl.2021.128453","article-title":"New bis- and tetrakis-1,2,3-triazole derivatives: Synthesis, DNA cleavage, molecular docking, antimicrobial, antioxidant activity and acid dissociation constants","volume":"55","author":"Nural","year":"2022","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"1949","DOI":"10.1002\/chem.201805555","article-title":"Interaction of Functionalized Naphthalenophanes with Abasic Sites in DNA: DNA Cleavage, DNA Cleavage Inhibition, and Formation of Ligand\u2013DNA Adducts","volume":"25","author":"Caron","year":"2019","journal-title":"Chem.\u2014Eur. J."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"108519","DOI":"10.1016\/j.dyepig.2020.108519","article-title":"Selenylated-oxadiazoles as promising DNA intercalators: Synthesis, electronic structure, DNA interaction and cleavage","volume":"180","author":"Rafique","year":"2020","journal-title":"Dye. Pigment."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"111851","DOI":"10.1016\/j.ejmech.2019.111851","article-title":"2-Styryl-4-aminoquinazoline derivatives as potent DNA-cleavage, p53-activation and in vivo effective anticancer agents","volume":"186","author":"Wei","year":"2020","journal-title":"Eur. J. Med. Chem."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"38695","DOI":"10.1039\/D0RA07486A","article-title":"Synthesis of novel calix[4]arene: P -benzazole derivatives and investigation of their DNA binding and cleavage activities with molecular docking and experimental studies","volume":"10","author":"Ozkan","year":"2020","journal-title":"RSC Adv."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"135","DOI":"10.1134\/S1070363220010211","article-title":"Synthesis of Some Indolyl Derivatives under Solvent Free Conditions, Their Cytotoxicity, and DNA Cleavage Studies","volume":"90","author":"Rathod","year":"2020","journal-title":"Russ. J. Gen. Chem."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"161","DOI":"10.1055\/s-0037-1610352","article-title":"10-Membered Azaenediyne Fused to a Benzothiophene through the Nicholas Macrocyclization: Synthesis and DNA Cleavage Ability","volume":"30","author":"Danilkina","year":"2019","journal-title":"Synlett"},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"7842","DOI":"10.1021\/jacs.9b01800","article-title":"DNA Binding and Cleavage Modes of Shishijimicin A","volume":"141","author":"Zhang","year":"2019","journal-title":"J. Am. Chem. Soc."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"495","DOI":"10.1016\/j.semarthrit.2018.03.003","article-title":"Comparing ultraviolet light A photo(chemo)therapy with Methotrexate protocol in childhood localized scleroderma: Evidence from systematic review and meta-analysis approach","volume":"48","author":"Marrani","year":"2018","journal-title":"Semin. Arthritis Rheum."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"501","DOI":"10.1111\/bjd.12645","article-title":"Photo(chemo)therapy in the management of atopic dermatitis: An updated systematic review with implications for practice and research","volume":"170","author":"Garritsen","year":"2014","journal-title":"Br. J. Dermatol."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"100341","DOI":"10.1016\/j.jphotochemrev.2020.100341","article-title":"Light-assisted and remote delivery of carbon monoxide to malignant cells and tissues: Photochemotherapy in the spotlight","volume":"42","author":"Pinto","year":"2020","journal-title":"J. Photochem. Photobiol. C Photochem. Rev."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"102831","DOI":"10.1016\/j.pdpdt.2022.102831","article-title":"Photodynamic therapy for treatment of infected burns","volume":"38","author":"Mencalha","year":"2022","journal-title":"Photodiagnosis Photodyn. Ther."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"102830","DOI":"10.1016\/j.pdpdt.2022.102830","article-title":"Targeting mitochondria for cancer photodynamic therapy","volume":"38","author":"Yaqoob","year":"2022","journal-title":"Photodiagnosis Photodyn. Ther."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"102858","DOI":"10.1016\/j.pdpdt.2022.102858","article-title":"Bringing the gentle properties of daylight photodynamic therapy indoors: A systematic review of efficacy and safety","volume":"39","author":"Heerfordt","year":"2022","journal-title":"Photodiagnosis Photodyn. Ther."},{"key":"ref_28","doi-asserted-by":"crossref","unstructured":"Mazur, A., Koziorowska, K., Dynarowicz, K., Aebisher, D., and Bartusik-Aebisher, D. (2022). Photodynamic Therapy for Treatment of Disease in Children\u2014A Review of the Literature. Children, 9.","DOI":"10.3390\/children9050695"},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"615","DOI":"10.1007\/s13555-021-00655-0","article-title":"Comparison of the Efficacy and Safety of Bexarotene and Photo(Chemo)Therapy Combination Therapy and Bexarotene Monotherapy for Cutaneous T-Cell Lymphoma","volume":"12","author":"Morita","year":"2022","journal-title":"Dermatol. Ther."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"250","DOI":"10.1016\/j.jconrel.2020.05.018","article-title":"Assemblies of indocyanine green and chemotherapeutic drug to cure established tumors by synergistic chemo-photo therapy","volume":"324","author":"Hu","year":"2020","journal-title":"J. Control. Release"},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"100688","DOI":"10.1016\/j.mtchem.2021.100688","article-title":"Target delivery of photo-triggered nanocarrier for externally activated chemo-photodynamic therapy of prostate cancer","volume":"23","author":"Ghosh","year":"2022","journal-title":"Mater. Today Chem."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"119211","DOI":"10.1016\/j.molliq.2022.119211","article-title":"Combination of chemo and photo dynamic therapy using pH triggered bio-coated spinels for treatment of breast cancer","volume":"358","author":"Zamani","year":"2022","journal-title":"J. Mol. Liq."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"308","DOI":"10.1089\/photob.2021.0167","article-title":"Photodynamic Therapy in Combination with Chemotherapy, Targeted, and Immunotherapy As a Successful Therapeutic Approach for Advanced Gastric Adenocarcinoma: A Case Report and Literature Review","volume":"40","author":"Ma","year":"2022","journal-title":"Photobiomodulation Photomed. Laser Surg."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"114168","DOI":"10.1016\/j.addr.2022.114168","article-title":"Enhanced antimicrobial activity through the combination of antimicrobial photodynamic therapy and low-frequency ultrasonic irradiation","volume":"183","author":"Wang","year":"2022","journal-title":"Adv. Drug Deliv. Rev."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"102876","DOI":"10.1016\/j.pdpdt.2022.102876","article-title":"Efficacy of curcumin-mediated antibacterial photodynamic therapy for oral antisepsis: A systematic review and network meta-analysis of randomized clinical trials","volume":"39","author":"Ferrisse","year":"2022","journal-title":"Photodiagnosis Photodyn. Ther."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"105425","DOI":"10.1016\/j.archoralbio.2022.105425","article-title":"Effect of the technique of photodynamic therapy against the main microorganisms responsible for periodontitis: A systematic review of in-vitro studies","volume":"138","author":"Sales","year":"2022","journal-title":"Arch. Oral Biol."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"1518","DOI":"10.1039\/c5pp00037h","article-title":"Resistance in antimicrobial photodynamic inactivation of bacteria","volume":"14","author":"Maisch","year":"2015","journal-title":"Photochem. Photobiol. Sci."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"67","DOI":"10.1016\/j.mib.2016.06.008","article-title":"Antimicrobial photodynamic inactivation: A bright new technique to kill resistant microbes","volume":"33","author":"Hamblin","year":"2016","journal-title":"Curr. Opin. Microbiol."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"12813","DOI":"10.1021\/acs.joc.0c01895","article-title":"Dyedauxiliary Groups, an Emerging Approach in Organic Chemistry. The Case of Arylazo Sulfones","volume":"85","author":"Qiu","year":"2020","journal-title":"J. Org. Chem."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"9790","DOI":"10.1021\/acs.chemrev.0c00278","article-title":"Generation of Alkyl Radicals: From the Tyranny of Tin to the Photon Democracy","volume":"120","author":"Crespi","year":"2020","journal-title":"Chem. Rev."},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"1672","DOI":"10.1039\/c3ob27313j","article-title":"Barton esters for initiator-free radical cyclisation with heteroaromatic substitution","volume":"11","author":"Coyle","year":"2013","journal-title":"Org. Biomol. Chem."},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"5903","DOI":"10.1021\/jo5008543","article-title":"Tandem reactions via barton esters with intermolecular addition and vinyl radical substitution onto indole","volume":"79","author":"Coyle","year":"2014","journal-title":"J. Org. Chem."},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"3563","DOI":"10.1016\/j.tet.2009.01.103","article-title":"The Barton ester free-radical reaction: A brief review of applications","volume":"65","author":"Saraiva","year":"2009","journal-title":"Tetrahedron"},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"305","DOI":"10.1016\/j.trechm.2022.01.009","article-title":"Designing Radical Chemistry by Visible-Light Promoted Homolysis","volume":"4","author":"Protti","year":"2022","journal-title":"Trends Chem."},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"727","DOI":"10.1016\/S0968-0896(98)00211-9","article-title":"Design, synthesis, and evaluation of N-aroyloxy-2-thiopyridones as DNA photocleaving reagents","volume":"7","author":"Blom","year":"1999","journal-title":"Bioorg. Med. Chem."},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"1463","DOI":"10.1039\/a702913f","article-title":"Photochemical cleavage of duplex DNA by N -benzoyloxy-2-thiopyridone linked to 9-aminoacridine","volume":"5","author":"Theodorakis","year":"1997","journal-title":"Chem. Commun."},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"1927","DOI":"10.1039\/cc9960001927","article-title":"N-Aroyloxy-2-thiopyridones as efficient oxygen-radical generators: Novel time-controlled DNA photocleaving reagents","volume":"16","author":"Theodorakis","year":"1996","journal-title":"Chem. Commun."},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"3383","DOI":"10.1016\/S0040-4039(98)00509-7","article-title":"On the Mechanism of Photo-induced Nucleic Acid Cleavage Using N-Aroyloxy-2-thiopyridones","volume":"39","author":"Theodorakis","year":"1998","journal-title":"Tetrahedron Lett."},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"6175","DOI":"10.1016\/S0040-4039(01)01214-X","article-title":"N-Aroyloxynaphthalimides as novel highly efficient DNA photocleavers: Substituent effects","volume":"42","author":"Qian","year":"2001","journal-title":"Tetrahedron Lett."},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"2335","DOI":"10.1016\/j.bmc.2004.02.013","article-title":"N-Aroyloxylthioxo-naphthalimides as DNA photocleavers of aroyloxyl oxygen radicals: Synthesis, evaluation, and substituents\u2019 effect","volume":"12","author":"Xu","year":"2004","journal-title":"Bioorg. Med. Chem."},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"2234","DOI":"10.1021\/jo7025542","article-title":"Photocyclization of iminyl radicals: Theoretical study and photochemical aspects","volume":"73","author":"Alonso","year":"2008","journal-title":"J. Org. Chem."},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"27","DOI":"10.1016\/S1010-6030(02)00174-0","article-title":"Investigation of the photochemical properties of an important class of photobase generators: The O-acyloximes","volume":"151","author":"Allonas","year":"2002","journal-title":"J. Photochem. Photobiol. A Chem."},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"8828","DOI":"10.1016\/j.tet.2010.09.078","article-title":"Photochemistry of acyloximes: Synthesis of heterocycles and natural products","volume":"66","author":"Alonso","year":"2010","journal-title":"Tetrahedron"},{"key":"ref_54","doi-asserted-by":"crossref","unstructured":"Walton, J.C. (2016). Functionalised oximes: Emergent precursors for carbon-, nitrogen- and oxygen-centred radicals. Molecules, 21.","DOI":"10.3390\/molecules21010063"},{"key":"ref_55","doi-asserted-by":"crossref","first-page":"11440","DOI":"10.1002\/anie.202004413","article-title":"NIR-Sensitized Activated Photoreaction between Cyanines and Oxime Esters: Free-Radical Photopolymerization","volume":"59","author":"Pang","year":"2020","journal-title":"Angew. Chem.\u2014Int. Ed."},{"key":"ref_56","doi-asserted-by":"crossref","first-page":"719","DOI":"10.1039\/C4MD00548A","article-title":"O-Benzoyl pyridine aldoxime and amidoxime derivatives: Novel efficient DNA photo-cleavage agents","volume":"6","author":"Karamtzioti","year":"2015","journal-title":"Medchemcomm"},{"key":"ref_57","doi-asserted-by":"crossref","first-page":"1778","DOI":"10.1021\/bc400060h","article-title":"Relationship between structure of conjugated oxime esters and their ability to cleave DNA","volume":"24","author":"Hwu","year":"2013","journal-title":"Bioconjug. Chem."},{"key":"ref_58","doi-asserted-by":"crossref","first-page":"898","DOI":"10.1016\/j.bmcl.2011.12.037","article-title":"Synthesis and DNA cleavage studies of novel quinoline oxime esters","volume":"22","author":"Bindu","year":"2012","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"ref_59","doi-asserted-by":"crossref","first-page":"1239","DOI":"10.1039\/c2pp25033k","article-title":"Synthesis, photophysical, photochemical, DNA cleavage\/binding and cytotoxic properties of pyrene oxime ester conjugates","volume":"11","author":"Chowdhury","year":"2012","journal-title":"Photochem. Photobiol. Sci."},{"key":"ref_60","doi-asserted-by":"crossref","unstructured":"Pasolli, M., Dafnopoulos, K., Andreou, N.P., Gritzapis, P.S., Koffa, M., Koumbis, A.E., Psomas, G., and Fylaktakidou, K.C. (2016). Pyridine and p-nitrophenyl oxime esters with possible photochemotherapeutic activity: Synthesis, DNA photocleavage and DNA binding studies. Molecules, 21.","DOI":"10.3390\/molecules21070864"},{"key":"ref_61","doi-asserted-by":"crossref","first-page":"30","DOI":"10.1016\/j.jphotobiol.2016.02.017","article-title":"Alkyl and aryl sulfonyl p-pyridine ethanone oximes are efficient DNA photo-cleavage agents","volume":"158","author":"Andreou","year":"2016","journal-title":"J. Photochem. Photobiol. B Biol."},{"key":"ref_62","doi-asserted-by":"crossref","first-page":"351","DOI":"10.1039\/c5pp00439j","article-title":"Evaluation of O-alkyl and aryl sulfonyl aromatic and heteroaromatic amidoximes as novel potent DNA photo-cleavers","volume":"15","author":"Papastergiou","year":"2016","journal-title":"Photochem. Photobiol. Sci."},{"key":"ref_63","doi-asserted-by":"crossref","first-page":"337","DOI":"10.3762\/bjoc.16.33","article-title":"P-Pyridinyl oxime carbamates: Synthesis, DNA binding, DNA photocleaving activity and theoretical photodegradation studies","volume":"16","author":"Gritzapis","year":"2020","journal-title":"Beilstein J. Org. Chem."},{"key":"ref_64","doi-asserted-by":"crossref","first-page":"5187","DOI":"10.1021\/acs.orglett.9b01788","article-title":"Visible-Light-Driven Synthesis of Arylstannanes from Arylazo Sulfones","volume":"21","author":"Lian","year":"2019","journal-title":"Org. Lett."},{"key":"ref_65","doi-asserted-by":"crossref","first-page":"5239","DOI":"10.1002\/adsc.201900953","article-title":"Visible Light-Driven, Photocatalyst-Free Arbuzov-Like Reaction via Arylazo Sulfones","volume":"361","author":"Qiu","year":"2019","journal-title":"Adv. Synth. Catal."},{"key":"ref_66","doi-asserted-by":"crossref","first-page":"7358","DOI":"10.1002\/ejoc.202001386","article-title":"Metal-Free Synthesis of Unsymmetrical Aryl Selenides and Tellurides via Visible Light-Driven Activation of Arylazo Sulfones","volume":"2020","author":"Liu","year":"2020","journal-title":"Eur. J. Org. Chem."},{"key":"ref_67","doi-asserted-by":"crossref","first-page":"4863","DOI":"10.1021\/acs.joc.2c00225","article-title":"Visible Light-Driven, Gold(I)-Catalyzed Preparation of Symmetrical (Hetero)biaryls by Homocoupling of Arylazo Sulfones","volume":"87","author":"Scaringi","year":"2022","journal-title":"J. Org. Chem."},{"key":"ref_68","doi-asserted-by":"crossref","first-page":"1243","DOI":"10.1055\/s-0037-1611648","article-title":"Visible-Light Promoted Formation of C-B and C-S Bonds under metal and photocatalyst-free conditions","volume":"51","author":"Blank","year":"2019","journal-title":"Synthesis"},{"key":"ref_69","doi-asserted-by":"crossref","first-page":"341","DOI":"10.1002\/adsc.202100951","article-title":"Visible-Light-Mediated Synthesis of Sulfonyl Fluorides from Arylazo Sulfones","volume":"364","author":"Bui","year":"2022","journal-title":"Adv. Synth. Catal."},{"key":"ref_70","doi-asserted-by":"crossref","first-page":"6487","DOI":"10.1039\/D1OB01028J","article-title":"A photocatalyst-free visible-light-mediated solvent-switchable route to stilbenes\/vinyl sulfones from \u03b2-nitrostyrenes and arylazo sulfones","volume":"19","author":"Chawla","year":"2021","journal-title":"Org. Biomol. Chem."},{"key":"ref_71","doi-asserted-by":"crossref","first-page":"1292","DOI":"10.1021\/acs.joc.0c02669","article-title":"Metal-Free Trifluoromethylthiolation of Arylazo Sulfones","volume":"86","author":"Li","year":"2021","journal-title":"J. Org. Chem."},{"key":"ref_72","doi-asserted-by":"crossref","first-page":"151898","DOI":"10.1016\/j.tetlet.2020.151898","article-title":"Photocatalyst-free visible light driven synthesis of (E)-vinyl sulfones from cinnamic acids and arylazo sulfones","volume":"61","author":"Chawla","year":"2020","journal-title":"Tetrahedron Lett."},{"key":"ref_73","doi-asserted-by":"crossref","first-page":"5747","DOI":"10.1039\/D1PY00928A","article-title":"Blue light driven free-radical polymerization using arylazo sulfones as initiators","volume":"12","author":"Nitti","year":"2021","journal-title":"Polym. Chem."},{"key":"ref_74","doi-asserted-by":"crossref","first-page":"e202200333","DOI":"10.1002\/chem.202200333","article-title":"Visible-Light Assisted Covalent Surface Functionalization of Reduced Graphene Oxide Nanosheets with Arylazo Sulfones","volume":"28","author":"Lombardi","year":"2022","journal-title":"Chem.\u2014Eur. J."},{"key":"ref_75","doi-asserted-by":"crossref","first-page":"2786","DOI":"10.1021\/acs.langmuir.9b03878","article-title":"Simultaneous Photografting of Two Organic Groups on a Gold Surface by using Arylazo Sulfones as Single Precursors","volume":"36","author":"Decorse","year":"2020","journal-title":"Langmuir"},{"key":"ref_76","doi-asserted-by":"crossref","first-page":"826","DOI":"10.1111\/php.13376","article-title":"6-Nitro-Quinazolin\u22124(3H)\u2212one Exhibits Photodynamic Effects and Photodegrades Human Melanoma Cell Lines. A Study on the Photoreactivity of Simple Quinazolin\u22124(3H)\u2212ones","volume":"97","author":"Panagopoulos","year":"2021","journal-title":"Photochem. Photobiol."},{"key":"ref_77","doi-asserted-by":"crossref","first-page":"e04733","DOI":"10.1016\/j.heliyon.2020.e04733","article-title":"9-phenyl acridine photosensitizes A375 cells to UVA radiation","volume":"6","author":"Hansda","year":"2020","journal-title":"Heliyon"},{"key":"ref_78","doi-asserted-by":"crossref","first-page":"6392","DOI":"10.1021\/bi00394a013","article-title":"Polycyclic Aromatic Hydrocarbons Physically Intercalate into Duplex Regions of Denatured DNA","volume":"26","author":"Wolfe","year":"1987","journal-title":"Biochemistry"},{"key":"ref_79","doi-asserted-by":"crossref","first-page":"618","DOI":"10.1016\/j.jinorgbio.2007.10.005","article-title":"Synthesis, structure and interactions with DNA of novel tetranuclear, [Mn4(II\/II\/II\/IV)] mixed valence complexes","volume":"102","author":"Dimitrakopoulou","year":"2008","journal-title":"J. Inorg. Biochem."},{"key":"ref_80","doi-asserted-by":"crossref","first-page":"923","DOI":"10.1016\/j.jinorgbio.2009.04.003","article-title":"Toward the development of metal-based synthetic nucleases: DNA binding and oxidative DNA cleavage of a mixed copper(II) complex with N-(9H-purin-6-yl)benzenesulfonamide and 1,10-phenantroline. Antitumor activity in human Caco-2 cells and Jurkat T lymphocy","volume":"103","author":"Alzuet","year":"2009","journal-title":"J. Inorg. Biochem."},{"key":"ref_81","doi-asserted-by":"crossref","first-page":"114","DOI":"10.1039\/b206079p","article-title":"Interaction of macrocyclic copper(II) complexes with calf thymus DNA: Effects of the side chains of the ligands on the DNA-binding behaviors","volume":"1","author":"Liu","year":"2003","journal-title":"Dalt. Trans."},{"key":"ref_82","doi-asserted-by":"crossref","unstructured":"Lakowicz, J.R. (2006). Principles of Fluorescence Spectroscopy, Springer.","DOI":"10.1007\/978-0-387-46312-4"},{"key":"ref_83","doi-asserted-by":"crossref","first-page":"4098","DOI":"10.1021\/bi00066a035","article-title":"The Search for Structure-Specific Nucleic Acid-Interactive Drugs: Effects of Compound Structure on RNA versus DNA Interaction Strength","volume":"32","author":"Wilson","year":"1993","journal-title":"Biochemistry"},{"key":"ref_84","doi-asserted-by":"crossref","first-page":"305","DOI":"10.1016\/0301-4622(93)E0101-A","article-title":"Fluorescence lifetime analysis of DNA intercalated ethidium bromide and quenching by free dye","volume":"50","author":"Heller","year":"1994","journal-title":"Biophys. Chem."},{"key":"ref_85","doi-asserted-by":"crossref","first-page":"214780","DOI":"10.1016\/j.ccr.2022.214780","article-title":"Strategies to construct efficient singlet oxygen-generating photosensitizers","volume":"472","author":"Pang","year":"2022","journal-title":"Coord. Chem. Rev."},{"key":"ref_86","doi-asserted-by":"crossref","first-page":"208","DOI":"10.1016\/S0022-2836(61)80047-8","article-title":"A procedure for the isolation of deoxyribonucleic acid from micro-organisms","volume":"3","author":"Marmur","year":"1961","journal-title":"J. Mol. Biol."},{"key":"ref_87","doi-asserted-by":"crossref","first-page":"3047","DOI":"10.1021\/ja01640a067","article-title":"A Further Examination of the Molecular Weight and Size of Desoxypentose Nucleic Acid","volume":"76","author":"Reichmann","year":"1954","journal-title":"J. Am. Chem. Soc."},{"key":"ref_88","doi-asserted-by":"crossref","first-page":"3826","DOI":"10.1002\/adsc.201700619","article-title":"A Visible-Light-Driven, Metal-free Route to Aromatic Amides via Radical Arylation of Isonitriles","volume":"359","author":"Malacarne","year":"2017","journal-title":"Adv. Synth. Catal."},{"key":"ref_89","doi-asserted-by":"crossref","first-page":"68","DOI":"10.1021\/acsorginorgau.1c00020","article-title":"A Dyedauxiliary Group Strategy for the a-Functionalization of Ketones and Esters","volume":"1","author":"Cola","year":"2021","journal-title":"ACS Org. Inorg. Au"},{"key":"ref_90","first-page":"70","article-title":"Suzuki\u2013Miyaura cross-coupling reaction of 1-aryltriazenes with arylboronic acids catalyzed by a recyclable polymer-supported N-heterocyclic carbene\u2013palladium complex catalyst","volume":"28","author":"Nan","year":"2010","journal-title":"Beilstein J. Org. Chem."},{"key":"ref_91","doi-asserted-by":"crossref","first-page":"349","DOI":"10.1080\/00304949809355295","article-title":"New Synthesis Of Phenylthioglycolic Acids Via Related Tri-azene Compounds","volume":"30","author":"Disli","year":"1998","journal-title":"Org. Prep. Proc. Int."},{"key":"ref_92","doi-asserted-by":"crossref","first-page":"1345","DOI":"10.1016\/S0040-4039(00)95366-8","article-title":"An SRN1 approach to some aromatic nitriles diazosulfides","volume":"28","author":"Novi","year":"1987","journal-title":"Tetrahedron Lett."},{"key":"ref_93","doi-asserted-by":"crossref","first-page":"1432","DOI":"10.1021\/ol200101x","article-title":"Pd-Catalyzed desulfitative Heck coupling with dioxygen as the terminal oxidant","volume":"13","author":"Zhou","year":"2011","journal-title":"Org. Lett."},{"key":"ref_94","unstructured":"Frisch, M.J., Trucks, G., Schlegel, H., Scuseria, G.E., Robb, M., Cheeseman, J., Scalmani, G., Barone, V., Mennucci, B., and Petersson, G. (2009). Gaussian 09, Gaussian Inc.. Revision B.01."},{"key":"ref_95","doi-asserted-by":"crossref","first-page":"535","DOI":"10.1016\/0022-2836(81)90009-7","article-title":"Structure of a B-DNA dodecamer. III. Geometry of hydration","volume":"151","author":"Drew","year":"1981","journal-title":"J. Mol. Biol."},{"key":"ref_96","doi-asserted-by":"crossref","first-page":"455","DOI":"10.1002\/jcc.21334","article-title":"Software news and update AutoDock Vina: Improving the speed and accuracy of docking with a new scoring function, efficient optimization, and multithreading","volume":"31","author":"Trott","year":"2010","journal-title":"J. Comput. Chem."},{"key":"ref_97","unstructured":"Schr\u00f6dinger LLC (2022). The PyMOL Molecular Graphics System, Schr\u00f6dinger LLC. Version 1.2r3pre."}],"container-title":["International Journal of Molecular Sciences"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1422-0067\/24\/3\/1834\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,10]],"date-time":"2025-10-10T18:08:22Z","timestamp":1760119702000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1422-0067\/24\/3\/1834"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2023,1,17]]},"references-count":97,"journal-issue":{"issue":"3","published-online":{"date-parts":[[2023,2]]}},"alternative-id":["ijms24031834"],"URL":"https:\/\/doi.org\/10.3390\/ijms24031834","relation":{},"ISSN":["1422-0067"],"issn-type":[{"value":"1422-0067","type":"electronic"}],"subject":[],"published":{"date-parts":[[2023,1,17]]}}}