Synthesis and antibacterial activity of alkyl derivatives of the glycopeptide antibiotic A40926 and their amides
Lipophilic alkylated derivatives of A40926 containing basic amides showed a strong increase in antibiotic activity. New derivatives of the glycopeptide antibiotic A40926 were synthesized and evaluated for antimicrobial activity against VRE. Deacylated A40926 was obtained by microbial transformation...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry letters 2005-08, Vol.15 (16), p.3801-3805 |
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| container_title | Bioorganic & medicinal chemistry letters |
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| creator | Maffioli, Sonia I. Ciabatti, Romeo Romanò, Gabriella Marzorati, Ettore Preobrazhenskaya, Maria Pavlov, Andrej |
| description | Lipophilic alkylated derivatives of A40926 containing basic amides showed a strong increase in antibiotic activity.
New derivatives of the glycopeptide antibiotic A40926 were synthesized and evaluated for antimicrobial activity against VRE. Deacylated A40926 was obtained by microbial transformation of the parent antibiotic with the use of
Actinoplanes teichomyceticus ATCC 31121. Regioselective synthesis of alkylated derivatives of Deacyl A40926 was carried out using lipophilic aliphatic and aromatic halides or aldehydes. Further modification of the two carboxylic acids was performed to increase antibiotic activity. Poor antimicrobial activity was observed for the derivatives obtained by lipophilic mono- or dialkylation of the amino groups present on the molecule, while simultaneous condensation of both carboxylic groups, in hydrophobic derivatives, with dibasic amines led to a strong increase in antibiotic activity. |
| doi_str_mv | 10.1016/j.bmcl.2005.05.076 |
| format | Article |
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New derivatives of the glycopeptide antibiotic A40926 were synthesized and evaluated for antimicrobial activity against VRE. Deacylated A40926 was obtained by microbial transformation of the parent antibiotic with the use of
Actinoplanes teichomyceticus ATCC 31121. Regioselective synthesis of alkylated derivatives of Deacyl A40926 was carried out using lipophilic aliphatic and aromatic halides or aldehydes. Further modification of the two carboxylic acids was performed to increase antibiotic activity. Poor antimicrobial activity was observed for the derivatives obtained by lipophilic mono- or dialkylation of the amino groups present on the molecule, while simultaneous condensation of both carboxylic groups, in hydrophobic derivatives, with dibasic amines led to a strong increase in antibiotic activity.</description><identifier>ISSN: 0960-894X</identifier><identifier>EISSN: 1464-3405</identifier><identifier>DOI: 10.1016/j.bmcl.2005.05.076</identifier><identifier>PMID: 15993054</identifier><language>eng</language><publisher>England: Elsevier Ltd</publisher><subject>Amides - chemical synthesis ; Amides - chemistry ; Amides - pharmacology ; Anti-Bacterial Agents - chemical synthesis ; Anti-Bacterial Agents - chemistry ; Anti-Bacterial Agents - pharmacology ; Antibiotic ; Enterococcus - drug effects ; Glycopeptides ; Glycopeptides - chemistry ; Microbial Sensitivity Tests ; Molecular Conformation ; Structure-Activity Relationship ; Teicoplanin - analogs & derivatives ; Teicoplanin - chemical synthesis ; Teicoplanin - chemistry ; Teicoplanin - pharmacology ; Vancomycin Resistance ; VRE</subject><ispartof>Bioorganic & medicinal chemistry letters, 2005-08, Vol.15 (16), p.3801-3805</ispartof><rights>2005 Elsevier Ltd</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c354t-330e24fa64160d06af4cea47006f3db503ed30d3e10d9823d87d7a986fc68e273</citedby><cites>FETCH-LOGICAL-c354t-330e24fa64160d06af4cea47006f3db503ed30d3e10d9823d87d7a986fc68e273</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.bmcl.2005.05.076$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,777,781,3537,27905,27906,45976</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/15993054$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Maffioli, Sonia I.</creatorcontrib><creatorcontrib>Ciabatti, Romeo</creatorcontrib><creatorcontrib>Romanò, Gabriella</creatorcontrib><creatorcontrib>Marzorati, Ettore</creatorcontrib><creatorcontrib>Preobrazhenskaya, Maria</creatorcontrib><creatorcontrib>Pavlov, Andrej</creatorcontrib><title>Synthesis and antibacterial activity of alkyl derivatives of the glycopeptide antibiotic A40926 and their amides</title><title>Bioorganic & medicinal chemistry letters</title><addtitle>Bioorg Med Chem Lett</addtitle><description>Lipophilic alkylated derivatives of A40926 containing basic amides showed a strong increase in antibiotic activity.
New derivatives of the glycopeptide antibiotic A40926 were synthesized and evaluated for antimicrobial activity against VRE. Deacylated A40926 was obtained by microbial transformation of the parent antibiotic with the use of
Actinoplanes teichomyceticus ATCC 31121. Regioselective synthesis of alkylated derivatives of Deacyl A40926 was carried out using lipophilic aliphatic and aromatic halides or aldehydes. Further modification of the two carboxylic acids was performed to increase antibiotic activity. Poor antimicrobial activity was observed for the derivatives obtained by lipophilic mono- or dialkylation of the amino groups present on the molecule, while simultaneous condensation of both carboxylic groups, in hydrophobic derivatives, with dibasic amines led to a strong increase in antibiotic activity.</description><subject>Amides - chemical synthesis</subject><subject>Amides - chemistry</subject><subject>Amides - pharmacology</subject><subject>Anti-Bacterial Agents - chemical synthesis</subject><subject>Anti-Bacterial Agents - chemistry</subject><subject>Anti-Bacterial Agents - pharmacology</subject><subject>Antibiotic</subject><subject>Enterococcus - drug effects</subject><subject>Glycopeptides</subject><subject>Glycopeptides - chemistry</subject><subject>Microbial Sensitivity Tests</subject><subject>Molecular Conformation</subject><subject>Structure-Activity Relationship</subject><subject>Teicoplanin - analogs & derivatives</subject><subject>Teicoplanin - chemical synthesis</subject><subject>Teicoplanin - chemistry</subject><subject>Teicoplanin - pharmacology</subject><subject>Vancomycin Resistance</subject><subject>VRE</subject><issn>0960-894X</issn><issn>1464-3405</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2005</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kE9LxDAQxYMo7rr6BTxIT966Tpo0bcGLiP9gwYMK3kI2mWrWdluT7EK_vam74E2YMMPM7z3II-ScwpwCFVer-bLVzTwDyOdjFeKATCkXPGUc8kMyhUpAWlb8fUJOvF8BUA6cH5MJzauKQc6npH8Z1uETvfWJWpv4gl0qHdBZ1SRxsFsbhqSrE9V8DU1i4mGr4hb9uIzK5KMZdNdjH6zBnd52werkhkOViV_XiFmXqDYS_pQc1arxeLbvM_J2f_d6-5gunh-ebm8WqWY5DyljgBmvleBUgAGhaq5R8QJA1Mwsc2BoGBiGFExVZsyUhSlUVYpaixKzgs3I5c63d933Bn2QrfUam0atsdt4KUoQBeUjmO1A7TrvHdayd7ZVbpAU5JizXMkxZznmLMcqRBRd7N03yxbNn2QfbASudwDGP24tOum1xbVGYx3qIE1n__P_AVo5j6s</recordid><startdate>20050815</startdate><enddate>20050815</enddate><creator>Maffioli, Sonia I.</creator><creator>Ciabatti, Romeo</creator><creator>Romanò, Gabriella</creator><creator>Marzorati, Ettore</creator><creator>Preobrazhenskaya, Maria</creator><creator>Pavlov, Andrej</creator><general>Elsevier Ltd</general><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>7X8</scope></search><sort><creationdate>20050815</creationdate><title>Synthesis and antibacterial activity of alkyl derivatives of the glycopeptide antibiotic A40926 and their amides</title><author>Maffioli, Sonia I. ; Ciabatti, Romeo ; Romanò, Gabriella ; Marzorati, Ettore ; Preobrazhenskaya, Maria ; Pavlov, Andrej</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c354t-330e24fa64160d06af4cea47006f3db503ed30d3e10d9823d87d7a986fc68e273</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2005</creationdate><topic>Amides - chemical synthesis</topic><topic>Amides - chemistry</topic><topic>Amides - pharmacology</topic><topic>Anti-Bacterial Agents - chemical synthesis</topic><topic>Anti-Bacterial Agents - chemistry</topic><topic>Anti-Bacterial Agents - pharmacology</topic><topic>Antibiotic</topic><topic>Enterococcus - drug effects</topic><topic>Glycopeptides</topic><topic>Glycopeptides - chemistry</topic><topic>Microbial Sensitivity Tests</topic><topic>Molecular Conformation</topic><topic>Structure-Activity Relationship</topic><topic>Teicoplanin - analogs & derivatives</topic><topic>Teicoplanin - chemical synthesis</topic><topic>Teicoplanin - chemistry</topic><topic>Teicoplanin - pharmacology</topic><topic>Vancomycin Resistance</topic><topic>VRE</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Maffioli, Sonia I.</creatorcontrib><creatorcontrib>Ciabatti, Romeo</creatorcontrib><creatorcontrib>Romanò, Gabriella</creatorcontrib><creatorcontrib>Marzorati, Ettore</creatorcontrib><creatorcontrib>Preobrazhenskaya, Maria</creatorcontrib><creatorcontrib>Pavlov, Andrej</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Bioorganic & medicinal chemistry letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Maffioli, Sonia I.</au><au>Ciabatti, Romeo</au><au>Romanò, Gabriella</au><au>Marzorati, Ettore</au><au>Preobrazhenskaya, Maria</au><au>Pavlov, Andrej</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and antibacterial activity of alkyl derivatives of the glycopeptide antibiotic A40926 and their amides</atitle><jtitle>Bioorganic & medicinal chemistry letters</jtitle><addtitle>Bioorg Med Chem Lett</addtitle><date>2005-08-15</date><risdate>2005</risdate><volume>15</volume><issue>16</issue><spage>3801</spage><epage>3805</epage><pages>3801-3805</pages><issn>0960-894X</issn><eissn>1464-3405</eissn><abstract>Lipophilic alkylated derivatives of A40926 containing basic amides showed a strong increase in antibiotic activity.
New derivatives of the glycopeptide antibiotic A40926 were synthesized and evaluated for antimicrobial activity against VRE. Deacylated A40926 was obtained by microbial transformation of the parent antibiotic with the use of
Actinoplanes teichomyceticus ATCC 31121. Regioselective synthesis of alkylated derivatives of Deacyl A40926 was carried out using lipophilic aliphatic and aromatic halides or aldehydes. Further modification of the two carboxylic acids was performed to increase antibiotic activity. Poor antimicrobial activity was observed for the derivatives obtained by lipophilic mono- or dialkylation of the amino groups present on the molecule, while simultaneous condensation of both carboxylic groups, in hydrophobic derivatives, with dibasic amines led to a strong increase in antibiotic activity.</abstract><cop>England</cop><pub>Elsevier Ltd</pub><pmid>15993054</pmid><doi>10.1016/j.bmcl.2005.05.076</doi><tpages>5</tpages></addata></record> |
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| issn | 0960-894X 1464-3405 |
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| source | MEDLINE; Elsevier ScienceDirect Journals |
| subjects | Amides - chemical synthesis Amides - chemistry Amides - pharmacology Anti-Bacterial Agents - chemical synthesis Anti-Bacterial Agents - chemistry Anti-Bacterial Agents - pharmacology Antibiotic Enterococcus - drug effects Glycopeptides Glycopeptides - chemistry Microbial Sensitivity Tests Molecular Conformation Structure-Activity Relationship Teicoplanin - analogs & derivatives Teicoplanin - chemical synthesis Teicoplanin - chemistry Teicoplanin - pharmacology Vancomycin Resistance VRE |
| title | Synthesis and antibacterial activity of alkyl derivatives of the glycopeptide antibiotic A40926 and their amides |
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