A fungal metabolite and tumor promoter
Technical Support & Resources

Visit our FAQ

Contact Us

Toll Free Phone (USA and Canada Only): (888) 526-5351
Direct Phone: (734) 975-3888

Request Technical Support

Technical Support Request

To streamline the process attach the appropriate questionnaire to your inquiry.

Download IHC QuestionnaireDownload WB Questionnaire

View Our Privacy Statement for details on how we use and protect your data. In addition, this site is protected by hCaptcha and its Privacy Policy and Terms of Service apply.

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
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
Recommended Products

Certificates of Analysis & Batch Specific Data

Provide batch numbers separated by commas to download or request available product inserts, QC sheets, certificates of analysis, data packs, and GC-MS data.

Download most recent Certificate of Analysis for this product

    1 mg

    $369

    Add

    5 mg

    $1,103

    Add
    Lipid Resource Center
    Discover Products & Resources for Lipid Research
    • High-purity lipid standards
    • Lipid roles in biology
    • Lipids in health & disease
    • Lipids for pharmaceutical development
    • Protocols, advice, & resources
    EXPLORE NOW
    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).