adenosine-kinase and clitocine

adenosine-kinase has been researched along with clitocine* in 2 studies

Other Studies

2 other study(ies) available for adenosine-kinase and clitocine

Article	Year
Synthesis and biological evaluation of clitocine analogues as adenosine kinase inhibitors. Bioorganic & medicinal chemistry letters, 2001, Sep-17, Volume: 11, Issue:18 Adenosine kinase (AK) is the primary enzyme responsible for adenosine metabolism. Inhibition of AK effectively increases extracellular adenosine concentrations and represents an alternative approach to enhance the beneficial actions of adenosine as compared to direct-acting receptor agonists. Clitocine (3), isolated from the mushroom Clitocybe inversa, has been found to be a weak inhibitor of AK. We have prepared a number of analogues of clitocine in order to improve its potency and demonstrated that 5'-deoxy-5'-amino-clitocine (7) improved AK inhibitory potency by 50-fold. Topics: Adenosine Kinase; Animals; Biochemistry; Drug Design; Drug Evaluation, Preclinical; Enzyme Inhibitors; Inhibitory Concentration 50; Pyrimidine Nucleosides; Rats; Structure-Activity Relationship	2001
Synthesis, intramolecular hydrogen bonding, and biochemical studies of clitocine, a naturally occurring exocyclic amino nucleoside. Journal of medicinal chemistry, 1988, Volume: 31, Issue:4 The total synthesis of clitocine [6-amino-5-nitro-4-(beta-D-ribofuranosylamino)pyrimidine] (1), a nucleoside recently isolated from the mushroom Clitocybe inversa, has been accomplished. Glycosylation of 4,6-diamino-5-nitropyrimidine (4) with 1-O-acetyl-2,3,5-tri-O-benzoyl-D-ribofuranose afforded the protected nucleoside 6-amino-5-nitro-4-[(2,3,5-tri-O-benzoyl-beta-D-ribofuranosyl) amino]pyrimidine (5) in good yield exclusively as the beta-anomer. Deprotection of 5 with NaOMe/MeOH gave 1 as an 11.5:1 mixture of the beta- and alpha-anomers, respectively. Recrystallization from MeOH, followed by chromatography, afforded 1 containing less than 1% of its alpha-anomer. X-ray crystal data revealed a planar aglycon moiety in clitocine with each oxygen atom of the nitro group intramolecularly hydrogen bonded to the hydrogen atoms of the two adjacent amino functions. Clitocine inhibited L1210 cells in vitro with an ID50 of 3 X 10(-8) M. Clitocine was also found to be a substrate and inhibitor of adenosine kinase with a Ki value of 3 X 10(-6) M. Topics: Adenosine Kinase; Animals; Antineoplastic Agents; Basidiomycota; Cell Survival; Chromatography, High Pressure Liquid; Glycosylation; Hydrogen Bonding; Leukemia L1210; Magnetic Resonance Spectroscopy; Models, Molecular; Pyrimidine Nucleosides; Structure-Activity Relationship; Tumor Cells, Cultured; X-Ray Diffraction	1988

Article

Year

Synthesis and biological evaluation of clitocine analogues as adenosine kinase inhibitors.

Bioorganic & medicinal chemistry letters, 2001, Sep-17, Volume: 11, Issue:18

Adenosine kinase (AK) is the primary enzyme responsible for adenosine metabolism. Inhibition of AK effectively increases extracellular adenosine concentrations and represents an alternative approach to enhance the beneficial actions of adenosine as compared to direct-acting receptor agonists. Clitocine (3), isolated from the mushroom Clitocybe inversa, has been found to be a weak inhibitor of AK. We have prepared a number of analogues of clitocine in order to improve its potency and demonstrated that 5'-deoxy-5'-amino-clitocine (7) improved AK inhibitory potency by 50-fold.

Topics: Adenosine Kinase; Animals; Biochemistry; Drug Design; Drug Evaluation, Preclinical; Enzyme Inhibitors; Inhibitory Concentration 50; Pyrimidine Nucleosides; Rats; Structure-Activity Relationship

2001

Synthesis, intramolecular hydrogen bonding, and biochemical studies of clitocine, a naturally occurring exocyclic amino nucleoside.

Journal of medicinal chemistry, 1988, Volume: 31, Issue:4

The total synthesis of clitocine [6-amino-5-nitro-4-(beta-D-ribofuranosylamino)pyrimidine] (1), a nucleoside recently isolated from the mushroom Clitocybe inversa, has been accomplished. Glycosylation of 4,6-diamino-5-nitropyrimidine (4) with 1-O-acetyl-2,3,5-tri-O-benzoyl-D-ribofuranose afforded the protected nucleoside 6-amino-5-nitro-4-[(2,3,5-tri-O-benzoyl-beta-D-ribofuranosyl) amino]pyrimidine (5) in good yield exclusively as the beta-anomer. Deprotection of 5 with NaOMe/MeOH gave 1 as an 11.5:1 mixture of the beta- and alpha-anomers, respectively. Recrystallization from MeOH, followed by chromatography, afforded 1 containing less than 1% of its alpha-anomer. X-ray crystal data revealed a planar aglycon moiety in clitocine with each oxygen atom of the nitro group intramolecularly hydrogen bonded to the hydrogen atoms of the two adjacent amino functions. Clitocine inhibited L1210 cells in vitro with an ID50 of 3 X 10(-8) M. Clitocine was also found to be a substrate and inhibitor of adenosine kinase with a Ki value of 3 X 10(-6) M.

Topics: Adenosine Kinase; Animals; Antineoplastic Agents; Basidiomycota; Cell Survival; Chromatography, High Pressure Liquid; Glycosylation; Hydrogen Bonding; Leukemia L1210; Magnetic Resonance Spectroscopy; Models, Molecular; Pyrimidine Nucleosides; Structure-Activity Relationship; Tumor Cells, Cultured; X-Ray Diffraction

1988