A fungal metabolite and tumor promoter
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Teleocidin A1

Item No. 25482

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
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(Learn about Variance in Solubility)
DMF: SolubleDMSO: SolubleEthanol: SolubleMethanol: 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
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
Certificates of Analysis & Batch Specific Data

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    1 mg

    $369

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    5 mg

    $1,103

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    Product Description

    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.1 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.2 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.3 It is a substrate for the methyltransferase TleD in Streptomyces where it is converted to teleocidin B.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Sakai, S.-I., Hitotsuyanagi, Y., Aimi, N., et al. Absolute configuration of lyngbyatoxin A (teleocidin A-1) and teleocidin A-2. Tetrahedron Lett. 27(43), 5219-5220 (1986).

    2. Fujiki, H., and Sugimura, T. New classes of tumor promoters: Teleocidin, aplysiatoxin, and palytoxin. Adv. Cancer Res. 49, 223-264 (1987).

    3. Sakamoto, H., Terada, M., Fujiki, H., et al. Stimulation of prostaglandin production and choline turnover in HeLa cells by lyngbyatoxin A and dihydroteleocidin B. Biochem. Biophys. Res. Commun. 102(1), 100-107 (1981).

    4. Yu, F., Li, M., Xu, C., et al. Crystal structure and enantioselectivity of terpene cyclization in SAM-dependent methyltransferase TleD. Biochem. J. 473(23), 4385-4397 (2016).