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Volumn 56, Issue 31, 2000, Pages 5699-5707

β-Lactamase-dependent prodrugs - Recent developments

Author keywords

Antibody directed enzyme prodrug therapy; NMR; Lactam

Indexed keywords

ANTIBIOTIC AGENT; BETA LACTAM ANTIBIOTIC; BETA LACTAMASE INHIBITOR; PRODRUG;

EID: 0034725844     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(00)00419-1     Document Type: Conference Paper
Times cited : (37)

References (71)
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    • For leading references see: (a) Svensson, H. P.; Frank, I. S.; Berry, K. K.; Senter, P. D. J. Med. Chem. 1998, 41, 1507-1512 and references cited therein. (b) Bagshawe, K. D.; Begent, R. H. J. Adv. Drug Delivery Rev. 1996, 22, 365-367. (c) Bagshawe, K. D.; Sharma, S. K.; Springer, C. J.; Antoniw, P. Tumour Targeting 1995, 1, 17-29. (d) Rodrigues, M. L.; Carter, P.; Wirth, C.; Mullins, S.; Lee, A.; Blackburn, B. K. Chem. Biol. 1995, 2, 223-227. (e) See also www.seattlegenetics.com/.
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    • This is a well established diagnostic pattern in β-lactam chemistry, see
    • This is a well established diagnostic pattern in β-lactam chemistry, see: Davis, A. M.; Jones, M.; Page. M. I. J. Chem. Soc. Perkin Trans. 2, 1991, 1219-1223.
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    • The value of 4.0 Å is taken from the crystal structure data on the penicillin compound bearing the sulfenimine sidechain (RSN=) which was prepared by Gordon and co-workers; see Ref 8
    • The value of 4.0 Å is taken from the crystal structure data on the penicillin compound bearing the sulfenimine sidechain (RSN=) which was prepared by Gordon and co-workers; see Ref 8.
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    • (a) The reaction of piperidine-1-sulfenyl chloride with diamines to yield (cyclic) thiadiazoles provides a key intramolecular example: Bryce, M. R. J. Chem. Soc., Perkin Trans. 1 1984, 2591-2593.
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    • 3) with primary and secondary amines is a relevant intermolecular example: Armitage, D. A.; Clark. M. J.; Kinsey, A. C. J. Chem. Soc. (C) 1971, 3867-3869.
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    • (c) See also: Capozzi, C.; Modena, G.; Pasquato, L. In The Chemistry of Sulphenic Acids and Derivatives; Patai, S., Ed.; Wiley: Chichester, 1990, Chapter 10. Hogg, D. R. In The Chemistry of Sulphenic Acids and Derivatives; Patai, S., Ed.; Wiley: Chichester, 1990, Chapter 9.
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    • (a) Supporting evidence for the interconversion of Inter-A and Inter-B is provided by the observed ready contraction of seven- and eight-membered cyclic sulfides to form fused bicyclic structures by the nucleophilic addition of the sulfur atom to a carbonium ion center: Cerè, V.; Peri, F.; Pollicino, S.; Antonio, A. J. Chem. Soc., Perkin Trans. 2 1998, 977-979. de Groot, A.; Boerma, J. A.; Wynberg, H. Tetrahedron Lett. 1968, 2365-2367.
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    • (b) For other examples of the transannular interaction of a sulfur atom with a carbonium ion center see: Tabushi, I.; Tamaru, Y.; Yoshida, Z-I; Sugimoto, T. J. Am. Chem. Soc. 1975, 97, 2886-2891. Block, E. Reactions of Organosulfur Compounds; Academic Press: NY, 1978; Chapter 4.
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    • A certain degree of enzyme inhibition also occurred with 4bm, however, the partition number in favour of turnover versus inhibition was 15 000; see Ref. 7a.
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    • It is not clear that 6′ will be generated from 8′ (see below and also refer to Scheme 5) in aqueous buffer; it is probable that the end products result from further hydrolysis reactions of 8′. Products derived from reactions of sulfenic acids in aqueous solution are described in
    • It is not clear that 6′ will be generated from 8′ (see below and also refer to Scheme 5) in aqueous buffer; it is probable that the end products result from further hydrolysis reactions of 8′. Products derived from reactions of sulfenic acids in aqueous solution are described in: Hogg, D. R.; Vipond, P.W. Int. J. Sulfur Chem. C 1971, 6, 17-22.
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    • Products derived from further hydrolytic reaction of an exo-methylene thiazine type structure, such as 16, are described in: Taibi-Tronche, P.; Massova, I.; Vakulenko, S. B.; Lerner, S. A.; Mobashery, S. J. Am. Chem. Soc. 1996, 118, 7441-7448.
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    • For details on the successful application of directed evolution to the production of cephalosporinase enzymes with considerably enhanced activity towards designated β-lactams see: (c) Stemmer, W. P. C. Nature 1994, 370, 389-391. (d) Crameri, A.; Raillard, S.-A.; Bermudez, E.; Stemmer, W. P. C. Nature 1998, 391, 288-291. (e) See also www. maxygen.com/.


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