3-Deazaadenosine
featured

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 581636

CAS#: 6736-58-9

Description: 3-Deazaadenosine is a potent inhibitor of adenosine deaminase, an enzyme that catalyzes the removal of the amine group from adenosine. This compound exhibits antitumor activity against a range of leukemia cell lines. 3-Deazaadenosine is an inhibitor of SAHH.


Chemical Structure

img
3-Deazaadenosine
CAS# 6736-58-9

Theoretical Analysis

MedKoo Cat#: 581636
Name: 3-Deazaadenosine
CAS#: 6736-58-9
Chemical Formula: C11H14N4O4
Exact Mass: 266.1015
Molecular Weight: 266.257
Elemental Analysis: C, 49.62; H, 5.30; N, 21.04; O, 24.04

Price and Availability

Size Price Availability Quantity
5.0mg USD 360.0 2 Weeks
10.0mg USD 610.0 2 Weeks
Bulk inquiry

Synonym: 3-Deazaadenosine; Deaza-Ado; Adenosine, 3-deaza-; 3dAdo.

IUPAC/Chemical Name: 1H-Imidazo(4,5-c)pyridin-4-amine, 1-beta-D-ribofuranosyl- (9CI)

InChi Key: DBZQFUNLCALWDY-PNHWDRBUSA-N

InChi Code: InChI=1S/C11H14N4O4/c12-10-7-5(1-2-13-10)15(4-14-7)11-9(18)8(17)6(3-16)19-11/h1-2,4,6,8-9,11,16-18H,3H2,(H2,12,13)/t6-,8-,9-,11-/m1/s1

SMILES Code: NC1=NC=CC2=C1N=CN2[C@H]3[C@@H]([C@@H]([C@@H](CO)O3)O)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: >3 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: 2934.99.03.00

Certificate of Analysis:

Safety Data Sheet (SDS):

Preparing Stock Solutions

The following data is based on the product molecular weight 266.257 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

Molarity Calculator

Calculate the mass, volume, or concentration required for a solution.
=
x
x
g/mol

*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

Reconstitution Calculator

The reconstitution calculator allows you to quickly calculate the volume of a reagent to reconstitute your vial. Simply enter the mass of reagent and the target concentration and the calculator will determine the rest.

=
÷

Dilution Calculator

Calculate the dilution required to prepare a stock solution.
x
=
x

1: Weseliński ŁJ, Begoyan V, Ferrier A, Tanasova M. Tuning Cross-Coupling Approaches to C3 Modification of 3-Deazapurines. ACS Omega. 2017 Oct 31;2(10):7002-7015. doi: 10.1021/acsomega.7b01159. Epub 2017 Oct 20. PubMed PMID: 30023537; PubMed Central PMCID: PMC6045343.

2: Zhang B, De Graef S, Nautiyal M, Pang L, Gadakh B, Froeyen M, Van Mellaert L, Strelkov SV, Weeks SD, Van Aerschot A. Family-wide analysis of aminoacyl-sulfamoyl-3-deazaadenosine analogues as inhibitors of aminoacyl-tRNA synthetases. Eur J Med Chem. 2018 Mar 25;148:384-396. doi: 10.1016/j.ejmech.2018.02.013. Epub 2018 Feb 14. PubMed PMID: 29477072.

3: Mairhofer E, Fuchs E, Micura R. Facile synthesis of a 3-deazaadenosine phosphoramidite for RNA solid-phase synthesis. Beilstein J Org Chem. 2016 Nov 28;12:2556-2562. doi: 10.3762/bjoc.12.250. eCollection 2016. PubMed PMID: 28144324; PubMed Central PMCID: PMC5238537.

4: Saito-Tarashima N, Kira H, Wada T, Miki K, Ide S, Yamazaki N, Matsuda A, Minakawa N. Groove modification of siRNA duplexes to elucidate siRNA-protein interactions using 7-bromo-7-deazaadenosine and 3-bromo-3-deazaadenosine as chemical probes. Org Biomol Chem. 2016 Nov 29;14(47):11096-11105. PubMed PMID: 27714245.

5: Krajczyk A, Zeidler J, Januszczyk P, Dawadi S, Boshoff HI, Barry CE 3rd, Ostrowski T, Aldrich CC. 2-Aryl-8-aza-3-deazaadenosine analogues of 5'-O-[N-(salicyl)sulfamoyl]adenosine: Nucleoside antibiotics that block siderophore biosynthesis in Mycobacterium tuberculosis. Bioorg Med Chem. 2016 Jul 15;24(14):3133-43. doi: 10.1016/j.bmc.2016.05.037. Epub 2016 May 20. PubMed PMID: 27265685; PubMed Central PMCID: PMC4914392.

6: Karoopongse E, Yeung C, Byon J, Ramakrishnan A, Holman ZJ, Jiang PY, Yu Q, Deeg HJ, Marcondes AM. The KDM2B- let-7b -EZH2 axis in myelodysplastic syndromes as a target for combined epigenetic therapy. PLoS One. 2014 Sep 16;9(9):e107817. doi: 10.1371/journal.pone.0107817. eCollection 2014. PubMed PMID: 25225797; PubMed Central PMCID: PMC4166605.

7: Fustin JM, Doi M, Yamaguchi Y, Hida H, Nishimura S, Yoshida M, Isagawa T, Morioka MS, Kakeya H, Manabe I, Okamura H. RNA-methylation-dependent RNA processing controls the speed of the circadian clock. Cell. 2013 Nov 7;155(4):793-806. doi: 10.1016/j.cell.2013.10.026. PubMed PMID: 24209618.

8: Kim JH, Kim JH, Kim SC, Yi YS, Yang WS, Yang Y, Kim HG, Lee JY, Kim KH, Yoo BC, Hong S, Cho JY. Adenosine dialdehyde suppresses MMP-9-mediated invasion of cancer cells by blocking the Ras/Raf-1/ERK/AP-1 signaling pathway. Biochem Pharmacol. 2013 Nov 1;86(9):1285-300. doi: 10.1016/j.bcp.2013.08.022. Epub 2013 Aug 28. PubMed PMID: 23994169.

9: Li Q, Zhu L, Yan Y, Chai D, Li J, Xue L. S-adenosyl homocysteine hydrolase (SAHH) accelerates flagellar regeneration in Dunaliella salina. Curr Microbiol. 2013 Aug;67(2):249-54. doi: 10.1007/s00284-013-0357-y. Epub 2013 Mar 27. PubMed PMID: 23532254.

10: Kim JH, Lee YG, Yoo S, Oh J, Jeong D, Song WK, Yoo BC, Rhee MH, Park J, Cha SH, Hong S, Cho JY. Involvement of Src and the actin cytoskeleton in the antitumorigenic action of adenosine dialdehyde. Biochem Pharmacol. 2013 Apr 15;85(8):1042-56. doi: 10.1016/j.bcp.2013.01.012. Epub 2013 Jan 24. PubMed PMID: 23353701.

11: Lee SY, Ko KW, Kang WK, Choe YJ, Kim YH, Kim IK, Kim J, Kim HS. Induction of the Intrinsic Apoptotic Pathway by 3-Deazaadenosine Is Mediated by BAX Activation in HL-60 Cells. Korean J Physiol Pharmacol. 2010 Dec;14(6):407-12. doi: 10.4196/kjpp.2010.14.6.407. Epub 2010 Dec 31. PubMed PMID: 21311682; PubMed Central PMCID: PMC3034121.

12: Hayden A, Johnson PW, Packham G, Crabb SJ. S-adenosylhomocysteine hydrolase inhibition by 3-deazaneplanocin A analogues induces anti-cancer effects in breast cancer cell lines and synergy with both histone deacetylase and HER2 inhibition. Breast Cancer Res Treat. 2011 May;127(1):109-19. doi: 10.1007/s10549-010-0982-0. Epub 2010 Jun 17. PubMed PMID: 20556507.

13: Yu X, Ling W, Mi M. Relationship of impairment induced by intracellular S-adenosylhomocysteine accumulation with DNA methylation in human umbilical vein endothelial cells treated with 3-deazaadenosine. Int J Exp Pathol. 2009 Dec;90(6):638-48. doi: 10.1111/j.1365-2613.2009.00687.x. PubMed PMID: 19958400; PubMed Central PMCID: PMC2803255.

14: Sedding DG, Tröbs M, Reich F, Walker G, Fink L, Haberbosch W, Rau W, Tillmanns H, Preissner KT, Bohle RM, Langheinrich AC. 3-Deazaadenosine prevents smooth muscle cell proliferation and neointima formation by interfering with Ras signaling. Circ Res. 2009 May 22;104(10):1192-200. doi: 10.1161/CIRCRESAHA.109.194357. Epub 2009 Apr 16. PubMed PMID: 19372464.

15: Matthews RP, Lorent K, Mañoral-Mobias R, Huang Y, Gong W, Murray IV, Blair IA, Pack M. TNFalpha-dependent hepatic steatosis and liver degeneration caused by mutation of zebrafish S-adenosylhomocysteine hydrolase. Development. 2009 Mar;136(5):865-75. doi: 10.1242/dev.027565. PubMed PMID: 19201949; PubMed Central PMCID: PMC2685951.

16: Yamasaki-Mann M, Demuro A, Parker I. cADPR stimulates SERCA activity in Xenopus oocytes. Cell Calcium. 2009 Mar;45(3):293-9. doi: 10.1016/j.ceca.2008.11.008. Epub 2009 Jan 7. PubMed PMID: 19131109; PubMed Central PMCID: PMC2688955.

17: Zhu WY, Yang YL, Fu SH, Wang LH, Zai YG, Tang Q, Liang GD. Substitutions of 169Lys and 173Thr in nonstructural protein 1 influence the infectivity and pathogenicity of XJ-160 virus. Arch Virol. 2009;154(2):245-53. doi: 10.1007/s00705-008-0298-0. Epub 2009 Jan 1. PubMed PMID: 19118404.

18: Seeger FH, Hess W, Sedding D, Becker G, Kinscherf R, Braun-Dullaeus RC, Viedt C, Kreuzer J. The nucleotide analogue 3-deazaadenosine prevents neointima-formation after balloon injury. Biochem Biophys Res Commun. 2009 Jan 23;378(4):826-31. doi: 10.1016/j.bbrc.2008.11.151. Epub 2008 Dec 12. PubMed PMID: 19070587.

19: Reddy MC, Kuppan G, Shetty ND, Owen JL, Ioerger TR, Sacchettini JC. Crystal structures of Mycobacterium tuberculosis S-adenosyl-L-homocysteine hydrolase in ternary complex with substrate and inhibitors. Protein Sci. 2008 Dec;17(12):2134-44. doi: 10.1110/ps.038125.108. Epub 2008 Sep 24. PubMed PMID: 18815415; PubMed Central PMCID: PMC2590921.

20: Dever JT, Elfarra AA. L-methionine toxicity in freshly isolated mouse hepatocytes is gender-dependent and mediated in part by transamination. J Pharmacol Exp Ther. 2008 Sep;326(3):809-17. doi: 10.1124/jpet.108.141044. Epub 2008 Jun 13. PubMed PMID: 18552130; PubMed Central PMCID: PMC2574759.