79886-50-3
Chemical Structure
1,2,3,6-Tetragalloylglucose
Synonym(s): TeGG
- CAS No.: 79886-50-3
- Formula:C34H28O22
- Molecular Weight:788.57
IUPAC Name: (2S,3R,4S,5R,6R)-5-hydroxy-6-(((3,4,5-trihydroxybenzoyl)oxy)methyl)tetrahydro-2H-pyran-2,3,4-triyl tris(3,4,5-trihydroxybenzoate)
InChIKey: RATQVALKDAUZBW-XPMKZLBQSA-N
SMILES: O=C(C1=CC(O)=C(O)C(O)=C1)O[C@@H]2[C@H]([C@@H]([C@@H](COC(C3=CC(O)=C(O)C(O)=C3)=O)O[C@H]2OC(C4=CC(O)=C(O)C(O)=C4)=O)O)OC(C5=CC(O)=C(O)C(O)=C5)=O
Biological Activity: 1,2,3,6-Tetragalloylglucose (TEgG) is a competitive inhibitor of UDP-glucuronyltransferase UGT1A1, targeting the competitive substrate binding site of UGT1A1. 1,2,3,6-Tetragalloylglucose inhibits UGT1A1-mediated β-estradiol 3-glucuronidation and SN-38 glucuronidation with IC50 of 6.01 μM and 4.31 μM, respectively, and binds to UGT1A1 with Ki of 3.55 μM. 1,2,3,6-Tetragalloylglucose also induces tumor cell apoptosis, inhibit cell proliferation, activates caspase-3 and induces DNA fragmentation in HL-60 cells. 1,2,3,6-Tetragalloylglucose also inhibits HIV integrase and reverse transcriptase, and inhibits HCV protease[1][2][3].
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1,2,3,6-Tetragalloylglucose | 99.08% | 1,2,3,6-Tetragalloylglucose (TEgG) is a competitive inhibitor of UDP-glucuronyltransferase UGT1A1, targeting the competitive substrate binding site of UGT1A1. 1,2,3,6-Tetragalloylglucose inhibits UGT1A1-mediated β-estradiol 3-glucuronidation and SN-38 glucuronidation with IC50 of 6.01 μM and 4.31 μM, respectively, and binds to UGT1A1 with Ki of 3.55 μM. 1,2,3,6-Tetragalloylglucose also induces tumor cell apoptosis, inhibit cell proliferation, activates caspase-3 and induces DNA fragmentation in HL-60 cells. 1,2,3,6-Tetragalloylglucose also inhibits HIV integrase and reverse transcriptase, and inhibits HCV protease. | ||||||||||||||||||||
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References
- [1]. Park JB, et al. Identification and characterization of in vitro inhibitors against UDP-glucuronosyltransferase 1A1 in uva-ursi extracts and evaluation of in vivo uva-ursi-drug interactions. Food Chem Toxicol. 2018 Oct;120:651-661. [Content Brief]
- [2]. Min Byung-Sun, et al. Apoptosis-inducing activity of galloylglucoses from Juglans mandshurica in human promyeloid leukemic HL-60 cells. Natural Product Sciences 10.1 (2004): 48-53.
- [3]. Zhang J, et al. Anti-cancer, anti-diabetic and other pharmacologic and biological activities of penta-galloyl-glucose. Pharm Res. 2009 Sep;26(9):2066-80. [Content Brief]
