Avermectin A2a
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| Category | Antibiotics |
| Catalog number | BBF-00613 |
| CAS | 50914-15-3 |
| Molecular Weight | 905.12 |
| Molecular Formula | C49H76O15 |
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Description
Avermectin A2a is produced by the strain of Streptomyces avermitilis. It stimulates nerve cells to release Y-aminobutyric acid (GABA), which blocks the transmission of signals from the central nervous system to the motor nerve. It is not resistant to bacteria and fungi, but has strong activity to nematode parasites such as ancylostoma and Pteria, as well as insects such as flies. Abamectin B1a had the highest activity. Ivermectin obtained by catalytic hydrogenation contains 22,23-dihydroabamectin B1a (above 80%) and 22,23 dioxabamectin B1b(below 20%). Less active than B1a but less toxic. Used as repellent (subcutaneous or oral) for cattle, sheep and pigs, it is also effective against human filariasis.
Specification
| Related CAS | 65195-53-1 |
| Synonyms | Avermectin A1a; SCHEMBL1681224 |
| IUPAC Name | (1R,4S,4'S,5'S,6R,6'R,8R,10E,12S,13S,14E,16E,20R,21R,24S)-6'-butan-2-yl-4',24-dihydroxy-12-[(2R,4S,5S,6S)-5-[(2S,4S,5S,6S)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy-4-methoxy-6-methyloxan-2-yl]oxy-21-methoxy-5',11,13,22-tetramethylspiro[3,7,19-trioxatetracyclo[15.6.1.14,8.020,24]pentacosa-10,14,16,22-tetraene-6,2'-oxane]-2-one |
| Canonical SMILES | CCC(C)C1C(C(CC2(O1)CC3CC(O2)CC=C(C(C(C=CC=C4COC5C4(C(C=C(C5OC)C)C(=O)O3)O)C)OC6CC(C(C(O6)C)OC7CC(C(C(O7)C)O)OC)OC)C)O)C |
| InChI | InChI=1S/C49H76O15/c1-12-25(2)43-29(6)36(50)23-48(64-43)22-34-19-33(63-48)17-16-27(4)42(61-40-21-38(55-10)45(31(8)59-40)62-39-20-37(54-9)41(51)30(7)58-39)26(3)14-13-15-32-24-57-46-44(56-11)28(5)18-35(47(52)60-34)49(32,46)53/h13-16,18,25-26,29-31,33-46,50-51,53H,12,17,19-24H2,1-11H3/b14-13+,27-16+,32-15+/t25?,26-,29-,30-,31-,33+,34-,35-,36-,37-,38-,39-,40-,41-,42-,43+,44+,45-,46+,48-,49+/m0/s1 |
| InChI Key | JVGWUGTWQIAGHJ-DFAYUBCLSA-N |
Properties
| Appearance | White Powder |
| Antibiotic Activity Spectrum | parasites |
Reference Reading
1. Alternative production of avermectin components in Streptomyces avermitilis by gene replacement
Joon-Hyoung Yong, Woo-Hyeon Byeon J Microbiol. 2005 Jun;43(3):277-84.
The avermectins are composed of eight compounds, which exhibit structural differences at three positions. A family of four closely-related major components, A1a, A2a, B1a and B2a, has been identified. Of these components, B1a exhibits the most potent antihelminthic activity. The coexistence of the "1" components and "2" components has been accounted for by the defective dehydratase of aveAI module 2, which appears to be responsible for C22-23 dehydration. Therefore, we have attempted to replace the dehydratase of aveAI module 2 with the functional dehydratase from the erythromycin eryAII module 4, via homologous recombination. Erythromycin polyketide synthetase should contain the sole dehydratase domain, thus generating a saturated chain at the C6-7 of erythromycin. We constructed replacement plasmids with PCR products, by using primers which had been derived from the sequences of avermectin aveAI and the erythromycin eryAII biosynthetic gene cluster. If the original dehydratase of Streptomyces avermitilis were exchanged with the corresponding erythromycin gene located on the replacement plasmid, it would be expected to result in the formation of precursors which contain alkene at C22-23, formed by the dehydratase of erythromycin module 4, and further processed by avermectin polyketide synthase. Consequently, the resulting recombinant strain JW3105, which harbors the dehydratase gene derived from erythromycin, was shown to produce only C22,23-unsaturated avermectin compounds. Our research indicates that the desired compound may be produced via polyketide gene replacement.
2. Avermectin Derivatives, Pharmacokinetics, Therapeutic and Toxic Dosages, Mechanism of Action, and Their Biological Effects
Gaber El-Saber Batiha, Ali Alqahtani, Omotayo B Ilesanmi, Abdullah A Saati, Amany El-Mleeh, Helal F Hetta, Amany Magdy Beshbishy Pharmaceuticals (Basel). 2020 Aug 17;13(8):196. doi: 10.3390/ph13080196.
Avermectins are a group of drugs that occurs naturally as a product of fermenting Streptomyces avermitilis, an actinomycetes, isolated from the soil. Eight different structures, including ivermectin, abamectin, doramectin, eprinomectin, moxidectin, and selamectin, were isolated and divided into four major components (A1a, A2a, B1a and B2a) and four minor components (A1b, A2b, B1b, and B2b). Avermectins are generally used as a pesticide for the treatment of pests and parasitic worms as a result of their anthelmintic and insecticidal properties. Additionally, they possess anticancer, anti-diabetic, antiviral, antifungal, and are used for treatment of several metabolic disorders. Avermectin generally works by preventing the transmission of electrical impulse in the muscle and nerves of invertebrates, by amplifying the glutamate effects on the invertebrates-specific gated chloride channel. Avermectin has unwanted effects or reactions, especially when administered indiscriminately, which include respiratory failure, hypotension, and coma. The current review examines the mechanism of actions, biosynthesis, safety, pharmacokinetics, biological toxicity and activities of avermectins.
3. Heterologous expression of Avermectins biosynthetic gene cluster by construction of a Bacterial Artificial Chromosome library of the producers
Qian Deng, Li Zhou, Meizhong Luo, Zixin Deng, Changming Zhao Synth Syst Biotechnol. 2017 Mar 24;2(1):59-64. doi: 10.1016/j.synbio.2017.03.001. eCollection 2017 Mar.
Avermectins, a group of polyketide natural products, are widely used as anthelmintics in agriculture. Metabolic engineering and combinatorial biosynthesis were extensively employed to improve Avermectins production and create novel Avermectin derivatives, including Ivermectin and Doramectin. It is labor intensive and time cost to genetically manipulate Avermectins producer Streptomyces avermitilis in vivo. Cloning and heterologous expression of Avermectins biosynthetic gene cluster will make it possible to tailor the cluster in vitro. We constructed a Bacterial Artificial Chromosome (BAC) library of S. avermitilis ATCC 31267 with inserted DNA fragments ranged from 100 to 130 Kb. Five recombinant BAC clones which carried the Avermectins biosynthetic gene cluster ave (81 Kb in size) were screened out from the library. Then, ave was hetero-expressed in S. lividans. Three Avermectin components, A2a, B1a and A1a were detected from the cell extracts of recombinant strains. It will facilitate the development of Avermectin derivatives by polyketide synthase domain swapping and provide functional element for Avermectins synthetic biology study.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
