SYNTHESIS OF 2"-AMINO-2"-DEOXYARBEKACIN AND ITS ANALOGS HAVING POTENT ACTIVITY AGAINST METHICILLIN-RESISTANT Staphylococcus aureus

Based on our studies on the enzymatic modifications of arbekacin by methicillin-resistant Staphylococcus aureus (MRSA), replacement of the 2"-hydroxyl group by an amino group in arbekacin was designed to synthesize derivatives that would be active against MRSA. 2"-Amino-2"-deoxyarbeka...

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Bibliographic Details
Published inJournal of antibiotics Vol. 47; no. 7; pp. 821 - 832
Main Authors KONDO, SHINICHI, IKEDA, YOKO, IKEDA, DAISHIRO, TAKEUCHI, TOMIO, USUI, TAKAYUKI, ISHII, MIYUKI, KUDO, TOSHIAKI, GOMI, SHUICHI, SHIBAHARA, SEUI
Format Journal Article
LanguageEnglish
Published TOKYO JAPAN ANTIBIOTICS RESEARCH ASSOCIATION 1994
JAPAN ANTIBIOT RES ASSN
Japan Antibiotics Research Association
Subjects
Antibacterial agents
Antibiotics. Antiinfectious agents. Antiparasitic agents
Biological and medical sciences
Biotechnology & Applied Microbiology
Carbohydrate Sequence
Dibekacin - analogs & derivatives
Dibekacin - chemical synthesis
Dibekacin - chemistry
Dibekacin - pharmacology
Gram-Negative Bacteria - drug effects
Immunology
Life Sciences & Biomedicine
Magnetic Resonance Spectroscopy
Medical sciences
Methicillin Resistance
Microbial Sensitivity Tests
Microbiology
Molecular Sequence Data
Pharmacology & Pharmacy
Pharmacology. Drug treatments
Science & Technology
Staphylococcus - drug effects
Staphylococcus aureus - drug effects
Structure-Activity Relationship
AMINOGLYCOSIDE ANTIBIOTICS
ARBEKACIN
Resistance
Sensitivity resistance
Structure activity relation
Analog
Bacteria
Micrococcales
Micrococcaceae
Antibacterial agent
Staphylococcus aureus
Gram negative bacteria
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Summary:Based on our studies on the enzymatic modifications of arbekacin by methicillin-resistant Staphylococcus aureus (MRSA), replacement of the 2"-hydroxyl group by an amino group in arbekacin was designed to synthesize derivatives that would be active against MRSA. 2"-Amino-2"-deoxyarbekacin and five analogs were synthesized starting from dibekacin. Among them, 2"-amino-2"-deoxyarbekacin and the 5-epiamino analog showed excellent antibacterial activities against not only MRSA but also Gram-negative bacteria including Pseudomonas, and lower toxicities than arbekacin.
ISSN:0021-8820
1881-1469
DOI:10.7164/antibiotics.47.821