Conversion of the anti-tumor agent tasidotin (ILX651) to its active metabolite by prolyl oligopeptidase

Simmons, 2005, Marine natural products as anticancer drugs, Mol Cancer Ther, 4, 333, 10.1158/1535-7163.333.4.2 Poncet, 1999, The dolastatins, a family of promising antineoplastic agents, Curr Pharm Des, 5, 139, 10.2174/1381612805666230109214008 Genzyme Corporation, Investigator's brochure for tasidotin HCl (ILX651); 2007. Garg, 2007, Preclinical analysis of tasidotin HCl in Ewing's sarcoma, rhabdomyosarcoma, synovial sarcoma, and osteosarcoma, Clin Cancer Res, 13, 5446, 10.1158/1078-0432.CCR-06-2661 Ebbinghaus, 2005, A phase I study of the dolastatin-15 analogue tasidotin (ILX651) administered intravenously daily for 5 consecutive days every three weeks in patients with advanced solid tumors, Clin Cancer Res, 11, 7807, 10.1158/1078-0432.CCR-05-0909 Cunningham, 2005, Phase I and pharmacokinetic study of the dolastatin-15 analogue tasidotin (ILX651) administered intravenously on days 1, 3, and 5 every 3 weeks in patients with advanced solid tumors, Clin Cancer Res, 11, 7825, 10.1158/1078-0432.CCR-05-0058 Mita, 2006, Phase I and pharmacokinetic study of tasidotin hydrochloride (LX651), a third-generation dolastatin-15 analogue, administered weekly for 3 weeks every 28 days in patients with advanced solid tumors, Clin Cancer Res, 12, 5207, 10.1158/1078-0432.CCR-06-0179 Ray, 2007, Mechanism of action of the microtubule-targeted antimitotic depsipeptide tasidotin (formerly ILX651) and its major metabolite tasidotin C-carboxylate, Cancer Res, 67, 3767, 10.1158/0008-5472.CAN-06-3065 Bonate, 2007, Pharmacokinetics in mice implanted with xenografted tumors after intravenous administration of tasidotin (ILX651) or its carboxylate metabolite, AAPS J, 9, E378, 10.1208/aapsj0903045 Polgár, 2002, The prolyl oligopeptidase family, Cell Mol Life Sci, 59, 349, 10.1007/s00018-002-8427-5 Goosens, 1996, Distribution of prolyl oligopeptidase in human peripheral tissues and body fluids, Eur J Chem Clin Biochem, 34, 17 Brandt, 2007, Suggested functions for prolyl oligopeptidase: a puzzling paradox, Clin Chim Acta, 377, 50, 10.1016/j.cca.2006.09.001 García-Horsman, 2007, On the role of prolyl oligopeptidase in health and disease, Neuropeptides, 41, 1, 10.1016/j.npep.2006.10.004 Gass, 2007, Prolyl endopeptidases, Cell Mol Life Sci, 64, 345, 10.1007/s00018-006-6317-y Rosenblum, 2003, Prolyl peptidases: a serine protease subfamily with high potential for drug discovery, Curr Opin Chem Biol, 7, 496, 10.1016/S1367-5931(03)00084-X Edens, 2005, Extracellular prolyl endoprotease from Aspergillus niger and its use in the debittering of protein hydrolysates, J Agric Food Chem, 53, 7950, 10.1021/jf050652c FitzGerald, 2006, Enzymatic debittering of food protein hydrolysates, Biotechnol Adv, 24, 234, 10.1016/j.biotechadv.2005.11.002 Lopez, 2005, Effective prevention of chill-haze in beer using an acid proline-specific endoprotease from Aspergillus niger, J Agric Food Chem, 53, 7944, 10.1021/jf0506535 Xiu, 2002, A new method for the preparation of human parathyroid hormone 1–34 peptides, Biotechnol Appl Biochem, 36, 111, 10.1042/BA20020015 Shan, 2004, Comparative biochemical analysis of three bacterial prolyl endopeptidases: implications for coeliac sprue, Biochem J, 383, 311, 10.1042/BJ20040907 Stepinak, 2006, Enzymatic gluten detoxification: the proof of the pudding is in the eating!, Trends Biotechnol, 24, 433, 10.1016/j.tibtech.2006.08.003 Ehren, 2008, Protein engineering of improved prolyl endopeptidases for celiac sprue therapy, Protein Eng Des Sel, 21, 699, 10.1093/protein/gzn050 Cunningham, 1997, Proline specific peptidases, Biochim Biophys Acta, 1343, 160, 10.1016/S0167-4838(97)00134-9 Yoshimoto, 1978, Proline specific endopeptidase from Flavobacterium, Agric Biol Chem, 42, 2417, 10.1271/bbb1961.42.2417 Smith, 1985, Measurement of protein using bicinchoninic acid, Anal Biochem, 150, 76, 10.1016/0003-2697(85)90442-7 Yoshimoto, 1980, Proline-specific endopeptidase from Flavobacterium: purification and properties, J Biol Chem, 255, 4786, 10.1016/S0021-9258(19)85566-7 Yoshimoto, 1979, Post-proline cleaving enzyme: synthesis of a new fluorogenic substrate and distribution of the endopeptidase in rat tissues and body fluids in man, Biochim Biophys Acta, 569, 184, 10.1016/0005-2744(79)90053-6 Koida, 1976, Post-proline cleaving enzyme: purification of this endopeptidase by affinity chromatography, J Biol Chem, 251, 7593, 10.1016/S0021-9258(17)32893-4 Segel, 1976 Sevillano Cabeza, 2003, Rapid fluorometric assay for primary amine groups in water samples, Anal Bioanal Chem, 376, 918, 10.1007/s00216-003-2004-0 Benson, 1975, o-Phthaladehyde: fluorogenic detection of primary amines in the picomole range, Comparison with fluorescamine and ninhydrin, Proc Natl Acad Sci U S A, 72, 619, 10.1073/pnas.72.2.619 Ikehara, 1994, Dipeptidyl peptidase IV from rat liver, Meth Enzymol, 244, 215, 10.1016/0076-6879(94)44018-2 Cushman, 1971, Spectrophotometric assay and properties of the angiotensin converting enzyme of rabbit lung, Biochem Pharmacol, 20, 1637, 10.1016/0006-2952(71)90292-9 Priestman, 1984, Prolidase deficiency: characteristics of human skin fibroblast prolidase using colorimetric and fluorometric assays, Clin Chim Acta, 142, 263, 10.1016/0009-8981(84)90385-1 Hofmann, 1976, Penicillocarboxylpeptidases S-1 and S-2, Meth Enzymol, 45, 587, 10.1016/S0076-6879(76)45052-8 Stöckel-Maschek, 2003, A continuous fluorometric assay for amino peptidase P: detailed analysis of product inhibition, Anal Biochem, 322, 60, 10.1016/S0003-2697(03)00464-0 Park, 2006, Prolyl endopeptidase inhibitory activity of unsaturated fatty acids, J Agric Food Chem, 54, 1238, 10.1021/jf052521h Je, 2007, Sulfated chitooligosaccharides as prolyl endopeptidase inhibitor, Int J Biol Macromol, 41, 529, 10.1016/j.ijbiomac.2007.07.003 Cunningham, 1998, A study of prolyl endopeptidase in bovine serum and its relevance to the tissue enzyme, Int J Biochem Cell Biol, 30, 109, 10.1016/S1357-2725(97)00076-9 Yaron, 1993, Proline-dependent structural and biological properties of peptides and proteins, Crit Rev Biochem Mol Biol, 28, 31, 10.3109/10409239309082572 Mamdani, 2007, No association between the PREP gene and lithium responsive bipolar disorder, BMC Psychiatry, 7, 9, 10.1186/1471-244X-7-9