A 32390A
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| Category | Antibiotics |
| Catalog number | BBF-03140 |
| CAS | 61241-59-6 |
| Molecular Weight | 396.39 |
| Molecular Formula | C18H24N2O8 |
| Purity | >98% |
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Description
A 32390A is an antibiotic produced by Pyrenochaeta sp. (NRRL-5786). It has anti-gram-positive bacteria and fungi activity. It also inhibits the activity of dopamine tetra-hydroxylase, can reduce the level of norepinephrine in the heart and adrenal glands, and has a hypotensive effect on hypertensive rats.
Specification
| Synonyms | 1,6-Di-O-2-isocyano-3-methylcrotonyl-D-mannitol; Antibiotic A 32390A; A32390A |
| Storage | Store at -20°C |
| IUPAC Name | [2,3,4,5-tetrahydroxy-6-(2-isocyano-3-methylbut-2-enoyl)oxyhexyl] 2-isocyano-3-methylbut-2-enoate |
| Canonical SMILES | CC(=C(C(=O)OCC(C(C(C(COC(=O)C(=C(C)C)[N+]#[C-])O)O)O)O)[N+]#[C-])C |
| InChI | InChI=1S/C18H24N2O8/c1-9(2)13(19-5)17(25)27-7-11(21)15(23)16(24)12(22)8-28-18(26)14(20-6)10(3)4/h11-12,15-16,21-24H,7-8H2,1-4H3 |
| InChI Key | YEMJVHOPMVQUGS-UHFFFAOYSA-N |
Properties
| Appearance | Crystal |
| Antibiotic Activity Spectrum | Gram-positive bacteria; fungi |
| Melting Point | 162°C |
| Solubility | Soluble in DMSO, DMF |
Reference Reading
1. A32390A, a new biologically active metabolite. II. Isolation and structure
G G Marconi, B B Molloy, R Nagarajan, J W Martin, J B Deeter, J L Occolowitz J Antibiot (Tokyo). 1978 Jan;31(1):27-32. doi: 10.7164/antibiotics.31.27.
An inhibitor of dopamine-beta-hydroxylase, designated A32390A, was isolated from the culture broth of a Pyrenochaeta species. The inhibitor showed antimicrobial activity against fungi and gram-positive bacteria. Spectroscopic analysis and chemical degradation studies indicated that the structure was 1,6-di-O-(2-isocyano-3-methylcrotonyl)-D-mannitol.
2. A32390A, a new biologically active metabolite. I. Discovery and fermentation studies
L D Boeck, M M Hoehn, T H Sands, R W Wetzel J Antibiot (Tokyo). 1978 Jan;31(1):19-26. doi: 10.7164/antibiotics.31.19.
A32390A is an isonitrile-containing derivative of diacyl D-mannitol. The compound is produced in fermentation as the major component of a metabolic complex known as A32390. A32390A inhibits dopamine-beta-hydroxylase reduces heart and adrenal norepinephrine levels, lowers blood pressure in hypertensive rats, and possesses antibiotic activity vs. Gram-positive bacteria and fungi, including Candida albicans. A32390 is produced in submerged culture by a mold, a species of Pyrenochaeta, NRRL-5786. Glucose and sucrose are among the best carbon sources for the biosynthesis of A32390. Mannitol, although a substituent of the A32390A molecule, supports little or no biosynthesis of the compound when employed as the major carbon source for the fermentation. The addition of crotonic acid derivatives. ethanol, or L-histidine to the fermentation medium enhances the level of A32390 produced.
3. A32390A, a new biologically active metabolite. III. In vitro and in vivo antifungal activity
J R Turner, T F Butler, R S Gordee, A L Thakkar J Antibiot (Tokyo). 1978 Jan;31(1):33-7. doi: 10.7164/antibiotics.31.33.
A32390A, an isonitrile-containing derivative of mannitol, represents a new class of antifungal antibiotics. In vitro antifungal activity of A32390A was found against Candida albicans, Cryptococcus neoformans and Histoplasma capsulatum. In vivo antifungal activity of A32390A was demonstrated in mice infected with C. albicans. Accumulative doses of 37.5 approximately 600 mg/kg, administered subcutaneously over a 24-hour period, showed significant activity without demonstrating toxicity. A32390A was effective, but not as effective as amphotericin B, in reducing the number of Candida cells isolated from the kidney of infected mice. Urinary excretion of A32390A accounted for only 10% of the administered dose. Improved bioavailability of A32390A was accomplished when the antibiotic was combined with polyvinyl pyrrolidone (PVP) in a solid dispersion. Administration of A32390A as a 10% dispersion in PVP resulted in increased urinary excretion of the drug and reduced the amount of drug required for in vivo activity.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
