Binding of benanomicin A to fungal cells in reference to its fungicidal action.
An antifungal antibiotic, benanomicin A, binds in the presence of Ca2+ to susceptible fungi and some bacteria, but not to antibiotic-resistant bacteria and mammalian cells. With the susceptible yeast Saccharomyces cerevisiae, benanomicin A binds similarly to whole cells and to protoplasts. Studies using benanomicin A and three structurally related derivatives suggested that a carboxylic acid in the D-alanine moiety and a sugar moiety in the benanomicin A molecule are essential for both binding and antifungal activities against growing S. cerevisiae. An amino substituent on the sugar moiety can be replaced with a hydroxyl group without the loss of activities. Benanomicin A binds to various yeast mannans which differ in glycosidic linkages. These results indicate that binding of benanomicin A to the mannan portion of fungal cells is essential for exertion of the antifungal activity.
Watanabe
M
M
Pharmaceutical Research Center, Meiji Seika Kaisha, Ltd., Yokohama, Japan.
Gomi
S
S
Tohyama
H
H
Ohtsuka
K
K
Shibahara
S
S
Inouye
S
S
Kobayashi
H
H
Suzuki
S
S
Kondo
S
S
Takeuchi
T
T
Yamaguchi
H
H
D018943:Anthracyclines; D000903:Antibiotics, Antineoplastic / Q000737:chemistry / Q000378:metabolism* / Q000494:pharmacology; D000935:Antifungal Agents / Q000737:chemistry / Q000378:metabolism* / Q000494:pharmacology; D002118:Calcium / Q000378:metabolism; D002176:Candida albicans / Q000187:drug effects / Q000378:metabolism; D008351:Mannans / Q000737:chemistry / Q000378:metabolism; D011523:Protoplasts / Q000187:drug effects; D012441:Saccharomyces cerevisiae / Q000187:drug effects / Q000378:metabolism; D013329:Structure-Activity Relationship; D015003:Yeasts / Q000737:chemistry / Q000187:drug effects / Q000378:metabolism*; D000095643:Pradimicins and Benanomicins
D018943:Anthracyclines; D000903:Antibiotics, Antineoplastic; D000935:Antifungal Agents; D002118:Calcium; D008351:Mannans; C056805:benanomicin A; D000095643:Pradimicins and Benanomicins; C056806:benanomicin B