Login Register Cart 0
Generic placeholder image

Current Pharmaceutical Design

Editor-in-Chief

ISSN (Print): 1381-6128
ISSN (Online): 1873-4286

Back
Journal Home About Journal Editorial Board Journal Insight Current Issue Volumes/Issues
Subscribe
Review Article

Docking Related Survey on Heterocyclic Compounds Based on Glucosamine-6- Phosphate Synthase Inhibitors and their Antimicrobial Potential

Author(s): Amit Lather, Sunil Sharma, Sarita Khatkar and Anurag Khatkar*

Volume 26, Issue 15, 2020

Page: [1650 - 1665] Pages: 16

DOI: 10.2174/1381612826666200217115211

Price: $65

Abstract

The synthetic heterocyclic compounds have their importance due to their wide applications in various fields of science. The heterocyclic compounds have been reported for their anticancer, antitubercular, insecticides, analeptics, analgesic, anti-bacterial, anti-viral, anti-fungal, and weedicidal activity. Researchers have tried various newer targets in search of better antimicrobials acting via novel mechanisms. Glucosamine-6-Phosphate synthase is an enzyme present in microbial cells. The inactivation of G-6-P synthase may serve as a novel approach to find better antimicrobials. The increasing demands development of newer and effective antimicrobial drugs has reported in search of newer techniques for the generation of new drugs. Hence, the molecular docking technique shall be explored to find or investigate the newer target finding the novel compounds which can be an active antimicrobial compound. The present review has focused on the reported heterocyclic compounds which have been evaluated for their antimicrobial potential using G-6-P synthase as a target. The results of in silico methods and in vitro methods have been compared and critically discussed.

Keywords: Antimicrobial, G-6-P synthase, heterocyclic, in silico, antitubercular, anticancer, microbial cells.

« Previous Next »
[1]
Alvarez-Builla J, Barluenga Jose. Heterocyclic compounds: an introduction. In: modern heterocyclic chemistry, first ed published by Wiley-VCH Verlag GmbH & Co KGaA. 2011; 1-10.
[2]
Weast RC, Astle MJ. CRC Handbook of chemistry and physics.63rd Ed. Florida USA: CRC Press, Inc. 1983.
[3]
McNaught AD. Advances in heterocyclic chemistry. In: Katritzky AR, Boulton AJ, Eds. 1976. 1-27: 175-319
[4]
Soni HI, Desai T. Synthesis and antimicrobial activity of some novel heterocyclic compounds. Int J Sci Res (Ahmedabad) 2014; 3(6): 2359-63.
[5]
El-Salam NMA, Mostafa MS, Ahmed GA, Alothman OY. Synthesis and antimicrobial activities of some new heterocyclic compounds based on 6-chloropyridazine-3 (2H) thione. J Chem 2013; 2013: 1-8.
[http://dx.doi.org/10.1155/2013/890617]
[6]
Azab ME, Youssef MM, El-Bordany EA. Synthesis and antibacterial evaluation of novel heterocyclic compounds containing a sulfonamido moiety. Molecules 2013; 18(1): 832-44.
[http://dx.doi.org/10.3390/molecules18010832] [PMID: 23344196]
[7]
Salem MS, Sakr SI, El-Senousy WM, Madkour HMF. Synthesis, antibacterial, and antiviral evaluation of new heterocycles containing the pyridine moiety. Arch Pharm (Weinheim) 2013; 346(10): 766-73.
[http://dx.doi.org/10.1002/ardp.201300183] [PMID: 24105721]
[8]
Cao X, Sun Z, Cao Y, et al. Design, synthesis, and structure-activity relationship studies of novel fused heterocycles-linked triazoles with good activity and water solubility. J Med Chem 2014; 57(9): 3687-706.
[http://dx.doi.org/10.1021/jm4016284] [PMID: 24564525]
[9]
El-Sawy ER, Ebaid MS, Abo-Salem HM, Al-Sehemi AG, Mandour AH. Synthesis, anti-inflammatory, analgesic and anticonvulsant activities of some new 4,6-dimethoxy-5-(heterocycles) benzofuran starting from naturally occurring visnagin. Arab J Chem 2013; 7: 914-23.
[http://dx.doi.org/10.1016/j.arabjc.2012.12.041]
[10]
Sweetman S. The complete drug reference. 34th ed. London: Pharmaceutical Press 2004.
[11]
Kruger GJ, Gafner G. The crystal structure of sulphathiazole II. Acta Crystallogr 1971; B27: 326-33.
[http://dx.doi.org/10.1107/S0567740871002176]
[12]
Peters JM. Factors affecting caffeine toxicity: a review of the literature. J Clin Pharmacol New Drugs 1967; 7: 131-41.
[http://dx.doi.org/10.1002/j.1552-4604.1967.tb00034.x]
[13]
Youngson, Robert M. London: Robinson Publishing 1997; p. 276.
[14]
Black MT. Evidence that the catalytic activity of prokaryote leader peptidase depends upon the operation of a serine-lysine catalytic dyad. J Bacteriol 1993; 175(16): 4957-61.
[http://dx.doi.org/10.1128/JB.175.16.4957-4961.1993] [PMID: 8394311]
[15]
Soper TS, Manning JM. Different modes of action of inhibitors of bacterial D-amino acid transaminase. A target enzyme for the design of new antibacterial agents. J Biol Chem 1981; 256(9): 4263-8.
[PMID: 7217082]
[16]
Black MT, Hodgson J. Novel target sites in bacteria for overcoming antibiotic resistance. Adv Drug Deliv Rev 2005; 57(10): 1528-38.
[http://dx.doi.org/10.1016/j.addr.2005.04.006] [PMID: 15949866]
[17]
Bockstael K, Aerschot AV. Antimicrobial resistance in bacteria. Cent Eur J Med 2009; 4(2): 141-55.
[18]
Kavya CC. Phytochemical evaluation and pharmacological screening of wedelia trilobata. Int Rev Appl Biotechnol Biochem 2014; 2(1): 239-49.
[19]
Komatsuzawa H, Fujiwara T, Nishi H, et al. The gate controlling cell wall synthesis in Staphylococcus aureus. Mol Microbiol 2004; 53(4): 1221-31.
[http://dx.doi.org/10.1111/j.1365-2958.2004.04200.x] [PMID: 15306023]
[20]
Chmara H, Zähner H, Borowski E, Milewski S. Inhibition of glucosamine-6-phosphate synthetase from bacteria by anticapsin. J Antibiot (Tokyo) 1984; 37(6): 652-8.
[http://dx.doi.org/10.7164/antibiotics.37.652] [PMID: 6430854]
[21]
Al-Juboori SB, Mahmood AAR. Synthesis, antimicrobial evaluation, density functional theory, and docking studies of some new 2-mercapto pyrimidine Schiff bases. Asian J Pharm Clin Res 2019; 12(2): 496-502.
[http://dx.doi.org/10.22159/ajpcr.2019.v12i2.30858]
[22]
Elkanzi NAA, Ghoneim AA, Bakr RB. Design, efficient synthesis and antimicrobial evaluation of some novel Pyrano[2, 3-b][1, 8]Naphthyridine and Pyrrolo [2,3-f][1,8] naphth- yridine derivatives. Pharma Chem 2019; 11(2): 6-13.
[23]
Abid SE, Abdula AM, Marjani MFA, Abdulhameed QM. Synthesis, antimicrobial, antioxidant and docking study of some novel 3,5-disubstituted-4,5-dihydro- 1H- pyrazoles incorporating imine moiety. Egypt J Chem 2019; 62(4): 1139-49.
[24]
Venkatesh T, Bodke YD, Kenchappa R, Telkar S. Synthesis, antimicrobial and antioxidant activity of chalcone derivatives containing thiobarbitone nucleus. Med Chem 2016; 6(7): 440-8.
[25]
Ripain IHA, Roslan N, Norshahimi NS, Salleh SSM, Bunnori NM, Ngah N. Synthesis and molecular docking of 2,4,5-Trisubstituted 1,3-Thiazole derivatives as antibacterial agents. Malays J Anal Sci 2019; 23(2): 237-46.
[26]
Khan SA, Asiri AM, Rahman RM, et al. Multistep synthesis of fluorine-substituted pyrazolopyrimidine derivatives with higher antibacterial efficacy based on in vitro molecular docking and density functional theory. J Heterocycl Chem 2017; 54(6): 3099-107.
[http://dx.doi.org/10.1002/jhet.2923]
[27]
Ezeokonkwo MA, Ogbonna ON, Okafor SN, Godwin-Nwakwasi EU, Ibeanu FN, Okoro UC. Angular phenozaxine ethers as potent multi-microbial targets inhibitors: design, synthesis, and molecular docking studies. Front Chem 2017; 5(107): 107.
[http://dx.doi.org/10.3389/fchem.2017.00107] [PMID: 29238706]
[28]
Ali R, Kumar S, Afzal O, Bawa S. In-vitro antimicrobial screening and molecular docking studies of synthesized 2-chloro-N-(4-phenylthiazol-2-yl) acetamide derivatives. Drug Develop Therapeu 2015; 6(2): 79.
[http://dx.doi.org/10.4103/2394-6555.162452]
[29]
Afifi TH, Riyadh SM, Deawaly AA, Naqvi A. Novel chromenes and benzochromenes bearing arylazo moiety: molecular docking, in-silico admet, in-vitro antimicrobial and anticancer screening. Med Chem Res 2019; 28(9): 1471-87.
[http://dx.doi.org/10.1007/s00044-019-02387-5]
[30]
Periyasami G, Kamalraj S, Padmanaban R, et al. Glucosamine-6-phosphate synthase inhibiting C3-β-cholesterol tethered spiro heterocyclic conjugates: Synthesis and their insight of DFT and docking study. Bioorg Chem 2019; 88102920
[http://dx.doi.org/10.1016/j.bioorg.2019.102920] [PMID: 30991194]
[31]
Aouad MR, Mayaba MM, Naqvi A, Bardaweel SK. Al blewi FF, Messali M, Rezki N. Design, synthesis, in silico and in vitro antimicrobial screenings of novel 1,2,4-triazoles carrying 1,2,3-triazole scafold with lipophilic side chain tether. CCJ 2017; 11: 117.
[PMID: 29159721]
[32]
Kumara HK, Suhas R, Vardhan DMS, Shobha M, Gowda DC. A correlation study of biological activity and molecular docking of Asp and Glu linked bishydrazones of quinazolinones. Royal Society of Chem 2018; 8: 10644-53.
[33]
Abdelgawad MA. Synthesis and antibacterial evaluation of new azo-pyrimidine derivatives. J Appl P’ceutical Sci 2019; 9(Suppl. 1): 9-16.
[34]
Ismail AH, Abdula AM, Taha MM, Al-Bayati RI. 1,3,5-Trisubstituted-1H-Pyrazole derivatives as new antimicrobial agents: synthesis, characterization and docking study. Int J Chem Sci 2017; 15(2): 126.
[35]
Sarojini BK, Krishna BG, Darshanraj CG, Bharath BR, Manjunatha H. Synthesis, characterization, in vitro and molecular docking studies of new 2,5-dichloro thienyl substituted thiazole derivatives for antimicrobial properties. Eur J Med Chem 2010; 45(8): 3490-6.
[http://dx.doi.org/10.1016/j.ejmech.2010.03.039] [PMID: 20451305]
[36]
Aswathanarayanappa C, Bheemappa E, Bodke YD, Bhovi VK, Ningegowda R. 5-phenyl-1-benzofuran-2-yl derivatives: synthesis, antimicrobial, and antioxidant activity. Med Chem Res 2013; 22: 78-87.
[http://dx.doi.org/10.1007/s00044-012-0017-y]
[37]
Wallace AC, Laskowski RA, Thornton JM. Sporulation in D-glucosamine auxotrophs of Saccharomyces cerevisiae: meiosis with defective ascospore wall formation. Protein Eng 1995; 8: 127-34.
[http://dx.doi.org/10.1093/protein/8.2.127] [PMID: 7630882]
[38]
Schüttelkopf AW, van Aalten DM, Ettelkopf S. PRODRG: a tool for high-throughput crystallography of protein-ligand complexes. Acta Crystallogr D Biol Crystallogr 2004; 60(Pt 8): 1355-63.
[http://dx.doi.org/10.1107/S0907444904011679] [PMID: 15272157]
[39]
Chmara H, Borowski E. Bacteriolytic effect of cessation of glucosamine supply, induced by specific inhibition of glucosamine-6-phosphate synthetase. Acta Microbiol Pol 1986; 35(1-2): 15-27.
[PMID: 2426923]
[40]
Morris GM, Huey R, Lindstrom W, et al. AutoDock4 and AutoDockTools4: Automated docking with selective receptor flexibility. J Comput Chem 2009; 30(16): 2785-91.
[http://dx.doi.org/10.1002/jcc.21256] [PMID: 19399780]
[41]
Bates CJ, Adams WR, Handschumacher RE. Control of the formation of uridine diphospho-N-acetyl-hexosamine and glycoprotein synthesis in rat liver. J Biol Chem 1966; 241(8): 1705-12.
[PMID: 5945845]
[42]
Mouilleron S, Badet-Denisot MA, Golinelli-Pimpaneau B. Ordering of C-terminal loop and glutaminase domains of glucosamine-6-phosphate synthase promotes sugar ring opening and formation of the ammonia channel. J Mol Biol 2008; 377(4): 1174-85.
[http://dx.doi.org/10.1016/j.jmb.2008.01.077] [PMID: 18295797]
[43]
Jayanna ND, Vagdevi HM, Dharshan JC, Raghavendra R, Telkar SB. Synthesis, antimicrobial, analgesic activity, and molecular docking studies of novel 1-(5,7-dichloro-1,3-benzoxazol-2-yl)-3-phenyl-1Hpyrazole-4-carbaldehyde derivatives. Med Chem Res 2013; 22: 5814-22.
[http://dx.doi.org/10.1007/s00044-013-0565-9]
[44]
Morris GM, Goodsell DS, Halliday RS, Huey R, Hart WE. Automated docking using a lamarckian genetic algorithm and an empirical binding free energy function. J Comput Chem 1998; 19: 1639-62.
[http://dx.doi.org/10.1002/(SICI)1096-987X(19981115)19:14<1639:AID-JCC10>3.0.CO;2-B]
[45]
Ghose AK, Crippen GM. Atomic physicochemical parameters for three-dimensional-structure-directed quantitative structure-activity relationships. 2. Modeling dispersive and hydrophobic interactions. J Chem Inf Comput Sci 1987; 27(1): 21-35.
[http://dx.doi.org/10.1021/ci00053a005] [PMID: 3558506]
[46]
Binkowski TA, Naghibzadeh S, Liang J. Computed atlas of surface topography of proteins. Nucleic Acids Res 2003; 31(13): 3352-5.
[http://dx.doi.org/10.1093/nar/gkg512] [PMID: 12824325]
[47]
Gasteiger J, Marsili M. Iterative partial equalization of orbital electro negativity. Tetrahedron 1980; 36: 3219-28.
[http://dx.doi.org/10.1016/0040-4020(80)80168-2]
[48]
Reya T, Clevers H. Wnt signalling in stem cells and cancer. Nature 2005; 434(7035): 843-50.
[http://dx.doi.org/10.1038/nature03319] [PMID: 15829953]
[49]
Jose G, Suresha Kumara TH, Nagendrappa G, et al. New polyfunctional imidazo[4,5-C]pyridine motifs: synthesis, crystal studies, docking studies and antimicrobial evaluation. Eur J Med Chem 2014; 77: 288-97.
[http://dx.doi.org/10.1016/j.ejmech.2014.03.019] [PMID: 24657565]
[50]
Roseman S. Reflections on glycobiology. J Biol Chem 2001; 276(45): 41527-42.
[http://dx.doi.org/10.1074/jbc.R100053200] [PMID: 11553646]
[51]
Milewski S, Janiak A, Wojciechowski M. Structural analogues of reactive intermediates as inhibitors of glucosamine-6-phosphate synthase and phosphoglucose isomerase. Arch Biochem Biophys 2006; 450(1): 39-49.
[http://dx.doi.org/10.1016/j.abb.2006.03.019] [PMID: 16631105]
[52]
Milewski S. Glucosamine-6-phosphate synthase--the multi-facets enzyme. Biochim Biophys Acta 2002; 1597(2): 173-92.
[http://dx.doi.org/10.1016/S0167-4838(02)00318-7] [PMID: 12044898]
[53]
Whelan WL, Ballou CEJ. Sporulation in D-glucosamine auxotrophs of Saccharomyces cerevisiae: meiosis with defective ascospore wall formation. J Bacteriol 1975; 124(3): 1545-57.
[http://dx.doi.org/10.1128/JB.124.3.1545-1557.1975] [PMID: 1104590]
[54]
Kenchappa R, Bodke YD, Peethambar SK, Telkar S, Bhovi VK. Synthesis of b-amino carbonyl derivatives of coumarin and benzofuran and evaluation of their biological activity. Med Chem Res 2013; 22: 4787-97.
[http://dx.doi.org/10.1007/s00044-013-0494-7]
[55]
Kenchappa R, Bodke YD, Asha B, Telkar S, Sindhe MA. Synthesis, antimicrobial, and antioxidant activity of benzofuran barbitone and benzofuran thiobarbitone derivatives. Med Chem Res 2014; 23: 3065-81.
[http://dx.doi.org/10.1007/s00044-013-0892-x]
[56]
Kenchappa R, Bodke YD, Chandrashekar A, Telkar S, Manjunatha KS. Synthesis of some 2, 6-bis (1-coumarin-2-yl)-4-(4-substituted phenyl) pyridine derivatives as potent biological agents. Arab J Chem 2017; 10(1): S1336-44.
[http://dx.doi.org/10.1016/j.arabjc.2013.03.020]
[57]
Krishna PKV, Harish BGV, Kumar SSR, Kumar GK. Antibacterial activity of leaf extract of delonix elata and molecular docking studies of luteolin. J Biochem Technol 2012; 3(5): S193-7.
[58]
Nagle P, Pawar Y, Sonawane A, Bhosale S, More D. Docking simulation, synthesis and biological evaluation of novel pyridazinone containing thymol as potential antimicrobial agents. Med Chem Res 2014; 23: 918-1026.
[http://dx.doi.org/10.1007/s00044-013-0685-2]
[59]
Satyendra RV, Vishnumurthy KA, Vagdevi HM, Rajesh KP, Manjunatha H. In vitro antimicrobial and molecular docking of dichloro substituted benzoxazole derivatives. Med Chem Res 2012; 21: 4193-9.
[http://dx.doi.org/10.1007/s00044-011-9963-z]
[60]
Siwek A, Stefańska J, Dzitko K, Ruszczak A. Antifungal effect of 4-arylthiosemicarbazides against Candida species. Search for molecular basis of antifungal activity of thiosemicarbazide derivatives. J Mol Model 2012; 18(9): 4159-70.
[http://dx.doi.org/10.1007/s00894-012-1420-5] [PMID: 22535361]
[61]
Berman HM, Westbrook J, Feng Z, et al. The protein data bank. Nucleic Acids Res 2000; 28(1): 235-42.
[http://dx.doi.org/10.1093/nar/28.1.235] [PMID: 10592235]
[62]
Trott O, Olson AJ. AutoDock Vina: improving the speed and accuracy of docking with a new scoring function, efficient optimization, and multithreading. J Comput Chem 2010; 31(2): 455-61.
[PMID: 19499576]
[63]
Isupov MN, Obmolova G, Butterworth S, et al. Substrate binding is required for assembly of the active conformation of the catalytic site in Ntn amidotransferases: evidence from the 1.8 A crystal structure of the glutaminase domain of glucosamine 6-phosphate synthase. Structure 1996; 4(7): 801-10.
[http://dx.doi.org/10.1016/S0969-2126(96)00087-1] [PMID: 8805567]
[64]
Tomi IHR, Al-Daraji AHR, Abdula AM, Al-Marjani MF. Synthesis, antimicrobial and docking study of three novel 2,4,5-triarylimidazole derivatives. J Saudi Chem Soc 2016; 20: S509-16.
[http://dx.doi.org/10.1016/j.jscs.2013.03.004]
[65]
Sander T, Freyss J, von Korff M, Reich JR, Rufener C. OSIRIS, an entirely in-house developed drug discovery informatics system. J Chem Inf Model 2009; 49(2): 232-46.
[http://dx.doi.org/10.1021/ci800305f] [PMID: 19434825]
[66]
Vijesh AM, Isloor AM, Telkar S, Arulmoli T, Fun HK. Molecular docking studies of some new imidazole derivatives for antimicrobial properties. Arab J Chem 2013; 6: 197-204.
[http://dx.doi.org/10.1016/j.arabjc.2011.10.007]

Rights & Permissions Print Cite
Article Metrics
19
4
© 2024 Bentham Science Publishers | Privacy Policy