GlpBio

Genipin

目录号: GN10116纯度: >98.00%同义词: 京尼平; (+)-Genipin
Genipin是从栀子中提取的一种特异性UCP2（解偶联蛋白2）抑制剂。
Genipin
Cas No.: 6902-77-8
规格价格库存数量操作
25mg¥381.00现货
1
50mg¥455.00现货
1
100mg¥548.00现货
1
10mM (in 1mL DMSO)¥419.00现货
1
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产品描述 Description

Genipin is a specific UCP2 (uncoupling protein 2) inhibitor extracted from the Gardenia jasminoides Ellis[1]. Genipin has been widely used for drug delivery due to its excellent biocompatibility, admirable biodegradability, and stable cross-linking attributes[2]. Genipin has also been used as a fingerprint collection reagent and a cross-linker for the preparation of immobilized enzymes[3][4].

Genipin (10mM, 2h) treatment led to the activation of IRS-1, PI3-K, and downstream signaling in mouse skeletal muscle cells (C2C12 myoblasts)[5]. Genipin (200μM, 24h) induces apoptosis in FaO rat hepatoma cells and human hepatocarcinoma Hep3B cells[6].

Genipin (25, 50, 100 and 200mg/kg; i.p.) markedly decreased hemorrhagic necrosis, portal inflammation and the mortality in hepatic apoptosis and liver failure mouse model[7]. Genipin (50mg/kg, 7 days, p.o.) exerts protective effects on ethanol-induced acute gastric injury in mice by inhibiting the activation of the NLRP3 inflammasome[8].

References:
[1] Piscopo M, Tenore GC, Notariale R, et al. Antimicrobial and antioxidant activity of proteins from Feijoa sellowiana Berg. fruit before and after in vitro gastrointestinal digestion. Natural product research. 2020 Sep 16;34(18):2607-11.
[2] Yu Y, Xu S, Li S, et al. Genipin-cross-linked hydrogels based on biomaterials for drug delivery: A review. Biomaterials science. 2021;9(5):1583-97.
[3] Zhou T, Liu H, Wen J, et al. Fragmentation study of iridoid glycosides including epimers by liquid chromatography‐diode array detection/electrospray ionization mass spectrometry and its application in metabolic fingerprint analysis of Gardenia jasminoides Ellis. Rapid Communications in Mass Spectrometry. 2010 Sep 15;24(17):2520-8.
[4] Pujana MA, Pérez-Álvarez L, Iturbe LC, et al. Water soluble folate-chitosan nanogels crosslinked by genipin. Carbohydrate polymers. 2014 Jan 30;101:113-20.
[5] Ma ChanJuan MC, Nie AiFang NA, Zhang ZhiJian ZZ, et al. Genipin stimulates glucose transport in C2C12 myotubes via an IRS-1 and calcium-dependent mechanism.
[6] Kim BC, Kim HG, Lee SA, et al. Genipin-induced apoptosis in hepatoma cells is mediated by reactive oxygen species/c-Jun NH2-terminal kinase-dependent activation of mitochondrial pathway. Biochemical pharmacology. 2005 Nov 1;70(9):1398-407.
[7] Kim SJ, Kim JK, Lee DU, et al. Genipin protects lipopolysaccharide-induced apoptotic liver damage in D-galactosamine-sensitized mice. European journal of pharmacology. 2010 Jun 10;635(1-3):188-93.
[8] Zhao T, Zhang Y, Mu S, et al. Protective effects of genipin on ethanol-induced acute gastric injury in mice by inhibiting NLRP3 inflammasome activation. European Journal of Pharmacology. 2020 Jan 15;867:172800.

Genipin是从栀子中提取的一种特异性UCP2（解偶联蛋白2）抑制剂[1]。Genipin以其出色的生物相容性、极佳的生物降解性和稳定的交联特性而被广泛用于药物输送[2]。Genipin还被用作指纹采集试剂和制备固定化酶的交联剂[3][4]。

Genipin（10mM，2h）处理可激活小鼠骨骼肌细胞（C2C12成肌细胞）中的IRS-1、PI3-K和下游信号传导[5]。Genipin（200μM，24h）可诱导FaO大鼠肝癌细胞和人肝癌Hep3B细胞凋亡[6]。

Genipin（25、50、100和200mg/kg，腹腔注射）显著减少出血性坏死、门脉炎症和肝细胞凋亡及肝衰竭小鼠模型中的死亡率[7]。Genipin（50mg/kg，7天，口服）通过抑制NLRP3炎症小体的激活，对小鼠乙醇诱导的急性胃损伤发挥保护作用[8]。

实验参考方法 Experimental Reference Method

Cell experiment [1]:

Cell lines

Mouse skeletal muscle C2C12 cells

Preparation Method

C2C12 cells were treated with 10 μM Genipin for 0.5h and 2h. The cell lysates were extracted with lysis buffer (RIPA, 1×PBS, 1% Nonidet P-40, 5mM EDTA, 0.1% SDS, 1mM sodium orthovanadate, 1% PMSF, complete protease inhibitor cocktail, and complete phosphatase inhibitors). The whole-cell lysates were centrifuged at 12000g at 4°C for 20min to remove the insoluble materials. For immunoprecipitation, supernatants were incubated with IRS-1 antibody at 4°C for 16h followed by incubation with protein A-agarose beads for 2h. The beads were washed in lysis buffer three times, boiled with Laemmli sample buffer for 5min, and then loaded onto SDS-PAGE.

Reaction Conditions

10mM; 0.5h, 2h

Applications

Genipin treatment led to the activation of IRS-1 in mouse skeletal muscle C2C12 cells.
Animal experiment [2]:

Animal models

Hepatic apoptosis and liver failure mouse model

Preparation Method

Male ICR mice (20-22g) were fasted overnight but given access to water ad libitum. In the Genipin-treated group, mice were administered Genipin (suspended in 10% Tween 80-saline) at 25, 50, 100 and 200mg/kg intraperitoneally 1h before the d-galactosamine (GalN)/lipopolysaccharide (LPS) treatment, while other groups received an equivalent volume of vehicle as the control. All animals (except for the normal control) were injected intraperitoneally with GalN (700mg/kg) and LPS (10μg/kg Escherichia coli 026:B6) dissolved in phosphate-buffered saline.

Dosage form

25, 50, 100 and 200mg/kg; i.p.

Applications

Genipin markedly decreased hemorrhagic necrosis, portal inflammation and the mortality in hepatic apoptosis and liver failure mouse model.

References:
[1] Ma ChanJuan MC, Nie AiFang NA, Zhang ZhiJian ZZ, et al. Genipin stimulates glucose transport in C2C12 myotubes via an IRS-1 and calcium-dependent mechanism.
[2] Kim SJ, Kim JK, Lee DU, et al. Genipin protects lipopolysaccharide-induced apoptotic liver damage in D-galactosamine-sensitized mice. European journal of pharmacology. 2010 Jun 10;635(1-3):188-93.

产品文档 Product Documents

Purity:>98.00%

化学性质Chemical Properties

CAS 号
6902-77-8
同义词
京尼平; (+)-Genipin
化学名
methyl (1R,4aS,7aS)-1-hydroxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate
SMILES
COC(=O)C1=COC(C2C1CC=C2CO)O
分子式
C11H14O5
分子量
226.23 g/mol
溶解性
≥ 9.8 mg/mL in DMSO, ≥ 101.6 mg/mL in EtOH, ≥ 5.97 mg/mL in Water
保存条件
4°C, protect from light
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°C，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。

计算工具摩尔浓度 / 稀释 / 分子量 / 单位换算 / 体内配方 / 溶解度

g/mol