I7000
5-Iodo-2′-deoxycytidine
Synonym(s):
5-Iododeoxycytidine
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About This Item
Empirical Formula (Hill Notation):
C9H12IN3O4
CAS Number:
Molecular Weight:
353.11
EC Number:
MDL number:
UNSPSC Code:
41106305
PubChem Substance ID:
NACRES:
NA.51
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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).
Signal Word
Warning
Hazard Statements
Precautionary Statements
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
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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
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
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
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
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
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