新型ATP 2-硫代衍生物的合成及生物活性
SYNTHESIS AND BIOLOGICAL ACTIVITY OF NOVEL 2-THIO DERIVATIVES OF ATP.
作者信息
Zimmet J, Järlebark L, Hammarberg T, van Galen P J M, Jacobson K A, Heilbronn E
机构信息
Unit of Neurochemistry and Neurotoxicology, Stockholm University, 106 91 Stockholm, Sweden.
Laboratory of Bioorganic Chemistry, National Institute of Diabetes and Digestive and Kidney Diseases, NIH, Bethesda, MD, 20892, USA.
出版信息
Nucleosides Nucleotides. 1993;12(1):1-20. doi: 10.1080/07328319308016190.
Abstract
2-Alkylthio analogues of adenosine 5'-triphosphate were synthesized and evaluated as P purinoceptor agonists. ATP and analogues transiently increased intracellular Ca levels in C6 glioma cells and in skeletal muscle derived myotubes in culture. Most derivatives were resistant to stepwise dephosphorylation by ecto-ATPases.
摘要
合成了腺苷 5'-三磷酸的 2-烷硫基类似物，并将其作为嘌呤受体激动剂进行评估。ATP 及其类似物可使培养的 C6 胶质瘤细胞和骨骼肌衍生的肌管中的细胞内钙水平短暂升高。大多数衍生物对胞外 ATP 酶的逐步去磷酸化具有抗性。
相似文献
1
SYNTHESIS AND BIOLOGICAL ACTIVITY OF NOVEL 2-THIO DERIVATIVES OF ATP.新型ATP 2-硫代衍生物的合成及生物活性
Nucleosides Nucleotides. 1993;12(1):1-20. doi: 10.1080/07328319308016190.
2
Identification of potent P2Y-purinoceptor agonists that are derivatives of adenosine 5'-monophosphate.鉴定作为5'-单磷酸腺苷衍生物的强效P2Y嘌呤受体激动剂。
Br J Pharmacol. 1996 Aug;118(8):1959-64. doi: 10.1111/j.1476-5381.1996.tb15630.x.
3
Sp-2-propylthio-ATP-α-B and Sp-2-propylthio-ATP-α-B,β-γ-dichloromethylene are novel potent and specific agonists of the human P2Y₁₁ receptor.Sp-2-丙基硫代-ATP-α-B 和 Sp-2-丙基硫代-ATP-α-B，β-γ-二氯亚甲基是新型强效和特异的人 P2Y₁₁ 受体激动剂。
Biochem Pharmacol. 2013 Sep 1;86(5):645-55. doi: 10.1016/j.bcp.2013.06.013. Epub 2013 Jun 25.
4
Identification of potent, selective P2Y-purinoceptor agonists: structure-activity relationships for 2-thioether derivatives of adenosine 5'-triphosphate.强效、选择性P2Y嘌呤受体激动剂的鉴定：三磷酸腺苷5'-硫醚衍生物的构效关系
J Med Chem. 1993 Nov 26;36(24):3937-46. doi: 10.1021/jm00076a023.
5
Potent agonist action of 2-thioether derivatives of adenine nucleotides at adenylyl cyclase-linked P2Y-purinoceptors.腺嘌呤核苷酸的2-硫醚衍生物对腺苷酸环化酶偶联的P2Y嘌呤受体具有强效激动作用。
Br J Pharmacol. 1995 Nov;116(6):2611-6. doi: 10.1111/j.1476-5381.1995.tb17215.x.
6
Ecto-nucleotide pyrophosphatase modulates the purinoceptor-mediated signal transduction and is inhibited by purinoceptor antagonists.胞外核苷酸焦磷酸酶调节嘌呤受体介导的信号转导，并受到嘌呤受体拮抗剂的抑制。
Br J Pharmacol. 2000 May;130(1):139-45. doi: 10.1038/sj.bjp.0703289.
7
Relative contribution of ecto-ATPase and ecto-ATPDase pathways to the biphasic effect of ATP on acetylcholine release from myenteric motoneurons.胞外ATP酶和胞外ATP二磷酸酶途径对ATP影响肌间运动神经元乙酰胆碱释放的双相效应的相对贡献。
Br J Pharmacol. 2009 Feb;156(3):519-33. doi: 10.1111/j.1476-5381.2008.00058.x. Epub 2009 Jan 13.
8
Two subtypes of G protein-coupled nucleotide receptors, P2Y(1) and P2Y(2) are involved in calcium signalling in glioma C6 cells.G蛋白偶联核苷酸受体的两种亚型，P2Y(1)和P2Y(2)，参与了胶质瘤C6细胞中的钙信号传导。
Br J Pharmacol. 2001 Jan;132(2):393-402. doi: 10.1038/sj.bjp.0703843.
9
The biphasic response of rat vesical smooth muscle to ATP.大鼠膀胱平滑肌对三磷酸腺苷的双相反应。
Br J Pharmacol. 1995 Apr;114(8):1557-62. doi: 10.1111/j.1476-5381.1995.tb14939.x.
10
Specific but noncompetitive inhibition by 2-alkylthio analogues of adenosine 5'-monophosphate and adenosine 5'-triphosphate of human platelet aggregation induced by adenosine 5'-diphosphate.5'-二磷酸腺苷诱导的人血小板聚集受到5'-单磷酸腺苷和5'-三磷酸腺苷的2-烷硫基类似物的特异性而非竞争性抑制。
Br J Pharmacol. 1982 Feb;75(2):397-400. doi: 10.1111/j.1476-5381.1982.tb08800.x.
引用本文的文献
1
Nucleotide P2Y receptor agonists are in vitro and in vivo prodrugs of A/A adenosine receptor agonists: implications for roles of P2Y and A/A receptors in physiology and pathology.核苷酸 P2Y 受体激动剂是体外和体内的 A/A 腺苷受体激动剂前药：对 P2Y 和 A/A 受体在生理和病理中的作用的影响。
Purinergic Signal. 2020 Dec;16(4):543-559. doi: 10.1007/s11302-020-09732-z. Epub 2020 Oct 31.
2
Strain Promoted Click Chemistry of 2- or 8-Azidopurine and 5-Azidopyrimidine Nucleosides and 8-Azidoadenosine Triphosphate with Cyclooctynes. Application to Living Cell Fluorescent Imaging.2-或8-叠氮嘌呤、5-叠氮嘧啶核苷以及8-叠氮三磷酸腺苷与环辛炔的应变促进点击化学。在活细胞荧光成像中的应用。
Bioconjug Chem. 2015 Aug 19;26(8):1519-32. doi: 10.1021/acs.bioconjchem.5b00300. Epub 2015 Jul 2.
3
Structure Activity Relationships for Derivatives of Adenosine-5'-Triphosphate as Agonists at P(2) Purinoceptors: Heterogeneity Within P(2X) and P(2Y) Subtypes.作为P(2)嘌呤受体激动剂的三磷酸腺苷-5'-衍生物的构效关系：P(2X)和P(2Y)亚型内的异质性
Drug Dev Res. 1994 Mar;31(3):206-219. doi: 10.1002/ddr.430310308. Epub 2004 Oct 5.
4
Activity of Novel Adenine Nucleotide Derivatives as Agonists and Antagonists at Recombinant Rat P2X Receptors.新型腺嘌呤核苷酸衍生物作为重组大鼠P2X受体激动剂和拮抗剂的活性
Drug Dev Res. 2000 Apr 1;49(4):253-259. doi: 10.1002/1098-2299(200004)49:4<253::AID-DDR4>3.0.CO;2-1. Epub 2000 Jun 12.
5
Attenuation of apoptosis in vitro and ischemia/reperfusion injury in vivo in mouse skeletal muscle by P2Y6 receptor activation.P2Y6受体激活对小鼠骨骼肌体外细胞凋亡及体内缺血/再灌注损伤的减轻作用。
Pharmacol Res. 2008 Sep-Oct;58(3-4):232-9. doi: 10.1016/j.phrs.2008.08.004. Epub 2008 Aug 30.
6
New insights on P2X purinoceptors.P2X嘌呤受体的新见解。
Naunyn Schmiedebergs Arch Pharmacol. 1995 Dec;352(6):585-96. doi: 10.1007/BF00171316.
7
Identification of potent, selective P2Y-purinoceptor agonists: structure-activity relationships for 2-thioether derivatives of adenosine 5'-triphosphate.强效、选择性P2Y嘌呤受体激动剂的鉴定：三磷酸腺苷5'-硫醚衍生物的构效关系
J Med Chem. 1993 Nov 26;36(24):3937-46. doi: 10.1021/jm00076a023.
8
Effects of ATP and UTP in pheochromocytoma PC12 cells: evidence for the presence of three P2 receptors, only one of which subserves stimulation of norepinephrine release.三磷酸腺苷（ATP）和尿苷三磷酸（UTP）对嗜铬细胞瘤PC12细胞的作用：存在三种P2受体的证据，其中只有一种参与去甲肾上腺素释放的刺激作用。
Cell Mol Neurobiol. 1994 Feb;14(1):27-47. doi: 10.1007/BF02088587.
本文引用的文献
1
Differentiated rat glial cell strain in tissue culture.组织培养中的分化大鼠神经胶质细胞系。
Science. 1968 Jul 26;161(3839):370-1. doi: 10.1126/science.161.3839.370.
2
A new generation of Ca2+ indicators with greatly improved fluorescence properties.新一代具有大大改善的荧光特性的钙离子指示剂。
J Biol Chem. 1985 Mar 25;260(6):3440-50.
3
Involvement of inositol 1,4,5-trisphosphate and calcium in the action of adenine nucleotides on aortic endothelial cells.肌醇1,4,5 -三磷酸和钙在腺嘌呤核苷酸对主动脉内皮细胞作用中的参与情况。
J Biol Chem. 1987 Dec 25;262(36):17461-6.
4
Adenosine 5'-(2-fluorodiphosphate) is a selective agonist at P2-purinoceptors mediating relaxation of smooth muscle.腺苷5'-(2-氟二磷酸)是一种选择性激动剂，作用于介导平滑肌舒张的P2嘌呤受体。
Eur J Pharmacol. 1988 Feb 16;147(1):131-6. doi: 10.1016/0014-2999(88)90642-5.
5
Externally applied adenosine-5'-triphosphate causes inositol triphosphate accumulation in cultured chick myotubes.外用腺苷-5'-三磷酸导致培养的鸡肌管中肌醇三磷酸积累。
Neurosci Lett. 1987 Feb 24;74(2):199-204. doi: 10.1016/0304-3940(87)90149-2.
6
Extracellular ATP activates polyphosphoinositide breakdown and Ca2+ mobilization in Ehrlich ascites tumor cells.细胞外ATP可激活艾氏腹水瘤细胞中的多磷酸肌醇分解和Ca2+动员。
Arch Biochem Biophys. 1986 Feb 15;245(1):84-95. doi: 10.1016/0003-9861(86)90192-x.
7
ATP-induced cation influx in myotubes is additive to cholinergic agonist action.三磷酸腺苷（ATP）诱导的肌管阳离子内流与胆碱能激动剂的作用具有相加性。
Acta Physiol Scand. 1985 Nov;125(3):389-93. doi: 10.1111/j.1748-1716.1985.tb07734.x.
8
Is there a basis for distinguishing two types of P2-purinoceptor?是否有依据区分两种类型的P2嘌呤受体？
Gen Pharmacol. 1985;16(5):433-40. doi: 10.1016/0306-3623(85)90001-1.
9
Adenosine derivatives with N6-alkyl, -alkylamine or -alkyladenosine substituents as probes for the A1-receptor.具有N6-烷基、-烷基胺或-烷基腺苷取代基的腺苷衍生物作为A1受体的探针。
FEBS Lett. 1987 Oct 19;223(1):197-201. doi: 10.1016/0014-5793(87)80535-5.
10
P2-purinoceptor-stimulated phosphoinositide turnover in chick myotubes. Calcium mobilization and the role of guanyl nucleotide-binding proteins.
FEBS Lett. 1988 Aug 1;235(1-2):133-6. doi: 10.1016/0014-5793(88)81248-1.
Zotero 插件