3484-65-9
Chemical Structure
Aspergillomarasmine A
- CAS No.: 3484-65-9
- Formula:C10H17N3O8
- Molecular Weight:307.26
IUPAC Name: ((S)-2-(((S)-2-amino-2-carboxyethyl)amino)-2-carboxyethyl)-L-aspartic acid
InChIKey: XFTWUNOVBCHBJR-ZLUOBGJFSA-N
SMILES: O=C(O)C[C@@H](C(O)=O)NC[C@H](NC[C@H](N)C(O)=O)C(O)=O
Biological Activity: Aspergillomarasmine A is a fungal secondary metabolite derived from natural amino acids, with inhibitory activity against metallo-β-lactamases. Aspergillomarasmine A selectively inhibits the metallo-β-lactamases NDM-1 and VIM-2, but shows weak inhibitory activity against IMP-7. Aspergillomarasmine A exhibits metal ion selectivity, which enables it to capture spontaneously dissociated Zn2+ from NDM-1, inducing the monozincation and inactivation of the enzyme; the inactivated metallo-β-lactamase undergoes protein degradation in the bacterial periplasm, thereby restoring the bacteriostatic efficacy of carbapenem antibiotics. Aspergillomarasmine A can be used in studies related to bacterial infections[1][2][3].
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Aspergillomarasmine A | Aspergillomarasmine A is a fungal secondary metabolite derived from natural amino acids, with inhibitory activity against metallo-β-lactamases. Aspergillomarasmine A selectively inhibits the metallo-β-lactamases NDM-1 and VIM-2, but shows weak inhibitory activity against IMP-7. Aspergillomarasmine A exhibits metal ion selectivity, which enables it to capture spontaneously dissociated Zn2+ from NDM-1, inducing the monozincation and inactivation of the enzyme; the inactivated metallo-β-lactamase undergoes protein degradation in the bacterial periplasm, thereby restoring the bacteriostatic efficacy of carbapenem antibiotics. Aspergillomarasmine A can be used in studies related to bacterial infections. | |||||||||||||||||||||
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References
- [1]. King AM, et al. Aspergillomarasmine A overcomes metallo-β-lactamase antibiotic resistance. Nature. 2014 Jun 26;510(7506):503-6.
- [2]. Zhang J, et al. Synthesis and biological evaluation of Aspergillomarasmine A derivatives as novel NDM-1 inhibitor to overcome antibiotics resistance. Bioorganic & medicinal chemistry. 2017 Oct 01;25(19):5133-5141.
- [3]. Sychantha D, et al. Aspergillomarasmine A inhibits metallo-β-lactamases by selectively sequestering Zn. The Journal of biological chemistry. 2021 Aug;297(2):100918. [Content Brief]
