TUBERCIDIN Chemical Properties

Melting point:

247-248 °C (decomp)(Solv: water (7732-18-5))

alpha 

D17 -67° (50% acetic acid)

Boiling point:

409.46°C (rough estimate)

Density 

1.2896 (rough estimate)

refractive index 

1.8340 (estimate)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

Soluble in DMSO

form 

powder

pka

12.44±0.70(Predicted)

color 

off-white

Merck 

13,9875

BRN 

38498

Stability:

Hygroscopic

InChIKey

HDZZVAMISRMYHH-UIRWVKCDSA-N

CAS DataBase Reference

69-33-0

Safety Information

Hazard Codes 

T+

Risk Statements 

28

Safety Statements 

36/37/39-45

RIDADR 

UN 3462 6.1/PG 2

WGK Germany 

3

RTECS 

UY8870000

F 

10

HazardClass 

6.1(a)

PackingGroup 

II

HS Code 

29419090

Toxicity

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

MSDS

• Language:English Provider:SigmaAldrich

TUBERCIDIN Usage And Synthesis

Chemical Properties

White crystal

Uses

Tubercidin is a nucleoside metabolite first isolated from Streptomyces tubericidus. Tubercidin, like other nucleosides, is a broad spectrum, potent chemotherapeutic agent active against viruses, bacteria, fungi, protozoans and tumours. Tubercidin acts at a diverse range of sites, such as RNA processing, nucleic acid and protein synthesis, and acts as a nucleoside mimic of adenosine.

Definition

ChEBI: 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.

Biological Activity

tubercidin is an adenosine analog antibiotic agent.nucleoside antibiotics are a family of natural products with various biological functions. their biosynthesis is a complex process via multistep enzymatic reactions.

in vitro

previous study showed that tubercidin alone had a dose-dependent inhibitory effect on myeloid and erythroid human bone marrow progenitor cells. bfu-e were more sensitive at higher doses of tubercidin than cfu-gm. the 99% complete inhibition of bfu-e colonies was observed at 10 nm tubercidin, whereas complete inhibition of cfu-gm occurred at 100 nm [1].

in vivo

animal toxicity study showed that four successive daily injections of tubercidin at 5 mg/kg per day could produce 100% mouse mortality within 3 to 5 days, with massive peritonitis and intestinal obstruction. in addition, coadministration of nbmpr-p at 25 mg/kg per day could protect the mice from the tubercidin lethality and allow the repetition of the regimen for a second time with 100% survival [1].

IC 50

3.4 and 3.7 nm for granulocyte-macrophage cfu (cfu-gm) and erythroid burst-forming units (bfu-e), respectively

Purification Methods

7-Deazaadenosine forms needles from hot H2O. It is soluble in H2O (0.33%), MeOH (0.5%) and EtOH (0.05%). It has UV max at 270nm ( 12,100) in 0.001N NaOH. The picrate has m 229-231o(dec). [Tolman et al. J Am Chem Soc 91 2102 1969, Mizuno et al. J Org Chem 28 3329 1963, IR: Anzai et al. J Antibiot (Japan) [9] 10 201 1957, Beilstein 26 IV 1117.]

References

[1] el kouni mh,diop d,o'shea p,carlisle r,sommadossi jp. prevention of tubercidin host toxicity by nitrobenzylthioinosine 5'-monophosphate for the treatment of schistosomiasis. antimicrob agents chemother.1989 jun;33(6):824-7.
[2] grage tb,rochlin db,weiss aj,wilson wl. clinical studies with tubercidin administered after absorption into human erythrocytes. cancer res.1970 jan;30(1):79-81.

TUBERCIDIN(69-33-0)Related Product Information

• API-2
• SANGIVAMYCIN
• 5-IODOTUBERCIDIN
• 4-AMINO-5-CYANO-7-(BETA-D-RIBOFURANOSYL)PYRROLO[2,3-D]PYRIMIDINE
• tubercidin 5'-phosphate,TUBERCIDIN-5'-O-MONOPHOSPHATE SODIUM SALT,tubercidin-5-monophosphat
• thiosangivamycin
• 7-DEAZA-A CEP
• Triciribine
• TUBERCIDIN
• tubercidin 3',5'-cyclic phosphate
• ara-tubercidin
• tubercidin 5'-triphosphate
• tubercidin-5'-diphosphate
• ara-tubercidin 5'-triphosphate
• tubercidin 5'-diphosphate-5'-1,2-dipalmitin
• TUBERCIDIN, [5-3H]
• SANGIVAMYCIN, [3H]-
• 7-DEAZA-7-CARBAMOYLADENOSINE HYDRATE