Aculeacin A
Aculeacin A is a β-1,3-glucan synthase inhibitor. Aculeacin A is an antifungal antibiotic. Aculeacin A inhibits cell wall glucan synthesis in growing yeast cells, induces cell lysis, osmotic fragility, cell aggregation and abnormal cell morphology, without affecting the synthesis of proteins, nucleic acids or mannan. Aculeacin A acts only on growing yeast cells and has a narrow antifungal spectrum, mainly targeting Candida and Torulopsis species. Aculeacin A shows reduced activity in human serum and exhibits a paradoxical dose-response pattern. Aculeacin A has an inoculum effect against some Candida albicans strains, and its activity is pH-stable. Aculeacin A can be used in studies of fungal infections, such as those caused by Candida, Torulopsis and other species.
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- CAS 番号: 58814-86-1
- 分子式: C50H81N7O16
- 分子量:1036.22
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保管条件:
Please store the product under the recommended conditions in the Certificate of Analysis.
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生物活性
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Lipopeptide |
Aculeacin A (0.05-0.5 μg/mL; up to 20 hours) completely inhibits the growth of Saccharomyces cerevisiae Hansen 0209 strain at a concentration of 0.5 μg/mL, and partially inhibits its growth at 0.2 μg/mL, when incubated in glucose-peptone medium for up to 20 hours[2].
Aculeacin A (0.5-50 μg/mL; up to 4 h) exhibits fungicidal activity against actively growing cells of Saccharomyces cerevisiae Hansen 0209 strain, and reduces cell viability within 2 h of incubation, but has no effect on the viability of non-growing resting cells even at the highest concentration of 50 μg/mL[2].
Aculeacin A (5 μg/mL; 1 hour) causes cell lysis at the budding tips of Saccharomyces cerevisiae Hansen 0209 strain within 1 hour of incubation in glucose-peptone medium[2].
Aculeacin A (5 μg/mL; 10 minutes pre-incubation, followed by incubation for up to 90 minutes) inhibits the incorporation of [U-14C]glucose into acid-insoluble fractions of Saccharomyces cerevisiae Hansen 0209 cells, but exerts no effect on the incorporation of [1-14C]leucine or [2-14C]uridine after up to 90 minutes of incubation with the radioactive precursors[2].
Aculeacin A (5 μg/mL; 10 minutes pre-incubation followed by 30 minutes treatment) selectively inhibits the incorporation of [U-14C] glucose into the glucan component of the cell wall of Saccharomyces cerevisiae Hansen 0209 strain, reducing the incorporation level to 45.7% of that in the control group, while exerting minimal effects on mannan synthesis[2].
Aculeacin A (10-100 μg/mL) weakly induces protoplast lysis of Saccharomyces cerevisiae Hansen 0209 only at the relatively high concentration of 100 μg/mL, while no effect is observed at 10 μg/mL[2].
Aculeacin A (5 μg/mL; 1 hour) induces membrane invagination and the formation of membranous spherical bodies in the gap between the cell wall and cytoplasm in intact Saccharomyces cerevisiae Hansen 0209 strain cells after 1 hour of incubation[2].
The inhibitory activity of Aculeacin A against 6 strains of Candida albicans is almost unaffected by variations in medium pH within the range of 3.0 to 8.0[3].
Aculeacin A (0.02-20 μg/mL; 6 hours) exhibits fungicidal activity against actively growing Candida albicans, Candida tropicalis, and Torulopsis glabrata, with its lethal activity peaking at concentrations ranging from 0.08 to 0.31 μg/mL, while higher concentrations reduce its fungicidal effect[3].
Aculeacin A (0.02-20 μg/mL; up to 6 hours) exerts paradoxical fungicidal and growth-inhibitory effects on exponentially growing Candida albicans MTU 12077 cells, with activity peaking at 0.08~1.25 μg/mL and decreasing at higher concentrations[4].
Studies show that Aculeacin A (0.31 μg/mL; 0-6 hours) exerts no effect on non-proliferating Candida albicans cells, but significantly reduces the viability of proliferating cells at the same concentration[4].
Aculeacin A (0.08-1.25 μg/mL; 30 minutes) induces visible aggregates in exponentially growing susceptible yeast cells, including Candida albicans, but does not induce aggregation in non-susceptible yeast strains[4].
Aculeacin A (0.08-20 μg/mL; 6 hours) induces concentration-dependent morphological changes in exponentially growing Candida albicans MTU 12077 cells. It causes cell lysis at concentrations ranging from 0.08 to 0.31 μg/mL, and induces abnormally large cell morphology at a concentration of 20 μg/mL[4].
Aculeacin A (0.31-20 μg/mL; 3 hours) induces osmotically sensitive cells in Candida albicans MTU 12077, with lower concentrations resulting in greater sensitivity, while osmotic stabilization inhibits the drug-induced cell aggregation[4].
Aculeacin A (0.01-100 μg/mL; 20 minutes pre-incubation) preferentially inhibits the synthesis of alkali-insoluble glucan in osmotically stabilized exponential-phase Candida albicans MTU 12077 cells (with an inhibition rate of approximately 80% at 0.31 μg/mL), and exhibits an anomalous dose-response: the inhibitory effect reaches a peak at 0.31 μg/mL, while the inhibition weakens at higher concentrations[4].
Aculeacin A (0.31-20 μg/mL; 3 hours) induces alkali-insoluble glucan-deficient Candida albicans MTU 12077 cells, with their glucan content reduced to ~20-23% of that in the control group, while other cellular components are minimally affected[4].
Aculeacin A (0.08-80 μg/mL; 60 minutes) inhibits β-(1,3)-glucan synthase activity in cell-free extracts of Candida albicans MTU 12077 and Saccharomyces cerevisiae MTU 09018 (with maximum inhibition rates of up to 64% at 8 μg/mL and up to 75% at 0.8 μg/mL), and the inhibitory effect weakens at higher concentrations[4].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
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Cell Line:Saccharomyces cerevisiae strain Hansen 0209 cells
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Concentration:0.05 μg/mL, 0.2 μg/mL, 0.5 μg/mL
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Incubation Time:up to 20 hours
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Result:Completely inhibited growth over the 20-hour incubation period at 0.5 μg/mL.
Partially reduced growth compared to untreated controls at 0.2 μg/mL.
Showed minimal growth inhibition relative to higher concentrations at 0.05 μg/mL.
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Cell Line:Saccharomyces cerevisiae strain Hansen 0209 cells
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Concentration:tested concentrations (growth-permissive medium); 5 μg/mL, 50 μg/mL (non-growth buffer)
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Incubation Time:up to 4 hours (growth-permissive medium); up to 4 hours (non-growth buffer)
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Result:Exerted a fungicidal effect at all tested concentrations in growth-permissive glucose-peptone medium, with a distinct decrease in viable cells occurring within the first 2 hours, followed by a gradual reduction in the rate of cell death.
Caused no decrease in viable cells at 5 μg/mL or 50 μg/mL over 4 hours in non-growth 0.1 M phosphate buffer.
化学情報
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CAS 番号 58814-86-1
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分子量 1036.22
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分子式 C50H81N7O16
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SMILES
CCCCCCCCCCCCCCCC(NC1C(NC(C(O)C)C(N2C(CC(O)C2)C(NC(C(O)C(O)C3=CC=C(O)C=C3)C(NC(C(O)C)C(N4C(C(O)C(C)C4)C(NC(O)C(O)C1)=O)=O)=O)=O)=O)=O)=O
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輸送条件
Room temperature in continental US; may vary elsewhere.
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保管条件
Please store the product under the recommended conditions in the Certificate of Analysis.
純度とドキュメンテーション
参考文献
[1]. Zhang F, et al. Biochemical and genetic characterization of fungal proline hydroxylase in echinocandin biosynthesis. Applied microbiology and biotechnology. 2018 Sep;102(18):7877-7890. [Content Brief]
[2]. Mizoguchi J, et al. On the mode of action of a new antifungal antibiotic, aculeacin A: inhibition of cell wall synthesis in Saccharomyces cerevisiae. The Journal of antibiotics. 1977 Apr;30(4):308-13. [Content Brief]
[3]. Iwata K et al. In vitro studies of aculeacin A, a new antifungal antibiotic. J Antibiot (Tokyo). 1982 Feb;35(2):203-9. [Content Brief]
[4]. Yamaguchi H et al. Studies on the mechanism of antifungal action of aculeacin A. J Antibiot (Tokyo). 1982 Feb;35(2):210-9. [Content Brief]
Calculators
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