For research use only. Not for therapeutic Use.
2′,3′,5′-Triacetyluridine(CAT: R021646) is a chemically modified form of uridine, featuring acetyl groups attached to the 2′, 3′, and 5′ positions of the ribose ring. This modification enhances the compound’s stability and cellular uptake, making it a valuable tool in biochemical and pharmaceutical research. 2′,3′,5′-Triacetyluridine is commonly used in studies related to nucleotide metabolism, neuroprotection, and cognitive enhancement. Its role in increasing uridine levels in the body makes it a potential therapeutic agent for conditions involving mitochondrial dysfunction, cognitive decline, and neurodegenerative diseases.
| CAS Number | 4105-38-8 |
| Synonyms | 2’,3’,5’-Tri-O-acetyluridine; PN 401; RG 2133; Tri-O-acetyl uridine; Uridine triacetate; Vistonuridine |
| Molecular Formula | C₁₅H₁₈N₂O₉ |
| Purity | ≥95% |
| Storage | Store at -20C |
| IUPAC Name | [(2R,3R,4R,5R)-3,4-diacetyloxy-5-(2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl acetate |
| InChI | InChI=1S/C15H18N2O9/c1-7(18)23-6-10-12(24-8(2)19)13(25-9(3)20)14(26-10)17-5-4-11(21)16-15(17)22/h4-5,10,12-14H,6H2,1-3H3,(H,16,21,22)/t10-,12-,13-,14-/m1/s1 |
| InChIKey | AUFUWRKPQLGTGF-FMKGYKFTSA-N |
| SMILES | O=C(C=CN1[C@H]2[C@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O2)NC1=O |
| Reference | </br> 1. Saydoff, Joel A.; Garcia, Rolando A. G.; Browne, Susan E.; Liu, Liansheng; Sheng, Jin; Brenneman, Denise; Hu, Zhongyi; Cardin, Sylvain; Gonzalez, Alexis; von Borstel, Reid W.; Gregorio, Jason; Burr, Holly; Beal, M. Flint. Oral uridine pro-drug PN401 is neuroprotective in the R6/2 and N171-82Q mouse models of Huntington/’s disease. Neurobiology of Disease (2006), 24(3), 455-465. CODEN: NUDIEM ISSN:0969-9961. CAN 146:266494 AN 2006:1245538 </br>2. Doroshow, James H.; McCoy, Sheryl; Macdonald, John S.; Issell, Brian F.; Patel, Taral; Cobb, Patrick W.; Yost, Kathleen J.; Abbruzzese, James L. Phase II trial of PN401, 5-FU, and leucovorin in unresectable or metastatic adenocarcinoma of the stomach: A Southwest Oncology Group study. Investigational New Drugs (2006), 24(6), 537-542. CODEN: INNDDK ISSN:0167-6997. CAN 146:414364 AN 2006:834313 </br>3. Saif, Muhammad Wasif; Borstel, Reid. 5-Fluorouracil dose escalation enabled with PN401 (triacetyluridine): toxicity reduction and increased antitumor activity in mice. Cancer Chemotherapy and Pharmacology (2006), 58(1), 136-142. CODEN: CCPHDZ ISSN:0344-5704. CAN 145:327796 AN 2006:375032 </br>4. Garcia, Rolando A. G.; Liu, Liansheng; Hu, Zhongyi; Gonzalez, Alexis; von Borstel, Reid W.; Saydoff, Joel A. Severe cytochrome c oxidase inhibition in vivo does not induce a pyrimidine deficiency; neuroprotective action of oral uridine prodrug PN401 requires supraphysiological levels of uridine. Brain Research (2005), 1066(1-2), 164-171. CODEN: BRREAP ISSN:0006-8993. CAN 144:81045 AN 2005:1319808 </br>5. Saydoff, J.; Liu, L.; Hu, Z.; von Borstel, R. Uridine prodrug PN401 is beneficial in APP2576 mice and models for chemical hypoxia and oxidative stress. Vascular Dementia, International Congress, 3rd, Prague, Czech Republic, Oct. 23-26, 2003 (2003), 241-245. CODEN: 69GVAS CAN 143:71599 AN 2005:397109 </br>6. Saydoff, Joel A.; Liu, Lian Sheng; Garcia, Rolando A. G.; Hu, Zhongyi; Li, Donna; von Borstel, Reid W. Oral uridine pro-drug PN401 decreases neurodegeneration, behavioral impairment, weight loss and mortality in the 3-nitropropionic acid mitochondrial toxin model of Huntington/’s disease. Brain Research (2003), 994(1), 44-54. CODEN: BRREAP ISSN:0006-8993. CAN 140:174995 AN 2003:923611 </br>7. Hidalgo, Manuel; Villalona-Calero, Miguel A.; Eckhardt, S. Gail; Drengler, Ronald L.; Rodriguez, Gladys; Hammond, Lisa A.; Diab, Sami G.; Weiss, Geoffrey; Garner, Allison M.; Campbell, Elizabeth; Davidson, Karen; Louie, Arthur; O/’Neil, James D.; Von Borstel, Reid; Von Hoff, Daniel D.; Rowinsky, Eric K. Phase I and pharmacologic study of PN401 and fluorouracil in patients with advanced solid malignancies. Journal of Clinical Oncology (2000), 18(1), 167-177. CODEN: JCONDN ISSN:0732-183X. CAN 132:102547 AN 2000:61094 </br>8. Kelsen, David P.; Martin, Dan; O/’neil, James; Schwartz, Gary; Saltz, Leonard; Sung, Michael T.; Von Borstel, Reid; Bertino, Joseph. Phase I trial of PN401, an oral prodrug of uridine, to prevent toxicity from fluorouracil in patients with advanced cancer. Journal of Clinical Oncology (1997), 15(4), 1511-1517. CODEN: JCONDN ISSN:0732-183X. CAN 126:325035 AN 1997:283216</br> |
