Ingenol Mebutate (Ingenol 3-angelate)

Name: Ingenol Mebutate (Ingenol 3-angelate)
SKU: GC31656
Availability: InStock
Rating: 5 (30 reviews)

(Synonyms: 巨大戟醇甲基丁烯酸酯; Ingenol 3-angelate; PEP005) 目录号 : GC31656

A natural cytotoxic diterpene ester

Ingenol Mebutate (Ingenol 3-angelate) Chemical Structure

Cas No.:75567-37-2

规格价格库存购买数量

10mM (in 1mL DMSO)	¥2,308.00	现货
1mg	¥775.00	现货
5mg	¥2,436.00	现货
10mg	¥4,024.00	现货

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Customer Reviews

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Sample solution is provided at 25 µL, 10mM.

GlpBio产品文献引用

Nature
610.7931 (2022): 366-372

Nature
618, 1017–1023 (2023)

Cell
183.7 (2020): 1867-1883

Cell Research
31, 1291–1307 (2021)

Cell Research
33, 273–287 (2023)

Cell Research
33, 546–561 (2023)

Molecular Cancer
21.1 (2022): 1-17

Molecular Cancer
21.1 (2022): 1-18

Cancer Cell
39 (2021): 1-16

Cell Host Microbe
30.8 (2022): 1124-1138

Cell Host Microbe
31.5 (2023): 766-780

Cell Host Microbe
31.3 (2023): 418-43

Cell Metabolism
34.2 (2022): 240-255

Ann Rheum Dis
82(4): 533-545 (2023)

Cell Mol Immunol
20, 264–276 (2023)

Adv Funct Mater
33.35 (2023): 2214998

产品描述实验参考方法化学性质产品文档相关产品

Description

Ingenol-3-angelate is a hydrophobic diterpene ester that can be isolated from the euphorb E. peplus. It rapidly induces cell death in proliferating keratinocytes through plasma membrane and mitochondrial disruption, although it can also initiate apoptosis in some cancer cell lines (LD₉₀ = ~190 ?M).¹ Secondarily, ingenol-3-angelate causes inflammation due, at least in part, to activation of PKC, leading to antibody-dependent cellular cytotoxicity.^2,3,4 These actions have relevance in diminishing actinic keratosis and, possibly, other cancers of the skin.^5,6

1.Ogbourne, S.M., Suhrbier, A., Jones, B., et al.Antitumor activity of 3-ingenyl angelate: Plasma membrane and mitochondrial disruption and necrotic cell deathCancer Res.64(8)2833-2839(2004) 2.Gillespie, S.K., Zhang, X.D., and Hersey, P.Ingenol 3-angelate induces dual modes of cell death and differentially regulates tumor necrosis factor-related apoptosis-inducing ligand-induced apoptosis in melanoma cellsMol. Cancer Ther.3(12)1651-1658(2004) 3.Li, L., Shukla, S., Lee, A., et al.The skin cancer chemotherapeutic agent ingenol-3-angelate (PEP005) is a substrate for the epidermal multidrug transporter (ABCB1) and targets tumor vasculatureCancer Res.70(11)4509-4519(2010) 4.Hasler, C.M., Acs, G., and Blumberg, P.M.Specific binding to protein kinase C by ingenol and its induction of biological responsesCancer Res.52(1)202-208(1992) 5.Lebwohl, M., Swanson, N., Anderson, L.L., et al.Ingenol mebutate gel for actinic keratosisN. Engl. J. Med.366(11)1010-1019(2012) 6.Micali, G., Lacarrubba, F., Nasca, M.R., et al.Topical pharmacotherapy for skin cancer. Part I. PharmacologyJ. Am. Acad. Dermatol.70(6)965.e961-956.e912(2014)

实验参考方法

Cell experiment:

KG1a cells are transiently transfected with EGFP-tagged mouse PKC-δ subcloned into pEGFP-N1 plasmid using an Amaxa nucleofection apparatus. Cells are treated with Ingenol Mebutate (0.2 μM-20 μM) 24 hours after transfection. Cell viability in EGFP-positive cells is assessed and loss of viability confirmed in the total cell culture by MTT assay after 3 days. Briefly, 24 hours after transfection, 2 × 104 cells are plated in 5 wells in 96-well plates and exposed to 0, 0.2, 2, and 20 μM Ingenol Mebutate. At 72 hours, 20 μL MTT substrate at 5 mg/mL is added and plates are incubated at 37°C. After 3 hours, 150 μL media is removed and replaced with 200 μL dimethyl sulfoxide (DMSO). Absorbance at an optical density (OD) of 550 nm is read on a plate reader and corrected for absorbance obtained from blank media controls[2].

References:

[1]. Kedei N, et al. Characterization of the interaction of ingenol 3-angelate with protein kinase C. Cancer Res. 2004 May 1;64(9):3243-55.
[2]. Hampson P, et al. PEP005, a selective small-molecule activator of protein kinase C, has potent antileukemic activity mediated via the delta isoform of PKC. Blood. 2005 Aug 15;106(4):1362-8.
[3]. Ghoul A, et al. Epithelial-to-mesenchymal transition and resistance to ingenol 3-angelate, a novel protein kinase C modulator, in colon cancer cells. Cancer Res. 2009 May 15;69(10):4260-9.

化学性质

Cas No.	75567-37-2	SDF
别名	巨大戟醇甲基丁烯酸酯; Ingenol 3-angelate; PEP005
Canonical SMILES	C/C=C(C)\C(O[C@H]1C(C)=C[C@]23[C@]1(O)[C@H](O)C(CO)=C[C@@](C3=O)([H])[C@@]4([H])[C@@](C4(C)C)([H])C[C@H]2C)=O
分子式	C₂₅H₃₄O₆	分子量	430.53
溶解度	DMSO : ≥ 100 mg/mL (232.27 mM)	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	2.3227 mL	11.6136 mL	23.2272 mL
	5 mM	0.4645 mL	2.3227 mL	4.6454 mL
	10 mM	0.2323 mL	1.1614 mL	2.3227 mL

摩尔浓度计算器
稀释计算器
分子量计算器

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

每只动物给药体积

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，注：如该浓度超过该批次药物DMSO溶解度，请先联系GLPBIO）；

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。

注意：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。

产品文档

Quality Control & SDS

View current batch:

Purity: >99.00%