Synonym
3-Deazauridine; 3Deazauridine; 3 Deazauridine; NSC126849; NSC-126849; NSC 126849
IUPAC/Chemical Name
1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-4-hydroxypyridin-2(1H)-one
InChi Key
CBOKZNLSFMZJJA-PEBGCTIMSA-N
InChi Code
InChI=1S/C10H13NO6/c12-4-6-8(15)9(16)10(17-6)11-2-1-5(13)3-7(11)14/h1-3,6,8-10,12-13,15-16H,4H2/t6-,8-,9-,10-/m1/s1
SMILES Code
O=C1C=C(C=CN1[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)O)O
Purity
>95% (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
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMF |
16.0 |
65.78 |
| DMSO |
10.0 |
41.12 |
| PBS (pH:7.2) |
5.0 |
20.56 |
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
243.22
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 |
1: Raynal NJ, Momparler LF, Rivard GE, Momparler RL. 3-Deazauridine enhances the antileukemic action of 5-aza-2'-deoxycytidine and targets drug-resistance due to deficiency in deoxycytidine kinase. Leuk Res. 2011 Jan;35(1):110-8. doi: 10.1016/j.leukres.2010.04.014. Epub 2010 May 26. PMID: 20510451.
2: Lockshin A, Mendoza JT, Giovanella BC, Stehlin JS Jr. Cytotoxic and biochemical effects of thymidine and 3-deazauridine on human tumor cells. Cancer Res. 1984 Jun;44(6):2534-9. PMID: 6722792.
3: Brockman RW, Shaddix SC, Williams M, Nelson JA, Rose LM, Schabel FM Jr. The mechanism of action of 3-deazauridine in tumor cells sensitive and resistant to arabinosylcytosine. Ann N Y Acad Sci. 1975 Aug 8;255:501-21. doi: 10.1111/j.1749-6632.1975.tb29254.x. PMID: 171997.
4: van Berg AA, Mooyer PA, van Lenthe H, Stet EH, De Abreu RA, van Kuilenburg AB, van Gennip AH. The IMP dehydrogenase inhibitor mycophenolic acid antagonizes the CTP synthetase inhibitor 3-deazauridine in MOLT-3 human leukemia cells: a central role for phosphoribosyl pyrophosphate. Biochem Pharmacol. 1995 Sep 28;50(7):1095-8. doi: 10.1016/0006-2952(95)00228-r. PMID: 7575666.
5: Momparler RL, Momparler LF. Chemotherapy of L1210 and L1210/ARA-C leukemia with 5-aza-2'-deoxycytidine and 3-deazauridine. Cancer Chemother Pharmacol. 1989;25(1):51-4. doi: 10.1007/BF00694338. PMID: 2480188.
6: Woodman DR, Williams JC. Effects of 2-deoxy-D-glucose and 3 deazauridine individually and in combination on the replication of Japanese B encephalitis virus. Antimicrob Agents Chemother. 1977 Mar;11(3):475-81. doi: 10.1128/AAC.11.3.475. PMID: 856001; PMCID: PMC352010.
7: Wang MC, Bloch A. Studies on the mode of action of 3-deazapyrimidines. 1. Metabolism of 3-deazauridine and 3-deazacytidine in microbial and tumor cells. Biochem Pharmacol. 1972 Apr 15;21(8):1063-73. doi: 10.1016/0006-2952(72)90100-1. PMID: 4624539.
8: Momparler RL, Veselý J, Momparler LF, Rivard GE. Synergistic action of 5-aza-2'-deoxycytidine and 3-deazauridine on L1210 leukemic cells and EMT6 tumor cells. Cancer Res. 1979 Oct;39(10):3822-7. PMID: 476619.
9: Sant ME, Lyons SD, Kemp AJ, McClure LK, Szabados E, Christopherson RI. Dual effects of pyrazofurin and 3-deazauridine upon pyrimidine and purine biosynthesis in mouse L1210 leukemia. Cancer Res. 1989 May 15;49(10):2645-50. PMID: 2713848.
10: Savickiene J, Gineitis A. 3-Deazauridine triggers dose-dependent apoptosis in myeloid leukemia cells and enhances retinoic acid-induced granulocytic differentiation of HL-60 cells. Int J Biochem Cell Biol. 2003 Oct;35(10):1482-94. doi: 10.1016/s1357-2725(03)00130-4. PMID: 12818243.
11: Shannon WM, Arnett G, Schabel FM Jr. 3-Deazauridine: inhibition of ribonucleic acid virus-induced cytopathogenic effects in vitro. Antimicrob Agents Chemother. 1972 Sep;2(3):159-63. doi: 10.1128/AAC.2.3.159. PMID: 4799550; PMCID: PMC444284.
