Penicillin-derived inhibitors that simultaneously target both metallo- and serine-β-lactamases
The synthesis and beta-lactamase inhibitory activity of four 6-(mercaptomethyl)penicillinates and the four corresponding 6-(hydroxymethyl)penicillinates are described. These penicillins include both C6 stereoisomers as well as the sulfide and sulfone oxidation states of the penam thiazolidine sulfur...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry letters 2004-03, Vol.14 (5), p.1299-1304 |
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| container_title | Bioorganic & medicinal chemistry letters |
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| creator | BUYNAK, John D HANSONG CHEN VOGETI, Lakshminaryana VENKAT RAO GADHACHANDA BUCHANAN, Christine A PALZKILL, Timothy SHAW, Robert W SPENCER, D. James WALSH, Timothy R |
| description | The synthesis and beta-lactamase inhibitory activity of four 6-(mercaptomethyl)penicillinates and the four corresponding 6-(hydroxymethyl)penicillinates are described. These penicillins include both C6 stereoisomers as well as the sulfide and sulfone oxidation states of the penam thiazolidine sulfur. All compounds were evaluated as inhibitors of representative metallo- and serine-beta-lactamases enzymes. Selected (mercaptomethyl)penicillinates are shown to inactivate both metallo- and serine-beta-lactamases and to display synergism with piperacillin against beta-lactamase producing strains. |
| doi_str_mv | 10.1016/j.bmcl.2003.12.037 |
| format | Article |
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Selected (mercaptomethyl)penicillinates are shown to inactivate both metallo- and serine-beta-lactamases and to display synergism with piperacillin against beta-lactamase producing strains.</description><identifier>ISSN: 0960-894X</identifier><identifier>EISSN: 1464-3405</identifier><identifier>DOI: 10.1016/j.bmcl.2003.12.037</identifier><identifier>PMID: 14980686</identifier><language>eng</language><publisher>Oxford: Elsevier</publisher><subject>Antibacterial agents ; Antibiotics. Antiinfectious agents. Antiparasitic agents ; beta-Lactamase Inhibitors ; beta-Lactamases - metabolism ; Biological and medical sciences ; Drug Delivery Systems - methods ; Humans ; Medical sciences ; Membrane Proteins - antagonists & inhibitors ; Penicillins - chemistry ; Penicillins - pharmacology ; Pharmacology. 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James</creatorcontrib><creatorcontrib>WALSH, Timothy R</creatorcontrib><title>Penicillin-derived inhibitors that simultaneously target both metallo- and serine-β-lactamases</title><title>Bioorganic & medicinal chemistry letters</title><addtitle>Bioorg Med Chem Lett</addtitle><description>The synthesis and beta-lactamase inhibitory activity of four 6-(mercaptomethyl)penicillinates and the four corresponding 6-(hydroxymethyl)penicillinates are described. These penicillins include both C6 stereoisomers as well as the sulfide and sulfone oxidation states of the penam thiazolidine sulfur. All compounds were evaluated as inhibitors of representative metallo- and serine-beta-lactamases enzymes. Selected (mercaptomethyl)penicillinates are shown to inactivate both metallo- and serine-beta-lactamases and to display synergism with piperacillin against beta-lactamase producing strains.</description><subject>Antibacterial agents</subject><subject>Antibiotics. Antiinfectious agents. Antiparasitic agents</subject><subject>beta-Lactamase Inhibitors</subject><subject>beta-Lactamases - metabolism</subject><subject>Biological and medical sciences</subject><subject>Drug Delivery Systems - methods</subject><subject>Humans</subject><subject>Medical sciences</subject><subject>Membrane Proteins - antagonists & inhibitors</subject><subject>Penicillins - chemistry</subject><subject>Penicillins - pharmacology</subject><subject>Pharmacology. Drug treatments</subject><subject>Protease Inhibitors - chemistry</subject><subject>Protease Inhibitors - pharmacology</subject><subject>Ribosomal Proteins - antagonists & inhibitors</subject><subject>Serine</subject><issn>0960-894X</issn><issn>1464-3405</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2004</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpFkM2KFDEURoMoTjv6Ai6kNrpLeW-SSqqWMow_MKALBXchlbqx06SqxiQtzGv5ID6T1XTDrO7mnI_LYew1QouA-v2hHWefWgEgWxQtSPOE7VBpxaWC7inbwaCB94P6ecVelHIAQAVKPWdXqIYedK93zH6jJfqYUlz4RDn-oamJyz6Osa65NHXvalPifEzVLbQeS3poqsu_qDbjWvfNTNWltPLGLVNTNn8h_u8vT85XN7tC5SV7Flwq9Opyr9mPj7ffbz7zu6-fvtx8uONeiqHyEY0DGrUwg_EGg8NOGZKCtJQ9CBQymODl6JXXCkPQw7QR6DRR0AYHec3enXfv8_r7SKXaORZPKZ3ftj2gMVJ2GyjOoM9rKZmCvc9xdvnBIthTVnuwp6z2lNWisFvWTXpzWT-OM02PyqXjBry9AK54l0J2i4_lkes66ACl_A9tzYN2</recordid><startdate>20040308</startdate><enddate>20040308</enddate><creator>BUYNAK, John D</creator><creator>HANSONG CHEN</creator><creator>VOGETI, Lakshminaryana</creator><creator>VENKAT RAO GADHACHANDA</creator><creator>BUCHANAN, Christine A</creator><creator>PALZKILL, Timothy</creator><creator>SHAW, Robert W</creator><creator>SPENCER, D. 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James</au><au>WALSH, Timothy R</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Penicillin-derived inhibitors that simultaneously target both metallo- and serine-β-lactamases</atitle><jtitle>Bioorganic & medicinal chemistry letters</jtitle><addtitle>Bioorg Med Chem Lett</addtitle><date>2004-03-08</date><risdate>2004</risdate><volume>14</volume><issue>5</issue><spage>1299</spage><epage>1304</epage><pages>1299-1304</pages><issn>0960-894X</issn><eissn>1464-3405</eissn><abstract>The synthesis and beta-lactamase inhibitory activity of four 6-(mercaptomethyl)penicillinates and the four corresponding 6-(hydroxymethyl)penicillinates are described. These penicillins include both C6 stereoisomers as well as the sulfide and sulfone oxidation states of the penam thiazolidine sulfur. All compounds were evaluated as inhibitors of representative metallo- and serine-beta-lactamases enzymes. 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| identifier | ISSN: 0960-894X |
| ispartof | Bioorganic & medicinal chemistry letters, 2004-03, Vol.14 (5), p.1299-1304 |
| issn | 0960-894X 1464-3405 |
| language | eng |
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| source | MEDLINE; Access via ScienceDirect (Elsevier) |
| subjects | Antibacterial agents Antibiotics. Antiinfectious agents. Antiparasitic agents beta-Lactamase Inhibitors beta-Lactamases - metabolism Biological and medical sciences Drug Delivery Systems - methods Humans Medical sciences Membrane Proteins - antagonists & inhibitors Penicillins - chemistry Penicillins - pharmacology Pharmacology. Drug treatments Protease Inhibitors - chemistry Protease Inhibitors - pharmacology Ribosomal Proteins - antagonists & inhibitors Serine |
| title | Penicillin-derived inhibitors that simultaneously target both metallo- and serine-β-lactamases |
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