Siccanin Chemical Properties

Melting point:

139-140°

alpha 

D20 -136° (c = 2 in chloroform)

Boiling point:

427.8±45.0 °C(Predicted)

Density 

1.18±0.1 g/cm3(Predicted)

storage temp. 

Store at -20°C

solubility 

DMF: Soluble; DMSO: Soluble; Ethanol: Soluble; Methanol: Soluble

form 

A solid

pka

10.9(at 25℃)

Safety Information

Toxicity

LD50 in mice, rats (mg/kg): >6000, >1000 orally; >3000, >600 s.c. or i.p. (Suzuki)

Siccanin Usage And Synthesis

Description

Siccanin is an inhibitor of mitochondrial complex II (succinate dehydrogenase; IC₅₀s = 0.87 and 9.3 μM for P. aeruginosa and rat mitochondria, respectively). It inhibits the growth of T. mentagrophytes (IC₅₀ = 0.3 μg/ml) via inhibition of succinate oxidation in the mitochondria. It also inhibits the growth of C. albicans strains with IC₅₀ values ranging from 5-40 and 80-90 μg/ml for aerobic and anaerobic conditions, respectively.

Uses

Siccanin is an unusual, fused, phenolic pentacycle first isolated from Helminthosporium siccans and reported in 1962 as a potent antifungal agent. Siccanin inhibits succinate dehydrogenase in the terminal electron transport system. More recent studies note the proximity of the siccanin binding site to the quinone-binding site of the enzyme. Species-selective inhibition by siccanin is unique among succinate dehydrogenase inhibitors and offers a lead for new chemotherapeutics.

Uses

Siccanin is an antifungal and SDHB (IP) inhibitor.

Definition

ChEBI: Siccanin is an organic heteropentacyclic compound. It has a role as an antifungal drug and a fungal metabolite.

Origin

Siccanin was found in the culture broth of Helminthosporium siccans by Sankyo Co. in 1962.

Biological Activity

Siccanin shows specific and strong ac tivity against the dermatophytes Trichophyton, Epidermophyton, and Microsporum, but ithas almost no activity against other fungi.

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