69-33-0 Usage
Description
Tubercidin, a nucleoside metabolite first isolated from Streptomyces tubericidus, is a broad-spectrum, potent chemotherapeutic agent with activity against various pathogens, including viruses, bacteria, fungi, protozoans, and tumors. It functions as a nucleoside mimic of adenosine and exerts its effects at multiple sites, such as RNA processing, nucleic acid, and protein synthesis.
Uses
Used in Antiviral Applications:
Tubercidin is used as an antiviral agent for its ability to inhibit viral replication and activity, providing a broad-spectrum approach to treating various viral infections.
Used in Antibacterial Applications:
In the field of antibacterial therapy, Tubercidin is used as a potent agent to combat bacterial infections, targeting essential cellular processes and inhibiting bacterial growth.
Used in Antifungal Applications:
Tubercidin is utilized as an antifungal agent, effective against a range of fungal species, disrupting their growth and proliferation.
Used in Antiprotozoan Applications:
As an antiprotozoan agent, Tubercidin is employed to treat infections caused by protozoan parasites, interfering with their life cycle and essential cellular functions.
Used in Anticancer Applications:
Tubercidin is used as an anticancer agent, targeting tumor cells and inhibiting their growth and proliferation by interfering with nucleic acid and protein synthesis, as well as RNA processing.
Used in Research Applications:
In research settings, Tubercidin serves as a valuable tool for studying the mechanisms of action of nucleoside analogs and their effects on various cellular processes, including those related to disease-causing organisms and cancer cells.
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.
Check Digit Verification of cas no
The CAS Registry Mumber 69-33-0 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 6 and 9 respectively; the second part has 2 digits, 3 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 69-33:
(4*6)+(3*9)+(2*3)+(1*3)=60
60 % 10 = 0
So 69-33-0 is a valid CAS Registry Number.
InChI:InChI=1/C11H14N4O4/c12-9-5-1-2-15(10(5)14-4-13-9)11-8(18)7(17)6(3-16)19-11/h1-2,4,6-8,11,16-18H,3H2,(H2,12,13,14)/t6-,7-,8-,11-/m1/s1
69-33-0Relevant articles and documents
NUCLEOSIDE ANALOGUES FOR THE TREATMENT OF PARASITIC INFECTIONS
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Page/Page column 40, (2019/05/10)
The present invention relates to novel nucleoside analogues and compositions containing said nucleoside analogues. Moreover, the present invention provides processes for the preparation of the disclosed compounds, as well as methods of using them, for instance as a medicine, in particular for the diagnosis, prevention and/or treatment of parasitic infections, more specifically for use in the diagnosis, prevention and/or treatment of a Trypanosoma infection.
Glycosylation of Pyrrolo[2,3- d]pyrimidines with 1- O-Acetyl-2,3,5-tri- O-benzoyl-β- d -ribofuranose: Substituents and Protecting Groups Effecting the Synthesis of 7-Deazapurine Ribonucleosides
Ingale, Sachin A.,Leonard, Peter,Seela, Frank
, p. 8589 - 8595 (2018/06/25)
Glycosylation of nonfunctionalized 6-chloro-7-deazapurine with commercially available 1-O-acetyl-2,3,5-tri-O-benzoyl-β-d-ribofuranose (45%) followed by amination and deprotection gave tubercidin in only two steps. Similar conditions applied for the synthe
CYCLIC DINUCLEOTIDES AS AGONISTS OF STIMULATOR OF INTERFERON GENE DEPENDENT SIGNALLING
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Paragraph 0278, (2018/09/26)
Disclosed herein are new cyclic dinucleotide compounds and compositions and their application as pharmaceuticals for the treatment of disease. Methods of modulation of immune response to disease, and induce Stimulator of Interferon Genes (STING) dependent type I interferon production and co-regulated genes in a human or animal subject are also provided for the treatment diseases such as cancer, particularly metastatic solid tumors and lymphomas, inflammation, allergic and autoimmune disease, infectious disease, and for use as anti-viral agents and vaccine adjuvants.