5-Chloro-2'-deoxyuridine

Names

[ CAS No. ]:
50-90-8

[ Name ]:
5-Chloro-2'-deoxyuridine

[Synonym ]:
5-CHLORODEOXYURIDINE
MFCD00006531
5-CHLORODESOXYURIDINE
5-Chloro-2'-deoxy-D-uridine
CLUDR
5-Chlorodeoxyuridin
CldU
2'-DEOXY-5-CHLOROURIDINE
Chlorodeoxyuridine

Biological Activity

[Description]:

5-Chloro-2'-deoxyuridine, a thymine analog, is to study the potential of hypochlorous acid damage to DNA and DNA precursors.

[Related Catalog]:

Signaling Pathways >> Others >> Others

Research Areas >> Neurological Disease

[In Vitro]

When 5-Chloro-2’-deoxyuridine (ClDU) is placed into tissue culture medium, mammalian cells incorporate the analog into DNA. It is observed that 10 μM concentration of 5-Chloro-2’-deoxyuridine in the media does not alter cell division kinetics. Previously it has been shown that 5-Chloro-2’-deoxyuridine is metabolized and incorporated into DNA using antibodies that bind selectively to DNA containing halogenated bases. In the studies reported here, 5-Chloro-2’-deoxyuridine is more similar to BrdU in acting as a T analog. The toxicity of 5-Chloro-2’-deoxyuridine could in part be attributed to inhibition of thymidylate synthase[1].

[Cell Assay]

Human erythroleukemia K-562 cells are used throughout the study. Cells are initially seeded at 1.0×105 cells/mL and treated with either 10 μM 5-Chloro-2’-deoxyuridine or 10 μM thymidine (negative control) for 63 h, or two cell doublings. Cells are counted by trypan blue exclusion, pelleted by centrifugation (500×g) and washed with 10 mL sterile PBS[1].

[Animal admin]

Rats[2] Adult, male Wistar rats, weighing 200-250 g are used. Firstly, the animals are allowed to self-administer methamphetamine at a dose of 0.05 mg/kg/injection under a fixed-ratio 1 (FR1) schedule for baseline sessions. After that, the rats are divided into four groups. Two groups of rats (long-access; LgA-4 days (d), LgA-13 d; n=7 per group) are allowed to self-administer 0.05 mg/kg/injection of methamphetamine for 6 h per day, whereas the other groups (short-access; ShA-4 d, ShA-13 d; n=7 per group) are allowed to do so for 1 h per day. All procedures are performed during the dark cycle. On day 5, ShA-4 d and LgA-4 d rats receive one injection of 50 mg/kg 5-chloro-2’-deoxyuridine and survive for 30 min. On day 14, ShA-13 d and LgA-13 d receive one injection of 50 mg/kg 5-Iodo-2’-deoxyuridine followed by 50 mg/kg 5-chloro-2’-deoxyuridine 2 h later. These rats also survive for 30 min after the 5-Chloro-2'-deoxyuridine injection. A parallel group of drug-naive rats (n=6) receive one injection of 50 mg/kg IdU followed by 50 mg/kg 5-Chloro-2'-deoxyuridine 2 h later. These rats also survive for 30 min after the 5-Chloro-2'-deoxyuridine injection[2].

[References]

[1]. Kim CH, et al. Polymerase incorporation and miscoding properties of 5-chlorouracil. Chem Res Toxicol. 2010 Apr 19;23(4):740-8.

[2]. Yuan CJ, et al. 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. Pharmacol Biochem Behav. 2011 Nov;100(1):98-108.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.67 g/cm3

[ Melting Point ]:
176-179ºC

[ Molecular Formula ]:
C₉H₁₁ClN₂O₅

[ Molecular Weight ]:
262.64700

[ Exact Mass ]:
262.03600

[ PSA ]:
104.55000

[ Index of Refraction ]:
1.644

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: YU7400000

CHEMICAL NAME :: Uridine, 5-chloro-2'-deoxy-

CAS REGISTRY NUMBER :: 50-90-8

LAST UPDATED :: 199709

DATA ITEMS CITED :: 7

MOLECULAR FORMULA :: C9-H11-Cl-N2-O5

MOLECULAR WEIGHT :: 262.67

WISWESSER LINE NOTATION :: T6NVMVJ EG A- ET5OTJ B1Q CQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 2 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

MUTATION DATA

TYPE OF TEST :: Mutation in mammalian somatic cells

TEST SYSTEM :: Rodent - hamster Ovary

DOSE/DURATION :: 500 nmol/L

REFERENCE :: ENMUDM Environmental Mutagenesis. (New York, NY) V.1-9, 1979-87. For publisher information, see EMMUEG. Volume(issue)/page/year: 4,301,1982 *** REVIEWS *** TOXICOLOGY REVIEW 32XPAD "Teratology," Berry, C.L., and D.E. Poswillo, eds., New York, Springer, 1975 Volume(issue)/page/year: -,49,1975

Safety Information

[ Symbol ]:

GHS07, GHS08

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302-H312-H332-H351

[ Precautionary Statements ]:
P280

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xn: Harmful;

[ Risk Phrases ]:
R20/21/22

[ Safety Phrases ]:
36/37/39-45

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
YU7400000

[ HS Code ]:
2942000000

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2942000000

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