Home>>Signaling Pathways>> Immunology/Inflammation>> Reactive Nitrogen Species>>Piloty's Acid

Piloty's Acid Sale

(Synonyms: 苯磺酰异羟肟酸) 目录号 : GC44644

A well-characterized nitroxy (HNO) donor

Piloty's Acid Chemical Structure

Cas No.:599-71-3

规格 价格 库存 购买数量
500mg
¥137.00
现货
1g
¥258.00
现货
5g
¥1,097.00
现货
10g
¥1,918.00
现货

电话:400-920-5774 Email: sales@glpbio.cn

Customer Reviews

Based on customer reviews.

Sample solution is provided at 25 µL, 10mM.

产品文档

Quality Control & SDS

View current batch:

产品描述

Nitric Oxide (NO) is a free radical gas that is involved in a variety of biological processes including regulation vascular tone, neuronal signaling, and host defense. Nitroxyl (HNO) is the one electron reduced form of nitric oxide. Piloty's acid is one of the best known and most widely used HNO donors. Under basic conditions Piloty's acid decomposes to HNO and benzenesulfinate anion. The rate of HNO release at pH 7 is very slow (t½ = 5,500 minutes) making its use most effective above pH 8.0. The half-life of Piloty's acid decreases with an increase in pH to 561, 90, and 33 minutes at pH 8.0, 9.0, and 10.0, respectively. Piloty's acid also inhibits yeast aldehyde dehydrogenase with an IC50 or 48 µM.

Chemical Properties

Cas No. 599-71-3 SDF
别名 苯磺酰异羟肟酸
Canonical SMILES ON([H])S(C1=CC=CC=C1)(=O)=O
分子式 C6H7NO3S 分子量 173.2
溶解度 DMF: 30 mg/ml,DMSO: 20 mg/ml,Ethanol: 30 mg/ml,PBS (pH7.2): 2 mg/ml 储存条件 Store at -20°C
General tips 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液;一旦配成溶液,请分装保存,避免反复冻融造成的产品失效。
储备液的保存方式和期限:-80°C 储存时,请在 6 个月内使用,-20°C 储存时,请在 1 个月内使用。
为了提高溶解度,请将管子加热至37℃,然后在超声波浴中震荡一段时间。
Shipping Condition 评估样品解决方案:配备蓝冰进行发货。所有其他可用尺寸:配备RT,或根据请求配备蓝冰。

溶解性数据

制备储备液
1 mg 5 mg 10 mg
1 mM 5.7737 mL 28.8684 mL 57.7367 mL
5 mM 1.1547 mL 5.7737 mL 11.5473 mL
10 mM 0.5774 mL 2.8868 mL 5.7737 mL
  • 摩尔浓度计算器

  • 稀释计算器

  • 分子量计算器

质量
=
浓度
x
体积
x
分子量
 
 
 
*在配置溶液时,请务必参考产品标签上、MSDS / COA(可在Glpbio的产品页面获得)批次特异的分子量使用本工具。

计算

动物体内配方计算器 (澄清溶液)

第一步:请输入基本实验信息(考虑到实验过程中的损耗,建议多配一只动物的药量)
给药剂量 mg/kg 动物平均体重 g 每只动物给药体积 ul 动物数量
第二步:请输入动物体内配方组成(配方适用于不溶于水的药物;不同批次药物配方比例不同,请联系GLPBIO为您提供正确的澄清溶液配方)
% DMSO % % Tween 80 % saline
计算重置

Research Update

Piloty's Acid and its hydrazide analogue: Insights from the density functional theory and vibrational spectroscopy on the conformational stability and chemical reactivity

Spectrochim Acta A Mol Biomol Spectrosc 2021 Mar 15;249:119317.PMID:33360061DOI:10.1016/j.saa.2020.119317.

N-hydroxybenzenesulfonamide (commonly known as Piloty's Acid) is considered a major source for nitroxyl (HNO) species which has potential biological and medicinal applications. In the present study, the conformational preferences and chemical reactivity of Piloty's Acid (PA) and its hydrazide analogue (benzenesulfonylhydrazide, BSH) were studied using spectroscopic and computational tools. Six stable conformations of each molecule were theoretically identified, and their structures were fully optimized at the DFT-B3LYP and MP2 levels. Both molecules in their most stable forms adopt the anti configuration with the NH bond of the secondary amine pointing away from the terminal hydroxyl and amine moieties in the acid and hydrazide molecules, respectively. Three stable gauche states facilitated by weak intramolecular interactions of the SO⋯HO and SO⋯HN types arise due to the internal rotation about the SN linkage. Reliable assignments of the vibrational modes and the calculated reaction coordinates support a two-step mechanistic pathway of the Piloty's Acid dissociation leading to the production of the nitroxyl (HNO) intermediate with moderate transition state barriers. Frontier molecular orbitals distributions, molecular electrostatic potential maps and condensed Fukui functions analysis of the molecules were employed to elucidate the agility of PA to dissociate to produce HNO and the absence of such a dissociation of BSH that would produce diazene (N2H2).

Decomposition of Piloty's Acid derivatives - Toward the understanding of factors controlling HNO release

Arch Biochem Biophys 2019 Jan;661:132-144.PMID:30448388DOI:10.1016/j.abb.2018.11.012.

The recent interest in the clinical applications of Piloty's Acid derivatives as HNO donors for the treatment of cardiovascular system dysfunction has led us to the examination of factors controlling HNO release from selected ortho-substituted N-hydroxysulfonamides. Here we present the kinetic and quantum mechanical studies on the mechanism of HNO release from selected ortho-substituted N-hydroxysulfonamides and in vivo examination of the antiaggregatory properties of N-hydroxy-(2-bromobenzene)sulfonamide complex with sodium salt of β-cyclodextrin sulfobutyl ethers-ethyl ethers as compared with Angeli's salt.

Piloty's Acid derivative with improved nitroxyl-releasing characteristics

Bioorg Med Chem Lett 2013 Apr 15;23(8):2340-3.PMID:23489625DOI:10.1016/j.bmcl.2013.02.062.

Recent studies have shown that nitroxyl (HNO) ((1)HNO/(3)NO(-)), which is the one-electron-reduced form of nitric oxide (NO), has unique biological activities, especially in the cardiovascular system, and HNO-releasing agents may have therapeutic potential. Since few HNO donors are available for use under physiological conditions, we synthesized and evaluated a series of Piloty's Acid (PA) derivatives and evaluated their HNO-releasing activity under physiological conditions. N-Hydroxy-2-nitrobenzenesulfonamide (17) was the most efficient HNO donor among our synthesized PA derivatives, including the lead compound, 2-bromo-N-hydroxybenzenesulfonamide (2). The high HNO-releasing activity is suggested to be due to electronic and steric effects. Compound 17 may be a useful tool for biological experiments.

Synthesis of Nitric Oxide Donors Derived from Piloty's Acid and Study of Their Effects on Dopamine Secretion from PC12 Cells

Pharmaceuticals (Basel) 2017 Sep 5;10(3):74.PMID:28872590DOI:10.3390/ph10030074.

This study investigated the mechanisms and kinetics of nitric oxide (NO) generation by derivatives of Piloty's Acid (NO-donors) under physiological conditions. In order to qualitatively and quantitatively measure NO release, electron paramagnetic resonance (EPR) was carried out with NO spin trapping. In addition, voltammetric techniques, including cyclic voltammetry and constant potential amperometry, were used to confirm NO release from Piloty's Acid and its derivatives. The resulting data showed that Piloty's Acid derivatives are able to release NO under physiological conditions. In particular, electron-withdrawing substituents favoured NO generation, while electron-donor groups reduced NO generation. In vitro microdialysis, performed on PC12 cell cultures, was used to evaluate the dynamical secretion of dopamine induced by the Piloty's Acid derivatives. Although all the studied molecules were able to induce DA secretion from PC12, only those with a slow release of NO have not determined an autoxidation of DA itself. These results confirm that the time-course of NO-donors decomposition and the amount of NO released play a key role in dopamine secretion and auto-oxidation. This information could drive the synthesis or the selection of compounds to use as potential drugs for the therapy of Parkinson's disease (PD).

Mechanistic Studies on the Reaction between Aquacobalamin and the HNO Donor Piloty's Acid over a Wide pH Range in Aqueous Solution

Inorg Chem 2021 Mar 1;60(5):2964-2975.PMID:33513014DOI:10.1021/acs.inorgchem.0c02968.

Detailed kinetic and mechanistic studies have been carried out on the reaction between aquacobalamin/hydroxocobalamin (CblOH2+/CblOH) and nitroxyl (HNO) generated by Piloty's Acid (PA, N-hydroxybenzenesulfonamide) over a wide pH range (3.5-13). The resulting data showed that in a basic solution HNO can react with hydroxocobalamin to form nitrosylcobalamin despite the inert nature of CblOH. It was shown that at low PA concentrations the rate-determining step is the decomposition of PhSO2NHO- to release HNO, whereas the reaction between CblOH and HNO becomes the rate-determining step at high PA concentrations. Data from kinetic studies on the reaction of CblOH with an excess of HNO enabled us to experimentally determine the pKa(HNO) value from initial rate data as a function of pH, giving pKa(HNO) = 11.47 ± 0.04. An especially interesting observation was made in the neutral pH range, where PA is stable and does not produce HNO. Under such conditions, rapid formation of CblNO was observed in the studied system. The obtained data suggest that CblOH2+ reacts directly with PA to form a Piloty's acid-bound cobalamin intermediate, which deprotonates rapidly at neutral pH followed by rate-determining S-N bond cleavage to give CblNO and release PhSO2-.