908130-61-0

Basic information

• Product Name: 7-Deaza-2'-deoxy-7-iodoadenosine
• Synonyms: 7-Deaza-2'-deoxy-7-iodoadenosine;7-Deaza-21-deoxy-7-iodoadenosine;(2S,3R,5S)-5-(4-AMino-5-iodo-7H-pyrrolo[2,3-d]pyriMidin-7-yl)-2-(hydroxyMethyl)tetrahydrofuran-3-ol;7-(2-Deoxy-beta-L-erythro-pentofuranosyl)-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-4-amine;(2S,3R,5S)-5-(4-amino-5-iodopyrrolo[2,3-d]pyrimidin-7-yl)-2-(hydroxymethyl)oxolan-3-ol
• CAS NO: 908130-61-0
• Molecular Formula: C11H13IN4O3
• Molecular Weight: 376.15039
• EINECS: 1806241-263-5
• Mol File: 908130-61-0.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 7-Deaza-2'-deoxy-7-iodoadenosine(CAS DataBase Reference)
• NIST Chemistry Reference: 7-Deaza-2'-deoxy-7-iodoadenosine(908130-61-0)
• EPA Substance Registry System: 7-Deaza-2'-deoxy-7-iodoadenosine(908130-61-0)

Safety Data

• Hazardous Substances Data: 908130-61-0(Hazardous Substances Data)

Usage

General Description

7-Deaza-2'-deoxy-7-iodoadenosine is a synthetic chemical compound that is derived from adenosine, a nucleoside found in DNA and RNA. It is a modified form of adenosine, with the substitution of iodine at the 7th position and the replacement of the nitrogen on the 7th carbon with a carbon atom. This modification gives 7-Deaza-2'-deoxy-7-iodoadenosine unique properties and potential uses in biochemical research and medical applications. It is being explored for its potential as an anticancer agent, as well as for its ability to inhibit nucleoside transporters and modify DNA structure. The compound is also being investigated for its potential as a radiolabeled tracer in positron emission tomography (PET) imaging. Overall, 7-Deaza-2'-deoxy-7-iodoadenosine shows promise as a versatile chemical with various potential applications in the fields of medicine and biology.

Upstream product

• 141846-57-3 3,5-di-O-(4-methylbenzoyl)-2-deoxy-α-L-erythro-pentofuranosyl chloride 
• 123148-78-7 4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine 
• 933995-40-5 4-chloro-7-(2-deoxy-β-L-erythro-pentofuranosyl)-5-iodo-7H-pyrrolo[2,3-d]pyrimidine 
• 4330-21-6 2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride 
• 178420-94-5 (2R,3S,5R)-5-(4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-2-(((4-methylbenzoyl)oxy)methyl)tetrahydrofuran-3-yl 4-methylbenzoate 
• 178995-71-6 9-(β-D-2'-deoxyribofuranosyl)-6-chloro-7-iodo-7-deazapurine 

Downstream Products

• 1810869-43-2 ((2R,3S,5R)-5-(4-amino-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-3-((tert-butyldimethylsilyl)oxy)tetrahydrofuran-2-yl)methanol 

Relevant articles and documents

9-(2-Deoxy-α-D-ribofuranosyl)-7-iodo-7-deazaadenine

The structure of 4-amino-7-(2-deoxy-α-D-erythropentofuranosyl)-5-iodo-7H-pyrrolo[2,3-d] pyrimidine, C11H13IN4C3, has been determined. The N-glycosidic bond torsion angle χ is in the anti range [128.7 (12)°]. Both, the bulky iodo substituent and the N atom of the 6-amino group lie out of the 7-deazapurine plane, with deviations of -0.013 (10) and -0.0632 (12) A, respectively.

Synthesis and photophysical evaluation of new fluorescent 7-arylethynyl-7-deazaadenosine analogs

Three new fluorescent 7-deaza-2′-deoxyadenosine analogs were synthesized via the Sonogashira cross-coupling reaction of 7-iodo-7-deaza-2′-deoxyadenosine with 1-ethynylpyrene, 2-ethynyl-6-methoxynaphthalene, and 9-ethynylphenanthrene. The spectral properties of these analogs were evaluated in dioxane, EtOH, and H2O to determine their potential for use as environmentally sensitive fluorescent probes. All three analogs displayed large solvatofluorochromicity in H2O, relative to their emission wavelengths in dioxane or EtOH. Moreover, all three analogs exhibited microenvironmental sensitivity of their fluorescence emission intensity, being moderate to high quantum yields in dioxane and EtOH and significantly lower in H2O. Various attempts to perform domino cross-coupling and annuation reactions on 7-deaza-7-alkynyladenine derivatives to form a new fused tricyclic adenine analog were unsuccessful.

Method and reagent for gene sequence analysis

Provided is a nucleic acid substrate which has nucleic acid substrate characteristics equivalent to those of dATP, has a low substrate specificity for luciferase, exerts no negative effect on enzymatic reactions such as a complementary-strand synthesis, and therefore is particularly suitable for the pyrosequencing method. As a nucleic acid substrate complementary to nucleotide T, a 7-substituted deoxyribonucleotide triphosphate whose 7-position of a purine group is modified by a substituent is used as a substitute for a nucleotide α-thiotriphosphate analog.