Broad-spectrum antiviral activity of adenosine analogues. 1984

E De Clercq, and D E Bergstrom, and A Holy, and J A Montgomery

In recent years certain aliphatic and carbocyclic adenosine analogues have been developed which are of potential clinical importance as antiviral agents. This includes (S)-9-(2,3-dihydroxypropyl)adenine [(S)-DHPA] and carbocyclic 3-deazaadenosine (C-c3Ado). (S)-DHPA and C-c3Ado are remarkably similar in their antiviral spectrum in that they are particularly active against (-) RNA viruses such as measles, para-influenza, respiratory syncytial virus, rabies virus, vesicular stomatitis virus and (+/-)RNA viruses such as reo- and rotavirus, whereas (+)RNA viruses such as polio, coxsackie and (+/-)DNA viruses such as herpes simplex are only minimally affected or not inhibited at all. In contrast with (S)-DHPA and C-c3Ado which are quite selective in their antiviral action, other adenosine analogues, i.e., 3-deazaadenosine and 7-deazaadenosine (tubercidin), exhibit little, if any, selectivity as antiviral agents. Also, tubercidin has a broader activity spectrum, encompassing (+)RNA viruses as well as herpes simplex in addition to the (-)RNA viruses. Considering the high antiviral potency of tubercidin, attempts have been undertaken to increase its selectivity, i.e., by chemical substitutions at C-5 of the pyrrolo(2,3-d)pyrimidine ring. These attempts have been partially successful.

UI MeSH Term Description Entries
D000241 Adenosine A nucleoside that is composed of ADENINE and D-RIBOSE. Adenosine or adenosine derivatives play many important biological roles in addition to being components of DNA and RNA. Adenosine itself is a neurotransmitter. Adenocard,Adenoscan
D000998 Antiviral Agents Agents used in the prophylaxis or therapy of VIRUS DISEASES. Some of the ways they may act include preventing viral replication by inhibiting viral DNA polymerase; binding to specific cell-surface receptors and inhibiting viral penetration or uncoating; inhibiting viral protein synthesis; or blocking late stages of virus assembly. Antiviral,Antiviral Agent,Antiviral Drug,Antivirals,Antiviral Drugs,Agent, Antiviral,Agents, Antiviral,Drug, Antiviral,Drugs, Antiviral
D013329 Structure-Activity Relationship The relationship between the chemical structure of a compound and its biological or pharmacological activity. Compounds are often classed together because they have structural characteristics in common including shape, size, stereochemical arrangement, and distribution of functional groups. Relationship, Structure-Activity,Relationships, Structure-Activity,Structure Activity Relationship,Structure-Activity Relationships
D014372 Tubercidin An antibiotic purine ribonucleoside that readily substitutes for adenosine in the biological system, but its incorporation into DNA and RNA has an inhibitory effect on the metabolism of these nucleic acids. 7-Deazaadenosine,4-Amino-7 beta-D-ribofuranosyl-7H-pyrrolo(2,3-d)pyrimidine,Deazaadenosine,7 Deazaadenosine
D014780 Viruses Minute infectious agents whose genomes are composed of DNA or RNA, but not both. They are characterized by a lack of independent metabolism and the inability to replicate outside living host cells. Animal Viruses,Zoophaginae,Animal Virus,Virus,Virus, Animal,Viruses, Animal

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