Altemicidin
(Synonyms: (-)-Altemicidin) 目录号 : GC49046
A monoterpene alkaloid with acaricidal and anticancer activities
Cas No.:125399-82-8
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
Altemicidin is a monoterpene alkaloid originally isolated from S. sioyaensis with acaricidal and anticancer activities.1 It is acaricidal to two-spotted spider mites (T. urticae) in a greenhouse pot test at concentrations of 10 and 100 ppm. Altemicidin inhibits the growth of murine L1210 lymphocytic leukemia and IMC carcinoma cells (IC50s = 0.84 and 0.82 µg/ml, respectively). It is toxic to mice with an LD50 value of 0.3 mg/kg.
1.Takahashi, A., Kurasawa, S., Ikeda, D., et al.Altemicidin, a new acaricidal and antitumor substance. I. Taxonomy, fermentation, isolation and physico-chemical and biological propertiesJ. Antibiot. (Tokyo)42(11)1556-1561(1989)
| Cas No. | 125399-82-8 | SDF | |
| 别名 | (-)-Altemicidin | ||
| Canonical SMILES | NS(CC(N[C@@]1([C@@]2([H])[C@@](C(C(N)=O)=CN(C2)C)([H])C[C@@H]1O)C(O)=O)=O)(=O)=O | ||
| 分子式 | C13H20N4O7S | 分子量 | 376.4 |
| 溶解度 | Ethanol: soluble | 储存条件 | -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 | 2.6567 mL | 13.2837 mL | 26.5675 mL |
| 5 mM | 0.5313 mL | 2.6567 mL | 5.3135 mL |
| 10 mM | 0.2657 mL | 1.3284 mL | 2.6567 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。
Dearomative Synthetic Entry into the Altemicidin Alkaloids
J Am Chem Soc 2021 Jun 2;143(21):7935-7939.PMID:34018391DOI:10.1021/jacs.1c04147.
Altemicidin and related Streptomyces-derived monoterpene alkaloids possess dense, highly polar azaindane cores as well as potent cytotoxic and tRNA synthetase inhibitory properties. The congested α-amino acid motif decorating their presumed iridoid-like core structure has proven to be both a synthetic challenge and a biosynthetic mystery to date. Herein, we report a distinct, abiotic strategy to these alkaloids resulting in a concise synthesis of Altemicidin from simple chemical feedstocks. Key chemical findings include the exploitation of a dearomative pyridinium addition and dipolar cycloaddition sequence to stereospecifically install the quaternary amine moiety, and a chemoselective molybdenum-mediated double reduction to establish the fully functionalized azaindane nucleus with minimal redox manipulations.
Altemicidin, a new acaricidal and antitumor substance. II. Structure determination
J Antibiot (Tokyo) 1989 Nov;42(11):1562-6.PMID:2584138DOI:10.7164/antibiotics.42.1562.
The structure of Altemicidin, a new acaricidal and antitumor agent, was determined to be (1R,2S,3aR,7aS)-4-carbamoyl-2-hydroxy-6-methyl-1-(sulfamo ylacetamido)-2,3,3a,6, 7,7a-hexahydro-6-azaindene-1-carboxylic acid by a combination of spectroscopic and X-ray crystallographic analysis of its derivatives. Altemicidin is a monoterpene alkaloid.
Altemicidin, a new acaricidal and antitumor substance. I. Taxonomy, fermentation, isolation and physico-chemical and biological properties
J Antibiot (Tokyo) 1989 Nov;42(11):1556-61.PMID:2584137DOI:10.7164/antibiotics.42.1556.
Screening of new insecticidal and acaricidal antibiotics was carried out with reference to anti-brine shrimp activity from actinomycete strains isolated from marine environments. Of 200 actinomycete isolates, one isolate was found to produce a new substance, Altemicidin. The strain was isolated from sea mud collected at Gamo, Miyagi Prefecture, Japan, and identified as Streptomyces sioyaensis SA-1758. Altemicidin was purified by Diaion CHP-20P and Sephadex LH-20 column chromatographies. The molecular formula was determined as C13H20N4O7S by elemental analysis, MS and 13C NMR spectrum. Altemicidin showed not only acaricidal activity but also antitumor activity. The compound showed no antimicrobial activity except the inhibitory activity to Xanthomonas strains.
Synthetic studies on Altemicidin: stereocontrolled construction of the core framework
Org Lett 2008 Jan 17;10(2):169-71.PMID:18081299DOI:10.1021/ol701940f.
The stereoselective synthesis of the key intermediate for Altemicidin has been accomplished. The synthesis commenced with a bicyclo[3.3.0] framework, which was readily obtained via an intramolecular C-H insertion reaction. A Curtius rearrangement was employed as a key step to stereoselectively construct the beta-hydroxyl alpha-disubstituted-alpha-amino acid structure. Synthesis of vinylogous urea was achieved using hydrolysis of nitrile intermediate.
Aminoacyl sulfonamide assembly in SB-203208 biosynthesis
Nat Commun 2019 Jan 14;10(1):184.PMID:30643149DOI:10.1038/s41467-018-08093-x.
Sulfonamide is present in many important drugs, due to its unique chemical and biological properties. In contrast, naturally occurring sulfonamides are rare, and their biosynthetic knowledge are scarce. Here we identify the biosynthetic gene cluster of sulfonamide antibiotics, Altemicidin, SB-203207, and SB-203208, from Streptomyces sp. NCIMB40513. The heterologous gene expression and biochemical analyses reveal unique aminoacyl transfer reactions, including the tRNA synthetase-like enzyme SbzA-catalyzed L-isoleucine transfer and the GNAT enzyme SbzC-catalyzed β-methylphenylalanine transfer. Furthermore, we elucidate the biogenesis of 2-sulfamoylacetic acid from L-cysteine, by the collaboration of the cupin dioxygenase SbzM and the aldehyde dehydrogenase SbzJ. Remarkably, SbzM catalyzes the two-step oxidation and decarboxylation of L-cysteine, and the subsequent intramolecular amino group rearrangement leads to N-S bond formation. This detailed analysis of the aminoacyl sulfonamide antibiotics biosynthetic machineries paves the way toward investigations of sulfonamide biosynthesis and its engineering.