2'-Deoxyinosine

Names

[ CAS No. ]:
890-38-0

[ Name ]:
2'-Deoxyinosine

[Synonym ]:
INOSINE, 2'-DEOXY-
Inosine,2'-deoxy
EINECS 212-964-1
9H-Purin-6-ol, 9-(2-deoxy-β-D-erythro-pentofuranosyl)-
2'-Deoxyinosine
9-(2-deoxy-b-D-erythro-pentofuranosyl)-Hypoxanthine
9-(2-deoxy-β-D-erythro-pentofuranosyl)-Hypoxanthine
9-(2-Deoxy-b-D-erythro-pentofuranosyl)-1,9-dihydro-6H-purin-6-one
9-((2R,4S,5R)-4-Hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-9H-purin-6-ol
Deoxyinosine
(-)-2'-Deoxyinosine
d-Ino
2'-DEOXYGUANOSINE-5'-TRIPHOSPHATE TRISODIUM SALT,DGTP
MFCD00005762

Biological Activity

[Description]:

2’-deoxyadenosine inhibits the growth of human colon-carcinoma cell lines and is found to be associated with purine nucleoside phosphorylase (PNP) deficiency.

[Related Catalog]:

Natural Products >> Saccharides and Glycosides

Research Areas >> Cancer

Research Areas >> Metabolic Disease

[Target]

Human Endogenous Metabolite

[In Vitro]

In the absence of deoxycoformycin, 2’-deoxyadenosine is primarily deaminated to 2’-deoxyinosine and then converted into hypoxanthine. In the presence of the inhibitor, the deoxynucleoside, in addition to a phosphorylation process, undergoes phosphorolytic cleavage giving rise to adenine. The conversion of 2’-deoxyadenosine to adenine might represent a protective device, emerging when the activity of adenosine deaminase is reduced or inhibited. There is much evidence to indicate that the enzyme catalyzing this processs may be distinct from methylthioadenosine phosphorylase and S-adenosyl homocysteine hydrolase, which are the enzymes reported to be responsible for the formation of adenine from 28-deoxyadenosine in mammals[1].

[Cell Assay]

Various amounts of cells, ranging from 1,000 to 900,000, suspended in 3 mL of standard medium, are plated in 35-mm dishes and incubated in the absence (control) and in the presence of both 1 μM dCF and 0.1 mM dAdo, as indicated in each experiment. dCf was added to the standard medium 30 min before 2’-deoxyadenosine (dAdo). Furthermore, an incubation is performed in which 0.1 mM 2’-deoxyadenosine alone is added to the standard medium. After 4 days of incubation, the standard medium is withdrawn, then 0.5 mL of 0.025% trypsin containing 0.02% EDTA is added and kept for few minutes at 37°C. The cells are collected, diluted in an appropriate volume of standard medium, and counted[1].

[References]

[1]. Bemi V, et al. Deoxyadenosine metabolism in a human colon-carcinoma cell line (LoVo) in relation to its cytotoxic effect in combination with deoxycoformycin. Int J Cancer. 1998 Mar 2;75(5):713-20.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.9±0.1 g/cm3

[ Boiling Point ]:
620.6±65.0 °C at 760 mmHg

[ Melting Point ]:
250 °C

[ Molecular Formula ]:
C₁₀H₁₂N₄O₄

[ Molecular Weight ]:
252.227

[ Flash Point ]:
329.1±34.3 °C

[ Exact Mass ]:
252.085861

[ PSA ]:
113.26000

[ LogP ]:
-1.43

[ Vapour Pressure ]:
0.0±1.9 mmHg at 25°C

[ Index of Refraction ]:
1.837

[ Storage condition ]:
-20°C

MSDS

Click to get detail MSDS

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Hazard Codes ]:
Xn,Xi

[ Risk Phrases ]:
R20/21/22

[ Safety Phrases ]:
S24/25

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ HS Code ]:
2934999090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2934999090

[ Summary ]:
2934999090. other heterocyclic compounds. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

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