WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H581078
CAS#: 4097-22-7
Description: Dideoxyadenosine is konwn as 2′,3′-Dideoxyadenosine (ddA), a specific adenylyl cyclase inhibitor, is useful in biological process and pathway studies involving adenylyl cyclase activity and cAMP pool modulation.
Hodoodo Cat#: H581078
Name: Dideoxyadenosine
CAS#: 4097-22-7
Chemical Formula: C10H13N5O2
Exact Mass: 235.11
Molecular Weight: 235.250
Elemental Analysis: C, 51.06; H, 5.57; N, 29.77; O, 13.60
Synonym: NSC 98700; NSC-98700; Dideoxyadenosine; CCRIS 428; D2A; DDA; ddAdo; 2′,3′-Dideoxyadenosine ;
IUPAC/Chemical Name: 2',3'-Dideoxyadenosine
InChi Key: WVXRAFOPTSTNLL-NKWVEPMBSA-N
InChi Code: InChI=1S/C10H13N5O2/c11-9-8-10(13-4-12-9)15(5-14-8)7-2-1-6(3-16)17-7/h4-7,16H,1-3H2,(H2,11,12,13)/t6-,7+/m0/s1
SMILES Code: Nc1ncnc2c1ncn2[C@@H]3O[C@@H](CC3)CO
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: |
The following data is based on the product molecular weight 235.25 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.
| 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: |
1: Lan X, Mingdao L, Huilin G, Wei G, Lvjiang H, Yan Z, Gang L. Simultaneous determination of 2',3'-dideoxyinosine and the active metabolite, 2',3'-dideoxyadenosine-5'-triphosphate in human peripheral-blood mononuclear cell by HPLC-MS/MS and the application to cell pharmacokinetics. J Chromatogr B Analyt Technol Biomed Life Sci. 2015 Oct 1;1002:337-42. doi: 10.1016/j.jchromb.2015.08.039. Epub 2015 Sep 5. PubMed PMID: 26350426.
2: Balzarini J, Kruining J, Wedgwood O, Pannecouque C, Aquaro S, Perno CF, Naesens L, Witvrouw M, Heijtink R, De Clercq E, McGuigan C. Conversion of 2',3'-dideoxyadenosine (ddA) and 2',3'-didehydro-2',3'-dideoxyadenosine (d4A) to their corresponding aryloxyphosphoramidate derivatives markedly potentiates their activity against human immunodeficiency virus and hepatitis B virus. FEBS Lett. 1997 Jun 30;410(2-3):324-8. PubMed PMID: 9237655.
3: Rosowsky A, Solan VC, Sodroski JG, Ruprecht RM. Synthesis of the 2-chloro analogues of 3'-deoxyadenosine, 2',3'-dideoxyadenosine, and 2',3'-didehydro-2',3'-dideoxyadenosine as potential antiviral agents. J Med Chem. 1989 May;32(5):1135-40. Erratum in: J Med Chem 1990 Apr;33(4):1270. PubMed PMID: 2785212.
4: Ponomar'ova AH, Iurenko IeP, Zhurakivs'kyĭ RO, Hovorun DM. [Conformational capacity of 2',3'-didehydro-2',3'-dideoxyadenosine as a key to understanding its biological activity: results of quantum chemical modelling]. Ukr Biokhim Zh (1999). 2011 Mar-Apr;83(2):74-84. Ukrainian. PubMed PMID: 21851049.
5: Pélicano H, Pierra C, Eriksson S, Gosselin G, Imbach JL, Maury G. Enzymatic properties of the unnatural beta-L-enantiomers of 2',3'-dideoxyadenosine and 2',3'-didehydro-2',3'-dideoxyadenosine. J Med Chem. 1997 Nov 21;40(24):3969-73. PubMed PMID: 9397178.
6: Ahluwalia GS, Cooney DA, Shirasaka T, Mitsuya H, Driscoll JS, Johns DG. Enhancement by 2'-deoxycoformycin of the 5'-phosphorylation and anti-human immunodeficiency virus activity of 2',3'-dideoxyadenosine and 2'-beta-fluoro-2',3'-dideoxyadenosine. Mol Pharmacol. 1994 Nov;46(5):1002-8. PubMed PMID: 7969062.
7: Yueh H, Pal A, Chang K, Schlegel MK, McLaughlin LW. Synthesis and NMR assignment of the two diastereomers of 8,6'-cyclo-2',6'-dideoxyadenosine. Nucleosides Nucleotides Nucleic Acids. 2013;32(6):320-32. doi: 10.1080/15257770.2013.778997. PubMed PMID: 23638925.
8: Haertle T, Carrera CJ, Wasson DB, Sowers LC, Richman DD, Carson DA. Metabolism and anti-human immunodeficiency virus-1 activity of 2-halo-2',3'-dideoxyadenosine derivatives. J Biol Chem. 1988 Apr 25;263(12):5870-5. PubMed PMID: 3258602.
9: Wientjes MG, Placke ME, Chang MJ, Page JG, Kluwe WM, Tomaszewski JE. Pharmacokinetics of 2',3'-dideoxyadenosine in dogs. Invest New Drugs. 1991 May;9(2):159-68. PubMed PMID: 1908444.
10: Ponomareva AG, Yurenko YP, Zhurakivsky RO, van Mourik T, Hovorun DM. Structural and energetic properties of the potential HIV-1 reverse transcriptase inhibitors d4A and d4G: a comprehensive theoretical investigation. J Biomol Struct Dyn. 2014;32(5):730-40. doi: 10.1080/07391102.2013.789401. Epub 2013 Jun 19. PubMed PMID: 23947531.
11: Gudmundsson KS, Daluge SM, Condreay LD, Johnson LC. Synthesis of novel 8-substituted carbocyclic analogs of 2',3'-dideoxyadenosine with activity against hepatitis B virus. Nucleosides Nucleotides Nucleic Acids. 2002 Nov-Dec;21(11-12):891-901. PubMed PMID: 12537029.
12: Pliyev BK, Dimitrieva TV, Savchenko VG. Diadenosine diphosphate (Ap₂A) delays neutrophil apoptosis via the adenosine A2A receptor and cAMP/PKA pathway. Biochem Cell Biol. 2014 Oct;92(5):420-4. doi: 10.1139/bcb-2014-0059. Epub 2014 Jul 18. PubMed PMID: 25179165.
13: Roth JS, Ford H Jr, Tanaka M, Mitsuya H, Kelley JA. Determination of 2'-beta-fluoro-2',3'-dideoxyadenosine, an experimental anti-AIDS drug, in human plasma by high-performance liquid chromatography. J Chromatogr B Biomed Sci Appl. 1998 Aug 7;712(1-2):199-210. PubMed PMID: 9698243.
14: Griffith TM, Chaytor AT, Edwards DH, Daverio F, McGuigan C. Enhanced inhibition of the EDHF phenomenon by a phenyl methoxyalaninyl phosphoramidate derivative of dideoxyadenosine. Br J Pharmacol. 2004 May;142(1):27-30. PubMed PMID: 15131001; PubMed Central PMCID: PMC1574937.
15: Müller MS, Fox R, Schousboe A, Waagepetersen HS, Bak LK. Astrocyte glycogenolysis is triggered by store-operated calcium entry and provides metabolic energy for cellular calcium homeostasis. Glia. 2014 Apr;62(4):526-34. doi: 10.1002/glia.22623. Epub 2014 Jan 24. PubMed PMID: 24464850.
16: Agarwal RP, Busso ME, Mian AM, Resnick L. Uptake of 2',3'-dideoxyadenosine in human immunodeficiency virus-infected and noninfected human cells. AIDS Res Hum Retroviruses. 1989 Oct;5(5):541-50. PubMed PMID: 2590557.
17: Ruxrungtham K, Boone E, Ford H Jr, Driscoll JS, Davey RT Jr, Lane HC. Potent activity of 2'-beta-fluoro-2',3'-dideoxyadenosine against human immunodeficiency virus type 1 infection in hu-PBL-SCID mice. Antimicrob Agents Chemother. 1996 Oct;40(10):2369-74. PubMed PMID: 8891146; PubMed Central PMCID: PMC163536.
18: Fujimori H, Pan-Hou H. Enhancement of cellular adenosine triphosphate levels in PC12 cells by 2,5-dideoxyadenosine, a P-site inhibitor of adenylate cyclase. Biol Pharm Bull. 2005 Feb;28(2):358-60. PubMed PMID: 15684499.
19: Nair V, Sells TB. Interpretation of the roles of adenylosuccinate lyase and of AMP deaminase in the anti-HIV activity of 2',3'-dideoxyadenosine and 2',3'-dideoxyinosine. Biochim Biophys Acta. 1992 Feb 26;1119(2):201-4. PubMed PMID: 1540653.
20: Zyuz'kov GN, Zhdanov VV, Udut EV, Miroshnichenko LA, Chaikovskii AV, Simanina EV, Polyakova TY, Minakova MY, Udut VV, Tolstikova TG, Shul'ts EE, Stavrova LA, Burmina YV, Suslov NI, Dygai AM. Role of cAMP- and IKK-2-Dependent Signaling Pathways in Functional Stimulation of Mesenchymal Progenitor Cells with Alkaloid Songorine. Bull Exp Biol Med. 2015 Sep;159(5):642-5. doi: 10.1007/s10517-015-3036-0. Epub 2015 Oct 16. PubMed PMID: 26472093.
