title: Antiviral and antimetabolic activities of neplanocins.
abstract: Of a series of carbocyclic analogs of adenosine, in which the ribose moiety was replaced by a cyclopentenyl ring, neplanocin A, or (-)-9-[trans-2, trans-3-dihydroxy-4-(hydroxymethyl)cyclopent-4-enyl]adenine proved particularly effective in inhibiting the multiplication of DNA viruses (i.e., vaccinia), (-)RNA viruses (i.e., parainfluenza, measles, and vesicular stomatitis), and double-stranded RNA viruses (i.e., reo) in vitro in cell culture. Depending on the cells used, the MIC of neplanocin A for these viruses ranged from 0.01 to 4 micrograms/ml, and depending on the parameter used to assess toxicity for the host cell, the specificity index of neplanocin A ranged from 50 to 4,000. As postulated before for other adenosine analogs, neplanocin A may owe its antiviral action to inhibition of S-adenosylhomocysteine hydrolase, hence perturbation of transmethylation reactions. In vivo, neplanocin A afforded only marginal protection against a lethal infection of mice with vesicular stomatitis virus.
mesh_terms: D000241:Adenosine / Q000031:analogs & derivatives / Q000494:pharmacology; D000818:Animals; D000903:Antibiotics, Antineoplastic / Q000494:pharmacology*; D000963:Antimetabolites / Q000494:pharmacology*; D000998:Antiviral Agents / Q000494:pharmacology*; D006367:HeLa Cells / Q000382:microbiology; D007668:Kidney; D051379:Mice; D011817:Rabbits; D018139:Simplexvirus / Q000187:drug effects; D014721:Vesicular stomatitis Indiana virus / Q000187:drug effects; D014777:Virus Diseases / Q000188:drug therapy; D014779:Virus Replication / Q000187:drug effects
chemical_list: D000903:Antibiotics, Antineoplastic; D000963:Antimetabolites; D000998:Antiviral Agents; C031098:neplanocin C; C031096:neplanocin A; D000241:Adenosine