Home Other Building Blocks 8-CHLOROADENOSINE

8-CHLOROADENOSINE

CAS No.:
34408-14-5
Catalog Number:
AG00BYFI
Molecular Formula:
C10H12ClN5O4
Molecular Weight:
301.6864
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Product Description
Catalog Number:
AG00BYFI
Chemical Name:
8-CHLOROADENOSINE
CAS Number:
34408-14-5
Molecular Formula:
C10H12ClN5O4
Molecular Weight:
301.6864
MDL Number:
MFCD01076457
IUPAC Name:
(2R,3R,4S,5R)-2-(6-amino-8-chloropurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
InChI:
InChI=1S/C10H12ClN5O4/c11-10-15-4-7(12)13-2-14-8(4)16(10)9-6(19)5(18)3(1-17)20-9/h2-3,5-6,9,17-19H,1H2,(H2,12,13,14)/t3-,5-,6-,9-/m1/s1
InChI Key:
MHDPPLULTMGBSI-UUOKFMHZSA-N
SMILES:
OC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1c(Cl)nc2c1ncnc2N
UNII:
PA05MFH3I7
Properties
Complexity:
367  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
4  
Defined Bond Stereocenter Count:
0
Exact Mass:
301.058g/mol
Formal Charge:
0
Heavy Atom Count:
20  
Hydrogen Bond Acceptor Count:
8  
Hydrogen Bond Donor Count:
4  
Isotope Atom Count:
0
Molecular Weight:
301.687g/mol
Monoisotopic Mass:
301.058g/mol
Rotatable Bond Count:
2  
Topological Polar Surface Area:
140A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
-0.1  
Literature
Title Journal
Regioselective enzymatic undecylenoylation of 8-chloroadenosine and its analogs with biomass-based 2-methyltetrahydrofuran as solvent. Bioresource technology 20120801
E2F1 enhances 8-chloro-adenosine-induced G2/M arrest and apoptosis in A549 and H1299 lung cancer cells. Biochemistry. Biokhimiia 20120301
Integrative gene expression profiling reveals G6PD-mediated resistance to RNA-directed nucleoside analogues in B-cell neoplasms. PloS one 20120101
A unique RNA-directed nucleoside analog is cytotoxic to breast cancer cells and depletes cyclin E levels. Breast cancer research and treatment 20100601
Intracellular succinylation of 8-chloroadenosine and its effect on fumarate levels. The Journal of biological chemistry 20100312
Preclinical activity of 8-chloroadenosine with mantle cell lymphoma: roles of energy depletion and inhibition of DNA and RNA synthesis. British journal of haematology 20091101
Inhibition of ATP synthase by chlorinated adenosine analogue. Biochemical pharmacology 20090915
Inhibition of CHK1 kinase by Gö6976 converts 8-chloro-adenosine-induced G2/M arrest into S arrest in human myelocytic leukemia K562 cells. Biochemical pharmacology 20090301
8-Chloro-adenosine-induced E2F1 promotes p14ARF gene activation in H1299 cells through displacing Sp1 from multiple overlapping E2F1/Sp1 sites. Journal of cellular biochemistry 20090215
Inhibition of topoisomerase II by 8-chloro-adenosine triphosphate induces DNA double-stranded breaks in 8-chloro-adenosine-exposed human myelocytic leukemia K562 cells. Biochemical pharmacology 20090201
Induction of p14ARF by E2F1 contributes to 8-chloro-adenosine-induced apoptosis in human lung cancer H1299 cells. Chemotherapy 20090101
Protein kinase A-independent inhibition of proliferation and induction of apoptosis in human thyroid cancer cells by 8-Cl-adenosine. The Journal of clinical endocrinology and metabolism 20080301
Multiple myeloma cell killing by depletion of the MET receptor tyrosine kinase. Cancer research 20071015
8-Chloro-adenosine inhibits growth at least partly by interfering with actin polymerization in cultured human lung cancer cells. Biochemical pharmacology 20060828
8-chloroadenosine induced HL-60 cell growth inhibition, differentiation, and G(0)/G(1) arrest involves attenuated cyclin D1 and telomerase and up-regulated p21(WAF1/CIP1). Journal of cellular biochemistry 20060101
The combination of sulfinosine and 8-Cl-cAMP induces synergistic cell growth inhibition of the human neuroblastoma cell line in vitro. Investigational new drugs 20060101
[Mechanisms of sensitization by 8-chloro-adenosine of human tumor cells to TRAIL-induced apoptosis]. Zhonghua zhong liu za zhi [Chinese journal of oncology] 20051001
8-Chloro-cyclic AMP-induced growth inhibition and apoptosis is mediated by p38 mitogen-activated protein kinase activation in HL60 cells. Cancer research 20050601
[Preparation of 8-chloro-adenosine long circulation liposomes and its pharmacokinetics in rats]. Yao xue xue bao = Acta pharmaceutica Sinica 20050401
8-Cl-cAMP and its metabolite, 8-Cl-adenosine induce growth inhibition in mouse fibroblast DT cells through the same pathways: protein kinase C activation and cyclin B down-regulation. Journal of cellular physiology 20041101
8-Chloro-adenosine sensitizes a human hepatoma cell line to TRAIL-induced apoptosis by caspase-dependent and -independent pathways. Oncology reports 20040701
[Inhibition of 8-chloroadenosine on proteasome activity of HL-60 cells]. Ai zheng = Aizheng = Chinese journal of cancer 20040201
Anti-cowpox virus activities of certain adenosine analogs, arabinofuranosyl nucleosides, and 2'-fluoro-arabinofuranosyl nucleosides. Nucleosides, nucleotides & nucleic acids 20040101
8-Cl-Adenosine enhances 1,25-dihydroxyvitamin D3-induced growth inhibition without affecting 1,25-dihydroxyvitamin D3-stimulated differentiation of primary mouse epidermal keratinocytes. BMC pharmacology 20040101
[The inhibitory effect of 8-chloroadenosine on tumor necrosis factor-induced proto-oncogene expression of retinal pigment epithelial cells]. [Zhonghua yan ke za zhi] Chinese journal of ophthalmology 20031201
RNA-directed actions of 8-chloro-adenosine in multiple myeloma cells. Cancer research 20031115
[8-Chloro-adenosine increases the activity of transcription factor CREB by modification of phosphorylation]. Ai zheng = Aizheng = Chinese journal of cancer 20030401
Anti-proliferative effects of 8-chloro-cAMP and other cAMP analogs are unrelated to their effects on protein kinase A regulatory subunit expression. Journal of cellular physiology 20020801
Plasma and cellular pharmacology of 8-chloro-adenosine in mice and rats. Cancer chemotherapy and pharmacology 20020801
Genome-wide expression profiling of 8-chloroadenosine- and 8-chloro-cAMP-treated human neuroblastoma cells using radioactive human cDNA microarray. Experimental & molecular medicine 20020731
Synthesis and hybridization properties of RNA containing 8-chloroadenosine. Nucleosides, nucleotides & nucleic acids 20020101
8-Cl-adenosine is an active metabolite of 8-Cl-cAMP responsible for its in vitro antiproliferative effects on CHO mutants hypersensitive to cytostatic drugs. Cancer chemotherapy and pharmacology 20011201
8-chloro-cAMP and 8-chloro-adenosine act by the same mechanism in multiple myeloma cells. Cancer research 20010715
8-Cl-adenosine mediated cytotoxicity and sensitization of T-lymphoblastic leukemia cells to TNFalpha-induced apoptosis is via inactivation of NF-kappaB. Leukemia research 20010501
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