An insight of spirooxindole-annulated thiopyran – DNA interaction: spectroscopic and docking approach of these biological materials

References

• Singh MP, Joseph T, Kumar S, et al. Synthesis and sequence-specific DNA binding of a topoisomerase inhibitory analog of Hoechst 33258 designed for altered base and sequence recognition. Chem Res Toxicol. 1992;5(5):597–607.10.1021/tx00029a003
   PubMed Web of Science ®Google Scholar
• Sparks J, Scholz C. Evaluation of a cationic poly(β-hydroxyalkanoate) as a plasmid DNA delivery system. Biomacromolecules. 2009;10(7):1715–1719. DOI:10.1021/bm900372x
   PubMed Web of Science ®Google Scholar
• Jw L. Lexitropsins: rational design of DNA sequence reading agents as novel anti-cancer agents and potential cellular probes. Anticancer Drug Des. 1988;3(1):25–40.
   PubMedGoogle Scholar
• Kundu P, Ghosh S, Chattopadhyay N. Exploration of the binding interaction of a potential nervous system stimulant with calf-thymus DNA and dissociation of the drug–DNA complex by detergent sequestration. Phys Chem Chem Phys. 2015;17(27):17699–17709. DOI:10.1039/C5CP02101D
   PubMed Web of Science ®Google Scholar
• Hossain M, Suresh Kumar G. Thermodynamic profiles of the DNA binding of benzophenanthridines sanguinarine and ethidium: a comparative study with sequence specific polynucleotides. J Chem Thermodyn. 2010;42(10):1273–1280. DOI:10.1016/j.jct.2010.05.005
   Web of Science ®Google Scholar
• Kabir A, Hossain M, Kumar GS. Thermodynamics of the DNA binding of biogenic polyamines: calorimetric and spectroscopic investigations. J Chem Thermodyn. 2013;57:445–453. DOI:10.1016/j.jct.2012.09.025
   Web of Science ®Google Scholar
• Ma Y, Zhang G, Pan J. Spectroscopic studies of DNA interactions with food colorant indigo carmine with the use of ethidium bromide as a fluorescence probe. J Agric Food Chem. 2012;60(43):10867–10875. DOI:10.1021/jf303698k
   PubMed Web of Science ®Google Scholar
• Erkkila KE, Odom DT, Barton JK. Recognition and reaction of metallointercalators with DNA. Chem Rev. 1999;99(9):2777–2796.10.1021/cr9804341
   PubMed Web of Science ®Google Scholar
• Carter MT, Rodriguez M, Bard AJ. Voltammetric studies of the interaction of metal chelates with DNA. 2. Tris-chelated complexes of cobalt(III) and iron(II) with 1,10-phenanthroline and 2,2’-bipyridine. J Am Chem Soc. 1989;111(24):8901–8911. DOI:10.1021/ja00206a020
   Web of Science ®Google Scholar
• Das S, Kumar GS. Molecular aspects on the interaction of phenosafranine to deoxyribonucleic acid: model for intercalative drug–DNA binding. J Mol Struct. 2008;872(1):56–63. DOI:10.1016/j.molstruc.2007.02.016
   Web of Science ®Google Scholar
• Bischoff G, Hoffmann S. DNA-binding of drugs used in medicinal therapies. Curr Med Chem. 2002;9(3):312–348.
   PubMed Web of Science ®Google Scholar
• Neidle S, Nunn CM. Crystal structures of nucleic acids and their drug complexes. Nat Prod Rep. 1998;15(1):1–15.10.1039/a815001y
   PubMed Web of Science ®Google Scholar
• Tsuboi M, Benevides JM, Thomas GJ Jr. The complex of ethidium bromide with genomic DNA: structure analysis by polarized raman spectroscopy. Biophys J. 2007;92(3):928–934. DOI:10.1529/biophysj.106.093633
   PubMed Web of Science ®Google Scholar
• Rohs R, Bloch I, Sklenar H, et al. Molecular flexibility in ab initio drug docking to DNA: binding-site and binding-mode transitions in all-atom Monte Carlo simulations. Nucleic Acids Res. 2005;33(22):7048–7057. DOI:10.1093/nar/gki1008
   PubMed Web of Science ®Google Scholar
• Carle JS, Christophersen C. Marine alkaloids. 2. Bromo alkaloids from a marine bryozoan Flustra foliacea. Isolation and structure elucidation. J Org Chem. 1980;45(9):1586–1589. DOI:10.1021/jo01297a007
   Web of Science ®Google Scholar
• Kamijo S, Yamamoto Y. A bimetallic catalyst and dual role catalyst: synthesis of N-(Alkoxycarbonyl)indoles from 2-(Alkynyl)phenylisocyanates. J Org Chem. 2003;68(12):4764–4771. DOI:10.1021/jo034254p
   PubMed Web of Science ®Google Scholar
• Brown MJ, Carter PS, Fenwick AE, et al. The antimicrobial natural product chuangxinmycin and some synthetic analogues are potent and selective inhibitors of bacterial tryptophanyl tRNA synthetase. Bioorg Med Chem Lett. 2002;12(21):3171–3174. DOI:10.1016/S0960-894X(02)00604-2
   PubMed Web of Science ®Google Scholar
• Quaglia W, Pigini M, Piergentili A, et al. Structure–activity relationships in 1,4-benzodioxan-related compounds. 7. Selectivity of 4-phenylchroman analogues for α1–adrenoreceptor subtypes. J Med Chem. 2002;45(8):1633–1643. DOI:10.1021/jm011066n
   PubMed Web of Science ®Google Scholar
• Majumdar KC, Ponra S, Nandi RK. One-pot efficient green synthesis of spirooxindole-annulated thiopyran derivatives via Knoevenagel condensation followed by Michael addition. Tetrahedron Lett. 2012;53(14):1732–1737. DOI:10.1016/j.tetlet.2012.01.099
   Web of Science ®Google Scholar
• Vardevanyan PO, Antonyan AP, Parsadanyan MA, et al. The binding of ethidium bromide with DNA: interaction with single- and double-stranded structures. Exp Mol Med. 2003;35(6):527–533. DOI:10.1038/emm.2003.68
   PubMed Web of Science ®Google Scholar
• Mandal A, Ghosh S, Bothra AK, et al. Synthesis of friedelan triterpenoid analogs with DNA topoisomerase IIα inhibitory activity and their molecular docking studies. Eur J Med Chem. 2012;54:137–143. DOI:10.1016/j.ejmech.2012.04.037
   PubMed Web of Science ®Google Scholar
• Marinelli L, Lavecchia A, Gottschalk K-E, et al. Docking studies on αvβ3 integrin ligands: pharmacophore refinement and implications for drug design. J Med Chem. 2003;46(21):4393–4404. DOI:10.1021/jm020577m
   PubMed Web of Science ®Google Scholar
• Stephanos JJ. Drug-protein interactions: two-site binding of heterocyclic ligands to a monomeric hemoglobin. J Inorg Biochem. 1996;62(3):155–169.10.1016/0162-0134(95)00144-1
   PubMed Web of Science ®Google Scholar
• Marty R, N’soukpoé-Kossi CN, Charbonneau D, et al. Structural analysis of DNA complexation with cationic lipids. Nucleic Acids Res. 2009;37(3):849–857. DOI:10.1093/nar/gkn1003
   PubMed Web of Science ®Google Scholar
• Benesi HA, Hildebrand JH. A spectrophotometric investigation of the interaction of iodine with aromatic hydrocarbons. J Am Chem Soc. 1949;71(8):2703–2707. DOI:10.1021/ja01176a030
   Web of Science ®Google Scholar
• Mariam J, Dongre PM, Kothari DC. Study of interaction of silver nanoparticles with bovine serum albumin using fluorescence spectroscopy. J Fluoresc. 2011;21(6):2193–2199. DOI:10.1007/s10895-011-0922-3
   PubMed Web of Science ®Google Scholar
• Lakowicz JR. Principles of fluorescence spectroscopy. Springer-Verlag: Springer; 2006. DOI: 10.1007/978-0-387-46312-4
   Google Scholar
• Pacheco ME, Bruzzone L. Interactions between imazethapyr and bovine serum albumin: spectrofluorimetric study. J Lumin. 2012;132(10):2730–2735. DOI:10.1016/j.jlumin.2012.05.023
   Web of Science ®Google Scholar
• Anbazhagan V, Renganathan R. Study on the binding of 2,3-diazabicyclo[2.2.2]oct-2-ene with bovine serum albumin by fluorescence spectroscopy. J Lumin. 2008;128(9):1454–1458. DOI:10.1016/j.jlumin.2008.02.004
   Web of Science ®Google Scholar
• Darban RA, Shareghi B, Asoodeh A, et al. Multi-spectroscopic and molecular modeling studies of interaction between two different angiotensin I converting enzyme inhibitory peptides from gluten hydrolysate and human serum albumin. J Biomol Struct Dyn. 2016;1–15. DOI:10.1080/07391102.2016.1264892
   Web of Science ®Google Scholar
• Psomas G, Tarushi A, Efthimiadou EK. Synthesis, characterization and DNA-binding of the mononuclear dioxouranium(VI) complex with ciprofloxacin. Polyhedron. 2008;27(1):133–138. DOI:10.1016/j.poly.2007.08.043
   Web of Science ®Google Scholar
• Min J, Meng-Xia X, Dong Z, et al. Spectroscopic studies on the interaction of cinnamic acid and its hydroxyl derivatives with human serum albumin. J Mol Struct. 2004;692(1–3):71–80. DOI:10.1016/j.molstruc.2004.01.003
   Web of Science ®Google Scholar
• Kandagal PB, Ashoka S, Seetharamappa J, et al. Study of the interaction of an anticancer drug with human and bovine serum albumin: spectroscopic approach. J Pharm Biomed Anal. 2006;41(2):393–399. DOI:10.1016/j.jpba.2005.11.037
   PubMed Web of Science ®Google Scholar
• Roy S, Nandi RK, Ganai S, et al. Binding interaction of phosphorus heterocycles with bovine serum albumin: a biochemical study. J Pharm Anal. 2017;7(1):19–26. DOI:10.1016/j.jpha.2016.05.009
   PubMed Web of Science ®Google Scholar
• Roy S, Das TK. Investigation of interaction between casein enzyme hydrolysate and biosynthesized silver nanoparticles by spectroscopy. Nanosci Nanotechnol Lett. 2014;6(7):547–554. DOI:10.1166/nnl.2014.1852
   Web of Science ®Google Scholar
• Roy S, Das TK. Interaction of biosynthesized gold nanoparticles with BSA and CTDNA: a multi-spectroscopic approach. Polyhedron. 2016;115:111–118. DOI:10.1016/j.poly.2016.05.002
   Web of Science ®Google Scholar
• Roy S, Saxena SK, Mishra S, et al. Evidence of bovine serum albumin-viologen herbicide binding interaction and associated structural modifications. J Mol Struct. 2017;1139:447–454. DOI:10.1016/j.molstruc.2017.03.058
   Web of Science ®Google Scholar
• Boger DL, Fink BE, Hedrick MP. Total synthesis of distamycin A and 2640 analogues: a solution-phase combinatorial approach to the discovery of new, bioactive DNA binding agents and development of a rapid, high-throughput screen for determining relative DNA binding affinity or DNA binding sequence selectivity. J Am Chem Soc. 2000;122(27):6382–6394. DOI:10.1021/ja994192d
   Web of Science ®Google Scholar
• Lee M, Rhodes AL, Wyatt MD, et al. GC base sequence recognition by oligoimidazolecarboxamide and C-terminus-modified analogs of distamycin deduced from circular dichroism, proton nuclear magnetic resonance, and methidiumpropylethylenediaminetetraacetate-iron(II) footprinting studies. Biochemistry. 1993;32(16):4237–4245. DOI:10.1021/bi00067a011
   PubMed Web of Science ®Google Scholar
• Roy S, Sadhukhan R, Ghosh U, et al. Interaction studies between biosynthesized silver nanoparticle with calf thymus DNA and cytotoxicity of silver nanoparticles. Spectrochim Acta Part A Mol Biomol Spectrosc. 2015;141:176–184. DOI:10.1016/j.saa.2015.01.041
   PubMed Web of Science ®Google Scholar
• Liu Y, Chen M, Luo Z, et al. Investigation on the site-selective binding of bovine serum albumin by erlotinib hydrochloride. J Biomol Struct Dyn. 2013;31(10):1160–1174. DOI:10.1080/07391102.2012.726532
   PubMed Web of Science ®Google Scholar
• Némethy G, Scheraga HA. The structure of water and hydrophobic bonding in proteins. Iii. The thermodynamic properties of hydrophobic bonds in proteins. J Phys Chem. 1962;66(10):1773–1789. DOI:10.1021/j100816a004
   Web of Science ®Google Scholar
• Ross PD, Subramanian S. Thermodynamics of protein association reactions: forces contributing to stability. Biochemistry. 1981;20(11):3096–3102.10.1021/bi00514a017
   PubMed Web of Science ®Google Scholar
• Shahabadi N, Fatahi A. Multispectroscopic DNA-binding studies of a tris-chelate nickel(II) complex containing 4,7-diphenyl 1,10-phenanthroline ligands. J Mol Struct. 2010;970(1–3):90–95. DOI:10.1016/j.molstruc.2010.02.048
   Web of Science ®Google Scholar
• Shahabadi N, Fili SM, Kheirdoosh F. Study on the interaction of the drug mesalamine with calf thymus DNA using molecular docking and spectroscopic techniques. J Photochem Photobiol, B. 2013;128:20–26. DOI:10.1016/j.jphotobiol.2013.08.005
   PubMed Web of Science ®Google Scholar
• Krishna AG, Kumar DV, Khan BM, et al. Taxol-DNA interactions: fluorescence and CD studies of DNA groove binding properties of taxol. Biochimica Et Biophysica Acta. 1998;1381(1):104–112.10.1016/S0304-4165(98)00019-1
   PubMed Web of Science ®Google Scholar
• Sahoo D, Bhattacharya P, Chakravorti S. Quest for mode of binding of 2-(4-(dimethylamino)styryl)-1-methylpyridinium Iodide with calf thymus DNA. J Phys Chem B. 2010;114(5):2044–2050. DOI:10.1021/jp910766q
   PubMed Web of Science ®Google Scholar
• Caruso F, Rossi M, Benson A, et al. Ruthenium-arene complexes of curcumin: X-ray and density functional theory structure, synthesis, and spectroscopic characterization, in vitro antitumor activity, and DNA docking studies of (p-cymene)ru(curcuminato)chloro. J Med Chem. 2012;55(3):1072–1081. DOI:10.1021/jm200912j
   PubMed Web of Science ®Google Scholar
• Shi J-H, Liu T-T, Jiang M, et al. Characterization of interaction of calf thymus DNA with gefitinib: spectroscopic methods and molecular docking. J Photochem Photobiol, B. 2015;147:47–55. DOI:10.1016/j.jphotobiol.2015.03.005
   PubMed Web of Science ®Google Scholar
• Kumari M, Maurya JK, Singh UK, et al. Spectroscopic and docking studies on the interaction between pyrrolidinium based ionic liquid and bovine serum albumin. Spectrochim Acta Part A Mol Biomol Spectrosc. 2014;124:349–356. DOI:10.1016/j.saa.2014.01.012
   PubMed Web of Science ®Google Scholar
• Selva Sharma A, Anandakumar S, Ilanchelian M. A combined spectroscopic and molecular docking study on site selective binding interaction of Toluidine blue O with Human and Bovine serum albumins. J Lumin. 2014;151:206–218. DOI:10.1016/j.jlumin.2014.02.009
   Web of Science ®Google Scholar