110988-86-8

Basic information

• Product Name: 2',2'-difluorodeoxycytidine 5'-triphosphate
• Synonyms: 2',2'-difluorodeoxycytidine 5'-triphosphate;2'-Deoxy-2',2'-difluorocytidine 5'-triphosphate sodium salt
• CAS NO: 110988-86-8
• Molecular Formula: C9H14F2N3O13P3
• Molecular Weight: 503.14
• Mol File: 110988-86-8.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 797.7°Cat760mmHg
• Flash Point: 436.2°C
• Appearance: /
• Density: 2.43g/cm³
• PKA: 0.80±0.50(Predicted)
• CAS DataBase Reference: 2',2'-difluorodeoxycytidine 5'-triphosphate(CAS DataBase Reference)
• NIST Chemistry Reference: 2',2'-difluorodeoxycytidine 5'-triphosphate(110988-86-8)
• EPA Substance Registry System: 2',2'-difluorodeoxycytidine 5'-triphosphate(110988-86-8)

Safety Data

• Hazardous Substances Data: 110988-86-8(Hazardous Substances Data)

Usage

Description

2',2'-Difluorodeoxycytidine 5'-triphosphate is a nucleoside triphosphate analog that features two fluorine atoms and is structurally akin to deoxycytidine, a fundamental component of DNA. This modified nucleotide is designed to be integrated into the DNA of cancer cells during replication, thereby disrupting the DNA's normal function and impeding the proliferation of cancer cells.

Uses

Used in Anticancer Applications:
2',2'-Difluorodeoxycytidine 5'-triphosphate is utilized as an anticancer agent for its ability to interfere with the DNA replication process in cancer cells. It is particularly being explored for its potential in treating various forms of cancer, including leukemia, lymphoma, and solid tumors, due to its mechanism of action that inhibits cancer cell growth.
Used in Viral Infection Treatments:
In the medical field, 2',2'-Difluorodeoxycytidine 5'-triphosphate is also considered for use as an antiviral agent, showing promise in the treatment of viral infections such as HIV and hepatitis B. Its incorporation into viral DNA during replication may lead to the disruption of viral replication processes, offering a potential therapeutic strategy against these infections.

Upstream product

• 1035495-83-0 C₁₇H₁₄F₈N₅O₈P 

Relevant articles and documents

Synthesis of gemcitabine triphosphate (dFdCTP) as a tris(triethylammonium) salt

First synthesis of gemcitabine triphosphate (dFdCTP) as a tris(triethylammonium) salt is reported.

Inactivation of lactobacillus leichmannii ribonucleotide reductase by 2',2'-difluoro2'-deoxycytidine s'-triphosphate: Covalent modification

Ribonucleotide reductase (RNR) from Lactobacillus leichmannii, a 76 kDa monomer using adenosylcobalamin (AdoCbl) as a cofactor, catalyzes the conversion of nucleoside triphosphates to deoxynucleotides and is rapidly ( 3H]- and [5-3H]F2CTP were synthesized and used independently to inactivate RNR. Sephadex G-50 chromatography of the inactivation mixture revealed that 0.47 equiv of a sugar was covalently bound to RNR and that 0.71 equiv of cytosine was released. Alternatively, analysis of the inactivated RNR by SDS-PAGE without boiling resulted in 33% of RNR migrating as a 110 kDa protein. Inactivation of RNR with a mixture of [1'-3H]F2CTP and [1'-2H]F 2CTP followed by reduction with NaBH4, alkylation with iodoacetamide, trypsin digestion, and HPLC separation of the resulting peptides allowed isolation and identification by MALDI-TOF mass spectrometry (MS) of a 3H/2H-labeled peptide containing C731 and C736 from the C-terminus of RNR accounting for 10% of the labeled protein. The MS analysis also revealed that the two cysteines were cross-linked to a furanone species derived from the sugar of F2CTP. Incubation of [1-3H]F2CTP with C119S-RNR resulted in 0.3 equiv of sugar being covalently bound to the protein, and incubation with NaBH4 subsequent to inactivation resulted in trapping of 2'-fluoro-2'-deoxycytidine. These studies and the ones in the preceding paper (DOI: 10.1021/bi9021318) allow proposal of a mechanism of inactivation of RNR by F2CTP involving multiple reaction pathways. The proposed mechanisms share many common features with F2CDP inactivation of the class I RNRs.