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TUBERCIDIN

Product Name
TUBERCIDIN
CAS No.
69-33-0
Chemical Name
TUBERCIDIN
Synonyms
(2R,3R,4S,5R)-2-(4-amino-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol;b120121;u-10071;CS-2599;nsc56408;ski26996;TUBERCIDIN;Aids051983;7-Deaza-Ar;7-Deaza-rA
CBNumber
CB0461137
Molecular Formula
C11H14N4O4
Formula Weight
266.25
MOL File
69-33-0.mol
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TUBERCIDIN Property

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
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Safety

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)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H300Fatal if swallowed

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P301+P310IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
T0642
Product name
Tubercidin
Purity
from
Packaging
10mg
Price
$227
Updated
2024/03/01
Sigma-Aldrich
Product number
T0642
Product name
Tubercidin
Purity
from
Packaging
50mg
Price
$337.6
Updated
2024/03/01
Sigma-Aldrich
Product number
T0642
Product name
Tubercidin
Purity
from
Packaging
250mg
Price
$2540
Updated
2024/03/01
TRC
Product number
T897070
Product name
TubercidinTrifluoroacetate
Packaging
100mg
Price
$970
Updated
2021/12/16
Usbiological
Product number
295770
Product name
7-Deazaadenosine
Packaging
10mg
Price
$355
Updated
2021/12/16
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TUBERCIDIN Chemical Properties,Usage,Production

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

Raw materials

Preparation Products

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View Lastest Price from TUBERCIDIN manufacturers

WUHAN FORTUNA CHEMICAL CO., LTD
Product
7-Deaza-adeonsine 69-33-0
Price
US $0.00-0.00/g
Min. Order
10g
Purity
97%min
Supply Ability
100kgs
Release date
2021-09-07
Career Henan Chemical Co
Product
TUBERCIDIN 69-33-0
Price
US $5.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
1ton
Release date
2019-08-02

69-33-0, TUBERCIDINRelated Search:

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

  • 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
  • antibiotic155b2t
  • antibioticxk101-1
  • b120121
  • nsc56408
  • 7-Deazaadenosine, XK 101-1, NSC 56408, SparsoMycin A, U 10071
  • Sparsamycin A
  • N7-Deazaadenosine
  • (2R,3R,4S,5R)-2-(4-amino-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol
  • 7H-Pyrrolo[2,3-d]pyrimidin-4-amine,7-b-D-ribofuranosyl-
  • ski26996
  • sparsomycina
  • u-10071
  • tubercidin from streptomyces tubercidicus
  • tubercidin from streptomyces*tubercidicus
  • 7-beta-CD-ribofuranosyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine
  • 4-AMINO-7-BETA-D-RIBOFURANOSYL-7H-PYROLLO(2,3-D)PYRIMIDINE
  • 7H-Pyrrolo2,3-dpyrimidin-4-amine, 7-.beta.-D-ribofuranosyl-
  • 7-Deaza-D-adenosine
  • 4-Amino-7-β-D-ribofuranosyl-7H-pyrrolo[2,3-d]pyrimidine
  • Sparsomycine A
  • 7-.beta.-D-ribofuranosyl-7H-pyrrolo-[2,3-d]pyrimidin-4-amine
  • 7-Deazadenosine
  • 7H-Pyrrolo(2,3-D)pyrimidine, 4-amino-7-beta-D-ribofuranosyl-
  • Aids051983
  • Aids-051983
  • 2-(4-aMinopyrrolo[2,3-d]pyriMidin-7-yl)-5-(hydroxyMethyl)oxolane-3,4-diol
  • 7-deaza-adenosin(Tubercidine)
  • 7-DEAZAADENOSINE
  • Tubercidin (7-Deazaadenosine
  • 7-Deaza-adeonsine
  • CS-2599
  • Tubercidin, >97%
  • 7H-Pyrrolo[2,3-d]pyrimidin-4-amine, 7-β-D-ribofuranosyl-
  • 7-Deazaadenosine, Tubercidin, Sparsomycine A
  • 4-Amino-7-(β-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine
  • TUBERCIDIN USP/EP/BP
  • 7-Deaza-Ar
  • 7-Deaza-rA
  • Tubercidin (6CI)
  • 4-Amino-7-(b-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine
  • 69-33-0
  • Antibiotics T-Z
  • Antibiotics
  • Antibiotics A to Z
  • BioChemical