9-Methylstreptimidone
(Synonyms: 9一甲基链霉戊二酰亚胺) 目录号 : GC42648
A microbial metabolite with antifungal and antiviral activities
Cas No.:51867-94-8
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
9-Methylstreptimidone is a microbial metabolite originally isolated from Streptomyces sp. S-885 that has antifungal and antiviral activities. It is active against several fungi, including S. sake, S. fragilis, R. rubra, T. rubra, and C. albidus (MICs = 4-20 μg/ml) and has antiviral activity against poliovirus, vesicular stomatitis virus (VSV), and Newcastle disease virus (NDV) in vitro (MIC = 0.02 μg/ml for all). 9-Methylstreptimidone increases survival in mouse models of infection with influenza A2 (H2N2) or C. albicans when administered prior to infection.
| Cas No. | 51867-94-8 | SDF | |
| 别名 | 9一甲基链霉戊二酰亚胺 | ||
| Canonical SMILES | C/C=C\C(C)=C\[C@@H](C(C[C@H](O)CC1CC(NC(C1)=O)=O)=O)C | ||
| 分子式 | C17H25NO4 | 分子量 | 307.4 |
| 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 | 3.2531 mL | 16.2655 mL | 32.5309 mL |
| 5 mM | 0.6506 mL | 3.2531 mL | 6.5062 mL |
| 10 mM | 0.3253 mL | 1.6265 mL | 3.2531 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。
Structure-activity relationship of 9-Methylstreptimidone, a compound that induces apoptosis selectively in adult T-cell leukemia cells
Oncol Res 2012;20(1):7-14.PMID:23035360DOI:10.3727/096504012x13425470196056.
We previously reported that 9-Methylstreptimidone, a piperidine compound isolated from a culture filtrate of Streptomyces, induces apoptosis selectively in adult T-cell leukemia cells. It was screened for a compound that inhibits LPS-induced NF-kappaB and NO production in mouse macrophages. However, 9-methystreptimidone is poorly obtained from the producing microorganism and difficult to synthesize. Therefore, in the present research, we studied the structure-activity relationship to look for new selective inhibitors. We found that the structure of the unsaturated hydrophobic portion of 9-Methylstreptimidone was essential for the inhibition of LPS-induced NO production. Among the 9-methylstreptimidone-related compounds tested, (+/-)-4,alpha-diepi-streptovitacin A inhibited NO production in macrophage-like cells as potently as 9-Methylstreptimidone and without cellular toxicity. Moreover, this compound selectively induced apoptosis in adult T-cell leukemia MT-1 cells.
Biosynthesis of 9-Methylstreptimidone involves a new decarboxylative step for polyketide terminal diene formation
Org Lett 2013 Mar 15;15(6):1278-81.PMID:23438151DOI:10.1021/ol400224n.
9-Methylstreptimidone is a glutarimide antibiotic showing antiviral, antifungal, and antitumor activities. Genome scanning, bioinformatics analysis, and gene inactivation experiments reveal a gene cluster responsible for the biosynthesis of 9-Methylstreptimidone in Streptomyces himastatinicus. The unveiled machinery features both acyltransferase- and thioesterase-less iterative use of module 5 as well as a branching module for glutarimide generation. Impressively, inactivation of smdK leads to a new carboxylate analogue unveiling a new mechanism for polyketide terminal diene formation.
Effect of an interferon inducer, 9-Methylstreptimidone, on Candida albicans infection in mice
Antimicrob Agents Chemother 1978 Jun;13(6):939-43.PMID:354522DOI:10.1128/AAC.13.6.939.
The protective effect of an interferon inducer with a low molecular weight, 9-Methylstreptimidone (9-MS), against Candida albicans infection in mice was investigated. The antibiotic was effective only when given prophylactically. When administered in such a manner, the growth of C. albicans in the kidneys and brain was inhibited at the initial stage of infection. The growth of C. albicans was not inhibited by the antibiotic in vitro, and no antifungal effect was obtained in a preparation containing induced interferon. These results suggest that the antifungal action of 9-Methylstreptimidone in mice might be manifested not by direct antifungal activity but rather by a host-mediated activity that excludes interferon-inducing capability.
Synthesis and biological evaluation on novel analogs of 9-Methylstreptimidone, an inhibitor of NF-kappaB
Bioorg Med Chem Lett 2009 Mar 15;19(6):1726-8.PMID:19231181DOI:10.1016/j.bmcl.2009.01.107.
Synthesis of 9-Methylstreptimidone analogs and their inhibitory activities against NF-kappaB (nuclear factor-kappaB) are reported. Among several active derivatives synthesized in this study, 8 with a relatively simple structure, exhibited inhibitory activity against LPS-induced NO production comparable to that of 9-Methylstreptimidone.
Antiviral and interferon-inducing activity of a new glutarimide antibiotic, 9-Methylstreptimidone
Antimicrob Agents Chemother 1976 Jul;10(1):14-9.PMID:984746DOI:10.1128/AAC.10.1.14.
The antiviral effect of 9-Methylstreptimidone (9-MS) was examined in mice infected with mouse-adapted influenza A(2) (H(2)N(2)) virus. Both a single and continuous prophylactic administration of 9-MS protected mice from virus infection, and comparison between the minimal effective and the 50% lethal dose gave a therapeutic index of 60. When the treatment was started after infection, however, no antiviral effect was demonstrated. After a single intraperitoneal administration of 9-MS, a highly potent virus-inhibitory factor was detected in the lungs (10 h later) and the sera (16 h later) of uninfected mice, which was assumed to be an interferon on the basis of the biological characteristics. These results suggest that the protective activity of the antibiotic is due to interferon induction in mice.