Teleocidin A1

Teleocidin A1, also known as lyngbyatoxin A, is a fungal metabolite that has been isolated from S. mediocidicus and is the R enantiomer of (S)-teleocidin A. It acts as a tumor promoter, inducing ornithine decarboxylase activity in mouse skin, increasing adhesion of HL-60 human leukemia cells (ED50 = 7 ng/ml), and inducing tumor formation in 87% of mice after 30 weeks when administered at a dose of 3 µg twice per week. Teleocidin A1 also increases the production of prostaglandins and the turnover of choline in HeLa cells when used at concentrations ranging from 6 to 20 ng/ml. It is a substrate for the methyltransferase TleD in Streptomyces where it is converted to teleocidin B.Formal Name: (2S,5S)-9-[(1R)-1-ethenyl-1,5-dimethyl-4-hexen-1-yl]-1,2,4,5,6,8-hexahydro-5-(hydroxymethyl)-1-methyl-2-(1-methylethyl)-3H-pyrrolo[4,3,2-gh]-1,4-benzodiazonin-3-one. CAS Number: 70497-14-2. Synonyms: Lyngbyatoxin A. Molecular Formula: C27H39N3O2. Formula Weight: 437.6. Purity: >98%. Formulation: (Request formulation change), A solid. Solubility: DMF: Soluble, DMSO: Soluble, Ethanol: Soluble, Methanol: Soluble. SMILES: O=C([C@@H](C(C)C)N1C)N[C@H](CO)CC2=CNC3=C([C@](C=C)(C)CC/C=C(C)/C)C=CC1=C32. InChi Code: InChI=1S/C27H39N3O2/c1-8-27(6,13-9-10-17(2)3)21-11-12-22-23-19(15-28-24(21)23)14-20(16-31)29-26(32)25(18(4)5)30(22)7/h8,10-12,15,18,20,25,28,31H,1,9,13-14,16H2,2-7H3,(H,29,32)/t20-,25+,27-/m0/s1. InChi Key: KISDGNGREAJPQR-FESMNKHTSA-N. Origin: Bacterium/Streptomyces.