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Teleocidin A1 (Synonyms: Lyngbyatoxin A)

Catalog No.GC40069

Teleocidin A1, also known as lyngbyatoxin A, is a fungal metabolite that has been isolated from S.

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Teleocidin A1 Chemical Structure

Cas No.: 70497-14-2

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1mg
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Sample solution is provided at 25 µL, 10mM.

Description of 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. [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]

Reference:
[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).

Chemical Properties of Teleocidin A1

Cas No. 70497-14-2 SDF
Synonyms Lyngbyatoxin A
Chemical 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
Canonical 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
Formula C27H39N3O2 M.Wt 437.6
Solubility DMF: Soluble, DMSO: Soluble, Ethanol: Soluble, Methanol: Soluble Storage Store at -20°C
General tips Please select the appropriate solvent to prepare the stock solution according to the solubility of the product in different solvents; once the solution is prepared, please store it in separate packages to avoid product failure caused by repeated freezing and thawing.Storage method and period of the stock solution: When stored at -80°C, please use it within 6 months; when stored at -20°C, please use it within 1 month.
To increase solubility, heat the tube to 37°C and then oscillate in an ultrasonic bath for some time.
Shipping Condition Evaluation sample solution: shipped with blue ice. All other sizes available: with RT, or with Blue Ice upon request.

Complete Stock Solution Preparation Table of Teleocidin A1

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1 mg 5 mg 10 mg
1 mM 2.2852 mL 11.426 mL 22.8519 mL
5 mM 0.457 mL 2.2852 mL 4.5704 mL
10 mM 0.2285 mL 1.1426 mL 2.2852 mL
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Average Rating: 5 ★★★★★ (Based on Reviews and 33 reference(s) in Google Scholar.)

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