2'-Deoxyadenosine
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MedKoo CAT#: 591120

CAS#: 958-09-8

Description: 2'-Deoxyadenosine is the DNA nucleoside A, which pairs with deoxythymidine (T) in double-stranded DNA.

Chemical Structure

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2'-Deoxyadenosine
CAS# 958-09-8
Instruction

Theoretical Analysis

MedKoo Cat#: 591120
Name: 2'-Deoxyadenosine
CAS#: 958-09-8
Chemical Formula: C10H13N5O3
Exact Mass: 251.10
Molecular Weight: 251.250
Elemental Analysis: C, 47.81; H, 5.22; N, 27.88; O, 19.10

Price and Availability

Size Price Availability Quantity
5g USD 350 2 Weeks
10g USD 550 2 Weeks
25g USD 850 2 Weeks
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Synonym: 2'-Deoxyadenosine; NSC 141848; NSC141848; NSC-141848

IUPAC/Chemical Name: Adenosine, 2'-deoxy,

InChi Key: OLXZPDWKRNYJJZ-RRKCRQDMSA-N

InChi Code: InChI=1S/C10H13N5O3/c11-9-8-10(13-3-12-9)15(4-14-8)7-1-5(17)6(2-16)18-7/h3-7,16-17H,1-2H2,(H2,11,12,13)/t5-,6+,7+/m0/s1

SMILES Code: OC[C@@H]1[C@H](C[C@H](N2C=NC3=C(N=CN=C32)N)O1)O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 251.25 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Murakami H, Aoyanagi T, Miki Y, Tomita H, Esaka Y, Inoue Y, Teshima N. Effects of hydrophilic monomers on sorptive properties of divinylbenzene-based reversed phase sorbents. Talanta. 2018 Aug 1;185:427-432. doi: 10.1016/j.talanta.2018.03.093. Epub 2018 Mar 30. PubMed PMID: 29759223.

2: Markowitz M, Sarafianos SG. 4'-Ethynyl-2-fluoro-2'-deoxyadenosine, MK-8591: a novel HIV-1 reverse transcriptase translocation inhibitor. Curr Opin HIV AIDS. 2018 Apr 24. doi: 10.1097/COH.0000000000000467. [Epub ahead of print] PubMed PMID: 29697468.

3: Stegmüller S, Schrenk D, Cartus AT. Formation and fate of DNA adducts of alpha- and beta-asarone in rat hepatocytes. Food Chem Toxicol. 2018 Jun;116(Pt B):138-146. doi: 10.1016/j.fct.2018.04.025. Epub 2018 Apr 11. PubMed PMID: 29654846.

4: Carlson ES, Upadhyaya P, Villalta PW, Ma B, Hecht SS. Analysis and Identification of 2'-Deoxyadenosine-Derived Adducts in Lung and Liver DNA of F-344 Rats Treated with the Tobacco-Specific Carcinogen 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone and Enantiomers of its Metabolite 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol. Chem Res Toxicol. 2018 Apr 19. doi: 10.1021/acs.chemrestox.8b00056. [Epub ahead of print] PubMed PMID: 29651838.

5: Lubecka K, Kaufman-Szymczyk A, Fabianowska-Majewska K. Inhibition of breast cancer cell growth by the combination of clofarabine and sulforaphane involves epigenetically mediated CDKN2A upregulation. Nucleosides Nucleotides Nucleic Acids. 2018 Apr 10:1-10. doi: 10.1080/15257770.2018.1453075. [Epub ahead of print] PubMed PMID: 29634384.

6: Tschirka J, Kreisor M, Betz J, Gründemann D. Substrate Selectivity Check of the Ergothioneine Transporter. Drug Metab Dispos. 2018 Jun;46(6):779-785. doi: 10.1124/dmd.118.080440. Epub 2018 Mar 12. PubMed PMID: 29530864.

7: Yanagi M, Suzuki A, Hudson RHE, Saito Y. A fluorescent 3,7-bis-(naphthalen-1-ylethynylated)-2'-deoxyadenosine analogue reports thymidine in complementary DNA by a large emission Stokes shift. Org Biomol Chem. 2018 Feb 28;16(9):1496-1507. doi: 10.1039/c8ob00062j. PubMed PMID: 29417128.

8: Steinmeyer J, Wagenknecht HA. Synthesis of DNA Modified with Boronic Acid: Compatibility to Copper(I)-Catalyzed Azide-Alkyne Cycloaddition. Bioconjug Chem. 2018 Feb 21;29(2):431-436. doi: 10.1021/acs.bioconjchem.7b00765. Epub 2018 Feb 9. PubMed PMID: 29397700.

9: Suzuki T, Ogishi A, Shinohara T, Suito S. Formation of 8-S-L-Cysteinyladenosine from 8-Bromoadenosine and Cysteine. Chem Pharm Bull (Tokyo). 2018;66(2):184-187. doi: 10.1248/cpb.c17-00731. PubMed PMID: 29386470.

10: Feng Y, Wang S, Wang H, Peng Y, Zheng J. Urinary Methyleugenol-deoxyadenosine Adduct as a Potential Biomarker of Methyleugenol Exposure in Rats. J Agric Food Chem. 2018 Feb 7;66(5):1258-1263. doi: 10.1021/acs.jafc.7b05186. Epub 2018 Jan 25. PubMed PMID: 29328669.

11: Tian Y, Wang CX, Qian ZM, Li Z, Zhou MX, Sun WY, Yao XS, Li WJ, Gao H. [Simultaneous determination of cordycepin and 2'-deoxyadenosine in Cordyceps genus by online SPE-HPLC]. Zhongguo Zhong Yao Za Zhi. 2017 May;42(10):1932-1938. doi: 10.19540/j.cnki.cjcmm.20170223.025. Chinese. PubMed PMID: 29090553.

12: Parashar NC, Parashar G, Nayyar H, Sandhir R. N(6)-adenine DNA methylation demystified in eukaryotic genome: From biology to pathology. Biochimie. 2018 Jan;144:56-62. doi: 10.1016/j.biochi.2017.10.014. Epub 2017 Oct 24. PubMed PMID: 29074394.

13: Navacchia ML, Marchesi E, Mari L, Chinaglia N, Gallerani E, Gavioli R, Capobianco ML, Perrone D. Rational Design of Nucleoside-Bile Acid Conjugates Incorporating a Triazole Moiety for Anticancer Evaluation and SAR Exploration. Molecules. 2017 Oct 12;22(10). pii: E1710. doi: 10.3390/molecules22101710. PubMed PMID: 29023408.

14: Yockey OP, Jha V, Ghodke PP, Xu T, Xu W, Ling H, Pradeepkumar PI, Zhao L. Mechanism of Error-Free DNA Replication Past Lucidin-Derived DNA Damage by Human DNA Polymerase κ. Chem Res Toxicol. 2017 Nov 20;30(11):2023-2032. doi: 10.1021/acs.chemrestox.7b00227. Epub 2017 Oct 23. PubMed PMID: 28972744; PubMed Central PMCID: PMC5696069.

15: Oliveira M, Brenner BG, Xu H, Ibanescu RI, Mesplède T, Wainberg MA. M184I/V substitutions and E138K/M184I/V double substitutions in HIV reverse transcriptase do not significantly affect the antiviral activity of EFdA. J Antimicrob Chemother. 2017 Nov 1;72(11):3008-3011. doi: 10.1093/jac/dkx280. PubMed PMID: 28961903; PubMed Central PMCID: PMC5890679.

16: He X, Ma L, Xia Q, Fu PP. 7-N-Acetylcysteine-pyrrole conjugate-A potent DNA reactive metabolite of pyrrolizidine alkaloids. J Food Drug Anal. 2016 Oct;24(4):682-694. doi: 10.1016/j.jfda.2016.08.001. Epub 2016 Sep 10. PubMed PMID: 28911605.

17: Zhang W, Gao Q, Wei S, Fu B, Yang Q, Ming X. Synthesis of 8-Substituted 2'-Deoxyisoguanosines via Unprotected 8-Brominated 2-Amino-2'-deoxyadenosine. Chem Biodivers. 2018 Jan;15(1). doi: 10.1002/cbdv.201700335. Epub 2017 Dec 27. PubMed PMID: 28853211.

18: Cao XF, Bai ZZ, Ma L, Ma S, Ge RL. Metabolic Alterations of Qinghai-Tibet Plateau Pikas in Adaptation to High Altitude. High Alt Med Biol. 2017 Sep;18(3):219-225. doi: 10.1089/ham.2016.0147. Epub 2017 Aug 28. PubMed PMID: 28846033.

19: Chiavarino B, Crestoni ME, Fornarini S, Scuderi D, Salpin JY. Undervalued N3 Coordination Revealed in the Cisplatin Complex with 2'-Deoxyadenosine-5'-monophosphate by a Combined IRMPD and Theoretical Study. Inorg Chem. 2017 Aug 7;56(15):8793-8801. doi: 10.1021/acs.inorgchem.7b00570. Epub 2017 Jul 18. PubMed PMID: 28718635.

20: Ahmad MF, Alam I, Huff SE, Pink J, Flanagan SA, Shewach D, Misko TA, Oleinick NL, Harte WE, Viswanathan R, Harris ME, Dealwis CG. Potent competitive inhibition of human ribonucleotide reductase by a nonnucleoside small molecule. Proc Natl Acad Sci U S A. 2017 Aug 1;114(31):8241-8246. doi: 10.1073/pnas.1620220114. Epub 2017 Jul 17. PubMed PMID: 28716944; PubMed Central PMCID: PMC5547592.