Antimycin A3

Antimycin A3, an antibiotic isolated from a number of Streptomyces species, shows antifungal activities. Antimycin A3 is a potent inhibitor of respiration. Antimycin A3 inhibits the electron transfer activity of ubiquinol-cytochrome c oxidoreductase. Antimycin A3 inhibits ATP-citrate lyase with a Ki value of 60.1 µM.

Product information

CAS Number: 522-70-3

Molecular Weight: 1041.14

Formula: C52H72N4O18

Chemical Name: (2R, 3S, 6S, 7R, 8R)-8-butyl-3-(3-formamido-2-hydroxybenzamido)-2, 6-dimethyl-4, 9-dioxo-1, 5-dioxonan-7-yl 2-methylbutanoate; (2R, 3S, 6S, 7R, 8R)-8-butyl-3-(3-formamido-2-hydroxybenzamido)-2, 6-dimethyl-4, 9-dioxo-1, 5-dioxonan-7-yl 3-methylbutanoate

Smiles: CC(C)CC(=O)O[C@@H]1[C@@H](CCCC)C(=O)O[C@H](C)[C@H](NC(=O)C2=CC=CC(NC=O)=C2O)C(=O)O[C@H]1C.CC(CC)C(=O)O[C@@H]1[C@@H](CCCC)C(=O)O[C@H](C)[C@H](NC(=O)C2=CC=CC(NC=O)=C2O)C(=O)O[C@H]1C

InChiKey: ZYHTWTRWVRQONG-GZAMZOJXSA-N

InChi: InChI=1S/2C26H36N2O9/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;1-6-8-10-18-22(37-24(32)14(3)7-2)16(5)36-26(34)20(15(4)35-25(18)33)28-23(31)17-11-9-12-19(21(17)30)27-13-29/h8,10-11,13-16,18,21,23,31H,6-7,9,12H2,1-5H3,(H,27,29)(H,28,32);9,11-16,18,20,22,30H,6-8,10H2,1-5H3,(H,27,29)(H,28,31)/t15-,16+,18-,21+,23+;14?,15-,16+,18-,20+,22+/m11/s1

Technical Data

Appearance: Solid Power

Purity: ≥98% (or refer to the Certificate of Analysis)

Solubility: Soluble in DMSO

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical or refer to Certificate of Analysis

Storage Condition: Dry, dark and -20 ^oC for 1 year or refer to the Certificate of Analysis.

Shelf Life: ≥360 days if stored properly.

Stock Solution Storage: 0 - 4 ^oC for 1 month or refer to the Certificate of Analysis.

Drug Formulation: To be determined

HS Tariff Code: 382200

How to use

In Vitro:

Antimycin A3 induces apoptosis of cancer cells by selectively killing cancer cells that expressed high levels of anti-apoptotic Bcl-2 and Bcl-XL.

References:

1. Ade Arsianti, et al. Synthesis and anticancer activity of polyhydroxylated 18-membered analogue of antimycin A3. Tetrahedron.Volume 68, Issue 13, 1 April 2012, Pages 2884-2891.
2. Miyoshi H, et al. Inhibition of electron transport of rat liver mitochondria by unnatural (-)-antimycin A3.
3. Barrow CJ, et al. Antimycins, inhibitors of ATP-citrate lyase, from a Streptomyces sp. J Antibiot (Tokyo). 1997 Sep;50(9):729-33.

Products are for research use only. Not for human use.