Potent angiotensin-converting enzyme inhibitory tripeptides identified by a computer-based approach

Journal of Molecular Graphics and Modelling

Volumn 53, Issue , 2014, Pages 206-211

  Hai Bang, Tran ^a   Shimizu, Kuniyoshi ^a  

^a KYUSHU UNIVERSITY   (Japan)

Author keywords

ACE inhibition; ADME prediction; Docking; Hypotensive peptides; Rational design

Indexed keywords

BIOCHEMISTRY; BLOOD; BLOOD PRESSURE; DOCKING; ENZYMES; PEPTIDES; SILICON COMPOUNDS;

ACE INHIBITION; ANGIOTENSIN-CONVERTING ENZYME; COMPUTER-BASED APPROACH; INHIBITORY ACTIVITY; RATIONAL DESIGN; RATIONAL DRUG DESIGNS; TAUTOMERIZATIONS; VIRTUAL SCREENING;

BLOOD VESSELS;

DIPEPTIDYL CARBOXYPEPTIDASE; DIPEPTIDYL CARBOXYPEPTIDASE INHIBITOR; ENALAPRILAT; LISINOPRIL; PERINDOPRILAT; PROLINE; TRANDOLAPRILAT; TRIPEPTIDE DERIVATIVE; OLIGOPEPTIDE; PROTEIN BINDING;

ANTIHYPERTENSIVE ACTIVITY; ARTICLE; COMPUTER ANALYSIS; DRUG BIOAVAILABILITY; DRUG IDENTIFICATION; DRUG INHIBITION; DRUG POTENCY; DRUG SCREENING; IC 50; IN VITRO STUDY; MOLECULAR DOCKING; PRIORITY JOURNAL; PROTOPLAST; TAUTOMERIZATION; VIRTUAL REALITY; AMINO ACID SEQUENCE; CHEMISTRY; ENZYME ACTIVE SITE; HYDROGEN BOND;

AMINO ACID SEQUENCE; ANGIOTENSIN-CONVERTING ENZYME INHIBITORS; CATALYTIC DOMAIN; DRUG EVALUATION, PRECLINICAL; HYDROGEN BONDING; MOLECULAR DOCKING SIMULATION; OLIGOPEPTIDES; PEPTIDYL-DIPEPTIDASE A; PROTEIN BINDING;

EID: 84906859557     PISSN: 10933263     EISSN: 18734243     Source Type: Journal    
DOI: 10.1016/j.jmgm.2014.08.002     Document Type: Article

References (31)

1. D.B. Matchar, D.C. McCrory, L.A. Orlando, M.R. Patel, U.D. Patel, and M.B. Patwardhan et al. Systematic review: comparative effectiveness of angiotensin-converting enzyme inhibitors and angiotensin II receptor blockers for treating essential hypertension Ann. Intern. Med. 148 2008 16 29 (Pubitemid 351664943)
2. E.M. Gordon, M.A. Gallop, and D.V. Patel Strategy and tactics in combinatorial organic synthesis. Applications to drug discovery Acc. Chem. Res. 29 1996 144 154 (Pubitemid 126477916)
3. H. Gohlke, and G. Klebe Approaches to the description and prediction of the binding affinity of small-molecule ligands to macromolecular receptors Angew. Chem. Int. Ed. Engl. 41 2002 2644 2676
4. W.P. Walters, M.T. Stahl, and M.A. Murcko Virtual screening - an overview Drug Discov. Today 3 1998 160 178 (Pubitemid 128715971)
5. S. Alam, and F. Khan QSAR and docking studies on xanthone derivatives for anticancer activity targeting DNA topoisomerase IIα Drug Des. Dev. Ther. 8 2014 183 195
6. Z. Antosova, M. Mackova, V. Kral, and T. Macek Therapeutic application of peptides and proteins: parenteral forever? Trends Biotechnol. 27 2009 628 635
7. Y. Hata, M. Yamamoto, M. Ohni, K. Nakajima, Y. Nakamura, and T. Takano A placebo-controlled study of the effect of sour milk on blood pressure in hypertensive subjects Am. J. Clin. Nutr. 64 1996 767
8. E.D. Marczak, H. Usui, H. Fujita, Y. Yang, M. Yokoo, and A.W. Lipkowski et al. New antihypertensive peptides isolated from rapeseed Peptides 24 2003 791 798 (Pubitemid 37020917)
9. S. Mizuno, K. Matsuura, T. Gotou, S. Nishimura, O. Kajimoto, and M. Yabune et al. Antihypertensive effect of casein hydrolysate in a placebo-controlled study in subjects with high-normal blood pressure and mild hypertension Br. J. Nutr. 94 2005 84 91 (Pubitemid 41357814)
10. T. Tavares, M.-Á. Sevilla, M.-J. Montero, R. Carrón, and F.X. Malcata Acute effect of whey peptides upon blood pressure of hypertensive rats, and relationship with their angiotensin-converting enzyme inhibitory activity Mol. Nutr. Food Res. 56 2012 316 324
11. P. Ruiz-Giménez, J.F. Marcos, G. Torregrosa, A. Lahoz, R. Fernández-Musoles, and S. Valles et al. Novel antihypertensive hexa- and heptapeptides with ACE-inhibiting properties: from the in vitro ACE assay to the spontaneously hypertensive rat Peptides 32 2011 1431 1438
12. E. Escudero, L. Mora, P.D. Fraser, M.-C. Aristoy, K. Arihara, and F. Toldrá Purification and identification of antihypertensive peptides in Spanish dry-cured ham J. Proteomics 78 2013 499 507
13. B. Hernández-Ledesma, M. del Mar Contreras, and I. Recio Antihypertensive peptides: production, bioavailability and incorporation into foods Adv. Colloid Interface Sci. 165 2011 23 35
14. M.A. Ondetti, B. Rubin, and D.W. Cushman Design of specific inhibitors of angiotensin-converting enzyme: new class of orally active antihypertensive agents Science 196 1977 441 444 (Pubitemid 8073845)
15. M. Fry Essential Biochemistry for Medicine 1st ed. 2011 Wiley-Blackwell West Sussex, UK
16. R. Natesh, S.L.U. Schwager, E.D. Sturrock, and K.R. Acharya Crystal structure of the human angiotensin-converting enzyme-lisinopril complex Nature 421 2003 551 554 (Pubitemid 36168450)
17. R. Thomsen, and M.H. Christensen MolDock: a new technique for high-accuracy molecular docking J. Med. Chem. 49 2006 3315 3321 (Pubitemid 43830529)
18. L.H. Lam, T. Shimamura, S. Manabe, M. Ishiyama, and H. Ukeda Assay of angiotensin I-converting enzyme-inhibiting activity based on the detection of 3-hydroxybutyrate with water-soluble tetrazolium salt Anal. Sci. 24 2008 1057 1060
19. P.K.A.A. Chauhan Ace inhibitors: a comprehensive review Int. J. Pharm. Sci. Res. 4 2013 532 549
20. K. Heikamp, and J. Bajorath The future of virtual compound screening Chem. Biol. Drug Des. 81 2013 33 40
21. L. Tan, H. Geppert, M.T. Sisay, M. Gütschow, and J. Bajorath Integrating structure- and ligand-based virtual screening: comparison of individual, parallel, and fused molecular docking and similarity search calculations on multiple targets ChemMedChem 3 2008 1566 1571
22. J. Wu, R.E. Aluko, and S. Nakai Structural requirements of angiotensin I-converting enzyme inhibitory peptides: quantitative structure-activity relationship study of di- and tripeptides J. Agric. Food Chem. 54 2006 732 738 (Pubitemid 43274109)
23. R. Norris, F. Casey, R.J. FitzGerald, D. Shields, and C. Mooney Predictive modelling of angiotensin converting enzyme inhibitory dipeptides Food Chem. 133 2012 1349 1354
24. C.A. Lipinski, F. Lombardo, B.W. Dominy, and P.J. Feeney Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings Adv. Drug Deliv. Rev. 46 2001 3 26 (Pubitemid 33653411)
25. Y. Nakamura, N. Yamamoto, K. Sakai, A. Okubo, S. Yamazaki, and T. Takano Purification and characterization of angiotensin I-converting enzyme inhibitors from sour milk J. Dairy Sci. 78 1995 777 783
26. A. Shimakage, M. Shinbo, and S. Yamada ACE inhibitory substances derived from soy foods J. Biol. Macromol. 12 2012 72 80
27. M. Kohmura, N. Nio, K. Kubo, Y. Minoshima, E. Munekata, and Y. Ariyoshi Inhibition of angiotensin-converting enzyme by synthetic peptides of human beta-casein Agric. Biol. Chem. 53 1989 2107 2114
28. D.J. Craik, D.P. Fairlie, S. Liras, and D. Price The future of peptide-based drugs Chem. Biol. Drug Des. 81 2013 136 147
29. M. Raimund, H. Kubinyi, and G. Folkers C. Sotriffer, Virtual Screening: Vol. 48 - Principles, Challenges, and Practical Guidelines 2011 John Wiley & Sons Federal Republic of Germany 550
30. J. Valjakka, A. Siltari, S. Kukkurainen, H. Vapaatalo, and R. Viitanen Does the cis/trans configuration of peptide bonds in bioactive tripeptides play a role in ACE-1 enzyme inhibition? Biol. Targets Ther. 2014 59 65
31. I.K. McDonald, and J.M. Thornton Satisfying hydrogen bonding potential in proteins J. Mol. Biol. 238 1994 777 793 (Pubitemid 24168633)