Genipin
(Synonyms: 京尼平; (+)-Genipin) 目录号 : GN10116
Genipin是从栀子中提取的一种特异性UCP2（解偶联蛋白2）抑制剂。
Cas No.:6902-77-8
Sample solution is provided at 25 µL, 10mM.
;)
,-1-7$$$37316672.jpg');)
;)
;)
$$$36806353.jpg');)
;33(7)%EF%BC%9A546-561$$$37156877.jpg');)
;)
;)
;)
%201124-1138.$$$35908550.jpg');)
%20766-780.$$$37100057.jpg');)
%20418-432.$$$36893736.jpg');)
%EF%BC%9A-240-255.$$$35108512.jpg');)
533-545$$$36543525.jpg');)
%201-13.$$$36600053.jpg');)
;)
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]。
| 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: | |
| Cas No. | 6902-77-8 | SDF | |
| 别名 | 京尼平; (+)-Genipin | ||
| 化学名 | methyl (1R,4aS,7aS)-1-hydroxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate | ||
| Canonical SMILES | COC(=O)C1=COC(C2C1CC=C2CO)O | ||
| 分子式 | C11H14O5 | 分子量 | 226.23 |
| 溶解度 | ≥ 9.8 mg/mL in DMSO, ≥ 101.6 mg/mL in EtOH, ≥ 5.97 mg/mL in Water | 储存条件 | 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℃，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。 | ||
| 制备储备液 | |||
 |
1 mg | 5 mg | 10 mg |
| 1 mM | 4.4203 mL | 22.1014 mL | 44.2028 mL |
| 5 mM | 0.8841 mL | 4.4203 mL | 8.8406 mL |
| 10 mM | 0.442 mL | 2.2101 mL | 4.4203 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。
Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet