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Calcimycin

Calcimycin is a pyrrole polyether antibiotic that exhibits antibacterial, antifungal, pro-inflammatory, and pro-allergic activities. Calcimycin is a divalent cation ionophore that increases intracellular Ca2+ levels, uncouples oxidative phosphorylation, and inhibits mitochondrial ATPase activity. Calcimycin is especially active against gram positive bacteria. In mast cells, calcimycin activates IKK2 and NF-κB and induces degranulation and pro-inflammatory cytokine production.

References PubMed ID::http://www.ncbi.nlm.nih.gov/pubmed/18846437

Cas No.

52665-69-7

Purity

≥98%

Formula

C29H37N3O6

Formula Wt.

523.62

Chemical Name

5-(Methylamino)-2-[[(2R,3R,6S,8S,9R,11R)-3,9,11- trimethyl-8-[(1S)-1-methyl-2-oxo-2-(1H-pyrrol-2-yl)- ethyl]-1,7-dioxaspiro[5.5]undec-2-yl]methyl]-4- benzoxazolecarboxylic acid

IUPAC Name

5-(methylamino)-2-[[(2S,3R,5R,8S,9S)-3,5,9-trimethyl-2-[1-oxo-1-(1H-pyrrol-2-yl)propan-2-yl]-1,7-dioxaspiro[5.5]undecan-8-yl]methyl]-1,3-benzoxazole-4-carboxylic acid

Synonym

Antibiotic A-23187; A-23187

Melting Point

181-182°C

Solubility

Soluble in ethyl acetate, chloroform, methanol or DMSO. Slightly soluble in water.

Appearance

White Powder

Hosokawa J, Suzuki K, Nakagomi D, et al. Role of calcium ionophore A23187-induced activation of IkappaB kinase 2 in mast cells. Int Arch Allergy Immunol. 2013;161 Suppl 2:37-43. PMID: 23711852.

Abbott BJ, Fukuda DS, Dorman DE, et al. Microbial transformation of A23187, a divalent cation ionophore antibiotic. Antimicrob Agents Chemother. 1979 Dec;16(6):808-12. PMID: 119484.

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