1402-82-0

Basic information

• Product Name: Amphomycin
• Synonyms: Amphomycin;Nsc267431
• CAS NO: 1402-82-0
• Molecular Formula: C58H91N13O20
• Molecular Weight: 1290.43
• EINECS: 215-760-0
• Mol File: 1402-82-0.mol
• Article Data: 0

Chemical Properties

• Boiling Point: 854.06°C (rough estimate)
• Flash Point: 977.9°C
• Appearance: /
• Density: 1.0985 (rough estimate)
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.6700 (estimate)
• Solubility: Soluble in DMSO
• CAS DataBase Reference: Amphomycin(CAS DataBase Reference)
• NIST Chemistry Reference: Amphomycin(1402-82-0)
• EPA Substance Registry System: Amphomycin(1402-82-0)

Safety Data

• Hazardous Substances Data: 1402-82-0(Hazardous Substances Data)

Usage

Description

Amphomycin is a lipopeptide antibiotic derived from Streptomycetes and Actinoplanes, initially discovered by researchers at Bristol-Myers in 1953 from Streptomyces canus. It was marketed as a complex of closely related analogues during the 1950s and 1960s, and its structure was elucidated in 2000. Amphomycin exhibits activity against Gram-positive bacteria by inhibiting peptidoglycan synthesis and blocking cell wall development. It is closely related to several "lost" antibiotics, such as aspartocin, crystallomycin, glumamycin, friulimicin, laspartocin, tsushimycin, and zaomycin. Interest in amphomycin has been rekindled due to the discovery of friulimicin's activity against antibiotic-resistant strains.

Uses

Used in Pharmaceutical Industry:
Amphomycin is used as an antibiotic for treating infections caused by Gram-positive bacteria. Its ability to inhibit peptidoglycan synthesis and block cell wall development makes it a valuable tool in combating bacterial infections.
Used in Research and Development:
Amphomycin is used as a research compound for studying the mechanisms of antibiotic resistance and the development of new antibiotics. Its close relationship with other "lost" antibiotics provides a basis for exploring potential synergistic effects and novel applications in the fight against antibiotic-resistant strains.
Used in Antibiotic Resistance Studies:
Amphomycin is utilized in the study of antibiotic resistance, particularly in the context of its related compound, friulimicin, which has shown activity against antibiotic-resistant strains. This research can lead to the development of new strategies and treatments for combating the growing issue of antibiotic resistance in various bacterial pathogens.

Originator

Amphocortrin CR,Warner Lambert,US,1963

Manufacturing Process

The process for producing amphomycin comprises cultivating a strain of Streptomyces canus in an aqueous, nutrient-containing carbohydrate solution under submerged aerobic conditions until substantial antibacterial activity is imparted to the solution and then recovering the so-produced amphomycin from the fermentation broth. The process of decolorizing solutions of amphomycin then involves treatment with activated charcoal, followed by the steps of (1) extracting the antibiotic into a water-immiscible organic solvent under strongly acid conditions or precipitating the amphomycin from aqueous solution by adjusting the pH to a point within the range of pH 3.0 to 4.0, (2) removing impurities from strongly acid, aqueous solution of amphomycin by extraction of the impurities with methyl isobutyl ketone and amyl acetate, (3) extracting the amphomycin from a strongly acid solution in butanol by the use of water having a pH higher than 4, (4) extracting the amphomycin from solution in water-immiscible organic solvent into water whose pH is greater than 6.0, (5) precipitating amphomycin from solution by formation of insoluble derivatives of the basic function, and (6) precipitating amphomycin from solution by formation of insoluble derivates of the acidic function. The amphomycin is then converted to the calcium salt with calcium hydroxide.

Therapeutic Function

Antibiotic

Biological Activity

amphomycin is a natural antibacterial lipopeptide.cyclic lipopeptides are a promising class of natural products with antibiotic properties. cyclic lipopeptides are amphiphilic molecules, composed of a fatty acid tail linked to a short oligopeptide which form a macrocylic ring structure.

Safety Profile

Poison by intravenous andintraperitoneal routes. Moderately toxic by ingestion.Induces hemolysis. Active against gram-positive bacteria.Suggested as a topical agent for animal and plantinfections. When heated to decomposition it emits acridsmoke and

in vitro

in previous study, calf brain endoplasmic reticulum membranes were incubated with varying concentrations of gdp-mannose in the presence and absence of amphomycin, results showed no significant difference in apparent km for gdp-mannose. however, the vmax was reduced in the presence of amphomycin as compared with in its absence. moreover, when mannosylphosphoryldolichol synthase activity was measured in the presence of amphomycin, the shape of the substrate velocity curve changed from a rectangular hyperbola to a sigmoid [1].

in vivo

the pk of lipopeptides, the semi-synthetic amphomycin analogues, were evaluated in mice and rats following single i.v. and oral administration. following oral administration at 50 mg/kg, plasma concentrations of amphomycin analogues were

references

[1] d. k. banerjee. amphomycin inhibits mannosylphosphoryldolichol synthesis by forming a complex with dolichylmonophosphate. the journal of biological chemisty 264(4), 2024-2028 (1989).[2] pasetka cj, erfle dj, cameron dr, clement jj, rubinchik e. novel antimicrobial lipopeptides with long in vivo half-lives. int j antimicrob agents. 2010 feb;35(2):182-5.

InChI:InChI=1/C58H91N13O20/c1-8-30(4)18-13-11-9-10-12-14-21-39(72)63-36(26-44(79)80)51(83)69-48-33(7)62-52(84)38-20-17-23-71(38)56(88)45(29(2)3)67-55(87)47(32(6)59)66-41(74)28-61-49(81)34(24-42(75)76)64-40(73)27-60-50(82)35(25-43(77)78)65-54(86)46(31(5)58(90)91)68-53(85)37-19-15-16-22-70(37)57(48)89/h12,14,29-38,45-48H,8-11,13,15-28,59H2,1-7H3,(H,60,82)(H,61,81)(H,62,84)(H,63,72)(H,64,73)(H,65,86)(H,66,74)(H,67,87)(H,68,85)(H,69,83)(H,75,76)(H,77,78)(H,79,80)(H,90,91)/b14-12-/t30?,31-,32?,33+,34-,35-,36-,37+,38-,45-,46-,47+,48-/m0/s1

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Amphomycin, a selective inhibitor of peptidoglycan synthesis of bacteria, inhibited the lipid intermediates accumulation and the peptidoglycan synthesis from UDP-N-acetylmuramyl-L-Ala-D-Glu-[3H]-meso-Dpm-D-Ala-D-Ala (UDP-MurNAc-pentapeptide) and UDP-N-acetylglucosamine (UDP-GlcNAc) with a partic...detailed

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