CAS 59-14-3|5-溴-2′-脱氧尿苷|5-BrdU|5-bromo-2'-deoxyuridine|5-溴脱氧尿苷|5-Bromo-2′-deoxyuridine|5-bromo-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dion...

General Information

Structure

Molecular Formula

C₉H₁₁BrN₂O₅

Molecular Mass

307.09804

Exact Mass

305.98513346

Charge

InChI

InChI=1S/C9H11BrN2O5/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

WOVKYSAHUYNSMH-RRKCRQDMSA-N

Canonic Smiles

OC[C@H]1O[C@H](C[C@@H]1O)n1cc(Br)c(=O)[nH]c1=O

Isomeric Smiles

c1c(c(=O)[nH]c(=O)n1[C@H]1C[C@@H]([C@H](O1)CO)O)Br

Calculated Properties

JChem

Acid pKa

7.040325

H Acceptors

H Donor

LogD (pH = 5.5)

-0.70130664

LogD (pH = 7.4)

-1.1950028

Log P

-0.68911046

Molar Refractivity

58.6642

Polarizability

23.204786

Polar Surface Area

99.1

Rotatable Bonds

Lipinski's Rule of Five

true

Data Source

Names and Identifiers

Synonyms

5-溴-2′-脱氧尿苷5-BrdUBUdR5-溴脱氧尿苷5-溴-1-(2-脱氧-β-D-呋喃核糖)尿嘧啶5-Bromo-2′-deoxyuridine5-Bromo-1-(2-deoxy-β-D-ribofuranosyl)uracil5-Bromouracil deoxyribosideBromouridine5-Bromo-2'-deoxyuridineBroxuridine5-BroMo-2'-deoxyuridine5-溴-2'-脱氧尿苷Radibud5-Bromo-1-(2-deoxy-beta-D-ribofuranosyl)uracil

IUPAC Traditional name

5-bromo-2'-deoxyuridine 5-bromo-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione

IUPAC name

5-bromo-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione

Names and Identifiers

Registration numbers

EC Number

200-415-9

PubChem SID

24892132242782702488847424850256162226665

CAS Number

MDL Number

Beilstein Number

PubChem CID

Merck Index

Registration numbers

Properties

Physical Property

Melting Point

191-194 °C (dec.)(lit.)

ca 190°C dec.

Solubility

NH4OH: soluble0.1 M at 20 °C, clear, colorless

Optical Rotation

[α]22/D +23.0°, c = 1 in H2O

[α]20/D +23±1°, c = 1% in H2O

+31 (c=1 in 0.1N HCl)

Pharmacology Properties

Mechanism of Action

Nucleoside antimetabolite

Incorporate into the DNA

Properties

Related Proteins

No Data Available

Click here to submit data

Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

Sigma Aldrich

858811

Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Biochem/physiol Actions
Thymidine analog used as a mutagen in genetic research. Selectively incorporated into cellular DNA during S-phase.
Packaging
100, 500 mg in glass bottle
5 g in glass bottle

16880

Biochem/physiol Actions
Thymidine analog used as a mutagen in genetic research. Selectively incorporated into cellular DNA during S-phase.
Other Notes
Thymidine analogue. Inhibitor of cell differentiation : Review1; Incorporation into DNA for flow cytometric analysis2

B5002

Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Biochem/physiol Actions
用作遗传研究中诱变剂的胸苷类似物。在 S 期可选择性结合到细胞 DNA 中。
包装
1, 5, 100 g in glass bottle
100, 250, 500 mg in glass bottle
Application
5-Bromo-2′-deoxyuridine (5-BrdU) is a thymidine analogue which is incorporated into DNA. 5-BrdU is routinely and extensively used to measure DNA synthesis and to label dividing cells. Consequently 5-BrdU is used to study cell signaling and other processes that induce cell proliferation.

B9285

Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Biochem/physiol Actions
用作遗传研究中诱变剂的胸苷类似物。在 S 期可选择性结合到细胞 DNA 中。
Application
5-Bromo-2′-deoxyuridine (5-BrdU) is a thymidine analogue which is incorporated into DNA. 5-BrdU is routinely and extensively used to measure DNA synthesis and to label dividing cells. Consequently 5-BrdU is used to study cell signaling and other processes that induce cell proliferation.

Molecule Details

References

PubChem Literature

From Data Sources

• Iball, J. et al., Nature (London), 1966, 209, 1230, (cryst struct)

• Hruska, F.E. et al., Can. J. Chem., 1974, 52, 497, (pmr)

• Davies, D.B., Stud. Biophys., 1976, 55, 29; CA, 85, 59065h, (cmr)

• Du Frain, R.J., Basic Life Sci., 1984, 29A, 41; 59; 83, (revs)

• Aoyama, H., Bull. Chem. Soc. Jpn., 1987, 60, 2073, (synth)

• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, BNC750

• Beltz, R.E. et al., J.A.C.S., 1955, 77, 736, (synth)

• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 3, 375A, (nmr)

• Asakura, J. et al., J.O.C., 1990, 55, 4928, (synth, pmr, uv)

• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 460

• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 816C, (ir)

• Thymidine analog, preferentially incorporated into cellular DNA in place of thymidine, producing increased radiosensitivity of the cell: Int. J. Radiat. Oncol. Biol. Phys., 10, 1399 (1984); 21, 709 (1991). Mutagen used in genetic research: Mutat. Res., 258, 161 (1991). Reviews on use in diagnostics and research: Histochem. J., 27, 339, 923 (1995; 28, 531 (1996).

References

Bioactivity

PubChem BioAssay

Bioactivity