Development of novel peptide inhibitor of Lipoxygenase based on biochemical and BIAcore evidences

Biochimica et Biophysica Acta - Proteins and Proteomics

Volumn 1784, Issue 11, 2008, Pages 1812-1817

  Somvanshi, Rishi Kumar ^a   Singh, Abhay Kumar ^a   Saxena, Meera ^a   Mishra, Biswajit ^a   Dey, Sharmistha ^a  

^a ALL INDIA INSTITUTE OF MEDICAL SCIENCES   (India)

Author keywords

Enzyme kinetics; Leukotrienes; Lipoxygenases; Peptide synthesis; Surface plasmon resonance

Indexed keywords

ALANYLGLYCYLARGINYLSERINE; ALANYLISOLEUCYLARGINYLSERINE; ALANYLISOLEUCYLGLUTAMYLSERINE; ALANYLISOLEUCYLTYROSYLTRYPTOPHAN; CURCUMIN; EPIGALLOCATECHIN; LEUCYLVALYLSERINE; LIPOXYGENASE; LIPOXYGENASE INHIBITOR; LYSYLTRYPTOPHAN; NORDIHYDROGUAIARETIC ACID; PHENYLALANYLTRYPTOPHAN; PHENYLALANYLTRYPTOPHANYLSERINE; PHENYLALANYLTRYPTOPHANYLTYROSINE; PHENYLALANYLTYROSYLSERINE; SERYLTRYPTOPHAN; TYROSYLTRYPTOPHAN; TYROSYLTRYPTOPHANYLGLYCINE; UNCLASSIFIED DRUG; VALYLALANYLSERINE;

ARTICLE; BREAST CANCER; CRYSTAL STRUCTURE; ENZYME ACTIVATION; ENZYME ACTIVE SITE; ENZYME ACTIVITY; HUMAN; HUMAN TISSUE; NONHUMAN; PRIORITY JOURNAL; PROTEIN BINDING;

12-HYDROXY-5,8,10,14-EICOSATETRAENOIC ACID; BREAST NEOPLASMS; DRUG DESIGN; DRUG SCREENING ASSAYS, ANTITUMOR; ENZYME ACTIVATION; FEMALE; HUMANS; HYDROXYEICOSATETRAENOIC ACIDS; KINETICS; LIPOXYGENASE; LIPOXYGENASE INHIBITORS; PROTEIN BINDING; SOYBEANS; SURFACE PLASMON RESONANCE;

GLYCINE MAX;

EID: 54049149323     PISSN: 15709639     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bbapap.2008.07.004     Document Type: Article

References (36)

1. Liu M.C., Dube L.M., and Lancaster J. Acute and chronic effects of a 5-lipoxygenase inhibitor in asthma: a 6-month randomized multicenter trial. J. Allergy Clin. Immunol. 98 (1996) 859-871
2. Gardner H.W. Recent investigations into the lipoxygenase pathway of plants. Biochim. Biophys. Acta. 1084 (1991) 221-239
3. Seidow J.N. Plant lipoxygenase: structure and function. Annual Review of Plant Physiology and Plant Molecular Biology 2 (1991) 145-188
4. Samuelsson B., Dahlen S.E., Lindgren J.A., Rouzer C.A., and Serhan C.N. Leukotrienes and lipoxins: structures, biosynthesis, and biological effects. Science 237 (1987) 1171-1176
5. Sigal E., Craik C.S., Highland E., Grunberger D., Costello L.L., Dixon R.A., and Nadel J.A. Molecular cloning and primary structure of human 15-Lipoxygenase. Biochem. Biophys. Res. Commun. 157 (1988) 457-464
6. Steele V.E., Holmes C.A., Hawk E.T., Kopelovich L., Lubet R.A., Crowell J.A., Sigman C.C., and Kelloff G.J. Lipoxygenase inhibitors as potential cancer chemopreventives. Cancer Epidemiol. Biomarkers Prev. 8 (1999) 467-483
7. Dailey L.A., and Imming P. 12-Lipoxygenase: classification, possible therapeutic benefits from inhibition and inhibitors. Curr. Med. Chem. 6 (1999) 389-398
8. Skrzypczak Jankun E., Amzel L.M., Kroa B.A., and Funk Jr. M.O. Three-dimensional structure of a purple Lipoxygenase. J. Am. Chem. Soc. 123 (2001) 10814-10820
9. Boyington J.C., Gaffney B.J., and Amzel L.M. The three-dimensional structure of an arachidonic acid 15-lipoxygenase. Science 260 (1993) 1482-1486
10. Gillmor S.A., Villasenor A., and Fletterick R. The structure of mammalian 15-lipoxygenase reveals similarity to the lipases and the determinants of substrate specificity. Nat. Struc. Biol. 4 (1997) 1003-1009
11. Minor W., Steczko J., Stec B., Otwinowski Z., Bolin J.T., Walter R., and Axelrod B. Crystal structure of soybean Lipoxygenase L-1 at 1.4 Angstrom resolution. Biochemistry 35 (1996) 10687-10701
12. Minor W., Steczko J., Stec B., Otwinowski Z., Bolin J.T., Walter R., and Axelrod B. Crystallographic determination of the active-site iron and its ligands in soybean Lipoxygenase L-1. Biochemistry 32 (1993) 6320-6323
13. Prigge S.T., Boyington J.C., Faig M., Doctor K.S., Gaffney B.J., and Amzel L.M. Structure and mechanism of Lipoxygenases. Biochimie 79 (1997) 629-636
14. Skrzypczak Jankun E., Kanging Z., Patrick N., McCabe Stevev H., and Selman J. Structure of curcumin in complex with lipoxygenase and its significance in cancer. Int. J. Mol. Med. 12 (2003) 17-24
15. Ruddat V.C., Mogul R., Chorny I., Chen C., Perrin N., Whitman S., Kenyon V., Jacobson M.P., Bernasconi C.F., and Holman T.R. Tryptophan 500 and arginine 707 define product and substrate active site binding in soybean lipoxygenase-1. Biochemistry 43 (2004) 13063-13071
16. Edwards C.M.B., Cohen M.A., and Bloom S.R. Peptides as drugs. QJM 92 (1992) 1-4
17. Chandra V., Jasti J., Kaur P., Dey S., Perbandt M., Srinivasan A., Betzel Ch., and Singh T.P. Crystal structure of a complex formed between a snake venom phospholipase A(2) and a potent peptide inhibitor Phe-Leu-Ser-Tyr-Lys at 1.8 A resolution. J. Biol. Chem. 277 (2002) 41079-41085
18. Church W.B., Inglis A.S., Tseng A., Duell R., Lei P.W., Bryant K.J., and Scott K.F. A novel approach to the design of inhibitors of human secreted phospholipase A2 based on native peptide inhibition. J. Biol. Chem. 276 (2001) 33156-33164
19. Somvanshi R.K., Kumar A., Kant S., Gupta D., Singh S.B., Das U., Srinivasan A., Singh T.P., and Dey S. Surface plasmon resonance studies and biochemical evaluation of a potent peptide inhibitor against cyclooxygenase-2 as an anti-inflammatory agent. Biochem. Biophys. Res. Commun. 361 (2007) 37-42
20. Lineweaver H., and Burk D. The determination of enzyme dissociation constants. J. Am. Chem. Soc. 56 (1934) 658-666
21. Veldink G.A., and Vliengenthart J.F.G. Lopoxygenases, non-heme iron containing enzyme. Adv. Inorg. Biochem. 6 (1984) 139-161
22. Axelrod B., Cheesborough T.M., and Laasko S. Lipoxygenase from soybean. Meth. Enzymol. 71 (1981) 441-451
23. Whitman S., Gezginci M., Timmermann B.N., and Holman T.R. Structure-activity relationship studies of nordihydroguaiaretic acid inhibitors toward soybean, 12 human, and 15-human Lipoxygenase. J. Med. Chem. 45 (2002) 2659-2666
24. Merrifield R.B. The synthesis of a tetrapeptide. J. Am. Chem. Soc. 85 (1963) 2149-2154
25. Neichi T., Koshihara Y., and Murota S. Inhibitory effect of esculetin on 5-lipoxygenase and leukotriene biosynthesis. Biochim. Biophys. Acta. 753 (1983) 130-132
26. Hamasaki Y., and Tai H.H. Gossypol, a potent inhibitor of arachidonate 5- and 12-lipoxygenases. Biochim. Biophys. Acta. 834 (1985) 37-41
27. Skrzypczak-Jankun E., Kangjing Z., and Jerzy J. Inhibition of Lipoxygenase by (-)- epigallocatechin gallate: X-ray analysis at 2.1A reveals degradation of EGCG and shows soybean LOX-3 complex with EGC instead. Int. J. Mol. Med. 12 (2003) 415-422
28. Koshihara Y., Neichi T., Murota S., Lao A., Fujimoto Y., and Tatsuno T. Caffeic acid is a selective inhibitor for leukotriene biosynthesis. Biochim. Biophys. Acta. 792 (1984) 92-97
29. Du L., Zhang Z., Luo X., Chen K., Shen X., and Jiang H. Binding investigation of human 5-lipoxygenase with its inhibitors by SPR technology correlating with molecular docking simulation. J. Biochem. 139 (2006) 715-723
30. Laemmli U.K. Cleavage of structural proteins during the assembly of the head of bacteriophage T4. Nature 227 (1970) 680-685
31. Boussac M., and Garin J. Calcium-dependent secretion in human neutrophils: a proteomic approach. Electrophoresis 21 (2000) 680-685
32. Kinter M., and Sherman N.E. Protein Sequencing and Identification Using Tandem Mass Spectrometry (2000), Wiley Intersciences series
33. Redgel D., Kuhn H., and Schewe Z.T. On the reaction specificity of the lipoxygenase from tomato fruits. Biochemical & Biophysics Acta 1210 (1994) 297-302
34. Otto A. Excitation of surface plasma waves in silver by the method of frustrated total reflection. Z. Phys. 216 (1968) 398-410
35. Kretschmann E., and Raether H. Radiative decay of non-radiative surface plasmons excited by light. Z. Naturforsch. 23 (1968) 2135-2136
36. Nylander C., Leidberg B., and Lind T. Gas-detection by means of surface-plasmon resonance. Sens. Actuators 3 (1982) 79-88