{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,5]],"date-time":"2026-10-05T13:48:44Z","timestamp":1791208124158,"version":"4.1.0"},"reference-count":58,"publisher":"American Chemical Society (ACS)","issue":"6","license":[{"start":{"date-parts":[[2015,11,13]],"date-time":"2015-11-13T00:00:00Z","timestamp":1447372800000},"content-version":"vor","delay-in-days":365,"URL":"https:\/\/pubs.acs.org\/page\/policy\/authorchoice_termsofuse.html"}],"funder":[{"DOI":"10.13039\/100000011","name":"Howard Hughes Medical Institute","doi-asserted-by":"publisher","award":["52007562"],"award-info":[{"award-number":["52007562"]}],"id":[{"id":"10.13039\/100000011","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100000057","name":"National Institute of General Medical Sciences","doi-asserted-by":"publisher","award":["NA"],"award-info":[{"award-number":["NA"]}],"id":[{"id":"10.13039\/100000057","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100005714","name":"Office of Experimental Program to Stimulate Competitive Research","doi-asserted-by":"publisher","award":["EPS-0903787"],"award-info":[{"award-number":["EPS-0903787"]}],"id":[{"id":"10.13039\/100005714","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100006545","name":"National Institute on Minority Health and Health Disparities","doi-asserted-by":"publisher","award":["1P20MD002725"],"award-info":[{"award-number":["1P20MD002725"]}],"id":[{"id":"10.13039\/100006545","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2015,2,12]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>Fisetin (3,7,3\u2032,4\u2032-tetrahydroxyflavone) and quercetin (3,5,7,3\u2032,4\u2032-pentahydroxyflavone) are the bioactive plant flavonoids that are potentially useful therapeutic drugs for the treatment of a broad spectrum of diseases, including atherosclerosis, cardiovascular disease, obesity, hypertension, and cancer. 3-Hydroxyflavone (3HF) and 7-hydroxyflavone (7HF) are the synthetic chromophores of fisetin and quercetin. We have exploited dual luminescence properties of fisetin and quercetin along with 3-HF and 7HF to examine their efficacy of binding and compare their interactions with DNA, which is one of the macromolecular targets of flavonoids in physiological systems. Following the sequence of the human telomeric DNA 5\u2032-d (CCCTAA-)n\/(-TTAGGG)n-5\u2032, two single-stranded DNA oligonucleotides, 5\u2032-d(C3TA2)3C3-3\u2032 and 5\u2032-d(T2AG3)4-3\u2032, and their duplex were used as receptors to study binding by the ligands quercetin, fisetin, and their chromophores. Circular dichroism, differential absorption, UV thermal melting, and size exclusion chromatographic studies indicated the formation of unusual DNA structures (such as C4 and G4 tetraplexes) for both the C- and G-rich single-stranded DNAs. Upon binding to DNA, dramatic changes were observed in the intrinsic fluorescence behavior of the flavonoids. Molecular docking studies were performed to describe the likely binding sites for the ligands. The spectroscopic studies on flavonoid\u2013DNA interactions described herein demonstrate a powerful approach for examining their DNA binding through exploiting the highly sensitive intrinsic fluorescence properties of the flavonoids as their own \u201creporter\u201d for their interactions with macromolecular targets.<\/jats:p>","DOI":"10.1021\/jp508599h","type":"journal-article","created":{"date-parts":[[2014,11,13]],"date-time":"2014-11-13T07:31:32Z","timestamp":1415863892000},"page":"2546-2556","source":"Crossref","is-referenced-by-count":43,"title":["Excited\nState Proton Transfer of Natural Flavonoids\nand Their Chromophores in Duplex and Tetraplex DNAs"],"prefix":"10.1021","volume":"119","author":[{"given":"Bidisha","family":"Sengupta","sequence":"first","affiliation":[{"name":"Tougaloo College , , , , ,","place":["Tougaloo, Mississippi, United States, 39174"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Samantha M.","family":"Reilly","sequence":"additional","affiliation":[{"name":"University of Mississippi , , , , ,","place":["University, Mississippi, United States, 38677"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"suffix":"Jr.","given":"Donald E.","family":"Davis","sequence":"additional","affiliation":[{"name":"Tougaloo College , , , , ,","place":["Tougaloo, Mississippi, United States, 39174"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Kisa","family":"Harris","sequence":"additional","affiliation":[{"name":"Tougaloo College , , , , ,","place":["Tougaloo, Mississippi, United States, 39174"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Randy M.","family":"Wadkins","sequence":"additional","affiliation":[{"name":"University of Mississippi , , , , ,","place":["University, Mississippi, United States, 38677"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Denise","family":"Ward","sequence":"additional","affiliation":[{"name":"Tougaloo College , , , , ,","place":["Tougaloo, Mississippi, United States, 39174"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"D\u2019Asia","family":"Gholar","sequence":"additional","affiliation":[{"name":"Tougaloo College , , , , ,","place":["Tougaloo, Mississippi, United States, 39174"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Cari","family":"Hampton","sequence":"additional","affiliation":[{"name":"Tougaloo College , , , , ,","place":["Tougaloo, Mississippi, United States, 39174"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2014,11,13]]},"reference":[{"key":"2026090306050846300_cit1","volume-title":"Plant Flavonoids\nin Biology and Medicine II: Biochemical, Cellular and Medicinal properties","author":"Harborne","year":"1988"},{"key":"2026090306050846300_cit2","doi-asserted-by":"crossref","first-page":"27","DOI":"10.1038\/138027a0","article-title":"Vitamin P:\nflavonols as vitamins","volume":"138","author":"Rusznya\u0301k","year":"1936","journal-title":"Nature"},{"key":"2026090306050846300_cit3","doi-asserted-by":"crossref","first-page":"248","DOI":"10.1038\/sj.ejcn.1602509","article-title":"Intakes\nand sources of soya foods and isoflavones in a UK population cohort\nstudy (EPIC-Norfolk)","volume":"61","author":"Mulligan","year":"2007","journal-title":"Eur. J. Clin. Nutr."},{"key":"2026090306050846300_cit4","doi-asserted-by":"crossref","first-page":"1523","DOI":"10.1016\/0140-6736(92)91277-F","article-title":"Wine, alcohol,\nplatelets, and the French paradox for\ncoronary heart disease","volume":"339","author":"Renaud","year":"1992","journal-title":"Lancet"},{"key":"2026090306050846300_cit58","doi-asserted-by":"crossref","first-page":"41","DOI":"10.1097\/00041433-200202000-00007","article-title":"Evidence that the\nantioxidant flavonoids in tea and\ncocoa are beneficial for cardiovascular health","volume":"13","author":"Kris-Etherton","year":"2002","journal-title":"Curr. Opin. Lipidol."},{"key":"2026090306050846300_cit5","doi-asserted-by":"crossref","first-page":"135","DOI":"10.3844\/ajidsp.2009.135.141","article-title":"The flavonoid, quercetin,\ninhibits HIV-1 infection in normal peripheral blood mononuclear cells","volume":"5","author":"Nair","year":"2009","journal-title":"Am. J. Infect. Dis."},{"key":"2026090306050846300_cit6","doi-asserted-by":"crossref","first-page":"481","DOI":"10.1016\/S0031-9422(00)00235-1","article-title":"Advances in flavonoid research since 1992","volume":"55","author":"Harborne","year":"2000","journal-title":"Phytochemistry"},{"key":"2026090306050846300_cit7","doi-asserted-by":"crossref","first-page":"484","DOI":"10.1016\/j.intimp.2007.12.012","article-title":"Suppressive effects of flavonoid\nfisetin on lipopolysaccharide-induced microglial activation and neurotoxicity","volume":"8","author":"Zheng","year":"2008","journal-title":"Int. Immunopharmacol."},{"key":"2026090306050846300_cit8","doi-asserted-by":"crossref","first-page":"288","DOI":"10.1016\/j.jinorgbio.2005.11.013","article-title":"Interactions of quercetin\nand its lanthane complex with double-stranded DNA\/RNA and single-stranded\nRNA. Spectrophotometric sensing of poly G","volume":"100","author":"Marini\u0301","year":"2006","journal-title":"J.\nInorg. Biochem."},{"key":"2026090306050846300_cit9","doi-asserted-by":"crossref","first-page":"213","DOI":"10.1007\/s003940070014","article-title":"Absorption\nand DNA protective effects of flavonoid glycosides from an onion meal","volume":"39","author":"Boyle","year":"2000","journal-title":"Eur. J. Nutr."},{"key":"2026090306050846300_cit10","first-page":"2273","article-title":"The characterization\nof flavone-DNA isoform interactions as a basis for anticancer drug\ndevelopment","volume":"29","author":"Ragazzon","year":"2009","journal-title":"Anticancer Res."},{"key":"2026090306050846300_cit11","doi-asserted-by":"crossref","first-page":"405","DOI":"10.1016\/0092-8674(85)90170-9","article-title":"Identification of a specific telomere\nterminal transferase\nactivity in tetrahymena extracts","volume":"43","author":"Greider","year":"1985","journal-title":"Cell"},{"key":"2026090306050846300_cit12","first-page":"166","article-title":"Telomeres\nof Human Chromosomes","volume":"1","author":"O\u2019Connor","year":"2008","journal-title":"Nat. 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Biol."},{"key":"2026090306050846300_cit16","doi-asserted-by":"crossref","first-page":"182","DOI":"10.1038\/nchem.1548","article-title":"Quantitative\nvisualization of DNA G-quadruplex structures in human cells","volume":"5","author":"Biffi","year":"2013","journal-title":"Nat. Chem."},{"key":"2026090306050846300_cit17","doi-asserted-by":"crossref","first-page":"3887","DOI":"10.1093\/nar\/gkl529","article-title":"Gene function correlates with potential for G4 DNA\nformation in the human genome","volume":"34","author":"Eddy","year":"2006","journal-title":"Nucleic Acids\nRes."},{"key":"2026090306050846300_cit18","doi-asserted-by":"crossref","first-page":"4182","DOI":"10.1093\/nar\/gki722","article-title":"Preferential binding\nof a G-quadruplex ligand to human\nchromosome ends","volume":"33","author":"Granotier","year":"2005","journal-title":"Nucleic Acids Res."},{"key":"2026090306050846300_cit19","doi-asserted-by":"publisher","first-page":"e65383","DOI":"10.1371\/journal.pone.0065383","article-title":"Prospect of bioflavonoid\nfisetin as a quadruplex DNA ligand: A biophysical approach","volume":"8","author":"Sengupta","year":"2013","journal-title":"PLoS One"},{"key":"2026090306050846300_cit20","doi-asserted-by":"crossref","first-page":"6833","DOI":"10.1128\/AEM.02057-13","article-title":"Probing\n3-Hydroxyflavone for in vitro glycorandomization of flavonols by YjiC","volume":"79","author":"Pandey","year":"2013","journal-title":"Appl. Environ. Microbiol."},{"key":"2026090306050846300_cit21","doi-asserted-by":"crossref","first-page":"624","DOI":"10.1016\/0006-291X(92)90792-J","article-title":"The inhibition of phosphatidylinositol\n3-kinase by quercetin and analogs","volume":"186","author":"Matter","year":"1992","journal-title":"Biochem.\nBiophys. Res. Commun."},{"key":"2026090306050846300_cit22","doi-asserted-by":"crossref","first-page":"2262","DOI":"10.1074\/jbc.271.4.2262","article-title":"Selected novel\nflavones inhibit the DNA binding or the DNA religation step of eukaryotic\ntopoisomerase I","volume":"271","author":"Boege","year":"1996","journal-title":"J. Biol. Chem."},{"key":"2026090306050846300_cit23","doi-asserted-by":"crossref","first-page":"1617","DOI":"10.1016\/0006-2952(89)90309-2","article-title":"Protein kinase\nC inhibition by plant\nflavonoids: Kinetic mechanisms and structure\u2013activity relationships","volume":"381","author":"Ferricola","year":"1989","journal-title":"Biochem. Pharmacol."},{"key":"2026090306050846300_cit24","doi-asserted-by":"crossref","first-page":"631","DOI":"10.1016\/0006-291X(92)91103-W","article-title":"Flavones are inhibitors of HIV-1\nproteinase","volume":"188","author":"Brinkworth","year":"1992","journal-title":"Biochem. Biophys. Res. Commun."},{"key":"2026090306050846300_cit25","doi-asserted-by":"crossref","first-page":"77","DOI":"10.1016\/j.febslet.2004.06.027","article-title":"Investigations\non the binding and\nantioxidant properties of the plant flavonoid fisetin in model biomembranes","volume":"570","author":"Sengupta","year":"2004","journal-title":"FEBS Lett."},{"key":"2026090306050846300_cit26","doi-asserted-by":"crossref","first-page":"954","DOI":"10.1016\/j.bbrc.2005.06.181","article-title":"Properties of normal and glycated human hemoglobin\nin presence and absence of antioxidant","volume":"334","author":"Sengupta","year":"2005","journal-title":"Biochem.\nBiophys. Res. Commun."},{"key":"2026090306050846300_cit27","doi-asserted-by":"crossref","DOI":"10.1007\/978-0-387-46312-4","volume-title":"Principles of Fluorescence\nSpectroscopy","author":"Lakowicz","year":"2006","edition":"3"},{"key":"2026090306050846300_cit28","doi-asserted-by":"crossref","first-page":"19518","DOI":"10.1021\/jp906522u","article-title":"DNA templates for\nfluorescent silver clusters and i-motif\nfolding","volume":"113","author":"Sengupta","year":"2009","journal-title":"J. Phys. Chem. C"},{"key":"2026090306050846300_cit29","doi-asserted-by":"crossref","first-page":"2785","DOI":"10.1002\/jcc.21256","article-title":"Autodock4\nand AutoDockTools4: Automated\ndocking with selective receptor flexiblity","volume":"30","author":"Morris","year":"2009","journal-title":"J. Comput. Chem."},{"key":"2026090306050846300_cit30","doi-asserted-by":"crossref","first-page":"8","DOI":"10.1002\/0471250953.bi0814s24","article-title":"Using autodock for ligand-receptor\ndocking","volume":"24","author":"Morris","year":"2008","journal-title":"Curr. Protoc. Bioinform."},{"key":"2026090306050846300_cit31","doi-asserted-by":"crossref","first-page":"1605","DOI":"10.1002\/jcc.20084","article-title":"UCSF Chimera\u2500a\nvisualization system for exploratory\nresearch and analysis","volume":"25","author":"Pettersen","year":"2004","journal-title":"J. Comput. Chem."},{"key":"2026090306050846300_cit32","doi-asserted-by":"crossref","first-page":"263","DOI":"10.1016\/0969-2126(93)90015-9","article-title":"Solution structure\nof the human telomeric repeat d[AG3(T2AG3)3] G-tetraplex","volume":"1","author":"Wang","year":"1993","journal-title":"Structure"},{"key":"2026090306050846300_cit33","doi-asserted-by":"crossref","first-page":"949","DOI":"10.1006\/jmbi.1998.1740","article-title":"An intramolecular\ni-motif: The solution\nstructure and base-pair opening kinetics of d(5mCCT3CCT3ACCT3CC)","volume":"278","author":"Han","year":"1998","journal-title":"J. Mol. Biol."},{"key":"2026090306050846300_cit34","doi-asserted-by":"crossref","first-page":"4154","DOI":"10.1021\/ja00089a002","article-title":"Multiple binding\nmodes of anticancer drug actinomycin\nD: X-ray, molecular modeling, and spectroscopic studies of d (GAAGCTTC)\n2-actinomycin D complexes and its host DNA","volume":"116","author":"Kamitori","year":"1994","journal-title":"J. Am. Chem. Soc."},{"key":"2026090306050846300_cit35","doi-asserted-by":"crossref","first-page":"1504","DOI":"10.1016\/0006-291X(72)90243-4","article-title":"Optimised parameters for A-DNA and B-DNA","volume":"47","author":"Arnott","year":"1972","journal-title":"Biochem. Biophys. Res. Commun."},{"key":"2026090306050846300_cit36","doi-asserted-by":"crossref","first-page":"138","DOI":"10.1093\/nar\/gni134","article-title":"Thermal difference\nspectra: A specific signature for nucleic acid structures","volume":"33","author":"Mergny","year":"2005","journal-title":"Nucleic Acids Res."},{"key":"2026090306050846300_cit37","doi-asserted-by":"crossref","first-page":"729","DOI":"10.1016\/j.ijbiomac.2011.07.004","article-title":"Influence\nof pH, temperature and the cationic porphyrin TMPyP4 on the stability\nof the i-motif formed by the 5\u2032-(C3TA2)4-3\u2032 sequence\nof the human telomere","volume":"49","author":"Ferna\u0301ndez","year":"2011","journal-title":"Int. J. Biol. Macromol."},{"key":"2026090306050846300_cit38","doi-asserted-by":"crossref","first-page":"691","DOI":"10.1002\/chir.22064","article-title":"Circular dichroism\nspectroscopy of DNA: From duplexes to quadruplexes","volume":"24","author":"Vorlickova","year":"2012","journal-title":"Chirality"},{"key":"2026090306050846300_cit39","doi-asserted-by":"crossref","first-page":"245","DOI":"10.1080\/07391102.2000.10506628","article-title":"Intramolecular i-Motif Structures of Telomeric DNA","volume":"17","author":"Phan","year":"2000","journal-title":"J. Biomol Struct. Dyn."},{"key":"2026090306050846300_cit40","doi-asserted-by":"crossref","first-page":"382","DOI":"10.1016\/0009-2614(79)87221-8","article-title":"Excited state proton-transfer spectroscopy of 3-hydroxyflavone and\nquercetin","volume":"68","author":"Sengupta","year":"1979","journal-title":"Chem. Phys. 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B"},{"key":"2026090306050846300_cit49","doi-asserted-by":"crossref","first-page":"61","DOI":"10.1002\/mas.1003","article-title":"Electrospray ionization\nmass spectrometry of oligonucleotide complexes with drugs, metals,\nand proteins","volume":"20","author":"Beck","year":"2001","journal-title":"Mass Spectrom. Rev."},{"key":"2026090306050846300_cit50","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1016\/j.jphotobiol.2013.03.013","article-title":"Drug\u2013DNA\ninteractions and their study by UV\u2013Visible,\nfluorescence spectroscopies and cyclic voltametry","volume":"124","author":"Sirajuddin","year":"2013","journal-title":"J. Photochem. Photobiol. B"},{"key":"2026090306050846300_cit51","doi-asserted-by":"crossref","first-page":"2451","DOI":"10.1021\/bi00124a002","article-title":"Interaction of the dye ethidium bromide\nwith DNA containing guanine repeats","volume":"31","author":"Guo","year":"1992","journal-title":"Biochemistry"},{"key":"2026090306050846300_cit52","doi-asserted-by":"crossref","first-page":"239","DOI":"10.1016\/j.sbi.2009.04.001","article-title":"The structures\nof quadruplex nucleic acids and their drug complexes","volume":"19","author":"Neidle","year":"2009","journal-title":"Current Opin. Struct. Biol."},{"key":"2026090306050846300_cit53","doi-asserted-by":"crossref","first-page":"127","DOI":"10.1089\/nat.2012.0342","article-title":"The interaction\nof telomeric DNA and C-myc22 G-quadruplex with 11 natural alkaloids","volume":"22","author":"Ji","year":"2012","journal-title":"Nucleic Acid Therapeutics"},{"key":"2026090306050846300_cit54","doi-asserted-by":"crossref","first-page":"692","DOI":"10.1042\/bst0290692","article-title":"Secondary\nDNA structures as molecular targets for cancer therapeutics","volume":"29","author":"Hurley","year":"2001","journal-title":"Biochem. Soc. Trans."},{"key":"2026090306050846300_cit55","doi-asserted-by":"crossref","first-page":"4188","DOI":"10.1021\/jm030650o","article-title":"Validation of automated docking programs for docking\nand database screening against RNA drug targets","volume":"47","author":"Detering","year":"2004","journal-title":"J. Med. 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