Indole-2-carboxylic acid
(Synonyms: 2-吲哚甲酸) 目录号 : GC39848
Indole-2-carboxylic acid is a strong inhibitor of lipid peroxidation.
Cas No.:1477-50-5
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >99.50%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Indole-2-carboxylic acid is a strong inhibitor of lipid peroxidation.
| Cas No. | 1477-50-5 | SDF | |
| 别名 | 2-吲哚甲酸 | ||
| Canonical SMILES | O=C(C(N1)=CC2=C1C=CC=C2)O | ||
| 分子式 | C9H7NO2 | 分子量 | 161.16 |
| 溶解度 | Soluble in DMSO | 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。 |
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| 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。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 6.205 mL | 31.0251 mL | 62.0501 mL |
| 5 mM | 1.241 mL | 6.205 mL | 12.41 mL |
| 10 mM | 0.6205 mL | 3.1025 mL | 6.205 mL |
| 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 | 只 |
| 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 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Design, synthesis and biological evaluation of Indole-2-carboxylic acid derivatives as IDO1/TDO dual inhibitors
Eur J Med Chem 2020 Feb 15;188:111985.PMID:31881488DOI:10.1016/j.ejmech.2019.111985.
Indoleamine 2,3-dioxygenase 1 (IDO1) and tryptophan 2,3-dioxygenase (TDO) are involved in the key steps of tryptophan metabolism and are potential new targets for tumor immunotherapy. In this work, a variety of Indole-2-carboxylic acid derivatives were synthesized, and their inhibitory activities against both enzymes along with structure-activity relationships were investigated. As a result, a number of 6-acetamido-indole-2-carboxylic acid derivatives were found to be potent dual inhibitors with IC50 values at low micromolar levels. Among them, compound 9o-1 was the most potent inhibitor with an IC50 value of 1.17 μM for IDO1, and 1.55 μM for TDO, respectively. In addition, a para-benzoquinone derivative 9p-O, resulted from the oxidation of compound 9p, was also identified and it showed strong inhibition against the two enzymes with IC50 values at the double digit nanomolar level. Using molecular docking and molecular dynamic simulations, we predicted the binding modes of this class of compounds within IDO1 and TDO binding pocket. The results provide insights for further structural optimization of this series of IDO1/TDO dual inhibitors.
Photophysics of Indole-2-carboxylic acid (I2C) and indole-5-carboxylic acid (I5C): heavy atom effect
Spectrochim Acta A Mol Biomol Spectrosc 2013 Dec;116:183-95.PMID:23933843DOI:10.1016/j.saa.2013.07.011.
In this study the effect of carboxylic group substitution in the 2 and 5 position of indole ring on the photophysics of the parent indole chromophore has been studied. The photophysical parameters crucial in triplet state decay mechanism of aqueous Indole-2-carboxylic acid (I2C) and indole-5-carboxylic acid (I5C) have been determined applying our previously proposed methodology based on the heavy atom effect and fluorescence and phosphorescence decay kinetics [Kowalska-Baron et al., 2012]. The determined time-resolved phosphorescence spectra of I2C and I5C are red-shifted as compared to that of the parent indole. This red-shift was especially evident in the case of I2C and may indicate the possibility of hydrogen bonded complex formation incorporating carbonyl CO, the NH group of I2C and, possibly, surrounding water molecules. The possibility of the excited state charge transfer process and the subsequent electronic charge redistribution in such a hydrogen bonded complex may also be postulated. The resulting stabilization of the I2C triplet state is manifested by its relatively long phosphorescence lifetime in aqueous solution (912 μs). The relatively short phosphorescence lifetime of I5C (56 μs) may be the consequence of more effective ground-state quenching of I5 C triplet state. This hypothesis may be strengthened by the significantly larger value of the determined rate constant of I5C triplet state quenching by its ground-state (4.4 × 10(8)M(-1)s(-1)) as compared to that for indole (6.8 × 10(7)M(-1)s(-1)) and I2C (2.3 × 10(7)M(-1)s(-1)). The determined bimolecular rate constant for triplet state quenching by iodide [Formula: see text] is equal to 1 × 10(4)M(-1)s(-1); 6 × 10(3)M(-1)s(-1) and 2.7 × 10(4)M(-1)s(-1) for indole, I2 C and I5 C, respectively. In order to obtain a better insight into iodide quenching of I2C and I5C triplet states in aqueous solution, the temperature dependence of the bimolecular rate constants for iodide quenching of the triplet states has been expressed in Arrhenius form. The linearity of the obtained Arrhenius plots clearly indicated the existence of one temperature-dependent non-radiative process for the de-excitation of I2C and I5C triplet state in the presence of iodide. This process may be attributed to the solute-quenching by iodide and, most probably, proceeds via reversibly formed exciplex. The activation energies obtained from linear Arrhenius plots (1.89 kcal/mol for I5 C; 2.55 kcal/mol for I2 C) are smaller as compared to that for diffusion controlled reactions in aqueous solution (about 4 kcal/mol), which may indicate the great importance of the electrostatic interactions between solute and iodide ions in lowering the energy barrier needed for the formation of the triplet-quencher complex. Based on the theoretical predictions (at the DFT(CAM-B3LYP)/6-31+G(d,p) level of theory) and careful analysis of the obtained FTIR spectra it may be concluded that in the solid state I2 C and I5 C molecules form associates by intermolecular NH · · · OC and OH · · · OC hydrogen bonding interactions, whereas the existence of intramolecular NH · · · OC interactions in the solid state of I2C and I5C is highly unlikely.
Self-assembly of Indole-2-carboxylic acid at graphite and gold surfaces
J Chem Phys 2015 Mar 14;142(10):101923.PMID:25770512DOI:10.1063/1.4908143.
Model systems are critical to our understanding of self-assembly processes. As such, we have studied the surface self-assembly of a small and simple molecule, Indole-2-carboxylic acid (I2CA). We combine density functional theory gas-phase (DFT) calculations with scanning tunneling microscopy to reveal details of I2CA assembly in two different solvents at the solution/solid interface, and on Au(111) in ultrahigh vacuum (UHV). In UHV and at the trichlorobenzene/highly oriented pyrolytic graphite (HOPG) interface, I2CA forms epitaxial lamellar structures based on cyclic OH⋯O carboxylic dimers. The structure formed at the heptanoic acid/HOPG interface is different and can be interpreted in a model where heptanoic acid molecules co-adsorb on the substrate with the I2CA, forming a bicomponent commensurate unit cell. DFT calculations of dimer energetics elucidate the basic building blocks of these structures, whereas calculations of periodic two-dimensional assemblies reveal the epitaxial effects introduced by the different substrates.
3-(2-Carboxyethyl)Indole-2-carboxylic acid Derivatives: Structural Requirements and Properties of Potent Agonists of the Orphan G Protein-Coupled Receptor GPR17
J Med Chem 2018 Sep 27;61(18):8136-8154.PMID:30048589DOI:10.1021/acs.jmedchem.7b01768.
The orphan receptor GPR17 may be a novel drug target for inflammatory diseases. 3-(2-Carboxyethyl)-4,6-dichloro-1 H-indole-2-carboxylic acid (MDL29,951, 1) was previously identified as a moderately potent GPR17 agonist. In the present study, we investigated the structure-activity relationships (SARs) of 1. Substitution of the indole 1-, 5-, or 7-position was detrimental. Only small substituents were tolerated in the 4-position while the 6-position accommodated large lipophilic residues. Among the most potent compounds were 3-(2-carboxyethyl)-1 H-indole-2-carboxylic acid derivatives containing the following substituents: 6-phenoxy (26, PSB-1737, EC50 270 nM), 4-fluoro-6-bromo (33, PSB-18422, EC50 27.9 nM), 4-fluoro-6-iodo (35, PSB-18484, EC50 32.1 nM), and 4-chloro-6-hexyloxy (43, PSB-1767, EC50 67.0 nM). (3-(2-Carboxyethyl)-6-hexyloxy-1 H-indole-2-carboxylic acid (39, PSB-17183, EC50 115 nM) behaved as a partial agonist. Selected potent compounds tested at human P2Y receptor subtypes showed high selectivity for GPR17. Docking into a homology model of the human GPR17 and molecular dynamic simulation studies rationalized the observed SARs.
Energetic Effect of the Carboxylic Acid Functional Group in Indole Derivatives
J Phys Chem A 2017 Apr 20;121(15):2980-2989.PMID:28358511DOI:10.1021/acs.jpca.7b00275.
The standard molar enthalpy of formation, in the gaseous phase, at T = 298.15 K, was calculated by combining, for each compound, the standard molar enthalpy of formation, in the crystalline phase, and the standard molar enthalpy of sublimation, yielding -(222.2 ± 3.5) kJ·mol-1 and -(234.1 ± 2.1) kJ·mol-1 for indole-3-carboxylic acid and 1-methylindole-3-carboxylic acid, respectively. Computational studies, at the G3(MP2) composite level, were conducted for indole-3-carboxylic acid and 1-methylindole-3-carboxylic acid as a complement of the experimental work, and they were also extended to the remaining isomers, Indole-2-carboxylic acid, 1-methylindole-2-carboxylic acid, 3-methylindole-2-carboxylic acid, and 2-methylindole-3-carboxylic acid, to provide reliable estimates of the corresponding thermochemical parameters. The agreement of the estimates of the standard gas-phase enthalpy of formation so obtained, Indole-2-carboxylic acid -(223.6 ± 0.8) kJ·mol-1, 1-methylindole-2-carboxylic acid -(223.7 ± 0.8) kJ·mol-1, 3-methylindole-2-carboxylic acid -(251.6 ± 1.0) kJ·mol-1, indole-3-carboxylic acid -(227.1 ± 1.1) kJ·mol-1, 1-methylindole-3-carboxylic acid -(238.0 ± 1.0) kJ·mol-1, and 2-methylindole-3-carboxylic acid -(267.2 ± 1.0) kJ·mol-1, with the available experimental data gives us additional confidence for the situations not studied experimentally. The enthalpic effect resulting from the entrance of the carboxyl group into the indole ring was discussed, and an enthalpic stabilization was found for indole and pyrrole derivatives when compared with other similar systems.