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Indole-3-carboxaldehyde Sale

(Synonyms: 吲哚-3-甲醛; 3-吲哚甲醛; 3-Formylindole) 目录号 : GC38918 复制 一键复制产品信息

Indole-3-carboxaldehyde是一种来自于板蓝根的吲哚类化合物。Indole-3-carboxaldehyde是芳烃受体(AhR)的激动剂。

Indole-3-carboxaldehyde Chemical Structure

Cas No.:487-89-8

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Sample solution is provided at 25 µL, 10mM.

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Description

Indole-3-carboxaldehyde is an indole compound derived from Isatis indigotica. Indole-3-carboxaldehyde acts as an aryl hydrocarbon receptor (AhR) agonist. Indole-3-carboxaldehyde enhances intestinal epithelial barrier function and exhibits anti-inflammatory activity. Indole-3-carboxaldehyde can be used in research related to intestinal protection mechanisms, inflammation regulation, and antibacterial effects[1-4].

In vitro, THP-1 macrophage-derived foam cells were treated with Indole-3-carboxaldehyde (50μM) for 24 hours. Indole-3-carboxaldehyde significantly upregulated the expression of miR-1271-5p, ABCA1, and ABCG1, downregulated HDAC9 expression, inhibited lipid accumulation, and alleviated inflammatory response[5]. RAW264.7 cells infected with RSV were treated with Indole-3-carboxaldehyde (10-50μM) for 24 hours. By downregulating TLR7 expression and inhibiting the activation of the TLR7-MyD88-dependent NF-κB signaling pathway, Indole-3-carboxaldehyde suppressed RSV-induced excessive secretion of IFN-α, while also reducing the expression of pro-inflammatory factors such as TNF-α, IL-1β, and IL-6[6].

In vivo, 8-week-old C57BL/6J mice were orally administered Indole-3-carboxaldehyde (50-200mg/kg) daily for three consecutive days, followed by intraperitoneal injection of acetaminophen (300mg/kg). Indole-3-carboxaldehyde significantly alleviated acetaminophen-induced liver injury[7]. C57BL/6 mice were administered Indole-3-carboxaldehyde (10-40mg/kg) by oral gavage for three consecutive days, followed by intraperitoneal injection of cisplatin (20mg/kg). Indole-3-carboxaldehyde significantly prevented cisplatin-induced body weight loss and reduced the increase in kidney coefficient[8].

References:
[1] Stutz RE. Enzymatic Formation of Indole-3-Carboxaldehyde from Indole-3-Acetic Acid. Plant Physiol. 1958 May;33(3):207-12.
[2] Lu Y, Yang W, Qi Z, et al. Gut microbe-derived metabolite indole-3-carboxaldehyde alleviates atherosclerosis. Signal Transduct Target Ther. 2023 Oct 4;8(1):378.
[3] Cheng L, Wu H, Cai X, et al. A Gpr35-tuned gut microbe-brain metabolic axis regulates depressive-like behavior. Cell Host Microbe. 2024 Feb 14;32(2):227-243.e6.
[4] Cao J, Bao Q, Hao H. Indole-3-Carboxaldehyde Alleviates LPS-Induced Intestinal Inflammation by Inhibiting ROS Production and NLRP3 Inflammasome Activation. Antioxidants (Basel). 2024 Sep 13;13(9):1107.
[5] Luo W, Meng J, Yu XH, et al. Indole-3-Carboxaldehyde Inhibits Inflammatory Response and Lipid Accumulation in Macrophages Through the miR-1271-5p/HDAC9 Pathway. J Cell Mol Med. 2024 Dec;28(24):e70263.
[6] Hou X, Zhang X, Bi J, et al. Indole-3-carboxaldehyde regulates RSV-induced inflammatory response in RAW264.7 cells by moderate inhibition of the TLR7 signaling pathway. J Nat Med. 2021 Jun;75(3):602-611.
[7] Liu X, Liu R, Wang Y. Indole-3-carboxaldehyde alleviates acetaminophen-induced liver injury via inhibition of oxidative stress and apoptosis. Biochem Biophys Res Commun. 2024 May 28;710:149880.
[8] Yuan P, Feng A, Wei Y, et al. Indole-3-carboxaldehyde alleviates cisplatin-induced acute kidney injury in mice by improving mitochondrial dysfunction via PKA activation. Food Chem Toxicol. 2024 Apr;186:114546.

Indole-3-carboxaldehyde是一种来自于板蓝根的吲哚类化合物。Indole-3-carboxaldehyde是芳烃受体(AhR)的激动剂。Indole-3-carboxaldehyde能够增强肠道上皮屏障功能和抗炎活性。Indole-3-carboxaldehyde可用于肠道保护机制、炎症调控和抗菌的相关研究[1-4]

在体外,Indole-3-carboxaldehyde(50μM)处理THP-1巨噬细胞来源的泡沫细胞24小时。Indole-3-carboxaldehyde显著上调miR-1271-5p、ABCA1和ABCG1表达,下调HDAC9表达,抑制脂质积累,并减轻炎症反应[5]。Indole-3-carboxaldehyde(10-50μM)处理RSV感染的RAW264.7细胞24小时。Indole-3-carboxaldehyde通过下调TLR7表达和抑制TLR7-MyD88依赖的NF-κB信号通路激活,抑制RSV诱导的IFN-α过度分泌,同时降低TNF-α、IL-1β和IL-6等促炎因子的表达[6]

在体内,Indole-3-carboxaldehyde(50-200mg/kg)每天口服给药连续三天,用于处理8周龄C57BL/6J小鼠,随后给予乙酰氨基酚(300mg/kg)腹腔注射。Indole-3-carboxaldehyde显著减轻了乙酰氨基酚诱导的肝损伤[7]。Indole-3-carboxaldehyde(10-40mg/kg)连续三天灌胃给药于C57BL/6小鼠,随后给予顺铂(20mg/kg)腹腔注射。Indole-3-carboxaldehyde显著防止了顺铂导致的体重减轻和肾脏系数增加[8]

实验参考方法

Cell experiment [1]:

Cell lines

THP-1 macrophage-derived foam cells (human monocyte line THP-1 differentiated into macrophages and converted to foam cells)

Preparation Method

THP-1 monocytes were differentiated into macrophages using 160nM PMA for 24h, then converted to lipid-rich foam cells after 48h incubation with 50μg/mL ox-LDL. THP-1 macrophage-derived foam cells were exposed to Indole-3-carboxaldehyde (50μM) or the vehicle (DMSO) for 24h.

Reaction Conditions

50μM; 24h

Applications

Indole-3-carboxaldehyde upregulated the expression of miR-1271-5p, ABCA1 and ABCG1, downregulated HDAC9 expression and inhibited macrophage lipid accumulation. Indole-3-carboxaldehyde treatment also facilitated macrophage polarisation to the M2 phenotype and alleviated inflammatory response, as evidenced by decreased IL-6 levels and increased IL-10 levels.

Animal experiment [2]:

Animal models

C57BL/6J mice

Preparation Method

Mice were orally administered Indole-3-carboxaldehyde (50, 100, or 200mg/kg) dissolved in 10% DMSO and 90% corn oil vehicle via daily gavage for three consecutive days. Following a 16h fast, mice were intraperitoneally injected with 300mg/kg APAP. Mice were euthanized 12h post-injection for sample collection. In a separate survival study, mice were administered a lethal dose of 800mg/kg APAP and observed for 24h.

Dosage form

50, 100, or 200mg/kg; oral gavage; daily for three days

Applications

Indole-3-carboxaldehyde pretreatment significantly mitigated APAP-induced liver injury, as evidenced by reduced serum ALT and AST levels, improved liver histopathology (reduced hepatocyte swelling, necrosis, and neutrophil infiltration), attenuated oxidative stress (increased GSH and SOD, decreased MDA, and upregulated Nrf2/NQO1/HO-1 pathway), and inhibited hepatocyte apoptosis (reduced TUNEL-positive cells, decreased Bax/Bcl-2 ratio and Caspase-3 activity). Indole-3-carboxaldehyde also improved survival in mice receiving a lethal dose of APAP.

References:
[1] Luo W, Meng J, Yu XH, et al. Indole-3-Carboxaldehyde Inhibits Inflammatory Response and Lipid Accumulation in Macrophages Through the miR-1271-5p/HDAC9 Pathway. J Cell Mol Med. 2024 Dec;28(24):e70263.
[2] Liu X, Liu R, Wang Y. Indole-3-carboxaldehyde alleviates acetaminophen-induced liver injury via inhibition of oxidative stress and apoptosis. Biochem Biophys Res Commun. 2024 May 28;710:149880.

化学性质

Cas No. 487-89-8 SDF
别名 吲哚-3-甲醛; 3-吲哚甲醛; 3-Formylindole
Canonical SMILES O=CC1=CNC2=C1C=CC=C2
分子式 C9H7NO 分子量 145.16
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1 mM 6.889 mL 34.4448 mL 68.8895 mL
5 mM 1.3778 mL 6.889 mL 13.7779 mL
10 mM 688.9 μL 3.4445 mL 6.889 mL
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