Nebularine,9 - (b-D-呋喃核糖)嘌呤

9-(b-D-Ribofuranosyl)purine

9-(b-D-Ribofuranosyl)purine (9-BRP) is a purine nucleoside that is used in the synthesis of dyes. It has been shown to be an effective inhibitor of the enzyme phosphodiesterase 3B, which breaks down cyclic adenosine monophosphate (cAMP), and therefore can prevent kidney fibrosis. 9-BRP has also been shown to inhibit the synthesis of collagen by binding to cAMP. In addition, 9-BRP binds to DNA and forms hydrogen bonds with nitrogen atoms on the phosphate groups in DNA. This interaction prevents the formation of hydrogen bonds between water molecules in water vapor and phosphate groups, thus slowing down their rate of dissociation from each other. 9-BRP also has a high affinity for Toll-like receptor 4 (TLR4), which is involved in the inflammatory response, making it an ideal therapeutic candidate for treating inflammation and renal fibrosis.

Title: Nebularine

CAS Registry Number: 550-33-4

CAS Name: 9-b-D-Ribofuranosyl-9H-purine

Molecular Formula: C10H12N4O4

Molecular Weight: 252.23

Percent Composition: C 47.62%, H 4.80%, N 22.21%, O 25.37%

Literature References: Isoln from the mushroom Clitocybe nebularis (Batsch.) Quel., Agaricaceae: Ehrenberg et al., Sven. Kem. Tidskr. 58, 269 (1946); Löfgren et al., Acta Chem. Scand. 8, 670 (1954); from a streptomycete: Isono, Suzuki, J. Antibiot. 13A, 270 (1960). In vitro toxicity towards sarcoma 180 cells, mouse embryonic fibroblasts and epithelial cells: J. J. Biescle et al., Cancer 8, 87 (1955). Synthesis: Brown, Weliky, J. Biol. Chem. 204, 1019 (1953); Fox et al., J. Am. Chem. Soc. 80, 1669 (1958); Hashizume, Iwamura, Tetrahedron Lett. 1966, 643; eidem, J. Org. Chem. 33, 1796 (1968). Crystal structure: T. Takeda, Acta Crystallogr. 30B, 825 (1974). Alternate syntheses: V. Nair, S. G. Richardson, Tetrahedron Lett. 1979, 1181; P. K. Gupta, D. S. Bhakuni, Indian J. Chem. 20B, 534 (1981). Toxicity studies: Truant, D'Amato, Fed. Proc. 14, 391 (1955).

Properties: Small rhombohedra from ethyl methyl ketone + methanol, mp 181-182°; needles from methanol, mp 182-183°. [a]D25 -48.6° (H2O). uv max (0.1N HCl): 262 nm (E1%1cm 232); (0.1N NaOH): 263 nm (E1%1cm 361). Considerably sol in water (about 10%). Slightly sol in cold ethanol. Very slightly sol in acetone, ether, chloroform. Aq solns may be sterilized by boiling without decompn. LD50 in rats, guinea pigs (mg/kg): 220, 15 s.c. (Truant, D'Amato).

Melting point: mp 181-182°; mp 182-183°

Optical Rotation: [a]D25 -48.6° (H2O)

Absorption maximum: uv max (0.1N HCl): 262 nm (E1%1cm 232); (0.1N NaOH): 263 nm (E1%1cm 361)

Toxicity data: LD50 in rats, guinea pigs (mg/kg): 220, 15 s.c. (Truant, D'Amato)