Fungichromin Chemical Properties

Melting point:

157-162° (dec)

alpha 

D20 -227.7° (c = 0.53 in DMF)

Boiling point:

914.0±65.0 °C(Predicted)

Density 

1.196±0.06 g/cm3(Predicted)

storage temp. 

Store at -20°C

solubility 

Soluble in DMSO

form 

solid

pka

12.77±0.70(Predicted)

Safety Information

Toxicity

LD50 in mice (mg/kg): 1624 orally; 33.3 i.p. (Umezawa, Tanaka)

Fungichromin Usage And Synthesis

Uses

Lagosin is a pentaene antifungal produced by Streptomyces, first isolated in 1958 by researchers at MIT in the USA. The discovery was soon followed by several independent isolations as lagosin and cogomyin. Initially these metabolites were thought to be isomeric, but Pandey and colleagues at NCI definitively demonstrated they were identical. Structurally, lagosin is 14-hydroxyfilipin III and the most polar member of the filipin family of fungicides. Lagosin exhibits broad spectrum antifungal and antitumor activity and, like filipin, acts via interaction with cell membrane sterols.

Definition

ChEBI: Fungichromin is a macrolide and an antibiotic antifungal drug.

Biological Activity

lagosin, a polyene macrolide antibiotic, has first been extracted from an isolate of a streptomyces species present in a sample of soil collected in lagos, nigeria [1]. it has been reported that the three polyene macrolide antibiotics, fungichromin, lagosin, and cogomycin, showed some stereochemical differences at one or more centers [1].lagosin was the most polar member of the filipin family of fungicides with broad spectrum antifungal and antitumor activity, acting via interaction with cell membrane sterols. the antibiotic lagosin, which appeared to be identical to, or a stereoisomer of, fungichromin, and was very similar in structure to the filipins [2]. the equilibrium constants for association of the polyene antibiotics with aqueous suspensions of cholesterol follow the order filipin iil > amphotericin b > nystatin > lagosin, in agreement with the order reported for the extent of damage these antibiotics cause in natural and model membranes [2].

References

[1] pandey r c, guenther e c, aszalos a a, et al. physicochemical and biological comparison of polyene macrolide antibiotics fungichromin, lagosin and cogomycin[j]. the journal of antibiotics, 1982, 35(8): 988-996.
[2] bittman r, fischkoff s a. fluorescence studies of the binding of the polyene antibiotics filipin iii, amphotericin b, nystatin, and lagosin to cholesterol[j]. proceedings of the national academy of sciences, 1972, 69(12): 3795-3799.

Fungichromin(6834-98-6)Related Product Information

• Fungichromin
• ETHYL (S)-3-HYDROXY-TETRADECANOATE
• FILIPIN III