Monactin

Names

[ Name ]:
Monactin

[Synonym ]:
Nonactin,5-demethyl-5-ethyl
5-ethyl-2,11,14,20,23,29,32-heptamethyl-4,13,22,31,37,38,39,40-octaoxapentacyclo[32.2.1.17,10.116,19.125,28]tetracontane-3,12,21,30-tetrone
Akd-1B

Biological Activity

[Description]:

Monactin is a mactrotetralide antibiotic and a non-selective ionophore for monovalent cations, including potassium, sodium, and lithium. Monactin is isolated from Streptomyces and has antiproliferative activity[1][2][3].

[Related Catalog]:

Research Areas >> Infection

Signaling Pathways >> Anti-infection >> Bacterial

[In Vitro]

Monactin displays strong antiproliferative activity against A2780 ovarian cancer cells (IC50 0.13 μM), A2058 melanoma cells (0.02 μM), and H522-T1 non small-cell cancer lung cells (0.01 μM)[3]. Monactin inhibits TCF/β-catenin transcriptional activity[4]. At a concentration of 10 μM, nigericin and monactin inhibited growth of Streptococcus faecalis, and the inhibition was reversed by addition of excess K(+)[5].

[In Vivo]

Monactin is potent uncoupler of oxidative phosphorylation and inducer of ATP hydrolysis in rat liver mitochondria[1].

[References]

[1]. Graven SN, et al. Antibiotics as tools for metabolic studies. VI. Damped oscillatory swelling of mitochondria induced by nonactin, monactin, dinactin, and trinactin. Biochemistry. 1966;5(5):1735-1742.

[2]. Murer H, et al. On the mechanism of sugar and amino acid interaction in intestinal transport. J Biol Chem. 1975;250(18):7392-7396.

[3]. Harinantenaina Rakotondraibe L, et al. Antiproliferative and antiplasmodial compounds from selected Streptomyces species. Bioorg Med Chem Lett. 2015;25(23):5646-5649.

[4]. Tamai, Y, et al. Nonactin and related compounds found in a screening program for wnt signal inhibitory activity. Heterocycles, 84(2), 1245-1250.

[5]. Harold FM, et al. Effects of nigericin and monactin on cation permeability of Streptococcus faecalis and metabolic capacities of potassium-depleted cells. J Bacteriol. 1968;95(3):816-823.

Chemical & Physical Properties

[ Density]:
1.035g/cm3

[ Boiling Point ]:
896.9ºC at 760 mmHg

[ Molecular Formula ]:
C₄₁H₆₆O₁₂

[ Molecular Weight ]:
750.95600

[ Flash Point ]:
353.8ºC

[ Exact Mass ]:
750.45500

[ PSA ]:
142.12000

[ LogP ]:
6.41210

[ Index of Refraction ]:
1.451