Tubercidin, 杀结核菌素

Antibiotic; RNA and DNA synthesis inhibitor; adenosine analogue.

Tubercidin is an antibiotic and adenosine analog isolated from the bacterium Streptomyces tubercidicus with potential antineoplastic activity. Tubercidin is incorporated into DNA and inhibits polymerases, thereby inhibiting DNA replication and RNA and protein synthesis. This agent also exhibits antifungal and antiviral activities. (NCI04)

Tubercidin is an N-glycosylpyrrolopyrimidine that is adenosine in which the in the 5-membered ring that is not attached to the ribose moiety is replaced by a carbon. Tubercidin is produced in the culture broth of Streptomyces tubericidus. It has a role as an antineoplastic agent, a bacterial metabolite and an antimetabolite. It is a N-glycosylpyrrolopyrimidine, a ribonucleoside and an antibiotic antifungal agent.

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.

Title: Tubercidin

CAS Registry Number: 69-33-0

CAS Name: 7-b-D-Ribofuranosyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine

Additional Names: 4-amino-7-b-D-ribofuranosyl-7H-pyrrolo[2,3-d]pyrimidine; 7-deazaadenosine; sparsamycin A

Manufacturers' Codes: U-10071

Molecular Formula: C11H14N4O4

Molecular Weight: 266.25

Percent Composition: C 49.62%, H 5.30%, N 21.04%, O 24.04%

Literature References: Antibiotic substance produced in the culture broth of Streptomyces tubericidus. Isoln: Anzai et al., J. Antibiot. 10A, 201 (1957). Structure: Susuki, Marumo, ibid. 14A, 34 (1961). Total synthesis: Tolman et al., J. Am. Chem. Soc. 91, 2102 (1969). Crystal structure: Stroud, Acta Crystallogr. 29B, 690 (1973); Abola, Sundaralingham, ibid. 697.

Properties: Needles from water, dec 247-248°. [a]D17 -67° (50% acetic acid). uv max (0.01N NaOH): 270 nm (e 12,100). Sol in acidic and alkaline soln. One gram dissolves in 330 ml water, 200 ml methanol, 2000 ml ethanol. Practically insol in acetone, ethyl acetate, chloroform, benzene, petr ether. LD50 i.v. in mice: 45 mg/kg (Anzai).

Optical Rotation: [a]D17 -67° (50% acetic acid)

Absorption maximum: uv max (0.01N NaOH): 270 nm (e 12,100)

Toxicity data: LD50 i.v. in mice: 45 mg/kg (Anzai)