Mensacarcin

Modify Date: 2024-01-14 22:48:08

Mensacarcin Structure
Mensacarcin structure
Common Name Mensacarcin
CAS Number 808750-39-2 Molecular Weight 420.410
Density 1.5±0.1 g/cm3 Boiling Point 656.8±55.0 °C at 760 mmHg
Molecular Formula C21H24O9 Melting Point N/A
MSDS N/A Flash Point 232.9±25.0 °C

 Use of 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)[1][2].

 Names

Name (1S,9S,10S,11S,12S,13S,14R)-11,12,14-Trihydroxy-7,9-dimethoxy-13-methyl-12-{[(2R,3S)-3-methyl-2-oxiranyl]carbonyl}-15-oxatetracyclo[8.4.1.01,10.03,8]pentadeca-3,5,7-trien-2-one
Synonym More Synonyms

 Mensacarcin Biological Activity

Description 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)[1][2].
Related Catalog
Target

Traditional Cytotoxic Agents

In Vitro Mensacarcin (0-100 μM; 24 hours) exhibits general cytostatic but type-specific cytotoxic effects for melanoma cells[1]. Mensacarcin (2-50 μM; 15 hours) induces rapid apoptotic cell death in melanoma cells[1]. 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[1]. Cell Viability Assay[1] Cell Line: SK-Mel-28 and SK-Mel-5 melanoma cells, HCT-116 colon cancer cells Concentration: 0.01, 0.1, 1, 10, 100 μM Incubation Time: 24 hours Result: Induced concentration- and time-dependent cell death in the two tested melanoma cell lines. HCT-116 colon carcinoma cells were strongly inhibited. Western Blot Analysis[1] Cell Line: SK-Mel-28, SK-Mel-5 cells Concentration: 2, 10, 50 μM Incubation Time: 15 hours Result: Induced the formation of 89-kDa PARP-1 fragments as well as caspase-3 activation in SK-Mel-28 and SK-Mel-5 beginning between 6 and 15 h after exposure.
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.

 Chemical & Physical Properties

Density 1.5±0.1 g/cm3
Boiling Point 656.8±55.0 °C at 760 mmHg
Molecular Formula C21H24O9
Molecular Weight 420.410
Flash Point 232.9±25.0 °C
Exact Mass 420.142029
LogP 5.48
Vapour Pressure 0.0±2.1 mmHg at 25°C
Index of Refraction 1.647

 Synonyms

(1S,9S,10S,11S,12S,13S,14R)-11,12,14-Trihydroxy-7,9-dimethoxy-13-methyl-12-{[(2R,3S)-3-methyl-2-oxiranyl]carbonyl}-15-oxatetracyclo[8.4.1.01,10.03,8]pentadeca-3,5,7-trien-2-one
4a,9a-Epoxyanthracen-9(10H)-one, 1,2,3,4-tetrahydro-1,3,4-trihydroxy-5,10-dimethoxy-2-methyl-3-[[(2R,3S)-3-methyloxiranyl]carbonyl]-, (1R,2S,3S,4S,4aS,9aS,10S)-