Novel Semisynthetic Derivative of Antibiotic Eremomycin Active against Drug-Resistant Gram-Positive Pathogens Including Bacillus anthracis
Five adamantyl-containing carboxamides of eremomycin or vancomycin were synthesized and their antibacterial activities against some Gram-positive clinical isolates were investigated in vitro and in vivo. The adamantyl-2 amide of glycopeptide antibiotic eremomycin (1a in Chart , AN0900) was the most...
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| Veröffentlicht in: | Journal of medicinal chemistry 2007-07, Vol.50 (15), p.3681-3685 |
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| creator | Maples, Kirk R Wheeler, Conrad Ip, Emily Plattner, Jacob J Chu, Daniel Zhang, Yong-Kang Preobrazhenskaya, Maria N Printsevskaya, Svetlana S Solovieva, Svetlana E Olsufyeva, Evgenia N Heine, Henry Lovchik, Julie Lyons, C. Richard |
| description | Five adamantyl-containing carboxamides of eremomycin or vancomycin were synthesized and their antibacterial activities against some Gram-positive clinical isolates were investigated in vitro and in vivo. The adamantyl-2 amide of glycopeptide antibiotic eremomycin (1a in Chart , AN0900) was the most active compound and showed high activity against several Gram-positive pathogens: vancomycin-susceptible staphylococci and enterococci, glycopeptide-intermediate-resistant Staphylococcus aureus, and glycopeptide-resistant enterococci. Compound 1a was equally active in vitro against both Ciprofloxacin-susceptible and -resistant Bacillus anthracis strains (MICs 0.25−0.5 μg/mL). It was distinguished by having a 2.8 h half-life (t 1/2) in mice and a volume of distribution of 2.18 L/kg. Compound 1a was active against Staphylococcus aureus in mice (iv) and provided complete protection against a lethal intravenous challenge with vegetative B. anthracis bacilli and also in a murine pulmonary anthrax model in which mice were challenged with Bacillus anthracis spores. |
| doi_str_mv | 10.1021/jm0700058 |
| format | Article |
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Richard</creator><creatorcontrib>Maples, Kirk R ; Wheeler, Conrad ; Ip, Emily ; Plattner, Jacob J ; Chu, Daniel ; Zhang, Yong-Kang ; Preobrazhenskaya, Maria N ; Printsevskaya, Svetlana S ; Solovieva, Svetlana E ; Olsufyeva, Evgenia N ; Heine, Henry ; Lovchik, Julie ; Lyons, C. Richard</creatorcontrib><description>Five adamantyl-containing carboxamides of eremomycin or vancomycin were synthesized and their antibacterial activities against some Gram-positive clinical isolates were investigated in vitro and in vivo. The adamantyl-2 amide of glycopeptide antibiotic eremomycin (1a in Chart , AN0900) was the most active compound and showed high activity against several Gram-positive pathogens: vancomycin-susceptible staphylococci and enterococci, glycopeptide-intermediate-resistant Staphylococcus aureus, and glycopeptide-resistant enterococci. Compound 1a was equally active in vitro against both Ciprofloxacin-susceptible and -resistant Bacillus anthracis strains (MICs 0.25−0.5 μg/mL). It was distinguished by having a 2.8 h half-life (t 1/2) in mice and a volume of distribution of 2.18 L/kg. Compound 1a was active against Staphylococcus aureus in mice (iv) and provided complete protection against a lethal intravenous challenge with vegetative B. anthracis bacilli and also in a murine pulmonary anthrax model in which mice were challenged with Bacillus anthracis spores.</description><identifier>ISSN: 0022-2623</identifier><identifier>EISSN: 1520-4804</identifier><identifier>DOI: 10.1021/jm0700058</identifier><identifier>PMID: 17608397</identifier><identifier>CODEN: JMCMAR</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Animals ; Anthrax - mortality ; Anthrax - prevention & control ; Anti-Bacterial Agents - chemical synthesis ; Anti-Bacterial Agents - chemistry ; Anti-Bacterial Agents - pharmacology ; Bacillus anthracis ; Bacillus anthracis - drug effects ; Drug Resistance, Bacterial ; Glycopeptides - chemical synthesis ; Glycopeptides - chemistry ; Glycopeptides - pharmacology ; Gram-Positive Bacteria - drug effects ; Mice ; Microbial Sensitivity Tests ; Staphylococcal Infections - mortality ; Staphylococcal Infections - prevention & control ; Staphylococcus aureus ; Staphylococcus aureus - drug effects ; Structure-Activity Relationship</subject><ispartof>Journal of medicinal chemistry, 2007-07, Vol.50 (15), p.3681-3685</ispartof><rights>Copyright © 2007 American Chemical Society</rights><rights>2008 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a412t-69186523c79578e2157bb6e09ca2955dc6ff551abe89081360c202019e1763923</citedby><cites>FETCH-LOGICAL-a412t-69186523c79578e2157bb6e09ca2955dc6ff551abe89081360c202019e1763923</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/jm0700058$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jm0700058$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2765,27076,27924,27925,56738,56788</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=18931123$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/17608397$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Maples, Kirk R</creatorcontrib><creatorcontrib>Wheeler, Conrad</creatorcontrib><creatorcontrib>Ip, Emily</creatorcontrib><creatorcontrib>Plattner, Jacob J</creatorcontrib><creatorcontrib>Chu, Daniel</creatorcontrib><creatorcontrib>Zhang, Yong-Kang</creatorcontrib><creatorcontrib>Preobrazhenskaya, Maria N</creatorcontrib><creatorcontrib>Printsevskaya, Svetlana S</creatorcontrib><creatorcontrib>Solovieva, Svetlana E</creatorcontrib><creatorcontrib>Olsufyeva, Evgenia N</creatorcontrib><creatorcontrib>Heine, Henry</creatorcontrib><creatorcontrib>Lovchik, Julie</creatorcontrib><creatorcontrib>Lyons, C. Richard</creatorcontrib><title>Novel Semisynthetic Derivative of Antibiotic Eremomycin Active against Drug-Resistant Gram-Positive Pathogens Including Bacillus anthracis</title><title>Journal of medicinal chemistry</title><addtitle>J. Med. Chem</addtitle><description>Five adamantyl-containing carboxamides of eremomycin or vancomycin were synthesized and their antibacterial activities against some Gram-positive clinical isolates were investigated in vitro and in vivo. The adamantyl-2 amide of glycopeptide antibiotic eremomycin (1a in Chart , AN0900) was the most active compound and showed high activity against several Gram-positive pathogens: vancomycin-susceptible staphylococci and enterococci, glycopeptide-intermediate-resistant Staphylococcus aureus, and glycopeptide-resistant enterococci. Compound 1a was equally active in vitro against both Ciprofloxacin-susceptible and -resistant Bacillus anthracis strains (MICs 0.25−0.5 μg/mL). It was distinguished by having a 2.8 h half-life (t 1/2) in mice and a volume of distribution of 2.18 L/kg. Compound 1a was active against Staphylococcus aureus in mice (iv) and provided complete protection against a lethal intravenous challenge with vegetative B. anthracis bacilli and also in a murine pulmonary anthrax model in which mice were challenged with Bacillus anthracis spores.</description><subject>Animals</subject><subject>Anthrax - mortality</subject><subject>Anthrax - prevention & control</subject><subject>Anti-Bacterial Agents - chemical synthesis</subject><subject>Anti-Bacterial Agents - chemistry</subject><subject>Anti-Bacterial Agents - pharmacology</subject><subject>Bacillus anthracis</subject><subject>Bacillus anthracis - drug effects</subject><subject>Drug Resistance, Bacterial</subject><subject>Glycopeptides - chemical synthesis</subject><subject>Glycopeptides - chemistry</subject><subject>Glycopeptides - pharmacology</subject><subject>Gram-Positive Bacteria - drug effects</subject><subject>Mice</subject><subject>Microbial Sensitivity Tests</subject><subject>Staphylococcal Infections - mortality</subject><subject>Staphylococcal Infections - prevention & control</subject><subject>Staphylococcus aureus</subject><subject>Staphylococcus aureus - drug effects</subject><subject>Structure-Activity Relationship</subject><issn>0022-2623</issn><issn>1520-4804</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2007</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqF0ctuEzEUBmALgWgoLHgB5A1ILAZ8Gd-WoS2lUlUiUiR2luN4EocZu9ieiLwCT43bRM0GiZVlnU-_7PMD8BqjDxgR_HEzIIEQYvIJmGBGUNNK1D4FE4QIaQgn9AS8yHlTCcWEPgcnWHAkqRIT8Ocmbl0P527weRfK2hVv4blLfmuK3zoYOzgNxS98vB9cJDfEYWd9gFP7MDcr40Mu8DyNq-abyz4XEwq8TGZoZjH7BzQzZR1XLmR4FWw_Ln1YwU_G-r4fM6x8neolvwTPOtNn9-pwnoLvny9uz740118vr86m141pMSkNV1hyRqgVignpCGZiseAOKWuIYmxpedcxhs3CSYUkphxZggjCytVfU0XoKXi3z71L8dfoctH179b1vQkujlkLJLiQ7f9hjeUKKVzh-z20KeacXKfvkh9M2mmM9H1D-rGhat8cQsfF4JZHeaikgrcHYLI1fZdMqMs5Oqkori1W1-xdXbn7_Tg36afmggqmb2dzfdPOfvC5bDU_5hqb9SaOKdQl_-OBfwG1NrOq</recordid><startdate>20070726</startdate><enddate>20070726</enddate><creator>Maples, Kirk R</creator><creator>Wheeler, Conrad</creator><creator>Ip, Emily</creator><creator>Plattner, Jacob J</creator><creator>Chu, Daniel</creator><creator>Zhang, Yong-Kang</creator><creator>Preobrazhenskaya, Maria N</creator><creator>Printsevskaya, Svetlana S</creator><creator>Solovieva, Svetlana E</creator><creator>Olsufyeva, Evgenia N</creator><creator>Heine, Henry</creator><creator>Lovchik, Julie</creator><creator>Lyons, C. Richard</creator><general>American Chemical Society</general><scope>BSCLL</scope><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7QL</scope><scope>7QO</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>P64</scope><scope>7X8</scope></search><sort><creationdate>20070726</creationdate><title>Novel Semisynthetic Derivative of Antibiotic Eremomycin Active against Drug-Resistant Gram-Positive Pathogens Including Bacillus anthracis</title><author>Maples, Kirk R ; Wheeler, Conrad ; Ip, Emily ; Plattner, Jacob J ; Chu, Daniel ; Zhang, Yong-Kang ; Preobrazhenskaya, Maria N ; Printsevskaya, Svetlana S ; Solovieva, Svetlana E ; Olsufyeva, Evgenia N ; Heine, Henry ; Lovchik, Julie ; Lyons, C. 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Richard</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Novel Semisynthetic Derivative of Antibiotic Eremomycin Active against Drug-Resistant Gram-Positive Pathogens Including Bacillus anthracis</atitle><jtitle>Journal of medicinal chemistry</jtitle><addtitle>J. Med. Chem</addtitle><date>2007-07-26</date><risdate>2007</risdate><volume>50</volume><issue>15</issue><spage>3681</spage><epage>3685</epage><pages>3681-3685</pages><issn>0022-2623</issn><eissn>1520-4804</eissn><coden>JMCMAR</coden><abstract>Five adamantyl-containing carboxamides of eremomycin or vancomycin were synthesized and their antibacterial activities against some Gram-positive clinical isolates were investigated in vitro and in vivo. The adamantyl-2 amide of glycopeptide antibiotic eremomycin (1a in Chart , AN0900) was the most active compound and showed high activity against several Gram-positive pathogens: vancomycin-susceptible staphylococci and enterococci, glycopeptide-intermediate-resistant Staphylococcus aureus, and glycopeptide-resistant enterococci. Compound 1a was equally active in vitro against both Ciprofloxacin-susceptible and -resistant Bacillus anthracis strains (MICs 0.25−0.5 μg/mL). It was distinguished by having a 2.8 h half-life (t 1/2) in mice and a volume of distribution of 2.18 L/kg. Compound 1a was active against Staphylococcus aureus in mice (iv) and provided complete protection against a lethal intravenous challenge with vegetative B. anthracis bacilli and also in a murine pulmonary anthrax model in which mice were challenged with Bacillus anthracis spores.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>17608397</pmid><doi>10.1021/jm0700058</doi><tpages>5</tpages></addata></record> |
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| subjects | Animals Anthrax - mortality Anthrax - prevention & control Anti-Bacterial Agents - chemical synthesis Anti-Bacterial Agents - chemistry Anti-Bacterial Agents - pharmacology Bacillus anthracis Bacillus anthracis - drug effects Drug Resistance, Bacterial Glycopeptides - chemical synthesis Glycopeptides - chemistry Glycopeptides - pharmacology Gram-Positive Bacteria - drug effects Mice Microbial Sensitivity Tests Staphylococcal Infections - mortality Staphylococcal Infections - prevention & control Staphylococcus aureus Staphylococcus aureus - drug effects Structure-Activity Relationship |
| title | Novel Semisynthetic Derivative of Antibiotic Eremomycin Active against Drug-Resistant Gram-Positive Pathogens Including Bacillus anthracis |
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