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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

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P264 - P270 - P301 + P312 - P501

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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S A Koch et al.
Pharmaceutical research, 4(4), 317-320 (1987-08-01)
Two Mannich-base prodrugs of 5-iodo-2'-deoxycytidine (5-IDC) have been synthesized. The prodrugs exhibit increased lipid solubility compared to 5-IDC and rapidly revert to 5-IDC in buffer. One of the prodrugs delivered about twice as much 5-IDC from isopropyl myristate (IPM) through
P W Hammond et al.
Molecular and cellular biology, 17(1), 296-308 (1997-01-01)
Telomerase is a ribonucleoprotein enzyme that adds telomeric sequence repeats to the ends of linear chromosomes. In vitro, telomerase has been observed to add repeats to a DNA oligonucleotide primer in a processive manner, leading to the postulation of a
D Sincholle et al.
Current eye research, 4(5), 627-629 (1985-05-01)
The study of the permeability of the cornea to 5-iodo-2'-deoxycytidine (IDC), an antiherpetic agent was performed in the rabbit. In a first experiment, using 125I-IDC eye-drops and a sustained contact between the drug and the cornea, we showed that the
[Superficial herpetic keratitis: comparative double-blind treatment with iododeoxycytidine and acyclovir].
J Colin
Bulletin des societes d'ophtalmologie de France, 84(11), 1283-1286 (1984-11-01)
R J DuFrain
Basic life sciences, 29 Pt A, 41-58 (1984-01-01)
This communication describes the use of 6 different halogenated pyrimidine analogues, bromodeoxyuridine (BrdUrd), chlorodeoxyuridine (CldUrd), iododeoxyuridine (IdUrd), bromodeoxycytidine (BrdCyd), chlorodeoxycytidine (CldCyd), and iododeoxycytidine (IdCyd), to achieve sister chromatid differentiation (SCD) and evaluate sister chromatid exchange (SCE) formation in mitogen-stimulated human
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