Molecular mechanism of the interactions between inhibitory tripeptides and angiotensin-converting enzyme

Biophysical Chemistry

Volumn 168-169, Issue , 2012, Pages 60-66

  Zhou, Min ^a   Du, Kun ^a   Ji, Peijun ^a   Feng, Wei ^a  

^a BEIJING UNIVERSITY OF CHEMICAL TECHNOLOGY   (China)

Author keywords

Angiotensin converting enzyme; Molecular dynamics simulation; Tripeptide

Indexed keywords

ALANINE; DIPEPTIDYL CARBOXYPEPTIDASE; ISOLEUCINE; LEUCINE; PHENYLALANINE; TRIPEPTIDE; VALINE;

AMINO TERMINAL SEQUENCE; ARTICLE; BINDING AFFINITY; BINDING SITE; CRYSTAL STRUCTURE; ENZYME INHIBITION; HYDROGEN BOND; HYDROPHOBIC INTERACTION CHROMATOGRAPHY; HYDROPHOBICITY; MOLECULAR DYNAMICS; MOLECULAR INTERACTION; PRIORITY JOURNAL; PROCESS OPTIMIZATION; QUANTUM MECHANICS; STATIC ELECTRICITY;

AMINO ACID SEQUENCE; ANGIOTENSIN-CONVERTING ENZYME INHIBITORS; BINDING SITES; CATALYTIC DOMAIN; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; MOLECULAR DYNAMICS SIMULATION; OLIGOPEPTIDES; PEPTIDYL-DIPEPTIDASE A; QUANTUM THEORY;

EID: 84864089650     PISSN: 03014622     EISSN: 18734200     Source Type: Journal    
DOI: 10.1016/j.bpc.2012.05.002     Document Type: Article

References (45)

1. C.S. Anthony, H.R. Corradi, S.L. Schwager, U.P. Redelinghuys, D. Georgiadis, V. Dive, K.R. Acharya, and E.D. Sturrock The N domain of human angiotensin-I-converting enzyme: the role of N-glycosylation and the crystal structure in complex with an N domain-specific phosphinic inhibitor, RXP407 Journal of Biological Chemistry 285 2010 35685 35693
2. X. Liu, C.O.C. Bellamy, B.A. Bailey, L.J. Mullins, D.R. Dunbar, C.J. Kenyon, G. Brooker, S. Kantachuvesiri, K. Maratou, A. Ashek, A.F. Clark, S. Fleming, and J.J. Mullins Angiotensin-converting enzyme is a modifier of hypertensive end organ damage Journal of Biological Chemistry 284 2009 15564 15572
3. K. Zou, T. Maeda, A. Watanabe, J. Liu, S. Liu, R. Oba, Y.I. Satoh, H. Komano, and M. Michikawa Aβ-42-to-Aβ-40 and angiotensin-converting activities in different domains of angiotensin-converting enzyme Journal of Biological Chemistry 284 2009 31914 31920
4. R. Natesh, S.L.U. Schwager, E.D. Sturrock, and K. Ravi Acharya Crystal structure of the human angiotensin-converting enzyme-lisinopril complex Nature 421 2003 551 554 (Pubitemid 36168450)
5. Z.L. Woodman, S.L. Schwager, P. Redelinghuys, A.J. Chubb, E.L. van der Merwe, M.R. Ehlers, and E.D. Sturrock Homologous substitution of ACE C-domain regions with N-domain sequences: effect on processing, shedding, and catalytic properties Journal of Biological Chemistry 387 2006 1043 1051 (Pubitemid 44200498)
6. H.R. Corradi, I. Chitapi, B.T. Sewell, D. Georgiadis, V. Dive, E.D. Sturrock, and K.R. Acharya The structure of testis angiotensin-converting enzyme in complex with the C domain-specific inhibitor RXPA380 Biochemistry 46 2007 5473 5478 (Pubitemid 46717270)
7. J.M. Watermeyer, W.L. Kroger, H.G. O'Neill, B.T. Sewell, and E.D. Sturrock Probing the basis of domain-dependent inhibition using novel ketone inhibitors of angiotensin-converting enzyme Biochemistry 47 2008 5942 5950 (Pubitemid 351770024)
8. H.R. Corradi, S.L.U. Schwager, A.T. Nchinda, E.D. Sturrock, and K.R. Acharya Crystal structure of the N domain of human somatic angiotensin I-converting enzyme provides a structural basis for domain-specific inhibitor design Journal of Molecular Biology 357 2006 964 974
9. T.F.T. Antonios, and G.A. Macgregor Angiotensin-converting enzyme-inhibitors in hypertension - potential problems Journal of Hypertension 1 1995 S11 S16
10. L. Vercruysse, J. Van Camp, and G. Smagghe ACE inhibitory peptides derived from enzymatic hydrolysates of animal muscle protein: a review Journal of Agricultural and Food Chemistry 53 2005 8106 8115 (Pubitemid 41564615)
11. M. Martin, A. Wellner, I. Ossowski, and T. Henle Identification and quantification of inhibitors for angiotensin-converting enzyme in hypoallergenic infant milk formulas Journal of Agricultural and Food Chemistry 56 2008 6333 6338
12. H. Li, and R.E. Aluko Identification and inhibitory properties of multifunctional peptides from pea protein hydrolysate Journal of Agricultural and Food Chemistry 58 2010 11471 11476
13. R.J. FitzGerald, and H. Meisel Milk protein-derived peptide inhibitors of angiotensin-I-converting enzyme British Journal of Nutrition 84 2000 S33 S37
14. S. Makinen, J. Kelloniemi, A. Pihlanto, K. Makinen, H. Korhonen, A. Hopia, and J.P.T. Valkonen Inhibition of angiotensin converting enzyme I caused by autolysis of potato proteins by enzymatic activities confined to different parts of the potato tuber Journal of Agricultural and Food Chemistry 56 2008 9875 9883
15. T. Nakamura, A. Yoshida, N. Komatsuzaki, T. Kawasumi, and J. Shima Isolation and characterization of a low molecular weight peptide contained in sourdough Journal of Agricultural and Food Chemistry 55 2007 4871 4876 (Pubitemid 46960918)
16. M. Terashima, T. Baba, N. Ikemoto, M. Katayama, T. Morimoto, and S. Matsumura Novel angiotensin-converting enzyme (ACE) inhibitory peptides derived from boneless chicken leg meat Journal of Agricultural and Food Chemistry 58 2010 7432 7436
17. M. Liu, M. Pazgier, C. Li, W. Yuan, C. Li, and W. Lu A left-handed solution to peptide inhibition of the p53-MDM2 interaction Angewandte Chemie (International Ed. in English) 49 2010 3649 3652
18. H. Fujita, K. Yokoyama, and M. Yoshikawa Classification and antihypertensive activity of angiotensin I-converting enzyme inhibitory peptides derived from food proteins Journal of Food Science 65 2000 564 569 (Pubitemid 30610519)
19. A. Papakyriakou, G.A. Spyroulias, E.D. Sturrock, E. Manessi-Zoupa, and P. Cordopatis Simulated interactions between angiotensin-converting enzyme and substrate gonadotropin-releasing hormone: novel insights into domain selectivity Biochemistry 46 2007 8753 8765 (Pubitemid 47204441)
20. N. Dimitropoulos, A. Papakyriakou, G.A. Dalkas, E.D. Sturrock, and G.A. Spyroulias A computational approach to the study of the binding mode of dual ACE/NEP inhibitors Journal of Chemical Information and Modeling 50 2010 388 396
21. X. Wang, S. Wu, D. Xu, D. Xie, and H. Guo Inhibitor and substrate binding by angiotensin-converting enzyme: quantum mechanical/molecular mechanical molecular dynamics studies Journal of Chemical Information and Modeling 51 2011 1074 1082
22. N. Guex, and M.C. Peitsch SWISS-MODEL and the Swiss-PdbViewer: an environment for comparative protein modeling Electrophoresis 18 1997 2714 2723 (Pubitemid 28059943)
23. J.C. Gordon, J.B. Myers, T. Folta, V. Shoja, L.S. Heath, and A. Onufriev H++: a server for estimating pKas and adding missing hydrogens to macromolecules Nucleic Acids Research 23 2005 368 371
24. B. Hess GROMACS 4: algorithms for highly efficient, load-balanced, and scalable molecular simulation Journal of Chemical Theory and Computation 4 2008 435 447
25. W.F. van Gunsteren, and H.J.C. Berendsen Gromos-87 manual, Biomos BV Nijenborgh 4, 9747 AG Groningen, The Netherlands 1987
26. M. Manna, and C. Mukhopadhyay Molecular dynamics simulations of the interactions of kinin peptides with an anionic POPG bilayer Langmuir 27 2011 3713 3722
27. M.A. Barhoover, T. Orban, D.O. Beck, M.A. Bukys, and M. Kalafatis Contribution of amino acid region 334-335 from factor Va heavy chain to the catalytic efficiency of prothrombinase Biochemistry 47 2008 6840 6850 (Pubitemid 351898939)
28. M. Pasi, L. Riccardi, P. Fantucci, L. De Gioia, and E. Papaleo Dynamic properties of a psychrophilic r-amylase in comparison with a mesophilic homologue The Journal of Physical Chemistry. B 113 2009 13585 13595
29. G.M. Morris, D.S. Goodsell, R.S. Halliday, R. Huey, W.E. Hart, R.K. Belew, and A.J. Olson Automated docking using a Lamarckian genetic algorithm and an empirical binding free energy function Journal of Computational Chemistry 19 1998 1639 1662 (Pubitemid 128590223)
30. 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)
31. A.A. Patchett, E. Harris, E.W. Tristam, M.J. Wyvratt, M.T. Wu, D. Taub, E.R. Peterson, T.J. Ikeler, J. Ten Broeke, L.G. Payne, D.L. Ondeyka, E.D. Thorsett, W.J. Greenlee, N.S. Lohr, R.D. Hoffsommer, H. Joshua, W.V. Ruyle, J.W. Rothrock, S.D. Aster, A.L. Maycock, F.M. Robinson, R. Hirschmann, C.S. Sweet, E.H. Ulm, D.M. Gross, T.C. Vassil, and C.A. Stone A new class of angiotensin-converting enzyme inhibitors Nature 288 1980 280 283 (Pubitemid 11165879)
32. X. Hu, and W.H. Shelver Docking studies of matrix metalloproteinase inhibitors: zinc parameter optimization to improve the binding free energy prediction Journal of Molecular Graphics and Modelling 22 2003 115 126 (Pubitemid 36976838)
33. O.A. Donini, and P.A. Kollman Calculation and prediction of binding free energies for the matrix metalloproteinases Journal of Medicinal Chemistry 43 2000 4180 4188
34. Y. Pang, K. Xu, J. Yazal, and F.G. Prendergast Successful molecular dynamics simulation of the zinc-bound farnesyltransferase using the cationic dummy atom approach Protein Science 9 2000 1857 1865
35. R.H. Stote, and M. Karplus Zinc binding in proteins and solution: a simple but accurate nonbonded representation Proteins 23 1995 12 31
36. S.C. Hoops, K.W. Anderson, and K.M. Merz Force field design for metalloproteins Journal of the American Chemical Society 113 1991 8262 8270
37. T.J. Hou, W. Zhang, and X.J. Xu Binding affinities for a series of selective inhibitors of gelatinase-A using molecular dynamics with a linear interaction energy approach The Journal of Physical Chemistry. B 105 2001 5304 5315 (Pubitemid 35372632)
38. S. Toba, K.V. Damodaran, and K.M. Jr Merz Binding preferences of hydroxamate inhibitors of the matrix metalloproteinase human fibroblast collagenase Journal of Medicinal Chemistry 42 1999 1225 1234 (Pubitemid 29181145)
39. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, V.G. Zakrzewski, J.A. Montgomery, R.E. Jr Stratmann, J.C. Burant, S. Dapprich, J.M. Millam, A.D. Daniels, K.N. Kudin, M.C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G.A. Petersson, P.Y. Ayala, Q. Cui, K. Morokuma, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J. Cioslowski, J.V. Ortiz, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P.M.W. Gill, B.G. Johnson, W. Chen, M.W. Wong, J.L. Andres, M. Head-Gordon, E.S. Replogle, and J.A. Pople Gaussian 98, Revision A.9 1998 Gaussian, Inc. Pittsburgh, PA
40. C.I. Bayly, P. Cieplak, W.D. Cornell, and P.A. Kollman A well-behaved electrostatic potential based method using charge restraints for deriving atomic charges: the RESP model Journal of Physical Chemistry 97 1993 10269 10280
41. H.J.C. Berendsen, J.P.M. Postma, A. DiNola, and J.R. Haak Molecular dynamics with coupling to an external bath Journal of Chemical Physics 81 1984 3684 3690
42. U. Essmann, L. Perera, M.L. Berkowitz, T. Darden, H. Lee, and L.G.A. Pedersen Smooth Particle mesh Ewald potential Journal of Chemical Physics 103 1995 8577 8592
43. J.M. Watermeyer, B.T. Sewell, S.L. Schwager, R. Natesh, H.R. Corradi, K.R. Acharya, and E.D. Sturrock Structure of testis ACE glycosylation mutants and evidence for conserved domain movement Biochemistry 45 2006 12654 12663 (Pubitemid 44630850)
44. M. Akif, D. Georgiadis, A. Mahajan, V. Dive, E.D. Sturrock, R.E. Isaac, and K.R. Acharya High-resolution crystal structures of Drosophila melanogaster angiotensin-converting enzyme in complex with novel inhibitors and antihypertensive drugs Journal of Molecular Biology 400 2010 502 517
45. L. Wei, E. Clauser, F. Alhenc-Gelas, and P. Corvol The two homologous domains of human angiotensin I-converting enzyme interact differently with competitive inhibitors Journal of Biological Chemistry 267 1992 13398 13405