Invitro antioxidant activity and Molecular modeling studies of nine chromone derivatives were carried out to optimize their inhibitory activity against Poly [ADP-ribose] polymerase. The biological activities of these analogs were correlated to different molecular properties. The AM1and PM3 semiempirical methods are used to estimate vertical ioniza-tion potentials (IPv’s), electron affinity (EA), electronegativity (χ), hardness (η), softness (S), electrophilic index (ω), parti-tion coefficient (LogP), hydration energy (HE), ionization potential (IP) and charges. The different modeled equations by regression analysis are proposed. The leave-one-out cross-validation method is used to estimate the predictive power of final QSAR equations. The hardness (η) was found to be indicative molecular property by regression analysis. Docking studies of chromone with Poly [ADP-ribose] polymerase are also made to support the finding of QSAR studies. Analysis of results of both QSAR and Docking studies suggested that remarkable inhibitory activity is exhibited by molecule 3 .The hydrogen bond interactions along with hydrophobic and electrostatic interactions are mapped to confirm their potencies.
| Published in | Modern Chemistry (Volume 1, Issue 1) |
| DOI | 10.11648/j.mc.20130101.12 |
| Page(s) | 8-17 |
| Creative Commons |
This is an Open Access article, distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution and reproduction in any medium or format, provided the original work is properly cited. |
| Copyright |
Copyright © The Author(s), 2024. Published by Science Publishing Group |
Chromone Derivatives, Semi Empirical Methods, Cross-Validation Method, Inhibitor, QSAR, Regression Analysis, Docking
| [1] | Miao H, Yang Z (2000) Regio-specific carbonylative annu-lation of iodophenol acetates and acetylenes to construct the flavones by a new catalyst of palladiu-Silva AMS, Pinto DCGA, Cavaleiro JAS, Levai A, Patonay T (2004) Synthesis and reactivity of styrylchromones. Arki-voc 106 (c) Levai A (2004) Synthesis of exocyclicα,β-unsaturated ketones. Arkivoc 15. |
| [2] | Cutting WC, Dreisbach R H, Azima M,NeffBJ, Brown BJ, Wray J (1951) Antiviral chemotherapy. V. Further report on flavonoids. Stanford Med Bull 9:236. |
| [3] | Mentzer C, MeunierP, Lecocq J, Billet D, Xuong D (1945) Bull Soc Chim Fr 12:430 (c) Cox JSG (1967) Nature, Lon-don 216: 1328 (d) Orr TSC, Pollard MC, Gwilliam J (1970) Cox JSG Mode of action of disodium Cromoglycate, studies on immediate type hypersensitivity reactions using `double sensitization' with two antigenetically distinct rat regains. Celin Exp Immunol 7: 745. |
| [4] | Valenti P, Bisi A, Rampa A, Belluti F, Gobbi S, Zampiron A, Carrara M(2000) Synthesis andbiological activity of some rigid analogues of flavone-8-acetic acid.Biorg Med Chem 239. |
| [5] | Lim LC, Kuo YC, Chou CJ (2000) Cytotoxic biflavonoids from Selaginelladelicatula. J Nat Prod63:627. |
| [6] | Shi YQ, Fukai T, Sakagami H, Chang WJ, Yang PQ, Wang FP, Nomura T (2001) Cytotoxic flavonoids with isoprenoid groups from Morusmongolica. J Nat Prod 64:181. |
| [7] | Larget R, Lockhart B, Renard P, Largeron M (2000) A Con-venient Extension of the Wessely Moser Rearrangement for the Synthesis of Substituted Alkyl amino flavones as Neu-roprotective Agents In Vitro Biorg Med Chem Lett 10: 835. |
| [8] | Groweiss A, Cardellins JH, Boyd MR (2000) HIV-Inhibitory prenylatedxanthones and flavones from Macluratinctoria. J Nat Prod 63:1537. |
| [9] | Deng Y, Lee JP, Ramamonjy MT, Synder JK, Des Etages SA, Kanada D, Synder MP,Turner CJ(2000) New antimicrobial flavanones from Physenamadagascariensis. J Nat Prod 63:1082. |
| [10] | Khan IA, Avery MA,Burandt CL, Goins DK, Mikell JR, Nash TE, Azadega A,Walker LA (2000) Antigiardial activity of isoflavones from Dalbergiafrutescens bark. J Nat Prod 63: 1414. |
| [11] | Mori K, Audran G, Monti H (1998) ChemInform Abstract: The First Synthesis of Coniochaetones A and (.+-.)-B: Two Benzopyranone Derivatives. Synlett 259. |
| [12] | Pietta PJ (2000) Flavonoids as antioxidants. J Nat Prod 63:1035. |
| [13] | (a)Beecher GR (2003) Overview of Dietary Flavonoids: Nomenclature, Occurrence and Intake J Nutr 133:3248S. (b) Hoult JRS, Moroney MA, Paya M (1994) Actions of flavo-noids and coumarinson lipoxygenase and cyclooxygenase. Methods Enzymol 234:443. |
| [14] | Horton DA, Bourne GT, Smythe ML (2003) The combina-torial synthesis of bicyclic privileged structures or privileged substructures. ChemRev 103: 893. |
| [15] | Grindlay D, Reynolds T (1986) The 2008 aloe vera pheno-menon. J Ethnopharmacology16:117. |
| [16] | Hirata T, Suga T (1978) Biosynthesis of Aloenin in Aloe arborescence var.natalensis. Bull Chem Soc Jap 51:842. |
| [17] | Womble D, Helderman JH (1988) Enhancement of allo-responsiveness of human lymphocytes by aceman-nan(carrisyn).Int J Immunopharmac 10: 967. |
| [18] | Yu D, Brossi A, Kilgore N, Wild C, Alloway G, Lee KH. (2003) Anti-HIV agents. Part 55: 3'R, 4’R- Di-(O)-(-)-camphanoyl-2', 2’-dimethyldihydropyrano [2, 3-f] chromone (DCP), a novel anti-HIV agent. Bioorg Med Chem Lett 13(9):1575. |
| [19] | (a) Bouanani H, Gayoso JCR (1973). Acad Sci Paris Ser C 273:399 (b) Saburi Y, Yoshimoto T, Minami K (1971) Nip-pon Kagaku Zaisshi 92: 552. |
| [20] | Dias MM, Machado NFL, Marques MPM (2011) Dietary Chromones as antioxidant agents-The Structural variable. Food and function 2:595. |
| [21] | Pal pacher, Csalba S, (2008) Role of the peroxynitrile-PARP pathwayin human disease. The American Journal of Pathol-ogy 1(173):2-13. |
| [22] | Winterbourn CC, Hawkins RE, Brian M, Carrell RW(1975) The estimation of red cell superoxideDismutase activity. J Lab Clin Med. Feb 85(2):337-41. |
| [23] | http://www.warezdestiny.com/free-hyp. |
| [24] | SPSS Software. Consult http://www.spss.com. |
| [25] | Roothan CCJ (1951) New Developments in Molecular Or-bital Theory. Rev Mod Phys 23:69. |
| [26] | Pople JA, Nesbet RK (1954) Self consistent Orbitals for Radicals. J Chem Phys 22:571. |
| [27] | McWeeny R, Dierksen G (1968) Interpolating functionals in relation to the transition state and transition operator methods. J Chem Phys 49: 4852. |
| [28] | Dewar MJS, Zoebisch EG, Healy EF, Stewart JJP (1985) The development and use of quantum mechanical molecular models 76. AMI: a new general purpose quantum mechanical molecular mode. J Am Chem Soc 107:3902. |
| [29] | Stewart JJP (1989) Optimization of parameters for semi empirical methods. J Comput Chem 10:209. |
| [30] | Kohn W, Becke AD, Parr RG Density Functional Theory of Electronic Structure. J Phys Chem10:12974. |
| [31] | Parr RG, Pearson RG (1983) Hardness, softness, and the Fukui function in the electronic theory of metals and catalysis. J Am Chem Soc 105:7512. |
| [32] | Rameshwar N, Krishna K, Ashok Kumar B, Parthasarathy T (2006) QSAR studies of N1-(5-chloro-2- pyridyl)-2-{[4-(alkyl methyl)] amino}-5-chlorobenzamide analoges. Bio org Med Chem 14:319-325. |
| [33] | Jones G, Willet P, Glen RC (1995) Molecular recognition of receptor sites using a genetic algorithm with a description of desolvation. J mol bio 245:43. |
| [34] | Thompson & Mark A. ArgusLab 4.0.1 www.arguslab.com Planaria Software LLC, Seattle WA. |
| [35] | Pogliani L (1994) Structure property relationships of amino acids and some dipeptides. AminoAcids. 6:14. |
| [36] | Schulz-Gasch T, Stahl M (2004) Scoring functions for pro-tein–ligand interactions": a critical perspective.Drug Discov Today. 1 (3):231-239. |
| [37] | Siemoneit U, Hofmann B, Kather L, Lamkemeyer T, Mad-lung J, Franke L, Schneider G, Jauch J, Poeckel D, Werz O (2008) Identification and functional analysis of cyclooxyge-nase-1 as a molecular target of boswellic acids. Bioche .Pharmacol. 71, 503 – 513. |
| [38] | Guex N, Peitsch MC. Swiss Model and the Swiss Pdb-Viewer: An environment for comparative protein modeling. Deep View/SwissPdbViewer3.7 (SP5) Electrophoresis. 18: 2714-2723. |
| [39] | Gilmann JJ (1997) Chemical and physical Hardness. Mater Res Innov 1:71-76. |
| [40] | Chattterjee S, Hadi AS, Price B (2000) Regression Analysis by Examples 3rd Ed Willy: New York. |
| [41] | Parr RG, Chattaraj PK (1991) Principle of maximum Hard-ness. J Am Chem Soc 113:1854. |
| [42] | Weerasak S, Patcharawee N, Jiraporn U(2008)3D-QSAR Investigation of Synthetic Antioxidant Chromone Derivatives by Molecular Field Analysis Int J Mol Sci March 9(3): 235–246. |
APA Style
Shanthi V., Ramesh M., Srimai V., Srinivas P., Parthasarathy T. (2013). QSAR, Docking and Invitro Antioxidant Activity Study of Novel Chromone Derivatives. Modern Chemistry, 1(1), 8-17. https://doi.org/10.11648/j.mc.20130101.12
ACS Style
Shanthi V.; Ramesh M.; Srimai V.; Srinivas P.; Parthasarathy T. QSAR, Docking and Invitro Antioxidant Activity Study of Novel Chromone Derivatives. Mod. Chem. 2013, 1(1), 8-17. doi: 10.11648/j.mc.20130101.12
AMA Style
Shanthi V., Ramesh M., Srimai V., Srinivas P., Parthasarathy T. QSAR, Docking and Invitro Antioxidant Activity Study of Novel Chromone Derivatives. Mod Chem. 2013;1(1):8-17. doi: 10.11648/j.mc.20130101.12
Share This Article
Twitter
Linked In
Facebook
Copy
Download@article{10.11648/j.mc.20130101.12,
author = {Shanthi V. and Ramesh M. and Srimai V. and Srinivas P. and Parthasarathy T.},
title = {QSAR, Docking and Invitro Antioxidant Activity Study of Novel Chromone Derivatives},
journal = {Modern Chemistry},
volume = {1},
number = {1},
pages = {8-17},
doi = {10.11648/j.mc.20130101.12},
url = {https://doi.org/10.11648/j.mc.20130101.12},
eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.mc.20130101.12},
abstract = {Invitro antioxidant activity and Molecular modeling studies of nine chromone derivatives were carried out to optimize their inhibitory activity against Poly [ADP-ribose] polymerase. The biological activities of these analogs were correlated to different molecular properties. The AM1and PM3 semiempirical methods are used to estimate vertical ioniza-tion potentials (IPv’s), electron affinity (EA), electronegativity (χ), hardness (η), softness (S), electrophilic index (ω), parti-tion coefficient (LogP), hydration energy (HE), ionization potential (IP) and charges. The different modeled equations by regression analysis are proposed. The leave-one-out cross-validation method is used to estimate the predictive power of final QSAR equations. The hardness (η) was found to be indicative molecular property by regression analysis. Docking studies of chromone with Poly [ADP-ribose] polymerase are also made to support the finding of QSAR studies. Analysis of results of both QSAR and Docking studies suggested that remarkable inhibitory activity is exhibited by molecule 3 .The hydrogen bond interactions along with hydrophobic and electrostatic interactions are mapped to confirm their potencies.},
year = {2013}
}
TY - JOUR T1 - QSAR, Docking and Invitro Antioxidant Activity Study of Novel Chromone Derivatives AU - Shanthi V. AU - Ramesh M. AU - Srimai V. AU - Srinivas P. AU - Parthasarathy T. Y1 - 2013/02/20 PY - 2013 N1 - https://doi.org/10.11648/j.mc.20130101.12 DO - 10.11648/j.mc.20130101.12 T2 - Modern Chemistry JF - Modern Chemistry JO - Modern Chemistry SP - 8 EP - 17 PB - Science Publishing Group SN - 2329-180X UR - https://doi.org/10.11648/j.mc.20130101.12 AB - Invitro antioxidant activity and Molecular modeling studies of nine chromone derivatives were carried out to optimize their inhibitory activity against Poly [ADP-ribose] polymerase. The biological activities of these analogs were correlated to different molecular properties. The AM1and PM3 semiempirical methods are used to estimate vertical ioniza-tion potentials (IPv’s), electron affinity (EA), electronegativity (χ), hardness (η), softness (S), electrophilic index (ω), parti-tion coefficient (LogP), hydration energy (HE), ionization potential (IP) and charges. The different modeled equations by regression analysis are proposed. The leave-one-out cross-validation method is used to estimate the predictive power of final QSAR equations. The hardness (η) was found to be indicative molecular property by regression analysis. Docking studies of chromone with Poly [ADP-ribose] polymerase are also made to support the finding of QSAR studies. Analysis of results of both QSAR and Docking studies suggested that remarkable inhibitory activity is exhibited by molecule 3 .The hydrogen bond interactions along with hydrophobic and electrostatic interactions are mapped to confirm their potencies. VL - 1 IS - 1 ER -