2'-Deoxyadenosine

2′-Deoxyadenosine is an adenine nucleoside that inhibits glucose-stimulated insulin release. 2′-Deoxyadenosine inhibits glucose-stimulated increases seen in islet cyclic AMP (cAMP) accumulation. 2'-Deoxyadenosine activates caspase-3 and promotes apoptosis. 2'-Deoxyadenosine inhibits the activity of S-adenosyl-L-homocysteine hydrolase (SAHH) . 2'-Deoxyadenosine inhibits the growth of various cells. 2'-Deoxyadenosine has an anticancer effect on colon cancer[1][2][3].

Product Specifications

CAS Number

[958-09-8]

UNSPSC

12352005

Hazard Statement

H301

Target

Apoptosis; Caspase; Endogenous Metabolite; Nucleoside Antimetabolite/Analog

Type

Natural Products

Related Pathways

Apoptosis; Cell Cycle/DNA Damage; Metabolic Enzyme/Protease

Applications

Metabolism-protein/nucleotide metabolism

Field of Research

Cancer; Endocrinology; Metabolic Disease

Assay Protocol

https://www.medchemexpress.com/_2R,3S,5R_-5-_6-Amino-9H-purin-9-yl_-2-_hydroxymethyl_tetrahydrofuran-3-ol.html

Purity

99.99

Solubility

DMSO : 100 mg/mL (ultrasonic) |H2O : 16.67 mg/mL (ultrasonic)

Smiles

NC1=NC=NC2=C1N=CN2[C@H]3C[C@H](O)[C@@H](CO)O3

Molecular Formula

C10H13N5O3

Molecular Weight

251.25

Precautions

H301

References & Citations

[1]Giannecchini M, et al. 2'-Deoxyadenosine causes apoptotic cell death in a human colon carcinoma cell line. J Biochem Mol Toxicol. 2003;17 (6) :329-37.|[2]Cass CE, et al. Effects of 2'-deoxyadenosine, 9-beta-D-arabinofuranosyladenine, and related compounds on S-adenosyl-L-homocysteine hydrolase activity in synchronous and asynchronous cultured cells. Cancer Res. 1982 Dec;42 (12) :4991-8.|[3]Iizuka H, et al. Effects of adenosine and 2'-deoxyadenosine on epidermal keratinocyte proliferation: its relation to cyclic AMP formation. J Invest Dermatol. 1984 Jun;82 (6) :608-12.|[4]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.|[5]Wakade AR, et al. 2'-deoxyadenosine induces apoptosis in rat chromaffin cells. J Neurochem. 1996 Dec;67 (6) :2273-81.|[6]Gao X, et al. Activation of apoptosis in early mouse embryos by 2'-deoxyadenosine exposure. Teratology. 1994 Jan;49 (1) :1-12. |[7]Kuttesch JF Jr, et al. Renal handling of 2'-deoxyadenosine and adenosine in humans and mice. Cancer Chemother Pharmacol. 1982;8 (2) :221-9. |[8]Iain L. Campbell, et al. Effects of adenosine, 2-deoxyadenosine and N6-phenylisopropyladenosine on rat islet function and metabolism. Biochem J (1982) 204 (3) : 689-696.