Virustomycin A
(Synonyms: AM 2604A) 目录号 : GC45594
A macrolide antibiotic
Cas No.:84777-85-5
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
Virustomycin A is a macrolide antibiotic originally isolated from Streptomyces.1,2 It is active against infectious and plant pathogenic fungi, including T. vaginalis and P. oryzae (MICs = 6.25 and 12.5 μg/ml, respectively), as well as the parasite T. foetus (MIC = 25 μg/ml).1 It also decreases plaque formation by RNA and DNA viruses (ED50 = 0.0003 μg/ml for all). Virustomycin A is active against the GUTat 3.1 strain of T. brucei brucei, but not the STIB900 strain of T. brucei rhodesiense (IC50s = 0.45 and 480 ng/ml, respectively), and induces cytotoxicity in human MRC-5 cells with an IC50 value of 80 ng/ml.3 It inhibits RNA, DNA, and protein synthesis in T. foetus.2
References
1. Omura, S., Shimizu, H., Iwai, Y., et al. AM-2604 A, a new antiviral antibiotic produced by a strain of Streptomyces. J. Antibiot. (Tokyo) 35(12), 1632-1637 (1982).
2. Omura, S., Otogguro, K., and Tanaka, H. The mode of action of a novel 18-membered macrolide, virustomycin A (AM-2604 A), on Trichomonas foetus. J. Antibiot. (Tokyo) 36(12), 1755-1761 (1983).
3. Otoguro, K., Ishiyama, A., Namatame, M., et al. Selective and potent in vitro antitrypanosomal activities of ten microbial metabolites. J.Antibiot.(Tokyo) 61(6), 372-378 (2008).
| Cas No. | 84777-85-5 | SDF | |
| 别名 | AM 2604A | ||
| Canonical SMILES | O=C1O[C@H]([C@@H](C)[C@@H](O)[C@H](C)[C@@]2(O)C[C@@H](OC(/C=C/C(NC3=C(O)CCC3=O)=O)=O)[C@H](C)[C@@H](/C=C\C)O2)[C@@H](OC)/C=C/C=C(C)/C[C@@H](C)[C@H](O)[C@H](CC)[C@H](O)[C@H](C)/C=C(C)\C=C1\OC | ||
| 分子式 | C48H71NO14 | 分子量 | 886.1 |
| 溶解度 | Chloroform: 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 | 1.1285 mL | 5.6427 mL | 11.2854 mL |
| 5 mM | 0.2257 mL | 1.1285 mL | 2.2571 mL |
| 10 mM | 0.1129 mL | 0.5643 mL | 1.1285 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。
The mode of action of a novel 18-membered macrolide, Virustomycin A (AM-2604 A), on Trichomonas foetus
J Antibiot (Tokyo) 1983 Dec;36(12):1755-61.PMID:6662816DOI:10.7164/antibiotics.36.1755.
The mode of action of Virustomycin A, a novel 18-membered macrolide, on Trichomonas foetus was investigated. The antibiotic inhibited the biosynthesis of RNA, DNA and protein in the organism. The inhibition of RNA biosynthesis was the most severe. Virustomycin A repressed the incorporation of [3H]uridine into both acid-soluble and insoluble fractions, whereas actinomycin D inhibited the incorporation of [3H]uridine into acid-insoluble fraction alone. Furthermore, it was found that Virustomycin A interfered with nucleotide formation from uridine and adenosine but not with their transport to the cells. On the other hand, the antibiotic did not inhibit the activities of uridine kinase and uracil phosphoribosyltransferase in a cell-free extract from the organism. These data suggest that the antibiotic interferes with the formation of phosphate donor(s) (possibly ATP-forming system) of the organism.
Isolation and structural elucidation of new 18-membered macrolide antibiotics, viranamycins A and B
J Antibiot (Tokyo) 1991 Dec;44(12):1294-9.PMID:1778781DOI:10.7164/antibiotics.44.1294.
Two cytotoxic antibiotics, designated viranamycins A and B, were isolated from the culture broth of Streptomyces sp. CH41. Their structures were elucidated as new 18-membered macrolides related to Virustomycin A and concanamycin A from NMR spectral analysis. Viranamycins A and B inhibited the growth of P388 mouse leukemia and KB human squamous-cell-carcinoma cells.
Selective and potent in vitro antitrypanosomal activities of ten microbial metabolites
J Antibiot (Tokyo) 2008 Jun;61(6):372-8.PMID:18667785DOI:10.1038/ja.2008.52.
More than 400 compounds isolated from soil microorganisms, and catalogued in the antibiotic library of the Kitasato Institute for Life Sciences, were screened against African trypanosomes. Ten compounds were found to have selective and potent antitrypanosomal activity in vitro: aureothin, cellocidin, destomycin A, echinomycin, hedamycin, irumamycin, LL-Z 1272beta, O-methylnanaomycin A, venturicidin A and Virustomycin A. Results of the in vitro assays using the GUTat 3.1 strain of Trypanosomal brucei brucei and the STIB900 strain of T. b. rhodesiense are presented. Cytotoxicity was determined using a human MRC-5 cell line. This is the first report of antitrypanosomal activities of the 10 microbial metabolites listed above.
Acyltransferase Domain Exchange between Two Independent Type I Polyketide Synthases in the Same Producer Strain of Macrolide Antibiotics
Chembiochem 2023 Mar 14;24(6):e202200670.PMID:36602093DOI:10.1002/cbic.202200670.
Streptomyces graminofaciens A-8890 produces two macrolide antibiotics, FD-891 and Virustomycin A, both of which show significant biological activity. In this study, we identified the Virustomycin A biosynthetic gene cluster, which encodes type I polyketide synthases (PKSs), ethylmalonyl-CoA biosynthetic enzymes, methoxymalony-acyl carrier protein biosynthetic enzymes, and post-PKS modification enzymes. Next, we demonstrated that the acyltransferase domain can be exchanged between the Vsm PKSs and the PKSs involved in FD-891 biosynthesis (Gfs PKSs), without any supply problems of the unique extender units. We exchanged the malonyltransferase domain in the loading module of Gfs PKS with the ethylmalonyltransferase domain and the methoxymalonyltransferase domain of Vsm PKSs. Consequently, the expected two-carbon-elongated analog 26-ethyl-FD-891 was successfully produced with a titer comparable to FD-891 production by the wild type; however, exchange with the methoxymalonyltransferase domain did not produce any FD-891 analogs. Furthermore, 26-ethyl-FD-891 showed potent cytotoxic activity against HeLa cells, like natural FD-891.