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I7000

Sigma-Aldrich

5-Iodo-2′-deoxycytidine

Synonym(s):

5-Iododeoxycytidine

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About This Item

Empirical Formula (Hill Notation):
C9H12IN3O4
CAS Number:
611-53-0
Molecular Weight:
353.11
EC Number:
210-269-8
MDL number:
MFCD00038063
UNSPSC Code:
41106305
PubChem Substance ID:
24896100
NACRES:
NA.51

biological source

synthetic (organic)

assay

≥99% (HPLC)

form

powder

solubility

water: 50 mg/mL, clear, colorless

storage temp.

−20°C

SMILES string

NC1=NC(=O)N(C=C1I)[C@H]2C[C@@H](O)[C@H](CO)O2

InChI

1S/C9H12IN3O4/c10-4-2-13(9(16)12-8(4)11)7-1-5(15)6(3-14)17-7/h2,5-7,14-15H,1,3H2,(H2,11,12,16)/t5?,6?,7-/m1/s1

InChI key

WEVJJMPVVFNAHZ-KPGICGJXSA-N

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Application

5-Iodo-2′-deoxycytidine (5-iododeoxycytidine) is used in the construction of DNA oligomers to enable structural studies and photoactivated cross-linking. 5-Iodo-2′-deoxycytidine is used in the synthesis of other modified nucleosides, such as 5-ethynylferrocenyl-2′-deoxycytidine used in semiconductor electrodes and 10-(2-deoxyβ-D-ribofuranosyl)pyrimido[4′,5′:4,5]pyrimido[1,6-a]indole-6,9(7H)-dione (dCPPI).

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

13 - Non Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Masahiro Mizuta et al.
The Journal of organic chemistry, 72(14), 5046-5055 (2007-06-09)
10-(2-Deoxy-beta-D-ribofuranosyl)pyrimido[4',5':4,5]pyrimido[1,6-a]indole-6,9(7H)-dione (dCPPI) and its derivatives were synthesized via the Suzuki-Miyaura coupling reaction of 5-iododeoxycytidine with 5-substituted N-Boc-indole-2-borates and characterized by UV-vis and fluorescence spectroscopy. The new fluorescent nucleosides showed rather large Stokes shifts (116-139 nm) in an aqueous buffer. The
Andrew R Pike et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 11(1), 344-353 (2004-11-20)
The ferrocenyl-nucleoside, 5-ethynylferrocenyl-2'-deoxycytidine (1) has been prepared by Pd-catalyzed cross-coupling between ethynylferrocene and 5-iodo-2'-deoxycytidine and incorporated into oligonucleotides by using automated solid-phase synthesis at both silica supports (CPG) and modified single-crystal silicon electrodes. Analysis of DNA oligonucleotides prepared and cleaved
Hereditary orotic aciduria, Lesch-Nyhan syndrome, and xeroderma pigmentosum probed by herpes simplex virus: 125I-iododeoxycytidine incorporation as an assay for viral growth.
J Campisi et al.
Journal of cellular physiology, 114(1), 21-28 (1983-01-01)
L Fox et al.
Antimicrobial agents and chemotherapy, 23(3), 465-476 (1983-03-01)
The incorporation into DNA of 5-bromocytosine and 5-iodocytosine, derived from their respective administered deoxyribonucleoside analogs, has been demonstrated in studies with cells infected with herpes simplex virus types 1 and 2 (HSV-1 and HSV-2) and in cells transformed with the
Sunil Kumar et al.
Scientific reports, 10(1), 1233-1233 (2020-01-29)
Inferring cell-signaling networks from high-throughput data is a challenging problem in systems biology. Recent advances in cytometric technology enable us to measure the abundance of a large number of proteins at the single-cell level across time. Traditional network reconstruction approaches
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