2'-Desoxyuridin
DU · deoxyuridine · 1-((2R,4S,5R)-4-Hydroxy-5-(hydroxyMethyl)tetrahydrofuran-2-yl)pyriMidine-2,4(1H,3H)-dione · URACIL DEOXYRIBOSIDE · 2'-dU · durd · NSC 23615 · Uracildeoxyr
Identifikatoren & physikalische Daten
| CAS No. | 951-78-0 |
|---|---|
| Summenformel | C9H12N2O5 |
| Durchschnittliche Molmasse | 228,2 g/mol |
| Monoisotopische Masse | 228,07462148 g/mol |
| SMILES | O=c1ccn([C@H]2C[C@H](O)[C@@H](CO)O2)c(=O)[nH]1 |
| InChIKey | MXHRCPNRJAMMIM-SHYZEUOFSA-N |
| PubChem CID | 13712 |
| ChEMBL | CHEMBL353955 |
| ChEBI | CHEBI:16450 |
| EC No. | 213-455-7 |
| DTXSID | DTXSID30883621 |
| Lokaler Name | 2'-Desoxyuridin |
Chemische & physikalische Eigenschaften
| XLogP | -1,6 |
|---|---|
| Polarare Oberfläche (TPSA) | 99,1 |
| H-Brücken-Donoren | 3 |
| H-Brücken-Akzeptoren | 5 |
| Frei drehbare Bindungen | 2 |
| Schwere Atome | 16 |
| Formalladung | 0 |
| Komplexität | 343 |
| Arzneimittel | Pharmaceuticals -> Listed in ZINC15 |
| SpringerMaterials Properties | Crystal structure |
| LogP (Verteilungskoeffizient) | -1.51 |
| Schmelzpunkt | 167 °C167-169 °C(lit.) |
| Physical Description | Solid |
| Collision Cross Section | 145.91 Ų [M-H]- [CCS Type: DTMethod: single field calibrated with Agilent tune mix (Agilent)]151.64 Ų [M-H]- [CCS Type: DTMethod: stepped-field]156.4 Ų [M+Na]+ [CCS Type: DTMethod: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]157.3 Ų [M+Na]+ |
| Siedepunkt | 370.01°C (rough estimate) |
| Dichte | 1.3705 (rough estimate) |
| Brechungsindex | 52 ° (C=1, 1mol/L NaOH) |
| Lagerbedingungen | Inert atmosphere,2-8°C |
| Löslichkeit | DMSO (Slightly), Methanol (Slightly, Heated), Water (Slightly)300 g/L (20 ºC) |
| Aggregatzustand | Powder |
| pKa (Säurekonstante) | pKa 9.3(H2O t = 25) (Uncertain) |
| Farbe | White to off-white |
| Biologische Quelle | synthetic (organic) |
| Merck | 14,2910 |
| BRN | 24433 |
| InChI | 1S/C9H12N2O5/c12-4-6-5(13)3-8(16-6)11-2-1-7(14)10-9(11)15/h1-2,5-6,8,12-13H,3-4H2,(H,10,14,15)/t5-,6+,8+/m0/s1 |
| InChIKey | MXHRCPNRJAMMIM-ATRFCDNQSA-N |
| SMILES | OC[C@H]1O[C@H](C[C@@H]1O)N2C=CC(=O)NC2=O |
| CAS Datenbank | 951-78-0(CAS DataBase Reference) |
| EPA chemische Informationen | Uridine, 2'-deoxy- (951-78-0) |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 20% (1 of 5) of reports.WarningH302 (40%): Harmful if swallowed [Warning Acute toxicity, oral]P261, P264, P264+P265, P270, P271, P273, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 5 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Hazard Classes and Categories | Acute Tox. 4 (40%) |
| F | 10-23 |
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| Zollcode | 29349990 |
| RTECS-Nr. | YU7490000 |
| R-Sätze (R) | 36/37/38 |
| Gefahrensymbole | Xn |
| hazard_note | Air Sensitive |
| Sicherheitshinweise (S) | 22-24/25-37/39-36/37/39-26 |
| Lagerklasse | 11 - Combustible Solids |
Anwendungen & Verwendung
Beschreibung
2'-Deoxyuridine is an intermediate in the synthesis of thymidylate, which is a precursor for DNA synthesis. It has been shown to inhibit the enzymatic activity of enzymes responsible for synthesizing uridine and thymidylate, leading to neuronal death. 2'-Deoxyuridine has been used as a fluorescence probe for nucleic acids and as a polymerase chain reaction (PCR) substrate. It is also known to bind with toll-like receptor 4 (TLR4), which is involved in inflammatory responses.
Verwenden
2'-Deoxyuridine is frequently halogenated to create thymidine analogues useful for studies of DNA synthesis and degradation mechanisms. Derivatized 2'-Deoxyuridines used as labeling substrates include chloro-2'-deoxyuridine (CldU), bromodeoxyuridine (BrdU) and/or iododeoxyuridine (IdU). Other useful analogues of 2'-deoxyuridine include 5-ethynyl-2'-deoxyuridine (DdU) and 5-hydroxymethyl-2'-deoxyuridine (HmdU). Laboratory suppression of deoxyuridine is used to diagnose megaloblastic anemias due to vitamin B12 and folate deficiencies. Deoxyuridine (dU) is used to indirectly determine if there are sufficient levels of folate and cobalamin in cell or tissue samples.