Antrimycin A

Antrimycin A

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Category Antibiotics
Catalog number BBF-00054
CAS 80801-26-9
Molecular Weight 685.72
Molecular Formula C28H47N9O11
Purity >98%

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Description

Antrimycin is a peptide antibiotic produced by Streptomyces xanthocidicus MG125-CF1. Antrimycin A has anti-Mycobamrimn smegmatis (Mycobamrimn smegmatis) and human Mycobacterium tuberculosis H37 Rv activity, and also has an effect on rifampicin and capreomycin-resistant bacteria.

Specification

Synonyms Antrimycin; Cirratiomycin B; L-Serine, 2-(hydroxymethyl)seryl-L-alanyl-L-erythro-alpha,beta-diaminobutyryl-L-2,3,4,5-tetrahydro-3-pyridazinecarbonyl-L-alanyl-(E)-2,3-didehydroisoleucyl-
Storage Store at -20°C
IUPAC Name (2S)-2-[[(E)-2-[[(2S)-2-[[(3S)-2-[(2S,3S)-3-amino-2-[[(2S)-2-[[2-amino-3-hydroxy-2-(hydroxymethyl)propanoyl]amino]propanoyl]amino]butanoyl]-4,5-dihydro-3H-pyridazine-3-carbonyl]amino]propanoyl]amino]-3-methylpent-2-enoyl]amino]-3-hydroxypropanoic acid
Canonical SMILES CCC(=C(C(=O)NC(CO)C(=O)O)NC(=O)C(C)NC(=O)C1CCC=NN1C(=O)C(C(C)N)NC(=O)C(C)NC(=O)C(CO)(CO)N)C
InChI InChI=1S/C28H47N9O11/c1-6-13(2)19(24(44)34-17(10-38)26(46)47)35-21(41)15(4)32-23(43)18-8-7-9-31-37(18)25(45)20(14(3)29)36-22(42)16(5)33-27(48)28(30,11-39)12-40/h9,14-18,20,38-40H,6-8,10-12,29-30H2,1-5H3,(H,32,43)(H,33,48)(H,34,44)(H,35,41)(H,36,42)(H,46,47)/b19-13+/t14-,15-,16-,17-,18-,20-/m0/s1
InChI Key JIGYSKMCUNIKPN-KYVSZOTASA-N

Properties

Appearance Colorless Amorphous Powder
Antibiotic Activity Spectrum mycobacteria; Gram-positive bacteria
Melting Point 183°C
Solubility Soluble in DMSO

Reference Reading

1. Antimycin A induced apoptosis in HCT-116 colorectal cancer cells through the up- and downregulation of multiple signaling pathways
Syed Rashel Kabir, Tofazzal Islam Med Oncol. 2022 Dec 17;40(1):51. doi: 10.1007/s12032-022-01901-x.
Colorectal cancer is the third most life-threatening cancer in the western countries. For the treatment, several chemotherapeutic drugs are using those that have severe side effects on the patient. So, finding alternative drugs is important. In the present research antimycin A was selected to evaluate the anticancer properties on the HCT-116 colorectal cancer cells. Antimycin A inhibited HCT-116 cells proliferation with the IC50 value of 29 µg/mL concentration. As a long-term effect, HCT-116 cells were incubated with 10-40 µg/mL concentration of antimycin A for 7 days. No colony was observed in the treated wells. Apoptotic features in HCT-116 cells were observed in antimycin A treated cells after being stained with Hoechst 33342 dye. Apoptosis was further confirmed by FITC-annexin V/PI. Role of caspase-3 protein in the apoptosis process was also confirmed by the caspase-3 inhibitor. After treatment of HCT-116 cells with antimycin A, apoptotic related gene expression was checked by reverse transcription polymerase chain reaction. p53 and caspase-9 genes were upregulated consequently mitogen-activated protein kinases (MAPK), poly(ADP-Ribose) polymerase (PARP), and nuclear factor kappa B (NF-κB) genes were downregulated. Molecular docking simulation indicated significant binding affinity of antimycin A with the five proteins. The results indicated antimycin A would be a promising anticancer agent for further anticancer research.
2. A Standalone β-Ketoreductase Acts Concomitantly with Biosynthesis of the Antimycin Scaffold
Asif Fazal, Glyn R Hemsworth, Michael E Webb, Ryan F Seipke ACS Chem Biol. 2021 Jul 16;16(7):1152-1158. doi: 10.1021/acschembio.1c00229. Epub 2021 Jun 20.
Antimycins are anticancer compounds produced by a hybrid nonribosomal peptide synthetase/polyketide synthase (NRPS/PKS) pathway. The biosynthesis of these compounds is well characterized, with the exception of the standalone β-ketoreductase enzyme AntM that is proposed to catalyze the reduction of the C8 carbonyl of the antimycin scaffold. Inactivation of antM and structural characterization suggested that rather than functioning as a post-PKS tailoring enzyme, AntM acts upon the terminal biosynthetic intermediate while it is tethered to the PKS acyl carrier protein. Mutational analysis identified two amino acid residues (Tyr185 and Phe223) that are proposed to serve as checkpoints controlling substrate access to the AntM active site. Aromatic checkpoint residues are conserved in uncharacterized standalone β-ketoreductases, indicating that they may also act concomitantly with synthesis of the scaffold. These data provide novel mechanistic insights into the functionality of standalone β-ketoreductases and will enable their reprogramming for combinatorial biosynthesis.
3. Zhaoshumycins A and B, Two Unprecedented Antimycin-Type Depsipeptides Produced by the Marine-Derived Streptomyces sp. ITBB-ZKa6
Zhikai Guo, Shiying Ma, Salman Khan, Hongjie Zhu, Bo Zhang, Shiqing Zhang, Ruihua Jiao 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-derived Streptomyces sp. 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 compounds 1 and 2 were 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 of 1-6 in MCF7 human breast cancer cells revealed that compounds 5 and 6 possess weak cytotoxic activity. Further structure-activity relationship analysis suggested the importance of the NH2 group at C-34 in 5 and 6 for cytotoxicity in MCF7 cells.

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