Premium
Die fungitoxische Wirkung von 2,2′:5′,2″‐Tertiophen‐Derivaten
Author(s) -
Mares D.,
Romagnoli C.,
Rossi R.,
Carpita A.,
Ciofalo M.,
Bruni A.
Publication year - 1994
Publication title -
mycoses
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.13
H-Index - 69
eISSN - 1439-0507
pISSN - 0933-7407
DOI - 10.1111/myc.1994.37.9-10.377
Subject(s) - terthiophene , thiophene , chemistry , substituent , stereochemistry , antifungal , asteraceae , biological activity , biology , organic chemistry , biochemistry , in vitro , microbiology and biotechnology , botany
Summary The dermatophyte Microsporum cookei Ajello was treated with nine new natural and synthetic 2,2′: 5′,2″‐terthiophenes to determine their possible antifungal activity. In the dark the thiophenes were inactive, while when photoactivated with UV‐A they induced a remarkable reduction in the growth rate of the fungus. The only exception was (E)‐ N ‐(2‐methylpropyl)‐3‐(2,2′: 5′,2″‐terthien‐5‐yl)‐propenamide, which was not fungistatic even at the highest dose tested (24 μ m ). The more active compounds were 3 1 ‐methoxy‐2,2′: 5′,2″‐terthiophene and 3′‐methylthio‐2,2′ : 5′,2″‐terthiophene, whose activity seems to be related to the presence of a substituent in the 3′ position of the central ring of thiophenes. Transmission electron microscopic observations demonstrated the photoactive nature of the synthetic molecules to be similar to that of α‐terthienyl, a natural thiophene present in some Asteraceae. The dark treatment caused only the accumulation of the compound in vacuoles, without other evident alterations. After UV‐A irradiation the activated thiophene causes severe modifications to the endomembrane system, probably via oxygen‐dependent mechanism.