Mensacarcin

Mensacarcin, a highly complex polyketide, strongly inhibits cell growth universally in cancer cell lines and potently induces apoptosis in melanoma cells. Mensacarcin targets to mitochondria, affects energy metabolism in mitochondria, and activates caspase-dependent apoptotic pathways. Mensacarcin, an antibiotic, can be used as a cytotoxic component of antibody-drug conjugates (ADCs).

Product information

CAS Number: 808750-39-2

Molecular Weight: 420.41

Formula: C21H24O9

Chemical Name: (1S, 9S, 10S, 11S, 12S, 13S, 14R)-11, 12, 14-trihydroxy-7, 9-dimethoxy-13-methyl-12-[(2R, 3S)-3-methyloxirane-2-carbonyl]-15-oxatetracyclo[8.4.1.0, .0, ]pentadeca-3, 5, 7-trien-2-one

Smiles: C[C@@H]1O[C@H]1C(=O)[C@@]1(O)[C@H](O)[C@@]23O[C@]2([C@H](O)[C@@H]1C)C(=O)C1=CC=CC(OC)=C1[C@@H]3OC

InChiKey: WWNXYRCJJRRWAQ-ALCXHWRFSA-N

InChi: InChI=1S/C21H24O9/c1-8-14(22)20-15(23)10-6-5-7-11(27-3)12(10)17(28-4)21(20,30-20)18(25)19(8,26)16(24)13-9(2)29-13/h5-9,13-14,17-18,22,25-26H,1-4H3/t8-,9-,13+,14+,17-,18-,19+,20+,21+/m0/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: ≥12 months 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:

Mensacarcin (0-100 μM; 24 hours) exhibits general cytostatic but type-specific cytotoxic effects for melanoma cells. Mensacarcin (2-50 μM; 15 hours) induces rapid apoptotic cell death in melanoma cells. Mensacarcin exhibits potent cytostatic properties (mean of 50% growth inhibition=0.2 μM) in almost all cell lines of the National Cancer Institute (NCI)-60 cell line screen and relatively selective cytotoxicity against melanoma cells. Mensacarcin is a highly oxygenated polyketide that was first isolated from soil-dwelling Streptomyces bacteria. Mensacarcin impairs mitochondrial function in melanoma cells.

References:

1. Birte Plitzko, et al. The natural product mensacarcin induces mitochondrial toxicity and apoptosis in melanoma cells. J Biol Chem. 2017 Dec 22;292(51):21102-21116.
2. Lutz F. Tietze, et al. Intramolecular Heck Reactions for the Synthesis of the Novel Antibiotic Mensacarcin: Investigation of Catalytic, Electronic and Conjugative Effects in the Preparation of the Hexahydroanthracene Core. Chemistry Europe. Volume2005, Issue9.

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