Maytansinol (Ansamitocin P-0)
(Synonyms: 美登醇,Ansamitocin P-0) 目录号 : GC32895
An ansa macrolide
Cas No.:57103-68-1
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >99.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Maytansinol is an ansa macrolide originally isolated from P. verrucose that has antimitotic and anticancer activities.1,2,3 It inhibits polymerization and induces depolymerization of bovine brain tubulin with EC50 values of 12 and 43 ?M, respectively.2 Maytansinol inhibits sea urchin egg mitosis when used at a concentration of 10 ?M and decreases proliferation of KB nasopharyngeal cancer cells (EC50 = 0.19 ?g/ml).3
1.Kupchan, S.M., Branfman, A.R., Sneden, A.T., et al.Novel maytansinoids. Naturally occurring and synthetic antileukemic esters of maytansinolJ. Am. Chem. Soc.97(18)5294-5295(1975) 2.Ikeyama, S., and Takeuchi, M.Antitubulin activities of ansamitocins and maytansinoidsBiochem. Pharmacol.30(17)2421-2425(1981) 3.Kupchan, S.M., Sneden, A.T., Branfman, A.R., et al.Structural requirements for antileukemic activity among the naturally occurring and semisynthetic maytansinoidsJ. Med. Chem.21(1)31-37(1978)
| Cas No. | 57103-68-1 | SDF | |
| 别名 | 美登醇,Ansamitocin P-0 | ||
| Canonical SMILES | C[C@]1([C@H](CC(N(C(C=C2C=C3OC)=C3Cl)C)=O)O)[C@H]([C@@H]([C@](OC4=O)([H])C[C@]([C@](/C=C/C=C(C)/C2)([H])OC)(N4)O)C)O1 | ||
| 分子式 | C28H37ClN2O8 | 分子量 | 565.06 |
| 溶解度 | DMSO : ≥ 35 mg/mL (61.94 mM) | 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 | 1.7697 mL | 8.8486 mL | 17.6972 mL |
| 5 mM | 0.3539 mL | 1.7697 mL | 3.5394 mL |
| 10 mM | 0.177 mL | 0.8849 mL | 1.7697 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。
Maytansinol Derivatives: Side Reactions as a Chance for New Tubulin Binders
Chemistry 2022 Jan 10;28(2):e202103520.PMID:34788896DOI:10.1002/chem.202103520.
Maytansinol is a valuable precursor for the preparation of maytansine derivatives (known as maytansinoids). Inspired by the intriguing structure of the macrocycle and the success in targeted cancer therapy of the derivatives, we explored the Maytansinol acylation reaction. As a result, we were able to obtain a series of derivatives with novel modifications of the maytansine scaffold. We characterized these molecules by docking studies, by a comprehensive biochemical evaluation, and by determination of their crystal structures in complex with tubulin. The results shed further light on the intriguing chemical behavior of maytansinoids and confirm the relevance of this peculiar scaffold in the scenario of tubulin binders.
Maytansinol Functionalization: Towards Useful Probes for Studying Microtubule Dynamics
Chemistry 2023 Jan 24;29(5):e202300069.PMID:36692211DOI:10.1002/chem.202300069.
Invited for the cover of this issue are the groups of Professors Passarella and Pieraccini at the University of Milan, in collaboration with some of the members of TubInTrain consortium. The image depicts work with the elements of nature, in particular the destabilising effect of Maytansinol (the constellation) on microtubules (the trees). Read the full text of the article at 10.1002/chem.202203431.
Maytansinol Functionalization: Towards Useful Probes for Studying Microtubule Dynamics
Chemistry 2023 Jan 24;29(5):e202203431.PMID:36468686DOI:10.1002/chem.202203431.
Maytansinoids are a successful class of natural and semisynthetic tubulin binders, known for their potent cytotoxic activity. Their wider application as cytotoxins and chemical probes to study tubulin dynamics has been held back by the complexity of natural product chemistry. Here we report the synthesis of long-chain derivatives and maytansinoid conjugates. We confirmed that bulky substituents do not impact their high activity or the scaffold's binding mode. These encouraging results open new avenues for the design of new maytansine-based probes.
Total Synthesis of (-)-Maytansinol
J Org Chem 1996 Oct 4;61(20):7133-7138.PMID:11667616DOI:10.1021/jo960363a.
A total synthesis of Maytansinol (1) was achieved, in a convergent way, using (3S,6S,7S)-aldehyde 4 and (S)-p-tolyl sulfoxide 3 as fragments. When the anion of 3 was condensed with aldehyde 4, some induction at C(10) was observed (60% de), giving the C(1)-N(19)-open-chain compound 7, after thermal elimination of sulfinate. Pure E/E stereochemistry of the 11,13-diene was obtained. Selective modifications of the functionalities permitted macrocyclization and further elaboration to Maytansinol.
Combinatorial effect of Maytansinol and radiation in Drosophila and human cancer cells
Dis Model Mech 2011 Jul;4(4):496-503.PMID:21504911DOI:10.1242/dmm.006486.
Combination therapy, in which two or more agents are applied, is more effective than single therapies for combating cancer. For this reason, combinations of chemotherapy with radiation are being explored in clinical trials, albeit with an empirical approach. We developed a screen to identify, from the onset, molecules that act in vivo in conjunction with radiation, using Drosophila as a model. Screens through two small molecule libraries from the NCI Developmental Therapeutics Program yielded microtubule poisons; this class of agents is known to enhance the effect of radiation in mammalian cancer models. Here we report an analysis of one microtubule depolymerizing agent, Maytansinol isobutyrate (NSC292222; Maytansinol), in Drosophila and in human cancer cells. We find that the effect of Maytansinol is p53 dependent in Drosophila cells and human cancer cells, that Maytansinol enhances the effect of radiation in both systems, and that the combinatorial effect of drug and radiation is additive. We also uncover a differential sensitivity to Maytansinol between Drosophila cells and Drosophila larvae, which illustrates the value of studying cell behavior in the context of a whole organism. On the basis of these results, we propose that Drosophila might be a useful model for unbiased screens through new molecule libraries to find cancer drugs for combination therapy.