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2002-35-9

2002-35-9 | Adenosine, 2'-deoxy-N-methyl-

CAS No: 2002-35-9 Catalog No: AG002CM4 MDL No:MFCD00055999

Product Description

Catalog Number:
AG002CM4
Chemical Name:
Adenosine, 2'-deoxy-N-methyl-
CAS Number:
2002-35-9
Molecular Formula:
C11H15N5O3
Molecular Weight:
265.2685
MDL Number:
MFCD00055999
IUPAC Name:
(2R,3S,5R)-2-(hydroxymethyl)-5-[6-(methylamino)purin-9-yl]oxolan-3-ol
InChI:
InChI=1S/C11H15N5O3/c1-12-10-9-11(14-4-13-10)16(5-15-9)8-2-6(18)7(3-17)19-8/h4-8,17-18H,2-3H2,1H3,(H,12,13,14)/t6-,7+,8+/m0/s1
InChI Key:
DYSDOYRQWBDGQQ-XLPZGREQSA-N
SMILES:
OC[C@H]1O[C@H](C[C@@H]1O)n1cnc2c1ncnc2NC
UNII:
48QZW2IR9H

Properties

Complexity:
321  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
3  
Defined Bond Stereocenter Count:
0
Exact Mass:
265.117g/mol
Formal Charge:
0
Heavy Atom Count:
19  
Hydrogen Bond Acceptor Count:
7  
Hydrogen Bond Donor Count:
3  
Isotope Atom Count:
0
Molecular Weight:
265.273g/mol
Monoisotopic Mass:
265.117g/mol
Rotatable Bond Count:
3  
Topological Polar Surface Area:
105A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
-0.2  

Literature

Title Journal
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Postsynaptic mechanisms of CO(2) responses in parafacial respiratory neurons of newborn rats. The Journal of physiology 20120401
P2Y1 purinoceptor inhibition reduces extracellular signal-regulated protein kinase 1/2 phosphorylation in spinal cord and dorsal root ganglia: implications for cancer-induced bone pain. Acta biochimica et biophysica Sinica 20120401
Dynamic mass redistribution assays decode surface influence on signaling of endogenous purinergic P2Y receptors. Assay and drug development technologies 20120201
P2Y1 receptor modulation of Ca2+-activated K+ currents in medium-sized neurons from neonatal rat striatal slices. Journal of neurophysiology 20120201
Functional contribution of P2Y1 receptors to the control of coronary blood flow. Journal of applied physiology (Bethesda, Md. : 1985) 20111201
Prevention of extracellular ADP-induced ATP accumulation of the cultured rat spinal astrocytes via P2Y(1)-mediated inhibition of AMPK. Neuroscience letters 20111010
Local Ca2+ detection and modulation of synaptic release by astrocytes. Nature neuroscience 20110911
Nucleotides control the excitability of sensory neurons via two P2Y receptors and a bifurcated signaling cascade. Pain 20110801
Regional functional specialization and inhibitory nitrergic and nonnitrergic coneurotransmission in the human esophagus. American journal of physiology. Gastrointestinal and liver physiology 20110501
ADP ribose is an endogenous ligand for the purinergic P2Y1 receptor. Molecular and cellular endocrinology 20110210
P2Y1 and P2Y13 purinergic receptors mediate Ca2+ signaling and proliferative responses in pulmonary artery vasa vasorum endothelial cells. American journal of physiology. Cell physiology 20110201
Purinergic receptor agonists modulate phagocytosis and clearance of apoptotic cells in macrophages. Immunobiology 20110101
Phosphodiesterase 7 inhibition preserves dopaminergic neurons in cellular and rodent models of Parkinson disease. PloS one 20110101
Involvement of P2X receptors in the regulation of insulin secretion, proliferation and survival in mouse pancreatic β-cells. Cellular physiology and biochemistry : international journal of experimental cellular physiology, biochemistry, and pharmacology 20110101
Platelet adhesion and degranulation induce pro-survival and pro-angiogenic signalling in ovarian cancer cells. PloS one 20110101
Metabolic regulation of coronary vascular tone: role of hydrogen peroxide, purinergic components, and angiotensin. European journal of pharmacology 20101025
TGF-β and LPS modulate ADP-induced migration of microglial cells through P2Y1 and P2Y12 receptor expression. Journal of neurochemistry 20101001
Facilitation of Ih channels by P2Y1 receptors activation in Mesencephalic trigeminal neurons. Neuroscience letters 20100927
Purinergic receptors in the rat lens: activation of P2X receptors following hyperosmotic stress. Investigative ophthalmology & visual science 20100801
Assessment and characterization of purinergic contractions and relaxations in the rat urinary bladder. Basic & clinical pharmacology & toxicology 20100701
Adenosine triphosphate stimulates RANKL expression through P2Y1 receptor-cyclo-oxygenase-dependent pathway in human periodontal ligament cells. Journal of periodontal research 20100601
P2Y1 receptors mediate apamin-sensitive and -insensitive inhibitory junction potentials in murine colonic circular smooth muscle. The Journal of pharmacology and experimental therapeutics 20100501
Two-pore potassium ion channels are inhibited by both G(q/11)- and G(i)-coupled P2Y receptors. Molecular and cellular neurosciences 20100401
AMP N(1)-oxide, a unique compound of royal jelly, induces neurite outgrowth from PC12 cells via signaling by protein kinase A independent of that by mitogen-activated protein kinase. Evidence-based complementary and alternative medicine : eCAM 20100301
Endogenous purinergic signaling is required for osmotic volume regulation of retinal glial cells. Journal of neurochemistry 20100301
Acetylsalicylic acid enhances purinergic receptor-mediated outward currents in rat megakaryocytes. American journal of physiology. Cell physiology 20100301
Axons and astrocytes release ATP and glutamate to evoke calcium signals in NG2-glia. Glia 20100101
CNGA2 contributes to ATP-induced noncapacitative Ca2+ influx in vascular endothelial cells. Journal of vascular research 20100101
Static magnetic field exposure reproduces cellular effects of the Parkinson's disease drug candidate ZM241385. PloS one 20100101
The P2Y(1) and P2Y(12) receptors mediate autoinhibition of transmitter release in sympathetic innervated tissues. Neurochemistry international 20091201
Increase of intracellular Ca2+ by P2Y but not P2X receptors in cultured cortical multipolar neurons of the rat. The Journal of comparative neurology 20091010
Extracellular ADP regulates lesion-induced in vivo cell proliferation and death in the zebrafish retina. Journal of neurochemistry 20091001
Role of P2Y1 receptor in astroglia-to-neuron signaling at dorsal spinal cord. Journal of neuroscience research 20090901
P2 receptor-mediated signaling in spherical bushy cells of the mammalian cochlear nucleus. Journal of neurophysiology 20090901
Role of purinergic P2Y1 receptors in regulation of vasopressin and oxytocin secretion. American journal of physiology. Regulatory, integrative and comparative physiology 20090801
Electrical stimulation of the mucosa evokes slow EPSPs mediated by NK1 tachykinin receptors and by P2Y1 purinoceptors in different myenteric neurons. American journal of physiology. Gastrointestinal and liver physiology 20090701
The NANC relaxation of the human ileal longitudinal and circular muscles is inhibited by MRS 2179, a P2 purinoceptor antagonist. Life sciences 20090619
Mechanism of activation and functional role of protein kinase Ceta in human platelets. The Journal of biological chemistry 20090515
Investigation of the role of adrenergic and non-nitrergic, non-adrenergic neurotransmission in the sheep isolated internal anal sphincter. Neurogastroenterology and motility : the official journal of the European Gastrointestinal Motility Society 20090301
Platelet responsiveness to yohimbine hydrochloride and MRS2179 in the context of the interaction between collagen and epinephrine in acute coronary syndrome. Blood cells, molecules & diseases 20090101
P2Y1 receptor activation elicits its partition out of membrane rafts and its rapid internalization from human blood vessels: implications for receptor signaling. Molecular pharmacology 20081201
Ca2+ signaling in injured in situ endothelium of rat aorta. Cell calcium 20080901
Effects of P2Y1 receptor on glial fibrillary acidic protein and glial cell line-derived neurotrophic factor production of astrocytes under ischemic condition and the related signaling pathways. Neuroscience bulletin 20080801
Contribution of P2Y(1) receptors to ADP signalling in mouse spinal cord cultures. Neuroscience letters 20080425
Functional evidence for purinergic inhibitory neuromuscular transmission in the mouse internal anal sphincter. American journal of physiology. Gastrointestinal and liver physiology 20080401
Involvement of P2Y1 and P2Y11 purinoceptors in parasympathetic inhibition of colonic smooth muscle. The Journal of pharmacology and experimental therapeutics 20080301
Acyl derivatives of coenzyme A inhibit platelet function via antagonism at P2Y1 and P2Y12 receptors: a new finding that may influence the design of anti-thrombotic agents. Platelets 20080301
P2Y1 receptors mediate inhibitory neuromuscular transmission and enteric neuronal activation in small intestine. Neurogastroenterology and motility : the official journal of the European Gastrointestinal Motility Society 20080201
Gi-coupled P2Y-ADP receptor mediates GSK-3 phosphorylation and beta-catenin nuclear translocation in granule neurons. Journal of neurochemistry 20080101
Possible role of extracellular nucleotides in ectopic ossification of human spinal ligaments. Journal of pharmacological sciences 20080101
GPR17: molecular modeling and dynamics studies of the 3-D structure and purinergic ligand binding features in comparison with P2Y receptors. BMC bioinformatics 20080101
Inhibition of ATP-induced glutamate release by MRS2179 in cultured dorsal spinal cord astrocytes. Pharmacology 20080101
Nucleotide P2Y1 receptor regulates EGF receptor mitogenic signaling and expression in epithelial cells. Journal of cell science 20071215
Pulses of somatostatin release are slightly delayed compared with insulin and antisynchronous to glucagon. Regulatory peptides 20071204
P2Y receptor-activating nucleotides modulate cellular reactive oxygen species production in dissociated hippocampal astrocytes and neurons in culture independent of parallel cytosolic Ca(2+) rise and change in mitochondrial potential. Journal of neuroscience research 20071115
The ADP receptor P2Y(1) mediates t-PA release in pigs during cardiac ischemia. Journal of thrombosis and thrombolysis 20071001
Reference curves for aggregation and ATP secretion to aid diagnose of platelet-based bleeding disorders: effect of inhibition of ADP and thromboxane A(2) pathways. Platelets 20070801
ATP release and hydrolysis contribute to rat pial arteriolar dilatation elicited by neuronal activation. Experimental physiology 20070701
Inhibitory neuromuscular transmission mediated by the P2Y1 purinergic receptor in guinea pig small intestine. American journal of physiology. Gastrointestinal and liver physiology 20070601
Evidence that ATP or a related purine is an excitatory neurotransmitter in the longitudinal muscle of mouse distal colon. British journal of pharmacology 20070501
Glycoprotein Ibalpha inhibition and ADP receptor antagonists, but not aspirin, reduce platelet thrombus formation in flowing blood exposed to atherosclerotic plaques. Thrombosis and haemostasis 20070301
Stimulation of adenosine A1 and A2A receptors by AMP in the submucosal plexus of guinea pig small intestine. American journal of physiology. Gastrointestinal and liver physiology 20070201
A novel mechanism of vasoregulation: ADP-induced relaxation of the porcine isolated coronary artery is mediated via adenosine release. FASEB journal : official publication of the Federation of American Societies for Experimental Biology 20070201
P2Y1 receptor modulation of the pre-Bötzinger complex inspiratory rhythm generating network in vitro. The Journal of neuroscience : the official journal of the Society for Neuroscience 20070131
ATP increases intracellular calcium in supraoptic neurons by activation of both P2X and P2Y purinergic receptors. American journal of physiology. Regulatory, integrative and comparative physiology 20070101
Mitochondrial calcium transport is regulated by P2Y1- and P2Y2-like mitochondrial receptors. Journal of cellular biochemistry 20061101
Regulation of death and survival in astrocytes by ADP activating P2Y1 and P2Y12 receptors. Biochemical pharmacology 20061016
P2Y1 receptors mediate inhibitory purinergic neuromuscular transmission in the human colon. American journal of physiology. Gastrointestinal and liver physiology 20061001
Enhanced food intake after stimulation of hypothalamic P2Y1 receptors in rats: modulation of feeding behaviour by extracellular nucleotides. The European journal of neuroscience 20061001
PAR4, but not PAR1, signals human platelet aggregation via Ca2+ mobilization and synergistic P2Y12 receptor activation. The Journal of biological chemistry 20060908
P2Y receptor-mediated excitation in the posterior hypothalamus. The European journal of neuroscience 20060901
Glucose induces glucagon release pulses antisynchronous with insulin and sensitive to purinoceptor inhibition. Endocrinology 20060701
Can the PFA-100 be modified to detect P2Y12 inhibition? Journal of thrombosis and haemostasis : JTH 20060601
Undetectable levels of N6-methyl adenine in mouse DNA: Cloning and analysis of PRED28, a gene coding for a putative mammalian DNA adenine methyltransferase. FEBS letters 20060529
Differential coupling of the P2Y1 receptor to Galpha14 and Galphaq/11 proteins during the development of the rat salivary gland. Archives of oral biology 20060501
Neurogenic secretion mediated by the purinergic P2Y1 receptor in guinea-pig small intestine. European journal of pharmacology 20060424
Activation of P2Y1 receptor triggers two calcium signaling pathways in bone marrow erythroblasts. European journal of pharmacology 20060318
Endothelium-dependent relaxation evoked by ATP and UTP in the aorta of P2Y2-deficient mice. British journal of pharmacology 20060301
Extracellular nucleotide signaling in adult neural stem cells: synergism with growth factor-mediated cellular proliferation. Development (Cambridge, England) 20060201
Supersensitivity of P2X receptors in cerebrocortical cell cultures after in vitro ischemia. Journal of neurochemistry 20051201
Metabotropic P2Y1 receptors inhibit P2X3 receptor-channels in rat dorsal root ganglion neurons. European journal of pharmacology 20051003
Dual presynaptic control by ATP of glutamate release via facilitatory P2X1, P2X2/3, and P2X3 and inhibitory P2Y1, P2Y2, and/or P2Y4 receptors in the rat hippocampus. The Journal of neuroscience : the official journal of the Society for Neuroscience 20050706
Inhibition of purinoceptors amplifies glucose-stimulated insulin release with removal of its pulsatility. Diabetes 20050701
The novel suramin analogue NF864 selectively blocks P2X1 receptors in human platelets with potency in the low nanomolar range. Naunyn-Schmiedeberg's archives of pharmacology 20050701
Metabotropic P2Y purinoceptor-mediated presynaptic and postsynaptic enhancement of cerebellar GABAergic transmission. The Journal of neuroscience : the official journal of the Society for Neuroscience 20050223
ADP acting on P2Y13 receptors is a negative feedback pathway for ATP release from human red blood cells. Circulation research 20050204
Direct excitation of inhibitory interneurons by extracellular ATP mediated by P2Y1 receptors in the hippocampal slice. The Journal of neuroscience : the official journal of the Society for Neuroscience 20041201
Regulation of rat hepatocyte function by P2Y receptors: focus on control of glycogen phosphorylase and cyclic AMP by 2-methylthioadenosine 5'-diphosphate. The Journal of pharmacology and experimental therapeutics 20041001
Stimulation of Xenopus P2Y1 receptor activates CFTR in A6 cells. Pflugers Archiv : European journal of physiology 20041001
Synergistic action between inhibition of P2Y12/P2Y1 and P2Y12/thrombin in ADP- and thrombin-induced human platelet activation. British journal of pharmacology 20040801
The P2Y1 receptor plays an essential role in the platelet shape change induced by collagen when TxA2 formation is prevented. Journal of thrombosis and haemostasis : JTH 20040601
Synthesis and biological activity of 2-alkylated deoxyadenosine bisphosphate derivatives as P2Y(1) receptor antagonists. Bioorganic & medicinal chemistry 20040401
ATP release triggered by activation of the Ca2+-activated K+ channel in human airway Calu-3 cells. American journal of respiratory cell and molecular biology 20040301
N(6)-Methyldeoxyadenosine, a nucleoside commonly found in prokaryotes, induces C2C12 myogenic differentiation. Biochemical and biophysical research communications 20040206
ATP modulates intracellular Ca2+ and firing rate through a P2Y1 purinoceptor in cane toad pacemaker cells. The Journal of physiology 20031101
Differential involvement of the P2Y1 and P2Y12 receptors in platelet procoagulant activity. Arteriosclerosis, thrombosis, and vascular biology 20031001
Nucleotide coronary vasodilation in guinea pig hearts. American journal of physiology. Heart and circulatory physiology 20030901
Nucleotide-mediated calcium signaling in rat cortical astrocytes: Role of P2X and P2Y receptors. Glia 20030901
Slow excitatory synaptic transmission mediated by P2Y1 receptors in the guinea-pig enteric nervous system. The Journal of physiology 20030715
The platelet P2Y receptors as targets for new antithrombotic drugs. Journal of thrombosis and haemostasis : JTH 20030601
Inhibition of localized thrombosis in P2Y1-deficient mice and rodents treated with MRS2179, a P2Y1 receptor antagonist. Journal of thrombosis and haemostasis : JTH 20030601
Induction of neurite outgrowth in PC12 cells by the bacterial nucleoside N6-methyldeoxyadenosine is mediated through adenosine A2a receptors and via cAMP and MAPK signaling pathways. Biochemical and biophysical research communications 20030516
P2Y receptor specific for diadenosine tetraphosphate in lung: selective inhibition by suramin, PPADS, Ip5I, and not by MRS-2197. European journal of pharmacology 20030502
Effects of inhibition of P2Y(1) and P2Y(12) on whole blood clotting, coagulum elasticity and fibrinolysis resistance studied with free oscillation rheometry. Thrombosis research 20030315
P2Y receptor-mediated inhibition of voltage-dependent Ca2+ channels in rat dorsal root ganglion neurons. Synapse (New York, N.Y.) 20030201
P2Y(1) receptor activation inhibits NMDA receptor-channels in layer V pyramidal neurons of the rat prefrontal and parietal cortex. Neurochemistry international 20030101
The P2Y(1) receptor as a target for new antithrombotic drugs: a review of the P2Y(1) antagonist MRS-2179. Cardiovascular drug reviews 20030101
The relative importance of the ADP receptors, P2Y12 and P2Y1, in thrombin-induced platelet activation. Thrombosis research 20030101
Activation of adenosine and P2Y receptors by ATP in human peripheral nerve. Naunyn-Schmiedeberg's archives of pharmacology 20021101
Effects of dinucleoside polyphosphates on regulation of coronary vascular tone. European journal of pharmacology 20020719
P2Y(1) and P2Y(2) receptors are coupled to the NO/cGMP pathway to vasodilate the rat arterial mesenteric bed. British journal of pharmacology 20020701
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2-Chloro N(6)-methyl-(N)-methanocarba-2'-deoxyadenosine-3',5'-bisphosphate is a selective high affinity P2Y(1) receptor antagonist. British journal of pharmacology 20020401
Novel antagonists acting at the P2Y(1) purinergic receptor: synthesis and conformational analysis using potentiometric and nuclear magnetic resonance titration techniques. Journal of medicinal chemistry 20020214
Nucleotide-mediated relaxation in guinea-pig aorta: selective inhibition by MRS2179. British journal of pharmacology 20020101
Effects of P2Y(1) and P2Y(12) receptor antagonists on ADP-induced shape change of equine platelets: comparison with human platelets. Platelets 20020101
The bacterial nucleoside N(6)-methyldeoxyadenosine induces the differentiation of mammalian tumor cells. Biochemical and biophysical research communications 20010720
Extracellular ADP is a powerful osteolytic agent: evidence for signaling through the P2Y(1) receptor on bone cells. FASEB journal : official publication of the Federation of American Societies for Experimental Biology 20010501
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Endothelium-dependent, MRS2179-independent actions of uridine 5'-triphosphate in guinea pig aorta. Proceedings of the Western Pharmacology Society 20010101

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