Synthesis, molecular docking and Brugia malayi thymidylate kinase (BmTMK) enzyme inhibition study of novel derivatives of [6]-shogaol

European Journal of Medicinal Chemistry

Volumn 93, Issue , 2015, Pages 74-82

  Singh, Vinay Kr ^a   Doharey, Pawan K ^a   Kumar, Vikash ^a   Saxena, J K ^a   Siddiqi, M I ^a   Rathaur, Sushma ^b   Narender, Tadigoppula ^a  

^a CENTRAL DRUG RESEARCH INSTITUTE   (India)

^b BANARAS HINDU UNIVERSITY   (India)

Author keywords

Brugia malayi; Enzyme inhibitor; Filariasis; Molecular modelling; Thymidylate kinase; Zingiber officinale; 6 Shogaol

Indexed keywords

1 (4 HYDROXY 3 METHOXYPHENYL) 5 (3 METHYLPYRIDIN 2 YLAMINO)DECAN 3 ONE; 1 (4 HYDROXY 3 METHOXYPHENYL) 5 (4 METHYLPYRIDIN 2 YLAMINO)DECAN 3 ONE; 1 (4 HYDROXY 3 METHOXYPHENYL) 5 (5 METHYLPYRIDIN 2 YLAMINO)DECAN 3 ONE; 1 [1 (4 HYDROXY 3 METHOXYPHENYL) 3 OXODECAN 5 YL] 5 METHYLPYRIMIDINE 2,4 (1H,3H)DIONE; 2 METHOXY 4 [5 (4 METHYLPYRIDIN 2 YLAMINO) 3 OXODECYL]PHENYL 6 CHLORO NICOTINATE; 2 METHOXY 4 [5 (5 METHYL 2,4 DIOXO 3,4 DIHYDROPYRIMIDIN 1 (2H)YL 3 OXODECYL]PHENYL 4 METHYLMENZENESULFONATE; 2 METHOXY 4 [5 (5 METHYL 2,4 DIOXO 3,4 DIHYDROPYRIMIDIN 1 (2H)YL) 3 OXODECYL]PHENYL 4 METHOXYBENZOATE; 2 METHOXY 4 [5 (5 METHYL 2,4 DIOXO 3,4 DIHYDROPYRIMIDIN 1 (2H)YL) 3 OXODECYL]PHENYL 6 CHLORONICOTINATE; 2 METHOXY 4 [5 (5 METHYL 2,4 DIOXO 3,4 DIHYDROPYRIMIDIN 1 (2H)YL) 3 OXODECYL]PHENYL METHANESULFONATE; 5 (6 AMINO 9H PURIN 9 YL) 1 (4 HYDROXY 3 METHOXYPHENYL)DECAN 3 ONE; 5 BROMO 1 [1 (4 HYDROXY 3 METHOXYPHENYL) 3 OXODECAN 5 YL]PYRIMIDINE 2,4 (1H,3H)DIONE; ADENINE; ANTIMALARIAL AGENT; ANTINEMATODAL AGENT; CATECHOL DERIVATIVE; DTMP KINASE; ENZYME INHIBITOR; NUCLEOSIDE MONOPHOSPHATE KINASE; PHARMACOLOGY; PHOSPHOTRANSFERASE INHIBITOR; RECOMBINANT PROTEIN; SHOGAOL; THYMIDINE PHOSPHATE; THYMIDYLATE KINASE INHIBITOR; THYMINE; UNCLASSIFIED DRUG; [6]SHOGAOL DERIVATIVE;

ANIMAL; ANTAGONISTS AND INHIBITORS; ARTICLE; BRUGIA MALAYI; CHEMICAL STRUCTURE; CHEMISTRY; CONTROLLED STUDY; DNA SYNTHESIS; DRUG DESIGN; DRUG EFFECTS; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME ACTIVITY; ENZYME INHIBITION; ENZYMOLOGY; GENETICS; GINGER; ISOLATION AND PURIFICATION; MOLECULAR DOCKING; NONHUMAN; PLASMODIUM FALCIPARUM; SYNTHESIS;

ANIMALS; ANTAGONISTS AND INHIBITORS; ANTINEMATODAL AGENTS; BRUGIA MALAYI; CATECHOLS; CHEMICAL SYNTHESIS; CHEMISTRY; DRUG DESIGN; DRUG EFFECTS; ENZYME INHIBITORS; ENZYMOLOGY; GENETICS; GINGER; ISOLATION AND PURIFICATION; MOLECULAR DOCKING SIMULATION; MOLECULAR STRUCTURE; NUCLEOSIDE-PHOSPHATE KINASE; PHARMACOLOGY; RECOMBINANT PROTEINS;

EID: 84964211609     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2015.01.035     Document Type: Article

References (41)

1. C.A. Behm M.M. Bendig J.P. McCarter A.E. Sluder RNAi-based discovery and validation of new drug targets in filarial nematodes Trends Parasitol. 21 2005 97
2. K.V. Sashidhara K.B. Rao V. Kushwaha R.K. Modukuri R. Verma P.K. Murti Synthesis and antifilarial activity of chalcone-thiazole derivatives against a human lymphatic filarial parasite, Brugia malayi Eur. J. Med. Chem. 81 2014 473
3. A.L. Carreño Otero L.Y. Vargas Méndez E.D.L. Jonny V.V. Kouznetsov Design, synthesis, acetylcholinesterase inhibition and larvicidal activity of girgensohnine analogs on Aedes aegypti, vector of dengue fever Eur. J. Med. Chem. 78 2014 392
4. R.L. Gaur M.K. Sahoo S. Dixit N. Fatma S. Rastog D.K. Kulshreshtha R.K. Chatterjee P.K. Murthy Antifilarial activity of Caesalpinia bonducella against experimental filarial infections Indian J. Med. Res. 128 2008 65
5. M.Y. Osei-Atweneboana J.K. Eng D.A. Boakye J.O. Gyapong P.K. Prichard Prevalence and intensity of onchocerca volvulus infection and efficacy of ivermectin in endemic communities in Ghana: a two-phase epidemiological study Lancet 369 2007 2021
6. A.E. Schwab T.S. Churcher A.J. Schwab M.G. Basanez R.K. Prichard An analysis of the population genetics of potential multi-drug resistance in Wuchereria bancrofti due to combination chemotherapy Parasitology 134 2007 1025
7. C.D. Ginger Enzyme Inhibitors in the Chemotherapy of Filariasis, Report of a Scientific Working Group on the Biochemistry of Filarial and Allied Parasites WHO/OCP/OCT/83.1 1983 World Health Organization Geneva
8. E. Anderson Nucleoside and nucleotide kinases third ed. P.D. Boyer The Enzymes vol. 8 1973 Academic Press New York 49 96
9. M. Kandeel A. Kato Y. Kitamura Y. Kitade Thymidylate kinase: the lost chemotherapeutic target Nucleic Acids Symp. Ser. Oxf. 53 2009 283
10. S. Van Calenbergh Structure-aided design of inhibitors of mycobacterium tuberculosis thymidylate kinase Verh. K. Acad. Geneeskd. Belg. 68 2006 223
11. P.K. Doharey M.K. Suthar A. Verma V. Kumar S. Yadav V.M. Balaramnavar S. Rathaur A.K. Saxena M.I. Siddiqi J.K. Saxena Molecular cloning and characterization of Brugia malayi thymidylate kinase Acta Trop. 133C 2014 83
12. M.S. Butt M.T. Sultan Ginger and its health claims: molecular aspects Crit. Rev. Food S. C. Nutr. 51 2011 383
13. B.H. Ali G. Blunden M.O. Tanira A. Nemmar Some phytochemical, pharmacological and toxicological properties of ginger (Zingiber officinale Roscoe): a review of recent research Food Chem. Toxicol. 46 2008 409
14. H.S. Lee E.Y. Seo N.E. Kang W.K. Kim [6]-Gingerol inhibits metastasis of MDA-MB-231 human breast cancer cells J. Nutr. Biochem. 19 2008 313
15. J. Rhode S. Fogoros S. Zick H. Wahl K.A. Griffith J. Huang J.R. Liu Ginger inhibits cell growth and modulates angiogenic factors in ovarian cancer cells BMC Complement. Altern. Med. 7 2007 44
16. F. Kiuchi S. Iwakami M. Shibuya F. Hanaoka U. Sankawa Inhibition of prostaglandin and leukotriene biosynthesis by gingerols and diarylheptanoids Chem. Pharm. Bull. 40 1992 387
17. Y. Yasuka Isa Y. Miyakawa M. Yanagisawa T. Goto M.-S. Kang T. Kawada Y. Morimitsu K. Kubota T. Tsuda 6-Shogaol and 6-gingerol, the pungent of ginger, inhibit TNF-alpha mediated down regulation of adiponectin expression via different mechanisms in 3T3-L1 adipocytes Biochem. Biophys. Res. Commun. 373 2008 429
18. Y. Iwasaki A. Morita T. Iwasawa K. Kobata Y. Sekiwa Y. Morimitsu K. Kubota T. Watanabe A nonpungent component of steamed ginger-[10]-shogaol-increases adrenaline secretion via the activation of TRPV1 Nutr. Neurosci. 9 2006 169
19. V.N. Dedov V.H. Tran C.C. Duke M. Connor M.J. Christie S. Mandadi B.D. Roufogalis Gingerols: a novel class of vanilloid receptor (VR1) agonists Br. J. Pharmacol. 137 2002 793
20. M. Bandell G.M. Story S.W. Hwang V. Viswanath S.R. Eid M.J. Petrus T.J. Earley A. Patapoutian Noxious cold ion channel TRPA1 is activated by pungent compounds and bradykinin Neuron 41 2004 849
21. M. Li Y. Yu J. Yang Structural biology of TRP channels Adv. Exp. Med. Biol. 704 2011 1
22. R. Vennekens G. Owsianik B. Nilius Vanilloid transient receptor potential cation channels: an overview Curr. Pharm. Des. 14 2008 18
23. G. Appendino A. Minassi A. Pagani A. Ech-Chahad The role of natural products in the ligand deorphanization of TRP channels Curr. Pharm. Des. 14 2008 2
24. K. Venkatachalam C. Montell TRP channels Annu. Rev. Biochem. 76 2007 387
25. L. Gharat A. Szallasi Medicinal chemistry of the vanilloid (Capsaicin) TRPV1 receptor: current knowledge and future perspectives Drug Dev. Res. 68 2007 477
26. B. Minke TRP channels and Ca2+ signalling Cell. Calcium 40 2006 261
27. C.H. Andrade K.F. Pasqualoto E.I. Ferreira A.J. Hopfinger 3D-Pharmacophore mapping of thymidine-based inhibitors of TMPK as potential antituberculosis agents J. Comput.-Aided Mol. Des. 24 2010 157
28. H. Cui L.M. Ruiz-Perez D. Gonzalez-Pacanowska I.H. Gilbert Potential application of thymidylate kinase in nucleoside analogue activation in Plasmodium falciparum Bioorg. Med. Chem. 18 2010 7302
29. O. Familiar H. Munier-Lehmann J.A. Ainsa M.J. Camarasa M.J. Perez-Perez Design, synthesis and inhibitory activity against Mycobacterium tuberculosis thymidine monophosphate kinase of acyclic nucleoside analogues with a distal imidazoquinolinone Eur. J. Med. Chem. 45 2010 5910
30. V. Frecer P. Seneci S. Miertus Computer-assisted combinatorial design of bicyclic thymidine analogs as inhibitors of Mycobacterium tuberculosis thymidine monophosphate kinase J. Comput.-Aided Mol. Des. 25 2011 31
31. C.H. Andrade K.F. Pasqualoto E.I. Ferreira A.J. Hopfinger Rational design and 3D-pharmacophore mapping of 5'-thiourea-substituted alpha-thymidine analogues as mycobacterial TMPK inhibitors J. Chem. Inf. Model. 49 2009 1070
32. D. Douguet H. Munier-Lehmann G. Labesse S. Pochet LEA3D: a computer-aided ligand design for structure-based drug design J. Med. Chem. 48 2005 2457
33. I. Van Daele H. Munier-Lehmann M. Froeyen J. Balzarini S. Van Calenbergh Rational design of 5g€2-thiourea-substituted alpha-thymidine analogues as thymidine monophosphate kinase inhibitors capable of inhibiting mycobacterial growth J. Med. Chem. 50 2007 5281
34. J.L. Whittingham J. Carrero-Lerida J.A. Brannigan L.M. Ruiz-Perez A.P. Silva M.J. Fogg A.J. Wilkinson I.H. Gilbert K.S. Wilson D. González-Pacanowska Structural basis for the efficient phosphorylation of AZT-MP (3g€2-azido-3g€2-deoxythymidine monophosphate) and dGMP by Plasmodium falciparum type I thymidylate kinase Biochem. J. 428 2010 499
35. C. Blondin L. Serina L. Weismuller A.M. Gilles O. Barzu Improved spectrophotometric assay of nucleoside monophosphate kinase activity using the pyruvate kinase/lactate dehydrogenase coupling system Anal. Biochem. 220 1994 219
36. I.H. Segel Enzyme Kinetics 1993 Wiley-Interscience Publications, John Wiley New York
37. G.M. Morris R. Huey W. Lindstrom M.F. Sanner R.K. Belew D.S. Goodsell A.J. Olson AutoDock4 and autodocktools4: automated docking with selective receptor flexibility J. Comput Chem. 30 2009 2785
38. http://www.chemaxon.com/products/marvin/marvinsketch/.
39. N. Ostermann I. Schlichting R. Brundiers M. Konrad J. Reinstein T. Veit R.S. Goody A. Lavie Insights into the phosphoryltransfer mechanism of human thymidylate kinase gained from crystal structures of enzyme complexes along the reaction coordinate Structure. 8 2000 629
40. G.M. Morris D.S. Goodsell R.S. Halliday R. Huey W.E. Hart R.K. Belew A.J. Olson Automated docking using a lamarckian genetic algorithm and an empirical binding free energy function J. Comput Chem. 19 1998 1639
41. E.F. Pettersen T.D. Goddard C.C. Huang G.S. Couch D.M. Greenblatt E.C. Meng T.E.U.C.S.F. Ferrin Chimera-a visualization system for exploratory research and analysis J. Comput Chem. 25 2004 1605