Biocatalytic modifications of ethynodiol diacetate by fungi, anti-proliferative activity, and acetylcholineterase inhibitory of its transformed products
| Autor: | Sharifah Nurfazilah Wan Yusop, Kamran Ashraf, Syahrul Imran, Sadia Sultan, Mohd Ilham Adenan |
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| Rok vydání: | 2021 |
| Předmět: |
Ketone
Metabolite Clinical Biochemistry 030209 endocrinology & metabolism Inhibitory postsynaptic potential Biochemistry Ethynodiol Diacetate 03 medical and health sciences chemistry.chemical_compound 0302 clinical medicine Endocrinology Molecular Biology Biotransformation Botrytis cinerea Pharmacology chemistry.chemical_classification biology Organic Chemistry biology.organism_classification Acetylcholinesterase Trichothecium roseum Enzyme chemistry 030220 oncology & carcinogenesis Hypocreales Botrytis |
| Zdroj: | Steroids. 171:108832 |
| ISSN: | 0039-128X |
| Popis: | The fungal transformations of ethynodiol diacetate (1) were investigated for the first-time using Botrytis cinerea, Trichothecium roseum, and R3-2 SP 17. The metabolites obtained are as following: 17α-Ethynyl-17β-acetoxyestr-4-en-3-one-15β-ol (2), 19-nor-17a-ethynyltestosterone (3), and 17α-ethynyl-3β-hydroxy-17β-acetoxyestr-4-ene (4). The new metabolite, 2 (IC50 = 104.8 µM), which has ketone group at C-3, and the β-hydroxyl group at C-15, resulted in an almost equipotent strength with the parent compound (IC50 = 103.3 µM) against proliferation of SH-SY5Y cells. The previously reported biotransformed product, 3, showed almost equal strength to 1 against acetylcholinesterase. Molecular modelling studies were carried out to understand the observed experimental activities, and also to obtain more information on the binding mode and the interactions between the biotransformed products, and enzyme. |
| Databáze: | OpenAIRE |
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