Document Type : Original Paper
Authors
- Leila Emami 1
- zeinab faghih 2
- Masood Fereidoonnezhad 3
- soghra khabnadideh 1
- Farnaz Salehi 4
- Amirhosein Abbasi 1
- Amir Hosein Sakhteman 4
1 1 Pharmaceutical Sciences Research Center, Shiraz University of Medical Sciences, Shiraz, Islamic Republic of Iran. 2 Department of Medicinal Chemistry, Faculty of Pharmacy, Shiraz University of Medical Sciences, Shiraz, Islamic Republic of Iran
2 1 Pharmaceutical Sciences Research Center, Shiraz University of Medical Sciences, Shiraz, Islamic Republic of Iran
3 3 Department of Medicinal Chemistry, School of Pharmacy, Ahvaz Jundishapur University of Medical Sciences, Ahvaz, Islamic Republic of Iran
4 2 Department of Medicinal Chemistry, Faculty of Pharmacy, Shiraz University of Medical Sciences, Shiraz, Islamic Republic of Iran
Abstract
Isatin and its analogues have been shown anticancer activity against various cancer cell lines via restrainting cancer cell proliferation and tumor growth. In this study, five different statistical methods such as MLR, PCR, FA-MLR, GA-MLR, and GA-PLS, were used to aquaire the Quantitative relevance between cytotoxicity activity and 37 isatinstructures. Quantitative structure activity models indicated that topological and gateway parameters have an adequate impact on the cytotoxic activity of the tested molecules. Among the applied QSAR models, GA-PLS and MLR gave significant results with high statistical quality for predicting the inhibitory activity of the molecules. Molecular docking studies of these compounds were also investigated, and promising results were obtained. There was a good correlation between QSAR and docking results. For the validity of the docking studies, molecular dynamics (MD) simulation was also done.
Keywords
- Veneis P, Wild CP. Causes and prevention, Wild CP Global cancer patterns. Lancet. 2013;32(4):465-78.
- Thun MJ, DeLancey JO, Center MM, Jemal A, Ward EM. The global burden of cancer: priorities for prevention. Carcinogenesis. 2010;31(1):100-10.
- Boyle P LB. World cancer report. RC Press. International Agency for Research on Cancer. 2008.
- Chopra R, Lopes G. Improving access to cancer treatments: the role of biosimilars. J Glob Oncol. 2017;3(5):596-610.
- Gangarapu K, Thumma G, Manda S, Jallapally A, Jarapula R, Rekulapally S. Design, synthesis and molecular docking of novel structural hybrids of substituted isatin based pyrazoline and thiadiazoline as antitumor agents. Med Chem Res. 2017;26(4):819-29.
- Thadhaney B, Sain D, Pemawat G, Talesara GL. Synthesis and antimicrobial evaluation of ethoxyphthalimide derivatized spiro [indole3,5′-(1,3)thiazolo(4,5-c)isoxazol]-2(1H)-ones via ring closure metathesis. Indian J Chem B. 2010;49: 368-373.
- Dmytro H, Borys Z, Roman L. Synthesis, Biological Activity of Thiazolidinones Bearing Indoline Moiety and Isatin Based Hybrids. Mini Rev Org Chem. 2015;12(1):66-87.
- Havrylyuk D, Zimenkovsky B, Vasylenko O, Gzella A, Lesyk R. Synthesis of New 4Thiazolidinone-, Pyrazoline-, and Isatin-Based Conjugates with Promising Antitumor Activity. J Med Chem. 2012;55 (20):8630-8641.
- Liang C, Xia J, Lei D, Li X, Yao Q, Gao J. Synthesis, in vitro and in vivo antitumor activity of symmetrical bis-Schiff base derivatives of isatin. Eur J Med Chem. 2014;74:742-750.
- Huong TT, Dung do TM, Oanh DT, Lan TT, Dung PT, Loi VD. 5-aryl-1,3,4thiadiazole-based hydroxamic acids as histone deacetylase inhibitors and antitumor agents: synthesis, bioevaluation and docking study. Med Chem Shariqah (United Arab Emirates). 2015;11(3):296-304.
- Lesyk R HD, Lelyukh M. Synthesis and anticancer activity of isatin, oxadiazole and 4thiazolidinone based conjugates. Chem Chem Technol. 2015;9(1):29-36.
- Varma RS, Khan IA. Potential biologically active agents. X. Synthesis of 3-arylimino-2indolinones, and their 1-methyl- and 1-morpholino/piperidinomethyl derivatives as excystment and cysticidal agents against Schizopyrenus russelli, Pol J Pharmacol Pharm.1977;29(5):549-54.
- Socca EA, Luiz-Ferreira A, de Faria FM, de Almeida AC, Dunder RJ, Manzo LP. Inhibition of tumor necrosis factor-alpha and cyclooxigenase-2 by Isatin: a molecular mechanism of protection against TNBS-induced colitis in rats. Chem Biol. 2014;209:48-55.
- Rad MNS, Behrouz S, Nekoei AR, Faghih Z, Khalafi-Nezhad A. Three-component synthesis of some novel N-heterocycle methyl-O-oxime ethers. Synthesis. 2011;2011(24):4068-76.
- Medvedev A, Buneeva O, Glover V. Biological targets for isatin and its analogues: Implications for therapy, Biologics. Targets Ther. 2007;1(2):151-162.
- Zhou L, Liu Y, Zhang W, Wei P, Huang C, Pei J. Isatin compounds as noncovalent SARS coronavirus 3C-like protease inhibitors, J Med Chem. 2006;49(12):3440-3443.
- Chapman JG, Magee WP, Stukenbrok HA., Beckius GE., MiliciA J. A novel nonpeptidic caspase-3/7 inhibitor. (S)-(+)-5-[1-(2-methoxymethylpyrrolidinyl) sulfonyl] isatin reduces myocardial ischemic injury. Euro J Pharm. 2002;456(3):59-68.
- Cao J, Gao H, Bemis G, Salituro F, Ledeboer M, Harrington E. Structure-based design and parallel synthesis of N-benzyl isatin oximes as JNK3 MAP kinase inhibitors. Bioorg Med Chem Lett. 2009;19(10):2891-2895.
- Cane A, Tournaire MC, Barritault D, Crumeyrolle-Arias M. The endogenous oxindoles 5-hydroxyoxindole and isatin are antiproliferative and proapoptotic. Biochem Bioph Res Co. 2000;276(1):379-384.
- Fereidoonnezhad M, Faghih Z, Mojaddami A, Rezaei Z, Sakhteman A. A comparative QSAR analysis, molecular docking and PLIF studies of some N-arylphenyl-2, 2-dichloroacetamide analogues as anticancer agents. Iran J Pharm Res. 2017;16(3):981.
- Hemmateenejad B, Emami L, Sharghi H. Multi-wavelength spectrophotometric determination of acidity constant of some newly synthesized Schiff bases and their QSPR study. Spectrochim Acta A. 2010;75(1):340–346.
- Teng YO, Zhao HY, Wang J, Liu H, Gao ML, Zhou Y. Synthesis and anti-cancer activity evaluation of 5-(2-carboxyethenyl)-isatin derivatives. Eur J Med Chem. 2016;112:145-56.
- Teng YO, Zhao HY, Wang J, Liu H, Gao ML, Zhou Y. Synthesis and anti-cancer activity evaluation of 5-(2-carboxyethenyl)-isatin derivatives. Eur J Med Chem. 2016;112:145-156.
- Fereidoonnezhad M, Faghih Z, Mojaddami A, SakhtemanA , Rezaei Z. A comparative docking studies of dichloroacetate analogues on four isozymes of pyruvate dehydrogenase kinase in humans. Indian J Pharm Educ.2016;50(4):S32-S8.
- Fereidoonnezhad M, Tabaei SMH, Sakhteman A, Seradj H, Faghih Z. Design, synthesis, molecular docking, biological evaluations and QSAR studies of novel dichloroacetate analogues as anticancer agent. J Mol Struc. 2020;1221:128689
- R. Leardi. Application of genetic algorithm–PLS for feature selection in spectral data sets. J Chemom. 2000;14(5):643-655.
- Emami L, Sabet R, Sakhteman A, Khoshnevis Zadeh M. Quantitative Structure–Activity Relationship and Molecular Docking Studies of Imidazolopyrimidine Amides as Potent Dipeptidyl Peptidase-4 (DPP4) Inhibitors. J Pharm Res Int. 2019;27(6):1-15.
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- Zare S, Fereidoonnezhad M, Afshar D, Ramezani Z. A comparative QSAR analysis and molecular docking studies of phenyl piperidine derivatives as potent dual NK1R antagonists/serotonin transporter (SERT) inhibitors. Comput Biol Chem. 2017;67:22-37.
- Emami L, Faghih Z, Sakhteman A, Rezaei Z, Faghih Z, Salehi F, et al. Design, synthesis, molecular simulation, and biological activities of novel quinazolinone-pyrimidine hybrid derivatives as dipeptidyl peptidase-4 inhibitors and anticancer agents. New J Chem. 2020;44(45):19515-31.
- Salentin S, Schreiber S, Haupt VJ, Adasme MF, Schroeder M. PLIP: fully automated protein-ligand interaction profiler. Nucleic acid res. 2015;43(W1):W443- W447.
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