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Merck
CN

G7548

Sigma-Aldrich

Penta-O-galloyl-β-D-glucose hydrate

≥96% (HPLC), apoptosis inducer, powder

别名:

1,2,3,4,6-Penta-O-galloyl-b-D-glucopyranose, 1,2,3,4,6-pentakis(3,4,5-trihydroxybenzoate)-b-D-Glucopyranose, Gallic acid, pentaester with b-D-glucopyranose, Glucopyranose, pentagallate, b-D, PGG, Penta-1,2,3,4,6-O-galloyl-b-D-glucose, Penta-O-galloyl-beta-D-glucose

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关于此项目

经验公式（希尔记法）:
C41H32O26 · xH2O
化学文摘社编号:
14937-32-7
分子量:
940.68 (anhydrous basis)
MDL编号:
MFCD18632553
UNSPSC代码:
12352200
PubChem化学物质编号:
329799964
NACRES:
NA.77

主要文件

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产品名称

Penta-O-galloyl-β-D-glucose hydrate, ≥96% (HPLC)

方案

≥96% (HPLC)

表单

powder

旋光性

[α]/D +14 to +26°, c = 0.2 in acetone-d6

颜色

light brown

溶解性

DMSO: ≥20 mg/mL

储存温度

2-8°C

SMILES字符串

O=C(O[C@H]([C@H]([C@@H]([C@@H](COC(C1=CC(O)=C(O)C(O)=C1)=O)O2)OC(C3=CC(O)=C(O)C(O)=C3)=O)OC(C4=CC(O)=C(O)C(O)=C4)=O)[C@@H]2OC(C5=CC(O)=C(O)C(O)=C5)=O)C6=CC(O)=C(O)C(O)=C6.O

InChI

1S/C41H32O26.H2O/c42-17-1-12(2-18(43)28(17)52)36(57)62-11-27-33(64-37(58)13-3-19(44)29(53)20(45)4-13)34(65-38(59)14-5-21(46)30(54)22(47)6-14)35(66-39(60)15-7-23(48)31(55)24(49)8-15)41(63-27)67-40(61)16-9-25(50)32(56)26(51)10-16;/h1-10,27,33-35,41-56H,11H2;1H2/t27-,33-,34+,35-,41+;/m1./s1

InChI key

JCJIMLXECAATFH-ZSJSDXHXSA-N

相关类别

应用

Penta-O-galloyl-β-D-glucose hydrate (PCG) has been used as an inhibitor of abdominal aortic aneurysms (AAA) and matrix metalloproteinase (MMP) related metastatic activity.

生化/生理作用

Autophagy inducer in human PC-3 and mouse TRAMP-C2 prostate cancer cells
PGG induces predominantly (caspase dependent) apoptosis in DU145 and LNCaP cells, while inducing autophagy in more resistant PC3 and TRAMP-C2 cells. It appears that PGG targeted signaling downstream of rather than the mTOR itself. Polyphenolic pyranoses were reported (J Biol Chem. 2010, 285 (11), 7892-902) to inhibit the plasminogen activator inhibitor type 1 (PAI-1).
Penta-O-galloyl-β-D-glucose hydrate (PCG) is a polyphenolic gallotannin compound produced by plants. It has an ability to inhibit matrix metalloproteinase (MMP) related metastatic activity. Thus, PCG can be used for treating metastatic activity in squamous cell carcinoma. In addition, it also acts as a potential drug for stabilizing small abdominal aneurysms.

特点和优势

This compound is a featured product for Apoptosis research. Click here to discover more featured Apoptosis products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

储存分类代码

11 - Combustible Solids

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable

法规信息

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分析证书(COA)

Lot/Batch Number
0000432700
0000432700
0000399139
0000399139
0000472222

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Hsiu-Chen Huang et al.
Journal of agricultural and food chemistry, 59(12), 6765-6775 (2011-05-24)
The F-box protein S-phase kinase-associated protein 2 (Skp2), which acts as an oncogene through targeting p27 for degradation, is overexpressed in many different human cancers. Skp2 can play an important role in breast cancer progression and may also be a
Hyo-Jung Lee et al.
Kidney international, 79(5), 538-545 (2010-11-19)
Adhesion of calcium oxalate (CaOx) crystals to kidney cells may be a key event in the pathogenesis of kidney stones associated with marked hyperoxaluria. Previously, we found that 1,2,3,4,6-penta-O-galloyl-β-D-glucose (PGG), isolated from a traditional medicinal herb, reduced CaOx crystal adhesion
Small molecule inhibition of matrix metalloproteinases as a potential therapeutic for metastatic activity in squamous cell carcinoma
Matias C, et al.
Oral cancer, 3(1-2), 1-8 (2019)
Melissa N Hempstead et al.
Journal of dairy science, 101(4), 3193-3204 (2018-02-06)
Cautery disbudding of goat kids is painful, but may be alleviated with pain mitigation. We therefore evaluated the effect of administering general anesthesia (isoflurane) or a nonsteroidal anti-inflammatory drug (meloxicam) on goat kid behavior and physiology following cautery disbudding. Trial
Mei-Hui Lin et al.
Antimicrobial agents and chemotherapy, 55(3), 1021-1027 (2010-12-22)
1,2,3,4,6-Penta-O-galloyl-β-D-glucopyranose (PGG) is an active ingredient in plants that are commonly used in Chinese medicine to treat inflammation. We demonstrate here that PGG, at 6.25 μM, does not inhibit the growth of Staphylococcus aureus, and yet it prevents biofilm formation
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