A mechanistic and kinetic study of the β-lactone hydrolysis of salinosporamide A (NPI-0052), a novel proteasome inhibitor

Journal of Pharmaceutical Sciences

Volumn 96, Issue 8, 2007, Pages 2037-2047

  Denora, Nunzio ^a,b   Potts, Barbara C M ^c   Stella, Valentino J ^a  

^a UNIVERSITY OF KANSAS   (United States)

^b UNIVERSITY OF BARI   (Italy)

^c Nereus Pharmaceuticals Inc   (United States)

Author keywords

Degradation; Hydrolysis; Kinetics; Mechanism; NPI 0052; Salinosporamide A

Indexed keywords

BETA CYCLODEXTRIN SULFOBUTYL ETHER; NPI 0052; NPI 2054; NPI 2055; PROTEASOME INHIBITOR; SALINOSPORAMIDE A; UNCLASSIFIED DRUG;

ARTICLE; CANCER; CATALYSIS; CLINICAL TRIAL; CONTROLLED STUDY; DRUG DEGRADATION; DRUG SOLUBILITY; DRUG STABILITY; DRUG STRUCTURE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HYDROLYSIS; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; PH; PHASE 1 CLINICAL TRIAL; SOLVENT EFFECT;

EID: 34548013292     PISSN: 00223549     EISSN: 15206017     Source Type: Journal    
DOI: 10.1002/jps.20835     Document Type: Article

References (22)

1. Richarson PG, Barlogie B, Berenson J, Singhal S, Jagannath S, Irwin D, Rajkumar SV, Srkalovic G, Alsina M, Alexanian R, Seigel D, Orlowski RZ, Kuter D, Limentani SA, Lee S, Hideshima DP, Anderson KC. 2003. A phase 2 study of bortezomib in relapsed, refractory myeloma. N Engl J Med 348:2609-2617.
2. Feling RH, Buchanan GO, Mincer TJ, Kauffman CA, Jensen PR, Fenical WF. 2003. Salinosporamide A: A highly cytotoxic proteasome inhibitor from a novel microbial source, a marine bacterium of the new genus Salinospora. Angew Chem Int Ed 42:355-357.
3. Chauhan D, Catley L, Li G, Podar K, Hideshima T, Mitsiades C, Ovaa H, Berkers C, Munshi N, Chao T, Nicholson B, Neuteboom ST, Richardson P, Palladino M, Anderson KC. 2005. A novel non-peptide and orally active proteasome inhibitor overcomes bortezomib-resistance in multiple myeloma cells. Cancer Cells 8:407.
4. Macherla VR, Mitchell SS, Manam RR, Reed KA, Chao TH, Nicholson B, Deyanat-Yazdi G, Mai B, Jensen PR, Fenical WF, Neuteboom STC, Lam KS, Palladino MA, Potts BCM. 2005. Structure-activity relationship studies of Salinosporamide A (NPI-0052), a novel marine derived proteasome inhibitor. J Med Chem 48:3684-3687.
5. Williams PG, Buchanan GO, Feling RH, Kauffman CA, Jensen PR, Fenical W. 2005. New cytotoxic salinosporamides from the marine actinomycete Salinospora tropica. J Org Chem 70:6196-6203.
6. Loftsson T, Ólafsdóttir BJ, Baldvinsdóttir J. 1992. Estramustine: Hydrolysis, solubilization, and stabilization in aqueous solutions. Int J Pharm 79:107-112.
7. Yokshioka S, Stella VJ. 2000. Stability of drugs and dosage forms, Chapter 2. Kluwer: Academic/Plenum Publishers, pp 44-45, 80-94.
8. Gandour RD, Schowen RL. 1978. Transition states of biochemical processes, Chapter 6. New York: Plenum Press, pp 225-279.
9. Stella VJ. 1986. Chemical and physical bases determining the instability and incompatibility of formulated injectable drugs. J Parent Sci Tech 40:142-163.
10. Fassberg J, Stella VJ. 1992. A kinetic and mechanistic study of the hydrolysis of camptothecin and some analogues. J Pharm Sci 81:676-684.
11. Hanson BA, Schowen RL, Stella VJ. 2003. A mechanistic and kinetic study of the E-ring hydrolysis and lactonization of a novel phosphoryloxymethyl prodrug of camptothecin. Pharm Res 20:1031-1038.
12. Jumaa M, Carlson B, Chimilio L, Silchenko S, Stella VJ. 2004. Kinetics and mechanism of degradation of epothilone-D: An experimental anticancer agent. J Pharm Sci 93:2953-2961.
13. Euranto EK. 1969. In the chemistry of carboxylic acids and esters In: Patai S, Editor. Interscience, Chapter 11. New York: pp 505-588.
14. Kaiser ET, Kézdy FJ. 1976. Hydrolysis of cyclic esters. Prog Bioorg Chem 4:239-267.
15. Groll M, Huber R, Potts BC. 2006. Crystal structures of Salinosporamide A (NPI-0052) and B (NPI-0047) in complex with the 20S proteasome reveal important consequences of β-lactone ring opening and a mechanism for irreversible binding. J Am Chem Soc 128:5136-5141.
16. 18oxygen-enriched water. J Pharm Sci 76:161-165.
17. (a) Schowen KB, Schowen RL. 1982. Solvent isotope effects of enzyme systems. Methods Enzymol 87c:551-606.
18. (b) Schowen RL. 1972. Prog Phys Org Chem 9:275-332.
19. 2O mixtures. Pure Appl Chem 8:243-258.
20. Minor SS, Schowen RL. 1973. One-proton bridge in the intramolecular carboxylate catalysis of ester hydrolysis. J Am Chem Soc p. 2279.
21. Maskill H. 1985. The physical basis of organic chemistry. London: Oxford University Press, p. 399.
22. Stella VJ, Anderson KW, Benedetti A, Waugh W, Killion RB. 1991. Stability of carmethizole hydrochloride (NSC-602668), an experimental cytotoxic agent. Int J Pharm 71:157-165.