{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T01:40:11Z","timestamp":1760146811697,"version":"build-2065373602"},"reference-count":94,"publisher":"MDPI AG","issue":"24","license":[{"start":{"date-parts":[[2024,12,18]],"date-time":"2024-12-18T00:00:00Z","timestamp":1734480000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"FCT"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["IJMS"],"abstract":"<jats:p>Cancer is a leading cause of death, so continuous efforts into cancer therapy are imperative. In tumor cells, telomerase and oncogene activity are key points for uncontrolled cell growth. Targeting these processes with ligands that inhibit telomerase and\/or reduce oncogene expression has been identified as a promising cancer therapy. This study evaluated the selectivity and affinity of the silverII complex of 5,10,15,20-tetrakis(N-methyl-4-pyridinium)porphyrin (AgTMPyP) to stabilize DNA sequences capable of forming G4 structures mimicking the telomeric and oncogene regions, using spectroscopic, biochemical methods and in vitro assays. The tetracationic silver complex was compared with the free base, H2TMPyP, and the zincII complex, ZnTMPyP. The results obtained from UV-Vis and fluorescence methods pointed to a great affinity and good selectivity of AgTMPyP to G4 structures, especially for the oncogene MYC. In general, an increase in the ability of the studied ligands for 1O2 generation when interacting with oncogenic and telomeric G4 sequences was found. The results of the PCR stop assays proved that AgTMPyP has the ability to inhibit Taq polymerase. Additionally, in vitro assays demonstrated that the silverII complex exhibits low cytotoxicity against HaCaT\u2014 an immortalized, non-tumorigenic, skin keratinocytes cell line\u2014and, although nonexclusive, AgTMPyP shows nuclear co-localization.<\/jats:p>","DOI":"10.3390\/ijms252413556","type":"journal-article","created":{"date-parts":[[2024,12,18]],"date-time":"2024-12-18T08:56:32Z","timestamp":1734512192000},"page":"13556","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["Is Silver a Precious Metal for G-Quadruplex Stabilization Mediated by Porphyrins?"],"prefix":"10.3390","volume":"25","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-9373-7006","authenticated-orcid":false,"given":"Nuno M. M.","family":"Moura","sequence":"first","affiliation":[{"name":"LAQV-REQUIMTE, Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal"}]},{"given":"Sofia","family":"Guedes","sequence":"additional","affiliation":[{"name":"LAQV-REQUIMTE, Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal"}]},{"given":"Diana","family":"Salvador","sequence":"additional","affiliation":[{"name":"CESAM-Centre for Environmental and Marine Studies, Department of Biology and CESAM, University of Aveiro, 3810-193 Aveiro, Portugal"},{"name":"CICECO, Aveiro Institute of Materials, Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4673-0696","authenticated-orcid":false,"given":"Helena","family":"Oliveira","sequence":"additional","affiliation":[{"name":"CESAM-Centre for Environmental and Marine Studies, Department of Biology and CESAM, University of Aveiro, 3810-193 Aveiro, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7953-8166","authenticated-orcid":false,"given":"M. Gra\u00e7a P. M. S.","family":"Neves","sequence":"additional","affiliation":[{"name":"LAQV-REQUIMTE, Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0200-2005","authenticated-orcid":false,"given":"Catarina I. V.","family":"Ramos","sequence":"additional","affiliation":[{"name":"LAQV-REQUIMTE, Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal"}]}],"member":"1968","published-online":{"date-parts":[[2024,12,18]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"28","DOI":"10.2174\/1568026620666200819160213","article-title":"Beyond DNA-targeting in Cancer Chemotherapy. Emerging Frontiers\u2014A Review","volume":"21","author":"Mbugua","year":"2021","journal-title":"Curr. Top. Med. Chem."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"521","DOI":"10.1021\/jm400528t","article-title":"Telomere maintenance as a target for drug discovery","volume":"57","author":"Sekaran","year":"2014","journal-title":"J. Med. Chem."},{"key":"ref_3","doi-asserted-by":"crossref","unstructured":"Xu, Y., and Goldkorn, A. (2016). Telomere and telomerase therapeutics in cancer. Genes, 7.","DOI":"10.3390\/genes7060022"},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"21858","DOI":"10.1016\/S0021-9258(17)31882-3","article-title":"Structure and stability of human telomeric sequence","volume":"269","author":"Balagurumoorthy","year":"1994","journal-title":"J. Biol. Chem."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"273","DOI":"10.1016\/S0092-8674(04)00038-8","article-title":"Beginning to understand the end of the chromosome","volume":"116","author":"Cech","year":"2004","journal-title":"Cell"},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"69","DOI":"10.1038\/nrm3505","article-title":"Finding the end: Recruitment of telomerase to telomeres","volume":"14","author":"Nandakumar","year":"2013","journal-title":"Nat. Rev. Mol. Cell Biol."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"24","DOI":"10.1016\/j.pharmthera.2016.03.017","article-title":"Functional and mechanistic analysis of telomerase: An antitumor drug target","volume":"163","author":"Chen","year":"2016","journal-title":"Pharmacol. Ther."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"2408","DOI":"10.1093\/nar\/gkl303","article-title":"Telomeres, chromosome instability and cancer","volume":"34","author":"Bailey","year":"2006","journal-title":"Nucleic Acids Res."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"787","DOI":"10.1016\/S0959-8049(97)00062-2","article-title":"A survey of telomerase activity in human cancer","volume":"33","author":"Shay","year":"1997","journal-title":"Eur. J. Cancer"},{"key":"ref_10","doi-asserted-by":"crossref","unstructured":"Wang, W., Hu, S., Gu, Y., Yan, Y., Stovall, D.B., Li, D., and Sui, G. (2020). Human MYC G-quadruplex: From discovery to a cancer therapeutic target. Biochim. Biophys. Acta\u2014Rev. Cancer, 1874.","DOI":"10.1016\/j.bbcan.2020.188410"},{"key":"ref_11","doi-asserted-by":"crossref","unstructured":"Bahls, B., Aljnadi, I.M., Em\u00eddio, R., Mendes, E., and Paulo, A. (2023). G-Quadruplexes in c-MYC Promoter as Targets for Cancer Therapy. Biomedicines, 11.","DOI":"10.3390\/biomedicines11030969"},{"key":"ref_12","doi-asserted-by":"crossref","unstructured":"(2012). Dang C V MYC on the path to cancer. Cell, 149, 22.","DOI":"10.1016\/j.cell.2012.03.003"},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"1024","DOI":"10.1158\/2159-8290.CD-15-0507","article-title":"MYC, Metabolism, and Cancer","volume":"5","author":"Stine","year":"2015","journal-title":"Cancer Discov."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"6009","DOI":"10.21873\/anticanres.14622","article-title":"Role of Oncogenes and Tumor-suppressor Genes in Carcinogenesis: A Review","volume":"40","author":"Kontomanolis","year":"2020","journal-title":"Anticancer Res."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"21","DOI":"10.2147\/ITT.S150586","article-title":"Oncogenes in immune cells as potential therapeutic targets","volume":"7","author":"Zakiryanova","year":"2018","journal-title":"ImmunoTargets Ther."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"141","DOI":"10.1016\/S0163-7258(99)00068-6","article-title":"G-quadruplexes as targets for drug design","volume":"85","author":"Hurley","year":"2000","journal-title":"Pharmacol. Ther."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"155","DOI":"10.1002\/bies.20523","article-title":"Physiological relevance of telomeric G-quadruplex formation: A potential drug target","volume":"29","author":"Oganesian","year":"2007","journal-title":"BioEssays"},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"899","DOI":"10.1002\/cmdc.201300566","article-title":"G-quadruplex structures and their interaction diversity with ligands","volume":"9","author":"Zhang","year":"2014","journal-title":"ChemMedChem"},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"15036","DOI":"10.1021\/ja204326w","article-title":"Contribution of Telomere G-Quadruplex Stabilization to the Inhibition of Telomerase-Mediated Telomere Extension by Chemical Ligands","volume":"133","author":"Chen","year":"2011","journal-title":"J. Am. Chem. Soc."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"1107","DOI":"10.1111\/j.1742-4658.2009.07464.x","article-title":"Human telomeric G-quadruplex: Structures of DNA and RNA sequences","volume":"277","author":"Phan","year":"2010","journal-title":"FEBS J."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"2536","DOI":"10.1093\/nar\/gkl286","article-title":"G-quadruplex formation within the promoter of the KRAS proto-oncogene and its effect on transcription","volume":"34","author":"Cogoi","year":"2006","journal-title":"Nucleic Acids Res."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"2898","DOI":"10.2174\/0929867325666171229132619","article-title":"The Interplay between G-quadruplex and Transcription","volume":"26","author":"Kim","year":"2019","journal-title":"Curr. Med. Chem."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"5536","DOI":"10.1021\/bi972681p","article-title":"Effect of DNA secondary structure on human telomerase activity","volume":"37","author":"Fletcher","year":"1998","journal-title":"Biochemistry"},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"11593","DOI":"10.1073\/pnas.182256799","article-title":"Direct evidence for a G-quadruplex in a promoter region and its targeting with a small molecule to repress c- MYC transcription","volume":"99","author":"Grand","year":"2002","journal-title":"Proc. Natl. Acad. Sci. USA"},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"167","DOI":"10.1016\/j.apcatb.2018.09.030","article-title":"Insights into rapid photodynamic inactivation mechanism of Staphylococcus aureus via rational design of multifunctional nitrogen-rich carbon-coated bismuth\/cobalt nanoparticles","volume":"241","author":"Wang","year":"2019","journal-title":"Appl. Catal. B"},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"218","DOI":"10.1038\/nchembio864","article-title":"An RNA G-quadruplex in the 5\u2032 UTR of the NRAS proto-oncogene modulates translation","volume":"3","author":"Kumari","year":"2007","journal-title":"Nat. Chem. Biol."},{"key":"ref_27","doi-asserted-by":"crossref","unstructured":"Reed, J.E., Neidle, S., and Vilar, R. (2007). Stabilisation of human telomeric quadruplex DNA and inhibition of telomerase by a platinum\u2013phenanthroline complex. Chem. Commun., 4366\u20134368.","DOI":"10.1039\/b709898g"},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"159","DOI":"10.1016\/j.dnarep.2016.05.022","article-title":"DNA damage processing at telomeres: The ends justify the means","volume":"44","author":"Fouquerel","year":"2016","journal-title":"DNA Repair"},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"189","DOI":"10.1016\/S0304-3835(02)00706-1","article-title":"Telomere repeat binding factors: Keeping the ends in check","volume":"194","author":"Karlseder","year":"2003","journal-title":"Cancer Lett."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"802","DOI":"10.1016\/j.bbrc.2004.08.150","article-title":"Stabilization of the c-myc gene promoter quadruplex by specific ligands\u2019 inhibitors of telomerase","volume":"323","author":"Lemarteleur","year":"2004","journal-title":"Biochem. Biophys. Res. Commun."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"275","DOI":"10.1007\/s10867-014-9348-x","article-title":"A spectroscopic investigation of the interaction between c-MYC DNA and tetrapyridinoporphyrazinatozinc(II)","volume":"40","author":"Hassani","year":"2014","journal-title":"J. Biol. Phys."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"105703","DOI":"10.1016\/j.bioorg.2022.105703","article-title":"Diketopyrrolo[3,4-c]pyrrole derivative as a promising ligand for the stabilization of G-quadruplex DNA structures","volume":"122","author":"Ramos","year":"2022","journal-title":"Bioorg. Chem."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"12368","DOI":"10.3390\/molecules181012368","article-title":"G-quadruplex structures in the human genome as novel therapeutic targets","volume":"18","author":"Bidzinska","year":"2013","journal-title":"Molecules"},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"8082","DOI":"10.1074\/jbc.M117.781906","article-title":"High-resolution three-dimensional NMR structure of the KRAS proto-oncogene promoter reveals key features of a G-quadruplex involved in transcriptional regulation","volume":"292","author":"Kerkour","year":"2017","journal-title":"J. Biol. Chem."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"ii","DOI":"10.1016\/B978-0-12-544952-6.50001-0","article-title":"Medicinal Chemistry: A Series of Monographs","volume":"2","author":"Rapozzi","year":"1964","journal-title":"Med. Chem."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"663","DOI":"10.1586\/17512433.2014.945909","article-title":"G-quadruplex interacting small molecules and drugs: From bench toward bedside","volume":"7","author":"Rodriguez","year":"2014","journal-title":"Expert Rev. Clin. Pharmacol."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"1163","DOI":"10.2174\/138955708785909880","article-title":"Design of selective G-quadruplex ligands as potential anticancer agents","volume":"8","author":"Tan","year":"2008","journal-title":"Mini-reviews Med. Chem."},{"key":"ref_38","doi-asserted-by":"crossref","unstructured":"Deiana, M., Matczyszyn, K., Massin, J., Olesiak-Banska, J., Andraud, C., and Samoc, M. (2015). Interactions of isophorone derivatives with DNA: Spectroscopic studies. PLoS ONE, 10.","DOI":"10.1371\/journal.pone.0133814"},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"525862","DOI":"10.4061\/2010\/525862","article-title":"\u201cOne Ring to Bind Them All\u201d\u2014Part I: The Efficiency of the Macrocyclic Scaffold for G-Quadruplex DNA Recognition","volume":"2010","author":"Monchaud","year":"2010","journal-title":"J. Nucleic Acids"},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"869","DOI":"10.1002\/cmdc.201700747","article-title":"Design of Modular G-quadruplex Ligands","volume":"13","author":"Duarte","year":"2018","journal-title":"ChemMedChem"},{"key":"ref_41","doi-asserted-by":"crossref","unstructured":"Ramos, C.I.V., Monteiro, A.R., Moura, N.M.M., Faustino, M.A.F., Trindade, T., and Neves, M.G.P.M.S. (2021). The interactions of h2tmpyp, analogues and its metal complexes with dna g-quadruplexes\u2014An overview. Biomolecules, 11.","DOI":"10.3390\/biom11101404"},{"key":"ref_42","doi-asserted-by":"crossref","unstructured":"Ramos, C.I.V., Almeida, S.P., Louren\u00e7o, L.M.O., Pereira, P.M.R., Fernandes, R., Faustino, M.A.F., Tom\u00e9, J.P.C., Carvalho, J., Cruz, C., and Neves, M.G.P.M.S. (2019). Multicharged Phthalocyanines as Selective Ligands for G-Quadruplex DNA Structures. Molecules, 24.","DOI":"10.3390\/molecules24040733"},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"1673","DOI":"10.2174\/092986707780830970","article-title":"Phthalocyanines Covalently Bound to Biomolecules for a Targeted Photodynamic Therapy","volume":"14","author":"Taquet","year":"2007","journal-title":"Curr. Med. Chem."},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"173","DOI":"10.1002\/jms.2048","article-title":"Charge and substituent effects on the stability of porphyrin\/G-quadruplex adducts","volume":"47","author":"Ramos","year":"2012","journal-title":"J. Mass Spectrom."},{"key":"ref_45","doi-asserted-by":"crossref","unstructured":"Moura, N.M.M., Cavaleiro, J.A.S., Neves, M.G.P.M.S., and Ramos, C.I.V. (2023). opp-Dibenzoporphyrin Pyridinium Derivatives as Potential G-Quadruplex DNA Ligands. Molecules, 28.","DOI":"10.3390\/molecules28176318"},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"900","DOI":"10.1016\/j.jcis.2022.07.075","article-title":"Interfacial assembly of zinc(II) phthalocyanines on graphene oxide (GO): Stable \u201cturn-off-on\u201d nanoplatforms to detect G-quadruplexes (G4)","volume":"627","author":"Monteiro","year":"2022","journal-title":"J. Colloid Interface Sci."},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"11184","DOI":"10.1021\/acsomega.8b01366","article-title":"Hybrids Based on Graphene Oxide and Porphyrin as Tools for Detection and Stabilization of DNA G-Quadruplexes","volume":"3","author":"Monteiro","year":"2018","journal-title":"ACS Omega"},{"key":"ref_48","doi-asserted-by":"crossref","unstructured":"Menilli, L., Monteiro, A.R., Lazzarotto, S., Morais, F.M.P., Gomes, A.T.P.C., Moura, N.M.M., Fateixa, S., Faustino, M.A.F., Neves, M.G.P.M.S., and Trindade, T. (2021). Graphene oxide and graphene quantum dots as delivery systems of cationic porphyrins: Photo-antiproliferative activity evaluation towards t24 human bladder cancer cells. Pharmaceutics, 13.","DOI":"10.3390\/pharmaceutics13091512"},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"2113","DOI":"10.1021\/jm970199z","article-title":"Inhibition of human telomerase by a G-Quadruplex-Interactive compound","volume":"40","author":"Sun","year":"1997","journal-title":"J. Med. Chem."},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"1310","DOI":"10.1016\/j.biochi.2011.06.008","article-title":"Improvement of porphyrins for G-quadruplex DNA targeting","volume":"93","author":"Romera","year":"2011","journal-title":"Biochimie"},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"627","DOI":"10.1039\/B714772B","article-title":"A hitchhiker\u2019s guide to G-quadruplex ligands","volume":"6","author":"Monchaud","year":"2008","journal-title":"Org. Biomol. Chem."},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"482","DOI":"10.1080\/10409238.2021.1926417","article-title":"Guanine quadruplexes and their roles in molecular processes","volume":"56","author":"Mishra","year":"2021","journal-title":"Crit. Rev. Biochem. Mol. Biol."},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"2","DOI":"10.1038\/s41598-017-11413-8","article-title":"Interaction between G-Quadruplex and Zinc Cationic Porphyrin: The Role of the Axial Water","volume":"7","author":"Yao","year":"2017","journal-title":"Sci. Rep."},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"902","DOI":"10.1016\/j.bbagen.2015.09.004","article-title":"Calorimetric and spectroscopic investigations of the binding of metallated porphyrins to G-quadruplex DNA","volume":"1860","author":"Dupont","year":"2016","journal-title":"Biochim. Biophys. Acta\u2014Gen. Subj."},{"key":"ref_55","doi-asserted-by":"crossref","first-page":"12807","DOI":"10.1021\/acs.jpcb.6b09827","article-title":"Interaction of a cationic porphyrin and its metal derivatives with G-quadruplex DNA","volume":"120","author":"Boschi","year":"2016","journal-title":"J. Phys. Chem. B"},{"key":"ref_56","doi-asserted-by":"crossref","first-page":"1297","DOI":"10.1016\/j.biochi.2011.05.038","article-title":"Induction of G-quadruplex DNA structure by Zn(II) 5,10,15,20-tetrakis(N- methyl-4-pyridyl)porphyrin","volume":"93","author":"Bhattacharjee","year":"2011","journal-title":"Biochimie"},{"key":"ref_57","doi-asserted-by":"crossref","first-page":"349","DOI":"10.1016\/j.ccr.2016.05.015","article-title":"Silver coordination compounds: A new horizon in medicine","volume":"327\u2013328","author":"Medici","year":"2016","journal-title":"Coord. Chem. Rev."},{"key":"ref_58","doi-asserted-by":"crossref","first-page":"2171","DOI":"10.1128\/AEM.02001-07","article-title":"Antibacterial Activity and Mechanism of Action of the Silver Ion in Staphylococcus aureus and Escherichia coli","volume":"74","author":"Jung","year":"2008","journal-title":"Appl. Environ. Microbiol."},{"key":"ref_59","doi-asserted-by":"crossref","first-page":"127199","DOI":"10.1016\/j.matlet.2019.127199","article-title":"Synthesis of a new binuclear silver(I) complex with the ability to interact with DNA molecule","volume":"262","author":"Gao","year":"2020","journal-title":"Mater. Lett."},{"key":"ref_60","doi-asserted-by":"crossref","first-page":"e202300116","DOI":"10.1002\/chem.202300116","article-title":"Silver-Based Terpyridine Complexes as Antitumor Agents","volume":"29","author":"Olmos","year":"2023","journal-title":"Chem.\u2014Eur. J."},{"key":"ref_61","doi-asserted-by":"crossref","unstructured":"Moura, N.M.M., Guedes, S., Salvador, D., Oliveira, H., Alves, M.Q., Paradis, N., Wu, C., Neves, M.G.P.M.S., and Ramos, C.I.V. (2024). Oncogenic and telomeric G-quadruplexes: Targets for porphyrin-triphenylphosphonium conjugates. Int. J. Biol. Macromol., 277.","DOI":"10.1016\/j.ijbiomac.2024.134126"},{"key":"ref_62","doi-asserted-by":"crossref","unstructured":"Kawauchi, K., Urano, R., Kinoshita, N., Kuwamoto, S., Torii, T., Hashimoto, Y., Taniguchi, S., Tsuruta, M., and Miyoshi, D. (2020). Photosensitizers based on g-quadruplex ligand for cancer photodynamic therapy. Genes, 11.","DOI":"10.3390\/genes11111340"},{"key":"ref_63","doi-asserted-by":"crossref","first-page":"13158","DOI":"10.1021\/acsami.9b02695","article-title":"G-Quadruplex\/Porphyrin Composite Photosensitizer: A Facile Way to Promote Absorption Redshift and Photodynamic Therapy Efficacy","volume":"11","author":"Cheng","year":"2019","journal-title":"ACS Appl. Mater. Interfaces"},{"key":"ref_64","doi-asserted-by":"crossref","first-page":"156","DOI":"10.1016\/j.bmcl.2016.11.094","article-title":"Photodynamic effect of meso-(aryl)porphyrins and meso-(1-methyl-4-pyridinium)porphyrins on HaCaT keratinocytes","volume":"27","author":"Slomp","year":"2017","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"ref_65","doi-asserted-by":"crossref","first-page":"759","DOI":"10.1111\/1523-1747.ep12345811","article-title":"Detection of telomerase activity in malignant and nonmalignant skin conditions","volume":"106","author":"Taylor","year":"1996","journal-title":"J. Investig. Dermatol. Apr."},{"key":"ref_66","doi-asserted-by":"crossref","first-page":"335","DOI":"10.1038\/s41467-021-24198-2","article-title":"Promoter G-quadruplexes and transcription factors cooperate to shape the cell type-specific transcriptome","volume":"12","author":"Lago","year":"2021","journal-title":"Nat. Commun."},{"key":"ref_67","doi-asserted-by":"crossref","unstructured":"Pavez Lorie, E., Stricker, N., Plitta-Michalak, B., Chen, I.-P., Volkmer, B., Greinert, R., Jauch, A., Boukamp, P., and Rapp, A. (2020). Characterisation of the novel spontaneously immortalized and invasively growing human skin keratinocyte line HaSKpw. Sci. Rep., 10.","DOI":"10.1038\/s41598-020-71315-0"},{"key":"ref_68","doi-asserted-by":"crossref","first-page":"6476","DOI":"10.1073\/pnas.93.13.6476","article-title":"Telomerase activity in the regenerative basal layer of the epidermis inhuman skin and in immortal and carcinoma-derived skin keratinocytes","volume":"93","author":"Boukamp","year":"1996","journal-title":"Proc. Natl. Acad. Sci. USA"},{"key":"ref_69","doi-asserted-by":"crossref","first-page":"144","DOI":"10.1002\/(SICI)1098-2744(199811)23:3<144::AID-MC3>3.0.CO;2-U","article-title":"Multiple stages and genetic alterations in immortalization, malignant transformation, and tumor progression of human skin keratinocytes","volume":"23","author":"Fusenig","year":"1998","journal-title":"Mol. Carcinog."},{"key":"ref_70","doi-asserted-by":"crossref","first-page":"5293","DOI":"10.1039\/c1cs15117g","article-title":"Methods for investigating G-quadruplex DNA\/ligand interactions","volume":"40","author":"Murat","year":"2011","journal-title":"Chem. Soc. Rev."},{"key":"ref_71","doi-asserted-by":"crossref","first-page":"1900","DOI":"10.2174\/138161212799958486","article-title":"Experimental methods for studying the interactions between G-quadruplex structures and ligands","volume":"18","author":"Jaumot","year":"2012","journal-title":"Curr. Pharm. Des."},{"key":"ref_72","doi-asserted-by":"crossref","first-page":"4509","DOI":"10.1021\/jm010246u","article-title":"Quadruplex-interactive agents as telomerase inhibitors: Synthesis of porphyrins and structure-activity relationship for the inhibition of telomerase","volume":"44","author":"Shi","year":"2001","journal-title":"J. Med. Chem."},{"key":"ref_73","doi-asserted-by":"crossref","first-page":"6681","DOI":"10.1021\/bi052356z","article-title":"A spectroscopic study on the interactions of porphyrin with G- quadruplex DNAs","volume":"45","author":"Wei","year":"2006","journal-title":"Biochemistry"},{"key":"ref_74","doi-asserted-by":"crossref","first-page":"37230","DOI":"10.1039\/C7RA05930B","article-title":"Exploring the preferential interaction of quercetin with VEGF promoter G-quadruplex DNA and construction of a pH-dependent DNA-based logic gate","volume":"7","author":"Bhattacharjee","year":"2017","journal-title":"RSC Adv."},{"key":"ref_75","first-page":"11","article-title":"Visualizing the Quadruplex: From Fluorescent Ligands to Light-Up Probes","volume":"330","author":"Largy","year":"2013","journal-title":"Top. Curr. Chem."},{"key":"ref_76","doi-asserted-by":"crossref","first-page":"37","DOI":"10.1007\/s12154-009-0029-3","article-title":"Hill coefficients, dose\u2013response curves and allosteric mechanisms","volume":"3","author":"Prinz","year":"2010","journal-title":"J. Chem. Biol."},{"key":"ref_77","doi-asserted-by":"crossref","first-page":"136","DOI":"10.1016\/S0165-6147(00)01457-7","article-title":"G-quadruplex DNA: A potential target for anti-cancer drug design","volume":"21","author":"Han","year":"2000","journal-title":"Trends Pharmacol. Sci."},{"key":"ref_78","doi-asserted-by":"crossref","first-page":"3419","DOI":"10.1007\/s00216-011-5018-z","article-title":"Development of a high-throughput G4-FID assay for screening and evaluation of small molecules binding quadruplex nucleic acid structures","volume":"400","author":"Largy","year":"2011","journal-title":"Anal. Bioanal. Chem."},{"key":"ref_79","unstructured":"Baumann, P. (2009). G4-FID: A Fluorescent DNA Probe Displacement Assay for Rapid Evaluation of Quadruplex Ligands. G-Quadruplex DNA\u2014Methods and Protocols, Humana Press."},{"key":"ref_80","doi-asserted-by":"crossref","first-page":"145","DOI":"10.1002\/(SICI)1099-1409(199803\/04)2:2<145::AID-JPP60>3.0.CO;2-2","article-title":"Singlet Oxygen Quantum Yields of Different Photosensitizers in Polar Solvents and Micellar Solutions","volume":"02","author":"Spiller","year":"1998","journal-title":"J. Porphyr. Phthalocyanines"},{"key":"ref_81","doi-asserted-by":"crossref","first-page":"853","DOI":"10.1016\/j.ejmech.2007.06.014","article-title":"Synthesis, properties and photodynamic inactivation of Escherichia coli by novel cationic fullerene C60 derivatives","volume":"43","author":"Spesia","year":"2008","journal-title":"Eur. J. Med. Chem."},{"key":"ref_82","doi-asserted-by":"crossref","first-page":"168","DOI":"10.1111\/j.1751-1097.2009.00647.x","article-title":"Synthesis, Properties and In Vitro Photodynamic Activity of Water-soluble Azaphthalocyanines and Azanaphthalocyanines","volume":"86","author":"Zimcik","year":"2010","journal-title":"Photochem. Photobiol."},{"key":"ref_83","doi-asserted-by":"crossref","first-page":"6433","DOI":"10.1039\/C7CS00525C","article-title":"Advancing porphyrin\u2019s biomedical utility via supramolecular chemistry","volume":"46","author":"Rajora","year":"2017","journal-title":"Chem. Soc. Rev."},{"key":"ref_84","doi-asserted-by":"crossref","first-page":"67","DOI":"10.1016\/j.ccr.2016.06.007","article-title":"Engineering of relevant photodynamic processes through structural modifications of metallotetrapyrrolic photosensitizers","volume":"325","author":"Pucelik","year":"2016","journal-title":"Coord. Chem. Rev."},{"key":"ref_85","doi-asserted-by":"crossref","first-page":"8","DOI":"10.1016\/j.ab.2008.04.044","article-title":"Study of the interaction between the G-quadruplex-forming thrombin-binding aptamer and the porphyrin 5,10,15,20-tetrakis-(N-methyl-4-pyridyl)-21,23H-porphyrin tetratosylate","volume":"379","author":"Gargallo","year":"2008","journal-title":"Anal. Biochem."},{"key":"ref_86","doi-asserted-by":"crossref","unstructured":"Litovchick, A., Tian, X., Monteiro, M.I., Kennedy, K.M., Gui\u00e9, M.-A., Centrella, P., Zhang, Y., Clark, M.A., and Keefe, A.D. (2019). Novel Nucleic Acid Binding Small Molecules Discovered Using DNA-Encoded Chemistry. Molecules, 24.","DOI":"10.3390\/molecules24102026"},{"key":"ref_87","doi-asserted-by":"crossref","first-page":"65","DOI":"10.1007\/978-1-59745-363-9_5","article-title":"Biochemical techniques for the characterization of Gquadruplex structures: EMSA, DMS footprinting, and DNA polymerase stop assay","volume":"608","author":"Sun","year":"2010","journal-title":"Methods Mol. Biol."},{"key":"ref_88","doi-asserted-by":"crossref","first-page":"239","DOI":"10.1007\/s11626-998-0130-x","article-title":"Application and evaluation of the alamarblue assay for cell growth and survival of fibroblasts","volume":"34","author":"Brightman","year":"1998","journal-title":"Vitr. Cell. Dev. Biol.\u2014Anim."},{"key":"ref_89","doi-asserted-by":"crossref","first-page":"12347","DOI":"10.3390\/s120912347","article-title":"Multiple Applications of Alamar Blue as an Indicator of Metabolic Function and Cellular Health in Cell Viability Bioassays","volume":"12","author":"Rampersad","year":"2012","journal-title":"Sensors"},{"key":"ref_90","doi-asserted-by":"crossref","first-page":"205","DOI":"10.1016\/S0022-1759(97)00043-4","article-title":"Assessment of the Alamar Blue assay for cellular growth and viability in vitro","volume":"204","author":"Nakayama","year":"1997","journal-title":"J. Immunol. Methods"},{"key":"ref_91","doi-asserted-by":"crossref","first-page":"109298","DOI":"10.1016\/j.dyepig.2021.109298","article-title":"Merging pyridine(s) with porphyrins and analogues: An overview of synthetic approaches","volume":"191","author":"Vallejo","year":"2021","journal-title":"Dye. Pigment."},{"key":"ref_92","doi-asserted-by":"crossref","first-page":"146418","DOI":"10.4061\/2010\/146418","article-title":"Effect of ionic strength on porphyrin drugs interaction with quadruplex DNA formed by the promoter region of C-myc and Bcl2 oncogenes","volume":"2010","author":"Nagesh","year":"2010","journal-title":"J. Nucleic Acids"},{"key":"ref_93","doi-asserted-by":"crossref","unstructured":"Lakowicz, J.R. (2006). Principles of Fluorescence Spectroscopy, Springer.","DOI":"10.1007\/978-0-387-46312-4"},{"key":"ref_94","doi-asserted-by":"crossref","first-page":"144","DOI":"10.1016\/j.molstruc.2011.05.023","article-title":"Fluorescence quenching and ligand binding: A critical discussion of a popular methodology","volume":"998","author":"Stella","year":"2011","journal-title":"J. Mol. Struct."}],"container-title":["International Journal of Molecular Sciences"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1422-0067\/25\/24\/13556\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,10]],"date-time":"2025-10-10T16:54:40Z","timestamp":1760115280000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1422-0067\/25\/24\/13556"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2024,12,18]]},"references-count":94,"journal-issue":{"issue":"24","published-online":{"date-parts":[[2024,12]]}},"alternative-id":["ijms252413556"],"URL":"https:\/\/doi.org\/10.3390\/ijms252413556","relation":{},"ISSN":["1422-0067"],"issn-type":[{"type":"electronic","value":"1422-0067"}],"subject":[],"published":{"date-parts":[[2024,12,18]]}}}