Teleocidin A1
(Synonyms: 杀鱼菌素A1,Lyngbyatoxin A) 目录号 : GC40069A fungal metabolite and tumor promoter
Cas No.:70497-14-2
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
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).
| Cas No. | 70497-14-2 | SDF | |
| 别名 | 杀鱼菌素A1,Lyngbyatoxin A | ||
| 化学名 | (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 | ||
| 分子式 | C27H39N3O2 | 分子量 | 437.6 |
| 溶解度 | DMF: Soluble, DMSO: Soluble, Ethanol: Soluble, Methanol: Soluble | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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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 |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Crystal structure and enantioselectivity of terpene cyclization in SAM-dependent methyltransferase TleD
Biochem J 2016 Dec 1;473(23):4385-4397.PMID:27613858DOI:10.1042/BCJ20160695.
TleD is a SAM (S-adenosyl-l-methionine)-dependent methyltransferase and acts as one of the key enzymes in the teleocidin B biosynthesis pathway. Besides methyl transferring, TleD also rearranges the geranyl and indole moieties of the precursor to form a six-membered ring. Moreover, it does not show homologies with any known terpenoid cyclases. In order to elucidate how such a remarkable reaction could be achieved, we determined the complex crystal structures of TleD and the cofactor analogue S-adenosyl-l-homocysteine with or without the substrate Teleocidin A1. A domain-swapped pattern via an additional N-terminal α-helix is observed in TleD hexamers. Structural comparison and alignment shows that this additional N-terminal α-helix is the common feature of SAM methyltransferase-like cyclases TleD and SpnF. The residue Tyr21 anchors the additional N-terminal α-helix to a 'core SAM-MT fold' and is a key residue for catalytic activity. Molecular dynamics simulation results suggest that the dihedral angle C23-C24-C25-C26 of Teleocidin A1 is preferred to 60-90° in the TleD and substrate complex structure, which tend to adopt a Re-face stereocenter at C25 position after reaction and is according to in vitro enzyme reaction experiments. Our results also demonstrate that methyl transfer can be a new chemical strategy for carbocation formation in the terpene cyclization, which is the key initial step.