Abstract
6'-Cyano-5',6'-didehydro-6'-deoxyhomoadenosine (E)-1, (Z)-1, and 6'-chloro-6'-cyano-5',6'-didehydro-6'-deoxyhomoadenosine (E)-2 were synthesized and tested as new mechanism-based inhibitors of AdoHcy hydrolase. Nucleoside (E)-1 was identified as a type I inhibitor of the enzyme, whereas inactivation of the enzyme by nucleosides (Z)-1 and (E)-2 was accompanied by the formation of a covalent labeling of AdoHcy hydrolase.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Adenosylhomocysteinase / antagonists & inhibitors*
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Adenosylhomocysteinase / chemistry
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Antineoplastic Agents / chemical synthesis*
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Antineoplastic Agents / chemistry
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Antineoplastic Agents / pharmacology
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Antiviral Agents / chemical synthesis*
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Antiviral Agents / chemistry
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Antiviral Agents / pharmacology
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Cells, Cultured
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Cytomegalovirus / drug effects
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Deoxyadenosines / chemical synthesis*
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Deoxyadenosines / chemistry
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Deoxyadenosines / pharmacology
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Herpesvirus 3, Human / drug effects
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Humans
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Nucleosides / chemical synthesis*
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Nucleosides / chemistry
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Nucleosides / pharmacology
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Stereoisomerism
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Structure-Activity Relationship
Substances
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6'-chloro-6'-cyano-5',6'-didehydro-6'-deoxyhomoadenosine
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6'-cyano-5',6'-didehydro-6'-deoxyhomoadenosine
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Antineoplastic Agents
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Antiviral Agents
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Deoxyadenosines
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Nucleosides
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Adenosylhomocysteinase