ATP | 56-65-5

• 物质功能分类: 生物化工 - 核酸类
• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷酸
• 英文名称: ATP
• 英文别名: O^5'-tetrahydroxy[1]triphosphoryl-adenosine；[[(2R,3S,4R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] phosphono hydrogen phosphate
• CAS: 56-65-5；653-60-1；3714-60-1；58175-53-4；70470-60-9；74427-34-2；74427-35-3
• 化学式: C₁₀H₁₆N₅O₁₃P₃
• 分子量: 507.184
• InChiKey: ZKHQWZAMYRWXGA-VTHZCTBJSA-N

物化性质

• 熔点：
  144°C (rough estimate)
• 沸点：
  951.4±75.0 °C(Predicted)
• 比旋光度：
  D22 -26.7° (c = 3.095)
• 密度：
  1.0 g/mL at 20 °C
• 溶解度：
  Soluble (water), Na and K salts are easily soluble in water, Ba salts are insoluble in water
• LogP：
  -4.180 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  -5.7
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  279
• 氢给体数：
  7
• 氢受体数：
  17

安全信息

• 安全说明：
  S22,S24/25
• WGK Germany：
  3
• 危险品运输编号：
  OTH
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

制备方法与用途

用途

5'-三磷酸腺苷是腺苷的一种的代谢物，一种多功能三磷酸核苷，在细胞中用作细胞内能量转移的辅酶它在细胞内运输化学能量进行新陈代谢。

生物活性

ATP dipotassium (Adenosine 5'-triphosphate) 是体内能量储存和代谢的重要物质，为代谢提供能量，同时在细胞中作为辅酶发挥作用。ATP 是免疫和炎症中重要的内源性信号分子。

靶点

Human Endogenous Metabolite

体外研究

ATP (5 mM; 1 hour) co-treatment with LPS (1 μg/mL) has a synergistic effect on the activation of the NLRP3 inflammasome in HGFs.
ATP (2 mM; 0.5-24 hours) induces secretion of IL-1β, KC and MIP-2 from BMDMs in a caspase-1 activation-dependent manner.
ATP promotes neutrophil chemotaxis in vitro.

体内研究

ATP (50 mg/kg; i.p.) protects mice against bacterial infection in vivo.
ATP induces the secretion of IL-1β, KC and MIP-2 and neutrophils recruitment in vivo.

Animal Model:	Four-week-old Kunming mice (18-22 g)
Dosage:	50 mg/kg
Administration:	Intraperitoneal injection, before bacterial ( E. coli ) challenge
Result:	Protected mice from bacterial infection.

类别

有毒物品

毒性分级

高毒

急性毒性

腹腔-大鼠 LD50; 200 毫克/公斤; 腹腔-小鼠 LD50: 2780 毫克/公斤

可燃性危险特性

可燃; 燃烧产生有毒氮氧化物和磷氧化物烟雾

储运特性

通风低温干燥; 与库房食品原料分开存放

灭火剂

干粉,泡沫,沙土,二氧化碳, 雾状水

反应信息

• 作为试剂：
  描述：

  2-氰基-6-羟基苯并噻唑 、 D-cysteine 在 ATP 、 magnesium chloride 、 zinc(II) chloride 、 luciferase 作用下， 以 aq. buffer 为溶剂， 反应 1.0h， 以27%的产率得到D-虫荧光素游离酸
  参考文献：
  名称：

  Strategy for Dual-Analyte Luciferin Imaging: In Vivo Bioluminescence Detection of Hydrogen Peroxide and Caspase Activity in a Murine Model of Acute Inflammation

  摘要：

  In vivo molecular imaging holds promise for understanding the underlying mechanisms of health, injury, aging, and disease, as it can detect distinct biochemical processes such as enzymatic activity, reactive small-molecule fluxes, or post-translational modifications. Current imaging techniques often detect only a single biochemical process, but, within whole organisms, multiple types of biochemical events contribute to physiological and pathological phenotypes. In this report, we present a general strategy for dual-analyte detection in living animals that employs in situ formation of firefly luciferin from two complementary caged precursors that can be unmasked by different biochemical processes. To establish this approach, we have developed Peroxy Caged Luciferin-2 (PCL-2), a H2O2-responsive boronic acid probe that releases 6-hydroxy-2-cyanobenzothiazole (HCBT) upon reacting with this reactive oxygen species, as well as a peptide-based probe, z-Ile-Glu-ThrAsp-D-Cys (IETDC), which releases D-cysteine in the presence of active caspase 8. Once released, HCBT and D-cysteine form firefly luciferin in situ, giving rise to a bioluminescent signal if and only if both chemical triggers proceed. This system thus constitutes an AND-type molecular logic gate that reports on the simultaneous presence of H2O2 and caspase 8 activity. Using these probes, chemoselective imaging of either H2O2 or caspase 8 activity was performed in vitro and in vivo. Moreover, concomitant use of PCL-2 and IETDC in vivo establishes a concurrent increase in both H2O2 and caspase 8 activity during acute inflammation in living mice. Taken together, this method offers a potentially powerful new chemical tool for studying simultaneous oxidative stress and inflammation processes in living animals during injury, aging, and disease, as well as a versatile approach for concurrent monitoring of multiple analytes using luciferin-based bioluminescence imaging technologies.

  DOI：

  10.1021/ja309078t