5-CHLORO-2'-DEOXYURIDINE

Bezeichnung:5-CHLORO-2'-DEOXYURIDINE

CAS-Nr50-90-8

Englisch Name:5-CHLORO-2'-DEOXYURIDINE

CBNumberCB0246956

SummenformelC9H11ClN2O5

Molgewicht262.65

MOL-Datei50-90-8.mol

5-CHLORO-2'-DEOXYURIDINE physikalisch-chemischer Eigenschaften

Schmelzpunkt	176-179°C
Dichte	1.5507 (rough estimate)
Brechungsindex	1.6500 (estimate)
storage temp.	-20°C
Löslichkeit	DMSO (Slightly), Methanol (Slightly), Water (Slightly)
Aggregatzustand	Solid
pka	7.73±0.10(Predicted)
Farbe	White to Off-White
InChI	InChI=1S/C9H11ClN2O5/c10-4-2-12(9(16)11-8(4)15)7-1-5(14)6(3-13)17-7/h2,5-7,13-14H,1,3H2,(H,11,15,16)/t5-,6+,7+/m0/s1
InChIKey	NJCXGFKPQSFZIB-RRKCRQDMSA-N
SMILES	OC[C@H]1O[C@@H](N2C=C(Cl)C(=O)NC2=O)C[C@@H]1O
CAS Datenbank	50-90-8(CAS DataBase Reference)

Sicherheit

Kennzeichnung gefährlicher	Xn
R-Sätze:	20/21/22-40
S-Sätze:	36/37/39-45
WGK Germany	3
RTECS-Nr.	YU7400000
HS Code	29349990
Speicherklasse	11 - Combustible Solids
Hazard Classifications	Acute Tox. 4 Dermal Acute Tox. 4 Inhalation Acute Tox. 4 Oral Carc. 2

Gefahreninformationscode (GHS)

5-CHLORO-2'-DEOXYURIDINE Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R20/21/22:Gesundheitsschädlich beim Einatmen,Verschlucken und Berührung mit der Haut.
R40:Verdacht auf krebserzeugende Wirkung.
S-Sätze Betriebsanweisung:
S36/37/39:Bei der Arbeit geeignete Schutzkleidung,Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
S45:Bei Unfall oder Unwohlsein sofort Arzt zuziehen (wenn möglich, dieses Etikett vorzeigen).
Beschreibung
5-Chloro-2''-deoxyuridine (CldU) is a thymidine analog that is readily incorporated, following phosphorylation, into newly synthesized DNA in place of thymidine. Like 5-bromo-2’-deoxyuridine and 5-iodo-2’-deoxyuridine, CldU can be detected immunologically in cells and tissues. CldU can also be added to cells or tissues sequentially with another thymidine analog to label temporally distinct populations. The insertion of thymidine analogs, including CldU, can significantly alter DNA processing and replication, so these analogs have also been used as mutagens, clastogens, and antiviral compounds.
Chemische Eigenschaften
White Needles
Verwenden
5-Chloro-2′-deoxyuridine (CldU) is used as a thymidine analog to study the miscoding potential of hypochlorous acid damage to DNA and DNA precursors. When used with antibody based immunofluorescent imaging, 5-Chloro-2′-deoxyuridine incorporation may be used in protocols to identify sites of DNA replication. CldU may be used as a labeling substrate in conjunction with other halogenated uridine labeling substrates such as iododeoxyuridine (IdU).
Verwenden
A halogenated uridine derivative used in pharmaceutical compositions.
Verwenden
5-Chloro-2'-deoxyuridine (CldU) is a thymidine analog that is readily incorporated, following phosphorylation, into newly synthesized DNA in place of thymidine. Like 5-bromo-2’-deoxyuridine and 5-iodo-2’-deoxyuridine, CldU can be detected immunologically in cells and tissues. CldU can also be added to cells or tissues sequentially with another thymidine analog to label temporally distinct populations. The insertion of thymidine analogs, including CldU, can significantly alter DNA processing and replication, so these analogs have also been used as mutagens, clastogens, and antiviral compounds.[Cayman Chemical]
Biochem/physiol Actions
DNA labeled with 5-chloro-2′-deoxyuridine (CldU) serves as an effective tool to analyze and quantify DNA replication, repair, and recombination. CldU is a potent mutagen, clastogen, and toxicant. It is used as a thymidine analog and is found to alter the dNTP pools and might lead to cell-cycle arrest. CldU produces sister-chromatid exchange but has less response to ionizing radiation compared to other thymine analogs. 5-Chloro-2′-deoxyuridine (CldU) is used to study the miscoding potential of hypochlorous acid damage to DNA and DNA precursors. When used with antibody based immunofluorescent imaging, 5-Chloro-2′-deoxyuridine incorporation may be used in protocols to identify sites of DNA replication. CldU may be used as a labeling substrate in conjunction with other halogenated uridine labeling substrates such as iododeoxyuridine (IdU).
Einzelnachweise
[1] AMRITRAJ PATRA. Structure, stability and function of 5-chlorouracil modified A:U and G:U base pairs.[J]. Nucleic Acids Research, 2013: 2689-2697. DOI: 10.1093/nar/gks1316
[2] CLARA J. YUAN . Extended access methamphetamine decreases immature neurons in the hippocampus which results from loss and altered development of neural progenitors without altered dynamics of the S-phase of the cell cycle[J]. Pharmacology Biochemistry and Behavior, 2011, 100 1: Pages 98-108. DOI: 10.1016/j.pbb.2011.08.004
[3] SILJE ANDA Beata G Erik Boye. Cell-cycle analyses using thymidine analogues in fission yeast.[J]. PLoS ONE, 2014: e88629. DOI: 10.1371/journal.pone.0088629
[4] MARíA LLORENS-MARTíN José L T Gonzalo S Tejeda. Differential regulation of the variations induced by environmental richness in adult neurogenesis as a function of time: a dual birthdating analysis.[J]. PLoS ONE, 2010: e12188. DOI: 10.1371/journal.pone.0012188
[5] ALEX H TUTTLE. Immunofluorescent detection of two thymidine analogues (CldU and IdU) in primary tissue.[J]. Jove-Journal of Visualized Experiments, 2010, 46. DOI: 10.3791/2166
[6] L M FOX. Capacity of deoxycytidine to selectively antagonize cytotoxicity of 5-halogenated analogs of deoxycytidine without loss of antiherpetic activity.[J]. Antimicrobial Agents and Chemotherapy, 1982, 22 3: 431-441. DOI: 10.1128/aac.22.3.431

5-CHLORO-2'-DEOXYURIDINE Upstream-Materialien And Downstream Produkte

5-CHLORO-2'-DEOXYURIDINE Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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