Molecular docking, synthesis, kinetics study, structure–activity relationship and ADMET analysis of morin analogous as Helicobacter pylori urease inhibitors
Tóm tắt
Từ khóa
Tài liệu tham khảo
Mobley HLT, Hausinger RP (1989) Microbial ureases: significance, regulation and molecular characterization. Microbiol Rev 53:85–103
Rotini OT (1935) Latrasformazione enzimatica dell' urea nel tereno. Annali Laboratorio Ricerca Spalllanzani 3:143–154
Tamaddon F, Ghazi S (2015) Urease: a highly biocompatible catalyst for switchable Biginelli reaction and synthesis of 1, 4-dihydropyridines from the in situ formed ammonia. Catal Commun 72:63–67
Mobley HLT, Island MD, Hausinger RP (1995) Molecular biology of microbial ureases. Microbiol Rev 59:451–480
Ha NC, Oh ST, Sung JY, Cha KA, Lee MH, Oh BH (2001) Supramolecular assembly and acid resistance of Helicobacter pylori urease. Nat Struct Biol 8:505–509
Jabri E, Carr MB, Hausinger RP, Karplus PA (1995) The crystal structure of urease from Klebsiella aerogenes. Science 268:998–1004
Jang HJ, Choi MH, Shin WG, Kim KH, Chung YW, Kim KO, Kim HY (2008) Has peptic ulcer disease changed during the past ten years in Korea? A prospective multi-center study. Dig Dis Sci 53(6):1527–1531
Mobley HL, Island MD, Hausinger RP (1995) Molecular biology of microbial ureases. Microbiol Rev 59(3):451–480
Collins CM, D’Orazio SE (1993) Bacterial ureases: structure, regulation of expression and role in pathogenesis. Mol Microbiol 9:907–913
Sujoy B, Aparna A (2013) Potential clinical significance of urease enzyme. Eur Sci J. https://doi.org/10.19044/esj.2013.v9n21p%25p
Ciurli S, Benini S, Rypniewski WR (1999) Structural properties of the nickel ions in urease: novel insights into the catalytic and inhibition mechanisms. Coord Chem Rev 192:331–355
Li HW, Zou TB, Jia Q (2016) Anticancer effects of morin-7-sulphate sodium, a flavonoid derivative, in mouse melanoma cells. Biomed Pharmacother 84:909–916
Galvez J, Coelho G, Crespo ME (2001) Intestinal anti-inflammatory activity of morin on chronic experimental colitis in the rat. Aliment Pharmacol Ther 15(12):2027–2039
Fang SH, Hou YC, Chang WC, Hsiu SL, Chao PD, Chiang BL (2003) Morin sulfates/glucuronides exert anti-inflammatory activity on activated macrophages and decreased the incidence of septic shock. Life Sci 74(6):743–756
Kim JW, Lee JH, Hwang BY (2009) Morin inhibits Fyn kinase in mast cells and IgE-mediated type I hypersensitivity response in vivo. Biochem Pharmacol 77(9):1506–1512
Dilshara MG, Jayasooriya RG, Lee S, Choi YH, Kim GY (2016) Morin downregulates nitric oxide and prostaglandin E 2 production in LPS-stimulated BV2 microglial cells by suppressing NF-κB activity and activating HO-1 induction. Environ Toxicol Pharmacol 44:62–68
Paoli P, Cirri P (1830) Caselli A (2013) The insulin-mimetic effect of Morin: a promising molecule in diabetes treatment. Biochim Biophys Acta Gen Subj 4:3102–3111
Lee HS, Jung KH, Hong SW (2008) Morin protects acute liver damage by carbon tetrachloride (CCl4) in rat. Arch Pharmacal Res 31(9):1160–1165
Pal R, Chaudhary MJ, Tiwari PC, Babu S, Pant KK (2015) Protective role of theophylline and their interaction with nitric oxide (NO) in adjuvant-induced rheumatoid arthritis in rats. Int Immunopharmacol 29(2):854–862
Mobley HL, Hausinger RP (1989) Microbial ureases: significance, regulation, and molecular characterization. Microbiol Rev 53(1):85–108
Awllia Jalaluddin JAJ, Al-Ghamdi M, Huwait E, Javaid S, Rasheed S, Iqbal Choudhary M (2016) Flavonoids as natural inhibitors of jack bean urease Enzyme. Lett Drug Des Discov 13(3):243–249
Aslam MAS, Mahmood SU, Shahid M, Saeed A, Iqbal J (2011) Synthesis, biological assay in vitro and molecular docking studies of new Schiff base derivatives as potential urease inhibitors. Eur J Med Chem 46(11):5473–5479
Ansari MM, Deshmukh SP, Khan R, Musaddiq M (2014) Synthesis antimicrobial and anticancer evaluation of 1-Aryl-5-(o-methoxyphenyl)-2-S-benzyl isothiobiurets. Int J Med Chem. https://doi.org/10.1155/2014/352626
Mughal EU, Ayaz M, Hussain Z, Hasan A, Sadiq A, Riaz M, Malik A, Hussain S, Choudhary MI (2006) Synthesis and antibacterial activity of substituted flavones, 4-thioflavones and 4-iminoflavones. Bioorg Med Chem 14(14):4704–4711
Brodowska K, Sykuła A, Garribba E, Łodyga-Chruścińska E, Sójka M (2016) Naringenin Schiff base: antioxidant activity, acid–base profile, and interactions with DNA. Transition Met Chem 41(2):179–189
Weatherburn MW (1967) Phenol-hypochlorite reaction for determination of ammonia. Anal Chem 39(8):971–974
Hanif M, Shoaib K, Saleem M, Hasan Rama N, Zaib S, Iqbal J (2012) Synthesis, urease inhibition, antioxidant, antibacterial, and molecular docking studies of 1, 3, 4-oxadiazole derivatives. ISRN Pharmacol 13:2012
Choudhary MI, Begum A, Abbaskhan A, Musharraf SG, Ejaz A (2008) Two new antioxidant phenylpropanoids from Lindelofia stylosa. Chem Biodivers 5(12):2676–2683
Friesner RA, Banks JL, Murphy RB, Halgren TA, Klicic JJ, Mainz DT, Repasky MP, Knoll EH, Shelley M, Perry JK, Shaw DE (2004) Glide: a new approach for rapid, accurate docking and scoring. 1. Method and assessment of docking accuracy. J Med Chem 47(7):1739–1749
Halgren TA, Murphy RB, Friesner RA, Beard HS, Frye LL, Pollard WT, Banks JL (2004) Glide: a new approach for rapid, accurate docking and scoring. Enrichment factors in database screening. J Med Chem 47(7):1750–1759
Glide, version 6.6, Schrödinger, LLC, New York, NY, 2015
Lee SK, Mbwambo ZH, Chung Luyengi L, Gamez EJ, Mehta RG, Kinghorn AD, Pezzuto JM (1998) Evaluation of the antioxidant potential of natural products. Comb Chem High Throughput Screening 1(1):35–46
Genheden S, Ryde U (2015) The MM/PBSA and MM/GBSA methods to estimate ligand-binding affinities. Exp Op Drug Disc 10:449–461
Godschalk F, Genheden S, Söderhjelm P, Ryde U (2013) Comparison of MM/GBSA calculations based on explicit and implicit solvent simulations. Phys Chem Chem Phy 15:7731–7739
Sengupta D, Verma D, Naik PK (2008) Docking-MM-GB/SA and ADME screening of HIV-1 NNRTI inhibitor: nevirapine and its analogues. Silico Biol 8:275–289
Cecchelli R, Berezowski V, Lundquist S, Culot M, Renftel M, Dehouck MP, Fenart L (2007) Modelling of the blood-brain barrier in drug discovery and development. Nat Rev Drug Discov 6:650–661
Lipinski CA, Lombardo F, Dominy BW, Feeney PJ (2012) Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv Drug Deliv Rev 64:4–17
Friesner RA, Murphy RB, Repasky MP, Frye LL, Greenwood JR, Halgren TA, Sanschagrin PC, Mainz DT (2006) Extra precision glide: docking and scoring incorporating a model of hydrophobic enclosure for protein-ligand complexes. J Med Chem 49:6177–6196
Hanif M, Saleem M, Hussain MT, Rama NH, Zaib S, Aslam MA, Jones PG, Iqbal J (2012) Synthesis, urease inhibition, antioxidant and antibacterial studies of some 4-amino-5-aryl-3H-1, 2, 4-triazole-3-thiones and their 3, 6-disubstituted 1, 2, 4-triazolo [3, 4-b] 1, 3, 4-thiadiazole derivatives. J Braz Chem Soc 23(5):854–860
Xiao ZP, Shi DH, Li HQ, Zhang LN, Xu C, Zhu HL (2007) Polyphenols based on isoflavones as inhibitors of Helicobacter pylori urease. Bioorg Med chem 15(11):3703–3710
Li HQ, Xiao ZP, Yan T, Lv PC, Zhu HL (2009) Amines and oximes derived from deoxybenzoins as Helicobacter pylori urease inhibitors. Eur J Med Chem 44(5):2246–2251
Xiao ZP, Wang XD, Peng ZY, Huang S, Yang P, Li QS, Zhou LH, Hu XJ, Wu LJ, Zhou Y, Zhu HL (2012) Molecular docking, kinetics study, and structure–activity relationship analysis of quercetin and its analogous as Helicobacter pylori urease inhibitors. J Agric Food Chem 60(42):10572–10577
Xiao ZP, Peng ZY, Dong JJ, He J, Ouyang H, Feng YT, Lu CL, Lin WQ, Wang JX, Xiang YP, Zhu HL (2013) Synthesis, structure–activity relationship analysis and kinetics study of reductive derivatives of flavonoids as Helicobacter pylori urease inhibitors. Eur J Med Chem 63:685–695