BIOMAT Database Logo BIOMAT Database Logo

Chemical modification of deltamycins. I. 4''-O-acyl analogs of deltamycins. 1980

Y Shimauchi, and K Hori, and M Sakamoto, and Y Mutoh, and Y Fukagawa, and S Hori, and T Ishikura, and J Lein

Using 4''-O-deacyldeltamycin as a starting material, various 4''-O-acyl derivatives were chemically synthesized by the following scheme: 2'-O-acetylation leads to 4''-O-acylation leads to 2'-O-deacetylation. 4''-O-Deacyldeltamycin is produced during the fermentation of deltamycin producing organisms or can be prepared by the biological deacylation of the deltamycins. 4''-O-Phenylacetyl-4''-O-deacyldeltamycin (PAD) showed good activity against various bacteria and mycoplasma. Among para-substituted PAD derivatives, NPAD (p-nitrophenylacetyl-) and SPAD (p-methylsulfonylphenylacetyl-) showed increased potency as compared to PAD against certain bacteria. The PAD was evaluated by in vivo experiments for plasma levels in mice and dogs and curative activity on the infected mice with Staphylococcus aureus Smith by subcutaneous or oral administration.

UI MeSH Term Description Entries
D007933 Leucomycins An antibiotic complex produced by Streptomyces kitasatoensis. The complex consists of a mixture of at least eight biologically active components, A1 and A3 to A9. Leucomycins have both antibacterial and antimycoplasmal activities.
D002621 Chemistry A basic science concerned with the composition, structure, and properties of matter; and the reactions that occur between substances and the associated energy exchange.
D002627 Chemistry, Physical The study of CHEMICAL PHENOMENA and processes in terms of the underlying PHYSICAL PHENOMENA and processes. Physical Chemistry,Chemistries, Physical,Physical Chemistries
D004285 Dogs The domestic dog, Canis familiaris, comprising about 400 breeds, of the carnivore family CANIDAE. They are worldwide in distribution and live in association with people. (Walker's Mammals of the World, 5th ed, p1065) Canis familiaris,Dog
D004352 Drug Resistance, Microbial The ability of microorganisms, especially bacteria, to resist or to become tolerant to chemotherapeutic agents, antimicrobial agents, or antibiotics. This resistance may be acquired through gene mutation or foreign DNA in transmissible plasmids (R FACTORS). Antibiotic Resistance,Antibiotic Resistance, Microbial,Antimicrobial Resistance, Drug,Antimicrobial Drug Resistance,Antimicrobial Drug Resistances,Antimicrobial Resistances, Drug,Drug Antimicrobial Resistance,Drug Antimicrobial Resistances,Drug Resistances, Microbial,Resistance, Antibiotic,Resistance, Drug Antimicrobial,Resistances, Drug Antimicrobial
D000284 Administration, Oral The giving of drugs, chemicals, or other substances by mouth. Drug Administration, Oral,Administration, Oral Drug,Oral Administration,Oral Drug Administration,Administrations, Oral,Administrations, Oral Drug,Drug Administrations, Oral,Oral Administrations,Oral Drug Administrations
D000818 Animals Unicellular or multicellular, heterotrophic organisms, that have sensation and the power of voluntary movement. Under the older five kingdom paradigm, Animalia was one of the kingdoms. Under the modern three domain model, Animalia represents one of the many groups in the domain EUKARYOTA. Animal,Metazoa,Animalia
D001419 Bacteria One of the three domains of life (the others being Eukarya and ARCHAEA), also called Eubacteria. They are unicellular prokaryotic microorganisms which generally possess rigid cell walls, multiply by cell division, and exhibit three principal forms: round or coccal, rodlike or bacillary, and spiral or spirochetal. Bacteria can be classified by their response to OXYGEN: aerobic, anaerobic, or facultatively anaerobic; by the mode by which they obtain their energy: chemotrophy (via chemical reaction) or PHOTOTROPHY (via light reaction); for chemotrophs by their source of chemical energy: CHEMOLITHOTROPHY (from inorganic compounds) or chemoorganotrophy (from organic compounds); and by their source for CARBON; NITROGEN; etc.; HETEROTROPHY (from organic sources) or AUTOTROPHY (from CARBON DIOXIDE). They can also be classified by whether or not they stain (based on the structure of their CELL WALLS) with CRYSTAL VIOLET dye: gram-negative or gram-positive. Eubacteria
D001681 Biological Assay A method of measuring the effects of a biologically active substance using an intermediate in vivo or in vitro tissue or cell model under controlled conditions. It includes virulence studies in animal fetuses in utero, mouse convulsion bioassay of insulin, quantitation of tumor-initiator systems in mouse skin, calculation of potentiating effects of a hormonal factor in an isolated strip of contracting stomach muscle, etc. Bioassay,Assay, Biological,Assays, Biological,Biologic Assay,Biologic Assays,Assay, Biologic,Assays, Biologic,Bioassays,Biological Assays
D013203 Staphylococcal Infections Infections with bacteria of the genus STAPHYLOCOCCUS. Infections, Staphylococcal,Staphylococcus aureus Infection,Staphylococcal Infection,Staphylococcus aureus Infections

Related Publications

Y Shimauchi, and K Hori, and M Sakamoto, and Y Mutoh, and Y Fukagawa, and S Hori, and T Ishikura, and J Lein
Chemical modification of sorbistin. I. N-acyl analogs of sorbistin.
December 1976, The Journal of antibiotics,
Y Shimauchi, and K Hori, and M Sakamoto, and Y Mutoh, and Y Fukagawa, and S Hori, and T Ishikura, and J Lein
Chemical modification of spiramycins. VI. Synthesis and antibacterial activities of 3,3''-di-O-acyl-4''-O-sulfonyl and 3,3''-di-O-acyl-4''-O-alkyl derivatives of spiramycin I.
October 1985, The Journal of antibiotics,
Y Shimauchi, and K Hori, and M Sakamoto, and Y Mutoh, and Y Fukagawa, and S Hori, and T Ishikura, and J Lein
Chemical modification of fumagillin. I. 6-O-acyl, 6-O-sulfonyl, 6-O-alkyl, and 6-O-(N-substituted-carbamoyl)fumagillols.
January 1992, Chemical & pharmaceutical bulletin,
Y Shimauchi, and K Hori, and M Sakamoto, and Y Mutoh, and Y Fukagawa, and S Hori, and T Ishikura, and J Lein
Chemical modification of acyl-CoA:cholesterol O-acyltransferase. 1. Identification of acyl-CoA:cholesterol O-acyltransferase subtypes by differential diethyl pyrocarbonate sensitivity.
September 1988, Biochemistry,
Y Shimauchi, and K Hori, and M Sakamoto, and Y Mutoh, and Y Fukagawa, and S Hori, and T Ishikura, and J Lein
Deltamycins, new macrolide antibiotics. III. Chemical structures.
September 1979, The Journal of antibiotics,
Y Shimauchi, and K Hori, and M Sakamoto, and Y Mutoh, and Y Fukagawa, and S Hori, and T Ishikura, and J Lein
Chemical modification of anthracycline antibiotics. I. Demethoxycarbonylation, 10-epimerization and 4-o-methylation of aclacinomycin A.
November 1980, The Journal of antibiotics,
Y Shimauchi, and K Hori, and M Sakamoto, and Y Mutoh, and Y Fukagawa, and S Hori, and T Ishikura, and J Lein
Chemical modification of streptovaricin C I. 19-O-substituted damavaricin C.
February 1976, The Journal of antibiotics,
Y Shimauchi, and K Hori, and M Sakamoto, and Y Mutoh, and Y Fukagawa, and S Hori, and T Ishikura, and J Lein
Chemical modification of acyl-CoA:cholesterol O-acyltransferase. 2. Identification of a coenzyme A regulatory site by p-mercuribenzoate modification.
September 1988, Biochemistry,
Y Shimauchi, and K Hori, and M Sakamoto, and Y Mutoh, and Y Fukagawa, and S Hori, and T Ishikura, and J Lein
Chemical modification of group IV graphene analogs.
January 2018, Science and technology of advanced materials,
Y Shimauchi, and K Hori, and M Sakamoto, and Y Mutoh, and Y Fukagawa, and S Hori, and T Ishikura, and J Lein
Platelet-activating factor analogs. II. Synthesis of the 1-O-(4-decyloxymethylphenyl)- and 1-O-(4-decyloxyphenylmethyl) analogs.
January 1986, Chemistry and physics of lipids,
Copied contents to your clipboard!