Kazusamycin A
(Synonyms: CL 1,957B, Hydroxyelactocin, Hydroxyleptomycin B, PD 114721) 目录号 : GC41236
An antitumor antibiotic
Cas No.:92090-94-3
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >95.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Kazusamycin A is an antibiotic from Streptomyces and a hydroxy analog of Leptomycin B that demonstrates cytotoxic activity against various human and mouse tumor lines. Additionally, at nanomolar concentrations, it inhibits nuclear export and translocation of Rev, a regulatory gene product in the HIV genome.
| Cas No. | 92090-94-3 | SDF | |
| 别名 | CL 1,957B, Hydroxyelactocin, Hydroxyleptomycin B, PD 114721 | ||
| Canonical SMILES | O=C1O[C@@H](/C=C/C(CC)=C\[C@H](C)C/C=C/C(C)=C/[C@@H](CO)C([C@@H](C)[C@H](O)[C@@H](C)C/C(C)=C/C(O)=O)=O)[C@@H](C)C=C1 | ||
| 分子式 | C33H48O7 | 分子量 | 556.7 |
| 溶解度 | Soluble in DMSO | 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 | 1.7963 mL | 8.9815 mL | 17.963 mL |
| 5 mM | 0.3593 mL | 1.7963 mL | 3.5926 mL |
| 10 mM | 0.1796 mL | 0.8981 mL | 1.7963 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。
First total synthesis of the antitumor compound (-)-kazusamycin A and absolute structure determination
Org Lett 2004 Aug 19;6(17):2845-8.PMID:15330629DOI:10.1021/ol049219z.
The first total synthesis of Kazusamycin A, a potent antitumor compound from an actinomycete, has been achieved, and its absolute structure was determined. Paterson's stereoselective aldol reaction was successfully applied to construct the contiguous chiral centers by using an originally designed optically active 2-acyl-1,3-propanediol derivative.
Design, synthesis, and evaluation of novel Kazusamycin A derivatives as potent antitumor agents
Bioorg Med Chem Lett 2006 Jun 15;16(12):3315-8.PMID:16617017DOI:10.1016/j.bmcl.2006.03.056.
Novel Kazusamycin A derivatives were designed in the viewpoint of decrease of reactivity at the alpha,beta-unsaturated delta-lactone moiety against Michael-type addition. Although 25-30 steps were required for the synthesis of each compound, their syntheses were achieved. Cytotoxicity against HPAC cell line was evaluated, and two of them exhibited comparable potency to Kazusamycin A. Hepatic toxicity of these designed compounds was much lower than that of Kazusamycin A.
[Studies on the new antibiotic kazusamycin and related substances]
Gan To Kagaku Ryoho 1987 Mar;14(3 Pt 2):858-64.PMID:3105461doi
Kazusamycins A and B and leptomycin B have a structure characteristic of an unsaturated, branched-chain fatty acid with a terminal delta-lactone ring, and show antibacterial activity on some kinds of fungi. Kazusamycin A (KZM-A) showed cytotoxic activity on mammalian cells at very low concentrations (ng/ml) in vitro. The antibiotic inhibited not only the growth of transplantable murine tumors and their metastases to the lung but also human mammary tumors inoculated into nude mice. KZM-A became immediately distributed to the main organs of mice, and a certain quantity of the antibiotic was inactivated by binding to high-molecular-weight substances such as albumin. A large quantity of KZM-A was carried to the liver and excreted into the bile, but was then reabsorbed by the small intestine. The growth of tumor metastases (L5178Y cells) in the liver was suppressed by KZM-A. The antibiotic induced severe diarrhea by causing necrosis and/or lysis of the mucous membrane of the small intestine. In contrast to this, the degree of myelotoxicity was relatively slight. The active site of the fatty acid of KZM-A appeared to consist of conjugated double bonds, carboxylic acid and hydroxyl moieties.
[Growth inhibitory effect of a new anticancer antibiotics, Kazusamycin A, on human transitional cancer cell lines in vitro]
Nihon Hinyokika Gakkai Zasshi 1992 May;83(5):627-35.PMID:1495200DOI:10.5980/jpnjurol1989.83.627.
Kazusamycin A (KZMA) is a new anticancer antibiotic, which has been proven to have strong anticancer effect and several characteristic features different from currently available anticancer antibiotics. However, there has as yet been no report which had concerned itself with the effect of KZMA on urological cancer. This study was undertaken to determine the inhibitory effects of KZMA on transitional cancer cells in vitro, the augmentation of the inhibitory effect by combining thermal treatment and the effect of KZMA upon DNA distribution. Human transitional cancer cells, KU-1, and T-24 were used as targets. Fifty % inhibitory concentration of KZMA was determined after these cells were exposed to graded concentrations of KZMA for 2 to 48 hours, and to the concentration of KZMA for 2 hours at the temperature of 42 degrees C. Viable cells were counted by dye exclusion assay (DEA) and by tetrazolium-based colorimetric assay (MTT-assay) exposure. KZMA inhibited the growth of the three transitional cancer cells strongly and this inhibitory effect appeared to be depend upon the exposure time and the concentration of KZMA. IC50s after 2-hour exposure at the temperature of 42 degrees C was shown to be decreased to 23 to 87% of that at the temperature of 37 degrees, indicating an augmentation of the inhibitory effect of KZMA by combining thermal treatment. MGH-U1 was the most sensitive to the combination of KZMA and hyperthermia. The cell cycle analysis showed that KZMA had G2-arresting and M-retarding effects, which were different compared with currently available anticancer antibiotics.(ABSTRACT TRUNCATED AT 250 WORDS)