الصفحة الرئيسية>>Natural Products>>1,2,3,4,6-pentagalloylglucose

1,2,3,4,6-pentagalloylglucose

رقم الكتالوجGN10059

1,2,3,4,6-pentagalloylglucose(Pentagalloylglucose; PGG) is a polyphenolic compound with powerful antioxidant, anti-inflammatory, antibacterial, antiviral, and antitumor effects.

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1,2,3,4,6-pentagalloylglucose التركيب الكيميائي

Cas No.: 14937-32-7

الحجم السعر المخزون الكميّة
10mM (in 1mL DMSO)
58٫00
متوفر
1mg
18٫00
متوفر
5mg
39٫00
متوفر
10mg
56٫00
متوفر
50mg
165٫00
متوفر
100mg
248٫00
متوفر

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Sample solution is provided at 25 µL, 10mM.

Description of 1,2,3,4,6-pentagalloylglucose

1,2,3,4,6-pentagalloylglucose(Pentagalloylglucose;PGG) is a polyphenolic compound with powerful antioxidant, anti-inflammatory, antibacterial, antiviral, and antitumor effects [1-2]. 1,2,3,4,6-pentagalloylglucose is a potent and cellular active inhibitor of the PALB2-BRCA2 protein-protein interaction (PPI). 1,2,3,4,6-pentagalloylglucose binds PALB2 at the BRCA2 binding site and significantly suppresses HR repair by inhibiting BRCA2 recruitment to the DNA damage site.

1,2,3,4,6-pentagalloylglucose (5, 10, or 20µM; 1h) blocked cGAS-STING pathway activation in bone marrow-derived macrophages (BMDMs) in vitro[3]. 1,2,3,4,6-pentagalloylglucose (10μM; 4h) suppresses HR-mediated DNA repair in U2OS cells[4]. 1,2,3,4,6-pentagalloylglucose (0-60µM; 24h) dose-dependently inhibited the proliferation of CNE1 and CNE2 cells. PGG regulated the cell cycle by altering p53, cyclin D1, CDK2, and cyclin E1 protein levels[5].

1,2,3,4,6-pentagalloylglucose (20 and 40mg/kg; i.p) treatment significantly reduced the alanine aminotransferase (ALT), aspartate aminotransferase (AST), and alkaline phosphatase (ALP) levels in mice with AILI, and protect Acetaminophen-induced acute liver injury in mice[3]. Pre-treatment with 1,2,3,4,6-pentagalloylglucose (5 and 10mg/kg; i.p; 7days) showed significant, and dose dependent protection against I/R-induced brain injury by alleviating all the behavioral, neurological, morphological, and histological changes induced by I/R. The protective effect of 1,2,3,4,6-pentagalloylglucose is thought to be due to its powerful antioxidant properties[6].

References:
[1]. Ashibe S, Ikeuchi K, et,al. Non-Enzymatic Oxidation of a Pentagalloylglucose Analogue into Members of the Ellagitannin Family. Angew Chem Int Ed Engl. 2017 Nov 27;56(48):15402-15406. doi: 10.1002/anie.201708703. Epub 2017 Nov 2. PMID: 29024258.
[2]. Mikolajczyk TP, Nosalski R, et,al. 1,2,3,4,6-Penta-O-galloyl-β-d-glucose modulates perivascular inflammation and prevents vascular dysfunction in angiotensin II-induced hypertension. Br J Pharmacol. 2019 Jun;176(12):1951-1965. doi: 10.1111/bph.14583. Epub 2019 Mar 14. PMID: 30658013; PMCID: PMC6534792.
[3]. Zheng C, Chen Y, et,al. Pentagalloylglucose alleviates acetaminophen-induced acute liver injury by modulating inflammation via cGAS-STING pathway. Mol Med. 2024 Sep 27;30(1):160. doi: 10.1186/s10020-024-00924-6. PMID: 39333876; PMCID: PMC11428449.
[4]. Zeng J, Han J, et,al. Pentagalloylglucose disrupts the PALB2-BRCA2 interaction and potentiates tumor sensitivity to PARP inhibitor and radiotherapy. Cancer Lett. 2022 Oct 10;546:215851. doi: 10.1016/j.canlet.2022.215851. Epub 2022 Aug 1. PMID: 35926819.
[5]. Fan CW, Tang J, et,al. Pentagalloylglucose suppresses the growth and migration of human nasopharyngeal cancer cells via the GSK3β/β-catenin pathway in vitro and in vivo. Phytomedicine. 2022 Jul 20;102:154192. doi: 10.1016/j.phymed.2022.154192. Epub 2022 May 21. PMID: 35636179.
[6]. Viswanatha GL, Shylaja H, et,al. Alleviation of transient global ischemia/reperfusion-induced brain injury in rats with 1,2,3,4,6-penta-O-galloyl-β-d-glucopyranose isolated from Mangifera indica. Eur J Pharmacol. 2013 Nov 15;720(1-3):286-93. doi: 10.1016/j.ejphar.2013.10.016. Epub 2013 Oct 22. PMID: 24157980.

Protocol of 1,2,3,4,6-pentagalloylglucose

Cell experiment [1]:

Cell lines

Bone marrow-derived macrophages (BMDMs)

Preparation Method

BMDMs were pretreated with 1,2,3,4,6-pentagalloylglucose (5, 10, or 20µM) for 1h and then stimulated with the cGAS agonist interferon stimulatory DNA (ISD) to model cGAS-STING activation.

Reaction Conditions

5, 10, or 20µM; 1h

Applications

1,2,3,4,6-pentagalloylglucose inhibits cGAS-STING pathway activation in BMDMs.
Animal experiment [1]:

Animal models

C57BL/6 mice(Acetaminophen-induced liver injury (AILI))

Preparation Method

Mice were fasted with water for 12h. Except for the control group, which was administered the corresponding volume of solvent, each group was injected intraperitoneally with 400mg/kg Acetaminophen dissolved in warm saline, and then injected with 20 and 40mg/kg 1,2,3,4,6-pentagalloylglucose 1h later. The mice were sacrificed after 24h, and serum and liver tissues were collected.

Dosage form

20 and 40mg/kg; i.p

Applications

1,2,3,4,6-pentagalloylglucose protect Acetaminophen-induced acute liver injury in mice.

References:
[1]. Zheng C, Chen Y, et,al. Pentagalloylglucose alleviates acetaminophen-induced acute liver injury by modulating inflammation via cGAS-STING pathway. Mol Med. 2024 Sep 27;30(1):160. doi: 10.1186/s10020-024-00924-6. PMID: 39333876; PMCID: PMC11428449.

Chemical Properties of 1,2,3,4,6-pentagalloylglucose

Cas No. 14937-32-7 SDF
Chemical Name [(2R,3R,4S,5R,6S)-3,4,5,6-tetrakis[(3,4,5-trihydroxybenzoyl)oxy]oxan-2-yl]methyl 3,4,5-trihydroxybenzoate
Canonical SMILES C1=C(C=C(C(=C1O)O)O)C(=O)OCC2C(C(C(C(O2)OC(=O)C3=CC(=C(C(=C3)O)O)O)OC(=O)C4=CC(=C(C(=C4)O)O)O)OC(=O)C5=CC(=C(C(=C5)O)O)O)OC(=O)C6=CC(=C(C(=C6)O)O)O
Formula C41H32O26 M.Wt 940.68
الذوبان ≥ 50.4mg/mL in DMSO Storage Store at 2-8°C,protect from light
General tips Please select the appropriate solvent to prepare the stock solution according to the solubility of the product in different solvents; once the solution is prepared, please store it in separate packages to avoid product failure caused by repeated freezing and thawing.Storage method and period of the stock solution: When stored at -80°C, please use it within 6 months; when stored at -20°C, please use it within 1 month.
To increase solubility, heat the tube to 37°C and then oscillate in an ultrasonic bath for some time.
Shipping Condition Evaluation sample solution: shipped with blue ice. All other sizes available: with RT, or with Blue Ice upon request.

Complete Stock Solution Preparation Table of 1,2,3,4,6-pentagalloylglucose

Prepare stock solution
1 mg 5 mg 10 mg
1 mM 1.0631 mL 5.3153 mL 10.6306 mL
5 mM 0.2126 mL 1.0631 mL 2.1261 mL
10 mM 0.1063 mL 0.5315 mL 1.0631 mL
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In vivo Formulation Calculator (Clear solution) of 1,2,3,4,6-pentagalloylglucose

Step 1: Enter information below (Recommended: An additional animal making an allowance for loss during the experiment)

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Method for preparing DMSO master liquid: mg drug pre-dissolved in μL DMSO ( Master liquid concentration mg/mL, Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug. )

Method for preparing in vivo formulation: Take μL DMSO master liquid, next addμL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O, mix and clarify.

Method for preparing in vivo formulation: Take μL DMSO master liquid, next add μL Corn oil, mix and clarify.

Note: 1. Please make sure the liquid is clear before adding the next solvent.
2. Be sure to add the solvent(s) in order. You must ensure that the solution obtained, in the previous addition, is a clear solution before proceeding to add the next solvent. Physical methods such as vortex, ultrasound or hot water bath can be used to aid dissolving.
3. All of the above co-solvents are available for purchase on the GlpBio website.

Product Documents

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