Antimycin A3
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| Category | Bioactive by-products |
| Catalog number | BBF-00554 |
| CAS | 522-70-3 |
| Molecular Weight | 520.57 |
| Molecular Formula | C26H36N2O9 |
| Purity | >98% by HPLC |
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Description
Antimycin A is a macrolide antibiotic produced by Streptomyces kitasawaensis, Str. griseus and Str. antibioticus. Antimycin A3 can inhibit atp-citrate lyase activity.
Specification
| Synonyms | Blastomycin |
| Storage | Store at -20°C |
| IUPAC Name | [(2R,3S,6S,7R,8R)-8-butyl-3-[(3-formamido-2-hydroxybenzoyl)amino]-2,6-dimethyl-4,9-dioxo-1,5-dioxonan-7-yl] 3-methylbutanoate |
| Canonical SMILES | CCCCC1C(C(OC(=O)C(C(OC1=O)C)NC(=O)C2=C(C(=CC=C2)NC=O)O)C)OC(=O)CC(C)C |
| InChI | InChI=1S/C26H36N2O9/c1-6-7-9-18-23(37-20(30)12-14(2)3)16(5)36-26(34)21(15(4)35-25(18)33)28-24(32)17-10-8-11-19(22(17)31)27-13-29/h8,10-11,13-16,18,21,23,31H,6-7,9,12H2,1-5H3,(H,27,29)(H,28,32)/t15-,16+,18-,21+,23+/m1/s1 |
| InChI Key | PVEVXUMVNWSNIG-PDPGNHKXSA-N |
| Source | Streptomyces sp. |
Properties
| Appearance | White Solid |
| Antibiotic Activity Spectrum | fungi; parasites; neoplastics (Tumor) |
| Boiling Point | 745.5°C at 760 mmHg |
| Melting Point | 174-175°C |
| Density | 1.25 g/cm3 |
| Solubility | Soluble in DMSO |
Reference Reading
1. Zhaoshumycins A and B, Two Unprecedented Antimycin-Type Depsipeptides Produced by the Marine-Derived Streptomyces sp. ITBB-ZKa6
Shiying Ma, Ruihua Jiao, Zhikai Guo, Shiqing Zhang, Hongjie Zhu, Salman Khan, Bo Zhang Mar Drugs . 2021 Nov 5;19(11):624. doi: 10.3390/md19110624.
Marine actinomycetes are prolific chemical sources of complex and novel natural products, providing an excellent chance for new drug discovery. The chemical investigation of the marine-derivedStreptomycessp. ITBB-ZKa6, from Zhaoshu island, Hainan, led to the discovery of two unique antimycin-type depsipeptides, zhaoshumycins A (1) and B (2), along with the isolation of the four known neoantimycins A (3), F (4), D (5), and E (6). The structures of the new compounds1and2were elucidated on the basis of the analysis of diverse spectroscopic data and biogenetic consideration. Zhaoshumycins A (1) and B (2) represent a new class of depsipeptides, featuring two neoantimycin monomers (only neoantimycin D or neoantimycins D and E) linked to a 1,4-disubstituted benzene ring via an imino group. Initial toxicity tests of1-6in MCF7 human breast cancer cells revealed that compounds5and6possess weak cytotoxic activity. Further structure-activity relationship analysis suggested the importance of the NH2group at C-34 in5and6for cytotoxicity in MCF7 cells.
2. Inhibition of electron transport of rat liver mitochondria by unnatural (-)-antimycin A3
I Saitoh, T Oritani, H Miyoshi, H Kondo, H Iwamura FEBS Lett . 1991 Nov 4;292(1-2):61-3. doi: 10.1016/0014-5793(91)80834-p.
The inhibition of electron transport by unnatural (-)-antimycin A3 was examined with rat liver mitochondria and compared with that of natural (+)-antimycin A3. (-)-Antimycin A3 inhibited respiration about 1/100th as strongly as natural (+)-antimycin A3. (-)-Antimycin A3 binding to the cytochrome bc1 complex did not seem to induce a conformational change in this proteinous complex. The binding site of (-)-antimycin A3 was probably the same as that of (+)-antimycin A3 (at the Qi center). However, the mode of interaction with the Qi center by (-)-antimycin A3 and (+)-antimycin A3 was somewhat different.
3. mmu-lncRNA 121686/hsa-lncRNA 520657 induced by METTL3 drive the progression of AKI by targeting miR-328-5p/HtrA3 signaling axis
Zhibiao He, Zhenyu Peng, Xiaozhou Li, Dongshan Zhang, Yijian Li, Jian Pan, Xudong Xiang, Jun Zhou, Junxiang Chen, Yunchang Yuan, Xiangfeng Liu, Xianming Tang, Huiling Li, Hongliang Zhang, Yuxin Xie Mol Ther . 2022 Dec 7;30(12):3694-3713. doi: 10.1016/j.ymthe.2022.07.014.
The pathogenesis of acute kidney injury (AKI) is still not fully understood, and effective interventions are lacking. Here, we explored whether methyltransferase 3 (METTL3) was involved in the progression of AKI via regulation of cell death. We reported that PT(proximal tubule)-METTL3-knockout (KO) noticeably suppressed ischemic-induced AKI via inhibition of renal cell apoptosis. Furthermore, we also found that the expression of mmu-long non-coding RNA (lncRNA) 121686 was upregulated in antimycin-treated Boston University mouse proximal tubule (BUMPT) cells and a mouse ischemia-reperfusion (I/R)-induced AKI model. Functionally, mmu-lncRNA 121686 could promote I/R-induced mouse renal cell apoptosis. Mechanistically, mmu-lncRNA 121686 acted as a competing endogenous RNA (ceRNA) to prevent microRNA miR-328-5p-mediated downregulation of high-temperature requirement factor A 3 (Htra3). PT-mmu-lncRNA 121686-KO mice significantly ameliorated the ischemic-induced AKI via the miR-328-5p/HtrA3 axis. In addition, hsa-lncRNA 520657, homologous with lncRNA 121686, sponged miR-328-5p and upregulated Htra3 to promote I/R-induced human renal cell apoptosis. Interestingly, we found that mmu-lncRNA 121686/hsa-lncRNA 520657 upregulation were dependent on METTL3 via N6-methyladenosine (m6A) modification. The mmu-lncRNA 121686/miR-328-5p or hsa-lncRNA 520657/miR-328-5p /HtrA3 axis was induced in vitro by METTL3 overexpression; in contrast, this effect was attenuated by METTL3 small interfering RNA (siRNA). Furthermore, we found that PT-METTL3-KO or METTL3 siRNA significantly suppressed ischemic, septic, and vancomycin-induced AKI via downregulation of the mmu-lncRNA 121686/miR-328-5p/HtrA3 axis. Taken together, our data indicate that the METTL3/mmu-lncRNA 121686/hsa-lncRNA 520657/miR-328-5p/HtrA3 axis potentially acts as a therapeutic target for AKI.
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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 ╳
