Synthesis and anti-DNA -virus activity of the 5'-monophosphate and the cyclic 3',5'-monophosphate of 9-(beta-D-xylofuranosyl) guanine. 1976

G R Revankar, and J H Huffman, and R W Sidwell, and R L Tolman, and R K Robins, and L B Allen

9-(beta-TD-xylofuranosyl)guanine (xylo-G) was converted chemically to the 9-(beta-D-xylofuranosyl)guanine 5'-monophosphate (xylo-GMP) and 9-(beta-D-xylofuranosyl)guanine cyclic 3',5'-monophosphate (c-xylo-GMP). These compounds were tested against a variety of DNA viruses in tissue culture in parallel with 9-(beta-D-arabinofuranosyl)adenine (ara-A). This evaluation revealed that xylo-G, xylo-GMP, and c-xylo-GMP were all moderately active but less effective than ara-A. When the four compounds were administered intracerebrally as a treatment for herpes virus, type 1 induced encephalitis in mice, c-xylo-GMP exhibited superior activity to that shown by the other three. When administered intraperitoneally, c-xylo-GMP was found to have a therapeutic index of about 4, which is less than that for ara-A (approximately 30) in the same system.

UI MeSH Term Description Entries
D009712 Nucleotides, Cyclic Cyclic Nucleotide,Cyclic Nucleotides,Nucleotide, Cyclic
D003588 Cytopathogenic Effect, Viral Visible morphologic changes in cells infected with viruses. It includes shutdown of cellular RNA and protein synthesis, cell fusion, release of lysosomal enzymes, changes in cell membrane permeability, diffuse changes in intracellular structures, presence of viral inclusion bodies, and chromosomal aberrations. It excludes malignant transformation, which is CELL TRANSFORMATION, VIRAL. Viral cytopathogenic effects provide a valuable method for identifying and classifying the infecting viruses. Cytopathic Effect, Viral,Viral Cytopathogenic Effect,Cytopathic Effects, Viral,Cytopathogenic Effects, Viral,Effect, Viral Cytopathic,Effect, Viral Cytopathogenic,Effects, Viral Cytopathic,Effects, Viral Cytopathogenic,Viral Cytopathic Effect,Viral Cytopathic Effects,Viral Cytopathogenic Effects
D004267 DNA Viruses Viruses whose nucleic acid is DNA. DNA Virus,Virus, DNA,Viruses, DNA
D004671 Encephalitis, Arbovirus Infections of the brain caused by arthropod-borne viruses (i.e., arboviruses) primarily from the families TOGAVIRIDAE; FLAVIVIRIDAE; BUNYAVIRIDAE; REOVIRIDAE; and RHABDOVIRIDAE. Life cycles of these viruses are characterized by ZOONOSES, with birds and lower mammals serving as intermediate hosts. The virus is transmitted to humans by the bite of mosquitoes (CULICIDAE) or TICKS. Clinical manifestations include fever, headache, alterations of mentation, focal neurologic deficits, and COMA. (From Clin Microbiol Rev 1994 Jan;7(1):89-116; Walton, Brain's Diseases of the Nervous System, 10th ed, p321) Arthropod-Borne Encephalitis,Australian Encephalitis,Encephalitis, Epidemic,Mosquito-Borne Encephalitis,Murray Valley Encephalitis,Arboviral Encephalitis,Arthropod-Borne Viral Encephalitis,Encephalitis, Arthropod-Borne,Encephalitis, Mosquito-Borne,Epidemic Encephalitis,Viral Encephalitis, Arthropod-Borne,Arboviral Encephalitides,Arbovirus Encephalitides,Arbovirus Encephalitis,Arthropod Borne Encephalitis,Arthropod Borne Viral Encephalitis,Arthropod-Borne Encephalitides,Arthropod-Borne Viral Encephalitides,Encephalitis, Arboviral,Encephalitis, Arthropod Borne,Encephalitis, Arthropod-Borne Viral,Encephalitis, Australian,Encephalitis, Mosquito Borne,Encephalitis, Murray Valley,Epidemic Encephalitides,Mosquito Borne Encephalitis,Mosquito-Borne Encephalitides,Valley Encephalitis, Murray,Viral Encephalitis, Arthropod Borne
D006150 Guanine Nucleotides Guanine Nucleotide,Guanosine Phosphates,Nucleotide, Guanine,Nucleotides, Guanine,Phosphates, Guanosine
D006152 Cyclic GMP Guanosine cyclic 3',5'-(hydrogen phosphate). A guanine nucleotide containing one phosphate group which is esterified to the sugar moiety in both the 3'- and 5'-positions. It is a cellular regulatory agent and has been described as a second messenger. Its levels increase in response to a variety of hormones, including acetylcholine, insulin, and oxytocin and it has been found to activate specific protein kinases. (From Merck Index, 11th ed) Guanosine Cyclic 3',5'-Monophosphate,Guanosine Cyclic 3,5 Monophosphate,Guanosine Cyclic Monophosphate,Guanosine Cyclic-3',5'-Monophosphate,3',5'-Monophosphate, Guanosine Cyclic,Cyclic 3',5'-Monophosphate, Guanosine,Cyclic Monophosphate, Guanosine,Cyclic-3',5'-Monophosphate, Guanosine,GMP, Cyclic,Guanosine Cyclic 3',5' Monophosphate,Monophosphate, Guanosine Cyclic
D006564 Herpesviridae A family of enveloped, linear, double-stranded DNA viruses infecting a wide variety of animals. Subfamilies, based on biological characteristics, include: ALPHAHERPESVIRINAE; BETAHERPESVIRINAE; and GAMMAHERPESVIRINAE. Mouse Thymic Virus,Murid herpesvirus 3,Thymic Group Viruses,Herpesviruses,Mouse Thymic Viruses,Thymic Virus, Mouse,Thymic Viruses, Mouse
D006566 Herpesviridae Infections Virus diseases caused by the HERPESVIRIDAE. Herpesvirus Infections,B Virus Infection,Infections, Herpesviridae,Infections, Herpesvirus,B Virus Infections,Herpesviridae Infection,Herpesvirus Infection,Infection, B Virus,Infection, Herpesviridae,Infection, Herpesvirus,Infections, B Virus
D000818 Animals Unicellular or multicellular, heterotrophic organisms, that have sensation and the power of voluntary movement. Under the older five kingdom paradigm, Animalia was one of the kingdoms. Under the modern three domain model, Animalia represents one of the many groups in the domain EUKARYOTA. Animal,Metazoa,Animalia
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

Related Publications

G R Revankar, and J H Huffman, and R W Sidwell, and R L Tolman, and R K Robins, and L B Allen
January 1973, Chemotherapy,
G R Revankar, and J H Huffman, and R W Sidwell, and R L Tolman, and R K Robins, and L B Allen
March 1974, Journal of medicinal chemistry,
G R Revankar, and J H Huffman, and R W Sidwell, and R L Tolman, and R K Robins, and L B Allen
March 1970, Journal of pharmaceutical sciences,
G R Revankar, and J H Huffman, and R W Sidwell, and R L Tolman, and R K Robins, and L B Allen
July 1984, The Journal of biological chemistry,
G R Revankar, and J H Huffman, and R W Sidwell, and R L Tolman, and R K Robins, and L B Allen
January 1967, Journal of medicinal chemistry,
G R Revankar, and J H Huffman, and R W Sidwell, and R L Tolman, and R K Robins, and L B Allen
November 1977, The Journal of organic chemistry,
G R Revankar, and J H Huffman, and R W Sidwell, and R L Tolman, and R K Robins, and L B Allen
January 2001, Nucleosides, nucleotides & nucleic acids,
G R Revankar, and J H Huffman, and R W Sidwell, and R L Tolman, and R K Robins, and L B Allen
December 1976, Antimicrobial agents and chemotherapy,
G R Revankar, and J H Huffman, and R W Sidwell, and R L Tolman, and R K Robins, and L B Allen
November 1980, Cancer research,
Copied contents to your clipboard!