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| | TUBERCIDIN Basic information |
| Product Name: | TUBERCIDIN | | Synonyms: | TUBERCIDIN;TUBERCIDINE;3-d)pyrimidin-4-amine,7-beta-d-ribofuranosyl-7h-pyrrolo(;3-d)pyrimidine,4-amino-7-beta-d-ribofuranosyl-7h-pyrrolo(;4-amino-7-(beta-d-ribofuranosyl)-pyrrolo(2,3-d)pyrimidine;4-amino-7-beta-d-ribofuranosyl-7h-pyrrolo(2,3-d)pyrimidine;7-beta-d-ribofuranosyl-7h-pyrrolo(2,3-d)pyrimidine-4-amine;7-deaza-adenosin | | CAS: | 69-33-0 | | MF: | C11H14N4O4 | | MW: | 266.25 | | EINECS: | 200-703-4 | | Product Categories: | | | Mol File: | 69-33-0.mol |  |
| | 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 | | pka | 12.44±0.70(Predicted) | | form | powder | | color | off-white | | Merck | 13,9875 | | BRN | 38498 | | Stability: | Hygroscopic | | InChIKey | HDZZVAMISRMYHH-UIRWVKCDSA-N | | CAS DataBase Reference | 69-33-0 |
| 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) |
| | 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 Preparation Products And Raw materials |
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