Structure-antifungal activity relationship of His-Phe-Arg-Trp-Gly-Lys-Pro-Val-NH2 and analogues

Bioorganic and Medicinal Chemistry

Volumn 16, Issue 8, 2008, Pages 4347-4358

  Masman, Marcelo F ^a   Somlai, Csaba ^b   Garibotto, Francisco M ^a   Rodríguez, Ana M ^a   de la Iglesia, Agustina ^c   Zacchino, Susana A ^c   Penke, Botond ^b   Enriz, Ricardo D ^a  

^a UNIVERSIDAD NACIONAL DE SAN LUIS   (Argentina)

^b UNIVERSITY OF SZEGED   (Hungary)

^c UNIVERSIDAD NACIONAL DE ROSARIO   (Argentina)

Author keywords

Antifungal peptides; Conformation; Electronic properties; Octapeptides; MSH analogues

Indexed keywords

AMPHOTERICIN B; ANTIFUNGAL AGENT; HISTIDYLPHENYLALANYLARGINYLTRYPTOPHANYLGLYCYLLYSYLPROLYLVALINAMIDE; HISTIDYLPHENYLALANYLARGINYLTRYPTOPHANYLGLYCYLLYSYLPROLYLVALINAMIDE DERIVATIVE; UNCLASSIFIED DRUG;

AMINO ACID SEQUENCE; ANTIFUNGAL ACTIVITY; ARTICLE; CANDIDA ALBICANS; CANDIDA TROPICALIS; CONTROLLED STUDY; CRYPTOCOCCUS NEOFORMANS; DRUG ANALYSIS; DRUG CONFORMATION; DRUG DESIGN; DRUG STRUCTURE; NONHUMAN; STRUCTURE ACTIVITY RELATION;

CANDIDA ALBICANS; CANDIDA TROPICALIS; FILOBASIDIELLA NEOFORMANS;

EID: 42349116821     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2008.02.072     Document Type: Article

References (60)

1. Vicente M.F., Basilio A., Cabello A., and Peláez F. Clin. Microbiol. Infect. 9 (2003) 15
2. McNeil M.M., Nash S.L., Hajjeh R.A., Phelan M.A., Conn L.A., Plikaytis B.D., and Warnock D.W. Clin. Infect. Dis. 33 (2001) 641
3. Pfaller M.A., and Diekema D.J. Clin. Microbiol. Rev. 20 (2007) 133
4. Walsh T.J., Groll A., Hiemenz J., Fleming R., Roilides E., and Anaissie E. Clin. Microbiol. Infect. 10 (2004) 48
5. Pfaller M.A., and Diekema D.J. J. Clin. Microbiol. 42 (2004) 4419
6. Weinberg A., Krisanaprakornkit S., and Dale B.A. Crit. Rev. Oral Biol. Med. 9 (1998) 399
7. Maly W.L., and Kari U.P. Biopolymers 37 (1995) 105
8. Epand R.M., and Vogel H.J. Biochim. Biophys. Acta 1462 (1999) 11
9. Tossi A., Sandri L., and Giangaspero A. Biopolymers 55 (2000) 4
10. Hancock R.E., Talla W.T., and Brown M.H. Adv. Microb. Physiol. 37 (1995) 135
11. Hancock R.E., and Leher R.I. Trends Biotechnol. 16 (1993) 82
12. Bulet P., and Stöcklin R. Protein Peptide Lett. 12 (2005) 3
13. Hancock R.E. Lancet 349 (1997) 418
14. Park C.B., Kim H.S., and Kim S.C. Biochem. Biophys. Res. Commun. 244 (1998) 253
15. Boman H.G., Agerberth B., and Boman A. Infect. Immun. 61 (1993) 2978
16. Cabiaux V., Agerberth B., Johansson J., Homble F., Goormaghtigh E., and Ruysschaert J.M. Eur. J. Biochem. 224 (1994) 1019
17. Cutuli M., Cristiani S., Lipton J.M., and Catania A.J. Leukocyte Biol. 67 (2000) 233
18. Grieco P., Rossi C., Colombo G., Gatti S., Novellino E., Lipton J.M., and Catania A. J. Med. Chem. 46 (2003) 850
19. Grieco P., Rossi C., Gatti S., Colombo G., Carlin A., Novellino E., Lama T., Lipton J.M., and Catania A. J. Med. Chem. 48 (2005) 1384
20. Carotenuto A., Saviello M.R., Auriemma L., Campiglia P., Catania A., Novellino E., and Grieco P. Chem. Biol. Drug Des. 69 (2007) 68
21. Kouznetsov V.V., Urbina J., Palma A., López S., Ribas J., Enriz R.D., and Zacchino S. Bioorg. Med. Chem. 8 (2000) 691
22. Vargas L.Y., Castelli M., Kouznetsov V., Urbina J.M., Lopez S., Sortino M., Enriz R.D., Ribas J.C., and Zacchino S. Bioorg. Med. Chem. 11 (2003) 1531
23. Suvire F.D., Sortino M., Kouznetsov V.V., Vargas M.L.Y., Zacchino S.A., Cruz U.M., and Enriz R.D. Bioorg. Med. Chem. 14 (2006) 1851
24. Masman M.F., Rodríguez A.M., Svetaz L., Zacchino S.A., Somlai C., Csizmadia I.G., Penke B., and Enriz R.D. Bioorg. Med. Chem. 14 (2006) 7604
25. Hruby V.J., Wilkes B.C., Hadley M.E., Al-Obeidi F., Sawyer T.K., Staples D.J., de Vaux A.E., Dym O., Castrucci A.M., Hintz M.F., Riehm J.P., and Ranga Rao K. J. Med. Chem. 30 (1987) 2126
26. Cai M., Mayorov A.V., Ying J., Stankova M., Trivedi D., Cabello C., and Hruby V.J. Peptides 26 (2005) 1481
27. Fung S., and Hruby V.J. Curr. Opin. Chem. Biol. 9 (2005) 352
28. Grieco P., Cai M., Mayorov A.V., Trivedi D., and Hruby V.J. Peptides 27 (2006) 472
29. Cain J.P., Mayorov A.V., Cai M., Wang H., Tan B., Chandler K., Lee Y.-S., Petrov R.R., Trivedi D., and Hruby V.J. Bioorg. Med. Chem. Lett. 16 (2006) 5462
30. Eberle A.N. The Melanotropins: Chemistry, Physiology and Mechanisms of Action (1988), Karger, Basel, Switzerland 393-394
31. Ripoll D.R., and Scheraga H.A. Biopolymers 27 (1988) 1283
32. Ripoll D.R., and Scheraga H.A. Biopolymers 30 (1990) 165
33. Vila J.A., Ripoll D.R., Baldoni H.A., and Scheraga H.A. J. Biol. NMR 24 (2002) 245
34. Sarai A.J. Theor. Biol. 140 (1989) 137
35. North A.C.T. J. Mol. Graphics. 7 (1989) 67
36. Politzer P., and Daiker K.C. In: Deb M.B. (Ed). The Force Concept in Chemistry (1981), Van Nostrand Reinhold Co., New York
37. Náray-Szabó G., and Ferenczy G.G. Chem. Rev. 95 (1995) 829
38. Murray S., and Politzer P. In: Sapse A.-M. (Ed). Molecular Orbital Calculations for Biological Systems (1998), Oxford University Press, New York 49-84
39. Otsuka H., and Inouye K. Bull. Chem. Soc. Jpn. 37 (1964) 289
40. Sugg E.E., Cody W.L., Abdel-Malek Z., Hadley M.E., and Hruby V.J. Biopolymers 25 (1986) 2029
41. Hiltz M.E., Catania A., and Lipton J.M. Peptides 12 (1991) 767
42. Peng P.J., Sahm U.G., Doherty R.V., Kinsman R.G., Moss S.H., and Pouton C.W. Peptides 18 (1997) 1001
43. Holder J.R., and Haskell-Luevano C. Med. Res. Rev. 24 (2004) 325
44. Sahm U.G., Olivier G.W., Branch S.K., Moss S.H., and Pouton C.W. Peptides 15 (1994) 1297
45. Kaiser E., Colescott R.L., Bossiuger C.D., and Cook P.I. Anal. Biochem. 34 (1970) 595
46. NCCLS, National Committee for Clinical Laboratory Standards, Method M27-A2, 2nd ed., Wayne Ed.; 2002, Vol. 22, pp 1-29.
47. Liwo A., Tempczyk A., Oldziej S., Shenderovich M.D., Hruby V.J., Talluri S., Ciarkowski J., Kasprzykowski S., Lankiewicz L., and Grzonka Z. Biopolymers 38 (1996) 157
48. Némethy G., Gibson K.D., Palmer K.A., Yoon C.N., Paterlini G., Zagari A., Rumsey S., and Scheraga H.A. J. Phys. Chem. 96 (1992) 6472
49. Vila J., Williams R.L., Vásquez M., and Scheraga H.A. Proteins Struct. Funct. Genet. 10 (1991) 199
50. Williams R.L., Vila J., Perrot G., and Scheraga H.A. Proteins Struct. Funct. Genet. 14 (1992) 110
51. Li Z., and Scheraga H.A. Proc. Natl. Acad. Sci. U.S.A. 84 (1987) 6611
52. Piela L., and Scheraga H.A. Biopolymers 26 (1987) S33
53. Metropolis N., Rosenbluth A.W., Rosenbluth M.N., Teller A.H., and Teller E.J. Chem. Phys. 21 (1953) 1087
54. Sidor M., Wójcik J., Pawlak D., and Izdebski J. Acta Biochim. Pol. 46 (1999) 641
55. Meadows, R. P.; Post, C. B.; Luxon, A. B.; Gorenstein, D. G. MORASS 2.1; Purdue University: W. Lafayette, 1994.
56. Post C.B., Meadows R.P., and Gorenstein D.G. J. Am. Chem. Soc. 112 (1990) 6796
57. Scheraga, H. A.; Ripoll, D. R.; Liwo, A.; Czaplewski, C. User Guide ECEPPAK and ANALYZE Programs.
58. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, revision B.01; Gaussian, Inc.: Wallingford, CT, 2004.
59. Flükiger, P.; Lüthi, H. P.; Portmann S.; Weber, J. MOLEKEL 4.0; Swiss Center for Scientific Computing: Manno, Switzerland, 2000.
60. Pettersen E.F., Goddard T.D., Huang C.C., Couch G.S., Greenblatt D.M., Meng E.C., and Ferrin T.E. J. Comput. Chem. 25 (2004) 1605