Novel semisynthetic antibiotics from caprazamycins A–G: caprazene derivatives and their antibacterial activity
| Autor: | Masayuki Igarashi, Seiko Hattori, Yoshiaki Takahashi, Norio Doi, Yuzuru Akamatsu, Naoko Nakagawa, Yoshiko Koyama, Toshiaki Miyake, Kanae Ishikawa, Kunio Inoue, Yasuhiro Komatsuki, Hiromi Soutome |
|---|---|
| Rok vydání: | 2013 |
| Předmět: |
medicine.drug_class
Antiparasitic Antibiotics Gram-Positive Bacteria Microbiology Mycobacterium tuberculosis Structure-Activity Relationship chemistry.chemical_compound Biosynthesis Gram-Negative Bacteria Drug Discovery medicine Uridine Pharmacology biology Chemical modification Nucleosides Azepines biology.organism_classification Lipids Glycopeptide Anti-Bacterial Agents chemistry Biochemistry Antibacterial activity Bacteria Mycobacterium avium |
| Zdroj: | The Journal of Antibiotics. 66:171-178 |
| ISSN: | 1881-1469 0021-8820 |
| Popis: | Acidic treatment of a mixture of caprazamycins (CPZs) A-G isolated from a screen of novel antimycobacterial agents gave caprazene, a core structure of CPZs, in high yield. Chemical modification of the resulting caprazene was performed to give its various derivatives. The structure-activity relationships of the caprazene derivatives against several mycobacterial species and pathogenic Gram-positive and Gram-negative bacteria were studied. Although caprazene showed no antibacterial activity, the antibacterial activity was restored for its 1'''-alkylamide, 1'''-anilide and 1'''-ester derivatives. Compounds 4b (CPZEN-45), 4d (CPZEN-48), 4f and 4g (CPZEN-51) exhibited more potent activities against Mycobacterium tuberculosis and M. avium complex strains than CPZ-B. These results suggest that caprazene would be a good precursor from which novel semisynthetic antibacterial antibiotics can be designed for the treatment of mycobacterial diseases such as tuberculosis and M. avium complex infection. |
| Databáze: | OpenAIRE |
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