Antimycin A1
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| Category | Bioactive by-products |
| Catalog number | BBF-00552 |
| CAS | 642-15-9 |
| Molecular Weight | 548.62 |
| Molecular Formula | C28H40N2O9 |
| 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 A1 can inhibit atp-citrate lyase activity.
Specification
| Synonyms | dihydrosamidin |
| Storage | Store at -20°C |
| IUPAC Name | [3-[(3-formamido-2-hydroxybenzoyl)amino]-8-hexyl-2,6-dimethyl-4,9-dioxo-1,5-dioxonan-7-yl] 3-methylbutanoate |
| Canonical SMILES | CCCCCCC1C(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/C28H40N2O9/c1-6-7-8-9-11-20-25(39-22(32)14-16(2)3)18(5)38-28(36)23(17(4)37-27(20)35)30-26(34)19-12-10-13-21(24(19)33)29-15-31/h10,12-13,15-18,20,23,25,33H,6-9,11,14H2,1-5H3,(H,29,31)(H,30,34) |
| InChI Key | UIFFUZWRFRDZJC-UHFFFAOYSA-N |
| Source | Streptomyces sp. |
Properties
| Appearance | White solid |
| Boiling Point | 777.8°C at 760 mmHg |
| Melting Point | 149-150°C |
| Density | 1.22 g/cm3 |
| Solubility | Soluble in ethanol, methanol, DMF or DMSO. Poor water solubility. |
Reference Reading
1. Inhibition of angiogenesis and HIF-1alpha activity by antimycin A1
Kiyoshi Egawa, Kiyoshi Nose, Masayuki Maeda, Motoko Shibanuma, Yuki Hasebe Biol Pharm Bull . 2006 Jul;29(7):1344-8. doi: 10.1248/bpb.29.1344.
We identified antimycin A1 as an inhibitor of the hypoxia-response element (HRE) from screening using a reporter under the control of HRE under hypoxic conditions. Antimycin A1 was effective at 20 pg/ml in inhibiting the reporter activity. The expression of vascular endothelial growth factor (VEGF) mRNA during hypoxia was also inhibited by antimycin A1. Angiogenesis induced by implantation of mouse sarcoma-180 cells was significantly inhibited by non-toxic doses of antimycin A1. Hypoxia inducible factor (HIF)-1alpha protein levels were significantly decreased by antimycin A1, but its mRNA level was not affected. Antimycin A1 is known to be an inhibitor of mitochondrial electron transport system, and depletion of mitochondria abolished antimycin A1-effect, at least in part. Inhibitors of proteasome or protein synthesis did not affect the decrease in HIF-1alpha level induced by antimycin A1. These results indicate that antimycin A1 inhibited angiogenesis through decrease in VEGF production caused by inhibition of HIF-1alpha activation.
2. Structure-activity-distribution relationship study of anti-cancer antimycin-type depsipeptides
Yupeng Miao, Xuejun Zhu, Jeremy Seidel, William Porterfield, Wei Min, Wenlong Cai, Fanghao Hu, Santi Bhattarai-Kline, Seong-Jong Kim, Wenjun Zhang Chem Commun (Camb) . 2019 Aug 1;55(63):9379-9382. doi: 10.1039/c9cc03051d.
Small-molecule natural products have been an essential source of pharmaceuticals to treat human diseases, but very little is known about their behavior inside dynamic, live human cells. Here, we demonstrate the first structure-activity-distribution relationship (SADR) study of complex natural products, the anti-cancer antimycin-type depsipeptides, using the emerging bioorthogonal Stimulated Raman Scattering (SRS) Microscopy. Our results show that the intracellular enrichment and distribution of these compounds are driven by their potency and specific protein targets, as well as the lipophilic nature of compounds.
3. The pharmacological regulation of cellular mitophagy
Michelangelo Campanella, Geoff Wells, Nikolaos D Georgakopoulos Nat Chem Biol . 2017 Jan 19;13(2):136-146. doi: 10.1038/nchembio.2287.
Small molecules are pharmacological tools of considerable value for dissecting complex biological processes and identifying potential therapeutic interventions. Recently, the cellular quality-control process of mitophagy has attracted considerable research interest; however, the limited availability of suitable chemical probes has restricted our understanding of the molecular mechanisms involved. Current approaches to initiate mitophagy include acute dissipation of the mitochondrial membrane potential (ΔΨm) by mitochondrial uncouplers (for example, FCCP/CCCP) and the use of antimycin A and oligomycin to impair respiration. Both approaches impair mitochondrial homeostasis and therefore limit the scope for dissection of subtle, bioenergy-related regulatory phenomena. Recently, novel mitophagy activators acting independently of the respiration collapse have been reported, offering new opportunities to understand the process and potential for therapeutic exploitation. We have summarized the current status of mitophagy modulators and analyzed the available chemical tools, commenting on their advantages, limitations and current applications.
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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 ╳
