Milbemycin A4
(Synonyms: 密灭汀A4) 目录号 : GC44194
An insecticidal antibiotic
Cas No.:51596-11-3
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
Milbemycin A4 is the prominent member of a complex family of macrocyclic lactones that contain a characteristic spiroketal group produced from the fermentation of soil bacterium S. hygroscopicus subsp. aureolacrimosus. As a compound that potentiates glutamate and GABA-gated chloride-channel opening, milbemycin 4 is used as a nematocide and insecticide.
| Cas No. | 51596-11-3 | SDF | |
| 别名 | 密灭汀A4 | ||
| Canonical SMILES | CC[C@H]([C@@H](C)CC1)O[C@]21C[C@](OC([C@@]3([H])[C@@]4(O)[C@@]5([H])[C@H](O)C(C)=C3)=O)([H])C[C@](C/C=C(C)/C[C@@H](C)/C=C/C=C4\CO5)([H])O2 | ||
| 分子式 | C32H46O7 | 分子量 | 542.7 |
| 溶解度 | DMF: soluble,DMSO: 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 | 1.8426 mL | 9.2132 mL | 18.4264 mL |
| 5 mM | 0.3685 mL | 1.8426 mL | 3.6853 mL |
| 10 mM | 0.1843 mL | 0.9213 mL | 1.8426 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。
Milbemycin A4 oxime as a probe of azole transport in Candida glabrata
FEMS Yeast Res 2014 Aug;14(5):755-61.PMID:24838041DOI:10.1111/1567-1364.12164.
Azole resistance in Candida glabrata, a pathogenic yeast, has prompted studies of compounds that have therapeutic potential by reversing azole resistance. Milbemycin A4 oxime blocked azole efflux and enhanced azole susceptibility fourfold in 28 clinical isolates of C. glabrata. Specificity of the Milbemycin A4 oxime effect depended on the drug transporter and the substrate being effluxed. The major effect of Milbemycin A4 oxime was inhibition of azole and rhodamine 6G efflux by the ATP-binding cassette (ABC) transporters CgCDR1 and PDH1. Milbemycin A4 oxime effect did not extend to oligomycin, transported by the ABC transporter YOR1 or to benomyl, transported by the major facilitator superfamily transporter, CgFLR1. Milbemycin A4 oxime did not suppress transcription of CgCDR1 but increased CgCDR1 expression 126-fold. Selectivity of the effect is compatible with the concept that Milbemycin A4 oxime may interact directly with one or more drug-binding sites of the major azole transporters.
Bioconversion of milbemycin-related compounds: biosynthetic pathway of milbemycins
J Antibiot (Tokyo) 1999 Feb;52(2):109-16.PMID:10344564DOI:10.7164/antibiotics.52.109.
Streptomyces hygroscopicus subsp. aureolacrimosus SANK 60286 and SANK 60576 produce many kinds of milbemycins. Among them, milbemycin alpha11, alpha14, A3, and A4 have the most effective acaricidal activity. In this study, we investigated the terminal biosynthetic pathway to milbemycin alpha14 and A4 which accumulated as the final products in these strains. Using cerulenin, a specific inhibitor of fatty acid and polyketide biosynthesis, we conducted bioconversion experiments with cultures of several mutants, including milbemycin A4- and alpha14-producing strains. The bioconversions of milbemycin beta6 to Milbemycin A4 and Milbemycin A4 to milbemycin alpha14 could be identified. For the biosynthesis of Milbemycin A4 from milbemycin beta6 in the milbemycin A4-high producing strain, there appeared to be two separate pathways exhibiting different sequences of furan ring formation and C-5 keto reduction steps.
Milbemycin alpha17 and related compounds synthesized from Milbemycin A4: synthetic procedure and acaricidal activities
J Antibiot (Tokyo) 2003 Oct;56(10):848-55.PMID:14700278DOI:10.7164/antibiotics.56.848.
Milbemycin alpha17, a 14-demethyl congener of Milbemycin A4, has been reported as a natural product. In this paper, we report the successful development of a chemical derivation method to synthesize milbemycin alpha17 from Milbemycin A4, as well as our use of a similar method to prepare 24-demethylmilbemycin A4 from the same precursor. The acaricidal activities of these compounds were assessed against the organophosphorus-sensitive two-spotted spider mites (Tetranychus urticae) on the primary leaves of cowpea plants (Vigna sinesis Savi species) by spraying.
Microbial conversion of milbemycins: oxidation of Milbemycin A4 and related compounds at the C-25 ethyl group by Circinella umbellata and Absidia cylindrospora
J Antibiot (Tokyo) 1995 Aug;48(8):831-7.PMID:7592029DOI:10.7164/antibiotics.48.831.
Microbial oxidation of Milbemycin A4 at the C-25 ethyl group was performed. Milbemycin A4 was converted to 31- and 32-hydroxy derivatives by Circinella umbellata SANK 44272 along with 24- and 30-hydroxy derivatives. Related compounds, 5-ketomilbemycin A4 5-oxime and 13 beta-fluoromilbemycin A4 were similarly converted to the hydroxylated compounds by this microorganism. Absidia cylindrospora SANK 31472 converted Milbemycin A4 to the corresponding 32-oic acid, 24-hydroxy derivative and a few oxygenated compounds including at the C-25 ethyl group.
Milbemycin derivatives: epoxidation of milbemycins
J Antibiot (Tokyo) 1994 Jul;47(7):812-20.PMID:8071127DOI:10.7164/antibiotics.47.812.
Epoxidation reactions (MCPBA epoxidation and Sharpless epoxidation) were examined as a means of chemically modifying milbemycins as part of our program for discovering anthelmintics. 8,9-Epoxy-, 14,15-epoxy-, 8,9-14,15-diepoxy-, and 3,4-8,9-14,15-triepoxymilbemycin A4 were selectively obtained from Milbemycin A4 and its derivatives, in which either the C-5 and C-7 hydroxyl groups or C-5 alone were protected as appropriate by a silyl ether (in the former case) or a carbonyl group. Further silylation or epoxidation on these epoxidized compounds indicated that the configuration of each epoxide moiety of the mono- and diepoxides is in accord with that of the corresponding epoxide moiety of the triepoxide. Furthermore, in order to confirm the absolute configurations of these epoxide functionalities, an X-ray analysis of a carbamate derivative from the triepoxymilbemycin was conducted.