d2T
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MedKoo CAT#: 464988

CAS#: 3416-05-5

Description: d2T is a nucleoside analog of thymidine that has antiviral activity. It inhibits HIV replication in infected human peripheral blood mononuclear cells (PBMCs; EC50 = 0.17 µM).2 3′-deoxy Thymidine (1, 3, 10, or 30 µM) reduces viral plaque formation in CV-1 cells infected with herpes simplex virus 1 (HSV-1).


Chemical Structure

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d2T
CAS# 3416-05-5

Theoretical Analysis

MedKoo Cat#: 464988
Name: d2T
CAS#: 3416-05-5
Chemical Formula: C10H14N2O4
Exact Mass: 226.0954
Molecular Weight: 226.232
Elemental Analysis: C, 53.09; H, 6.24; N, 12.38; O, 28.29

Price and Availability

Size Price Availability Quantity
25.0mg USD 210.0 2 Weeks
50.0mg USD 340.0 2 Weeks
100.0mg USD 540.0 2 Weeks
250.0mg USD 850.0 2 Weeks
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Synonym: d2T; ddThd; 2’,3’-Dideoxythymidine; 3′-deoxy Thymidine; 3′ deoxy Thymidine;

IUPAC/Chemical Name: 1-((2R,5S)-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione

InChi Key: XKKCQTLDIPIRQD-JGVFFNPUSA-N

InChi Code: InChI=1S/C10H14N2O4/c1-6-4-12(10(15)11-9(6)14)8-3-2-7(5-13)16-8/h4,7-8,13H,2-3,5H2,1H3,(H,11,14,15)/t7-,8+/m0/s1

SMILES Code: [H][C@]1(O[C@@H](CC1)CO)N2C(NC(C(C)=C2)=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: To be determined

Shelf Life: >2 years if stored properly

Drug Formulation: To be determined

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

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMF 25.0 110.51
DMF:PBS (pH 7.2) (1:5) 0.16 0.71
DMSO 20.0 88.4

Preparing Stock Solutions

The following data is based on the product molecular weight 226.232 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

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1: Dilmore CR, DeStefano JJ. HIV Reverse Transcriptase Pre-Steady-State Kinetic Analysis of Chain Terminators and Translocation Inhibitors Reveals Interactions between Magnesium and Nucleotide 3'-OH. ACS Omega. 2021 May 25;6(22):14621-14628. doi: 10.1021/acsomega.1c01742. PMID: 34124485; PMCID: PMC8190884.

2: Khorsandgolchin G, Sanche L, Cloutier P, Wagner JR. Strand Breaks Induced by Very Low Energy Electrons: Product Analysis and Mechanistic Insight into the Reaction with TpT. J Am Chem Soc. 2019 Jul 3;141(26):10315-10323. doi: 10.1021/jacs.9b03295. Epub 2019 Jun 22. PMID: 31244176.

3: Hamlow LA, Devereaux ZJ, Roy HA, Cunningham NA, Berden G, Oomens J, Rodgers MT. Impact of the 2'- and 3'-Sugar Hydroxyl Moieties on Gas-Phase Nucleoside Structure. J Am Soc Mass Spectrom. 2019 May;30(5):832-845. doi: 10.1007/s13361-019-02155-0. Epub 2019 Mar 8. PMID: 30850972.

4: Akula HK, Lakshman MK. Facile Modifications at the C4 Position of Pyrimidine Nucleosides via In Situ Amide Activation with 1H-Benzotriazol-1-yloxy- tris(dimethyl-amino)phosphonium Hexafluorophosphate. Curr Protoc Nucleic Acid Chem. 2019 Mar;76(1):e73. doi: 10.1002/cpnc.73. Epub 2019 Jan 28. PMID: 30688408; PMCID: PMC6834435.

5: Martinez SE, Bauman JD, Das K, Arnold E. Structure of HIV-1 reverse transcriptase/d4TTP complex: Novel DNA cross-linking site and pH-dependent conformational changes. Protein Sci. 2019 Mar;28(3):587-597. doi: 10.1002/pro.3559. Epub 2018 Dec 22. PMID: 30499174; PMCID: PMC6371216.

6: Mucha P, Ruczynski J, Dobkowski M, Backtrog E, Rekowski P. Capillary electrophoresis study of systemin peptides spreading in tomato plant. Electrophoresis. 2019 Jan;40(2):336-342. doi: 10.1002/elps.201800206. Epub 2018 Oct 11. PMID: 30259532.

7: Yuan S, Shi Y, Guo K, Tang SJ. Nucleoside Reverse Transcriptase Inhibitors (NRTIs) Induce Pathological Pain through Wnt5a-Mediated Neuroinflammation in Aging Mice. J Neuroimmune Pharmacol. 2018 Jun;13(2):230-236. doi: 10.1007/s11481-018-9777-6. Epub 2018 Feb 10. PMID: 29429030; PMCID: PMC5930064.

8: Agarwal HK, Chhikara BS, Doncel GF, Parang K. Synthesis and anti-HIV activities of unsymmetrical long chain dicarboxylate esters of dinucleoside reverse transcriptase inhibitors. Bioorg Med Chem Lett. 2017 May 1;27(9):1934-1937. doi: 10.1016/j.bmcl.2017.03.031. Epub 2017 Mar 16. PMID: 28351588.

9: Orozco Rodriguez JM, Nesrini M, Christiansen LS, Knecht W. Expression of tomato thymidine kinase 1 by means of the baculovirus expression vector system. Nucleosides Nucleotides Nucleic Acids. 2016 Dec;35(10-12):691-698. doi: 10.1080/15257770.2016.1139126. PMID: 27906616.

10: Bondarev IE, Khavinson VK. [Suppression of alternative telomere lengthening in cancer cells with reverse transcriptase inhibitors]. Adv Gerontol. 2016;29(2):218-221. Russian. PMID: 28514537.

11: Beni Y, Dash C, Parang K. Synthesis of β-triphosphotriester pronucleotides. Tetrahedron Lett. 2015 Apr 22;56(17):2247-2250. doi: 10.1016/j.tetlet.2015.03.036. Epub 2015 Mar 16. PMID: 26661734; PMCID: PMC4675357.

12: Pertusati F, McGuigan C, Serpi M. Symmetrical diamidate prodrugs of nucleotide analogues for drug delivery. Curr Protoc Nucleic Acid Chem. 2015 Mar 9;60:15.6.1-15.6.10. doi: 10.1002/0471142700.nc1506s60. PMID: 25754890.

13: Yoshida VM, Balcão VM, Vila MM, Oliveira Júnior JM, Aranha N, Chaud MV, Gremião MP. Zidovudine-poly(L-lactic acid) solid dispersions with improved intestinal permeability prepared by supercritical antisolvent process. J Pharm Sci. 2015 May;104(5):1691-700. doi: 10.1002/jps.24377. Epub 2015 Feb 10. PMID: 25676038.

14: Sun R, Eriksson S, Wang L. Zidovudine induces downregulation of mitochondrial deoxynucleoside kinases: implications for mitochondrial toxicity of antiviral nucleoside analogs. Antimicrob Agents Chemother. 2014 Nov;58(11):6758-66. doi: 10.1128/AAC.03613-14. Epub 2014 Sep 2. PMID: 25182642; PMCID: PMC4249380.

15: Dobkowski M, Szychowska A, Pieszko M, Miszka A, Wojciechowska M, Alenowicz M, Ruczyński J, Rekowski P, Celewicz L, Barciszewski J, Mucha P. 'Click' chemistry synthesis and capillary electrophoresis study of 1,4-linked 1,2,3-triazole AZT-systemin conjugate. J Pept Sci. 2014 Sep;20(9):696-703. doi: 10.1002/psc.2653. Epub 2014 May 28. PMID: 24889517.

16: Pemmaraju B, Agarwal HK, Oh D, Buckheit KW, Buckheit RW Jr, Tiwari R, Parang K. Synthesis and Biological Evaluation of 5'-O-Dicarboxylic Fatty Acyl Monoester Derivatives of Anti-HIV Nucleoside Reverse Transcriptase Inhibitors. Tetrahedron Lett. 2014 Mar 19;55(12):1983-1986. doi: 10.1016/j.tetlet.2014.02.001. PMID: 24791029; PMCID: PMC4001930.

17: National Toxicology Program. Toxicology and Carcinogenesis Studies of Mixtures of 3'-Azido-3'-Deoxythymidine (AZT), Lamivudine (3TC), and Nevirapine (NVP) (CAS Nos. 30516-87-1, 134678-17-4, 129618-40-2) in Genetically Modified C3B6.129F1-Trp53(tm1Brd) N12 Haploinsufficient Mice (in utero and postnatal gavage studies). Natl Toxicol Program Genet Modif Model Rep. 2013 Oct;(16):1-236. PMID: 24503698.

18: National Toxicology Program. Toxicology and carcinogenesis of 3´-azido-3´-deoxythymidine (AZT) (CAS No. 30516-87-1) in genetically modified C3B6.129F1-Trp53(tm1Brd) N12 haploinsufficient mice (in utero and postnatal gavage studies). Natl Toxicol Program Genet Modif Model Rep. 2013 Oct;(14):1-200. PMID: 24503641.

19: Yang J, Geng W, Zhang M, Han X, Shang H. Discordance between genotypic resistance and pseudovirus phenotypic resistance in AIDS patients after long- term antiretroviral therapy and virological failure. J Basic Microbiol. 2014 Oct;54(10):1120-5. doi: 10.1002/jobm.201300415. Epub 2013 Dec 11. PMID: 24338739.

20: Singh RK, Miazga A, Dąbrowska A, Lipniacki A, Piasek A, Kulikowski T, Shugar D. Myristoylated derivatives of 2',3'-didehydro-2',3'-dideoxythymidine (stavudine) bi-functional prodrugs with potent anti-HIV-1 activity and low cytotoxicity. Antivir Chem Chemother. 2014 Dec 16;23(6):231-5. doi: 10.3851/IMP2679. PMID: 23985753.

d2T

25.0mg / USD 210.0