Glucopiericidin A

Glucopiericidin A is a natural piericidin compound obtained from a marine-derived Streptomyces strain. Glucopiericidin A serves as a glucose transporter (GLUT) chemical probe and suppresses glycolysis. Glucopiericidin A inhibits ATP-dependent filopodia protrusion with Piericidin A (PA; HY-114936) and has no effect alone. Glucopiericidin A induces cell apoptosis through reducing the reactive oxygen species (ROS) level by increasing PRDX1 and exhibits potent antitumor efficacy in ACHN mice xenografts.

Product information

CAS Number: 108073-65-0

Molecular Weight: 577.71

Formula: C31H47NO9

Chemical Name: (2R, 3R, 4S, 5S, 6R)-2-{[(2E, 4R, 5R, 6E, 8E, 11E)-13-(4-hydroxy-5, 6-dimethoxy-3-methylpyridin-2-yl)-3, 5, 7, 11-tetramethyltrideca-2, 6, 8, 11-tetraen-4-yl]oxy}-6-(hydroxymethyl)oxane-3, 4, 5-triol

Smiles: C[C@H](/C=C(\C)/C=C/C/C(/C)=C/CC1=NC(OC)=C(OC)C(O)=C1C)[C@@H](O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)/C(/C)=C/C

InChiKey: YQOARHMNLCWEPG-DFTUVXBYSA-N

InChi: InChI=1S/C31H47NO9/c1-9-19(4)28(41-31-27(37)26(36)25(35)23(16-33)40-31)20(5)15-18(3)12-10-11-17(2)13-14-22-21(6)24(34)29(38-7)30(32-22)39-8/h9-10,12-13,15,20,23,25-28,31,33,35-37H,11,14,16H2,1-8H3,(H,32,34)/b12-10+,17-13+,18-15+,19-9+/t20-,23-,25-,26+,27-,28+,31+/m1/s1

Technical Data

Appearance: Solid Power

Purity: ≥98% (or refer to the Certificate of Analysis)

Solubility: Soluble in DMSO

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical or refer to Certificate of Analysis

Storage Condition: Dry, dark and -20 ^oC for 1 year or refer to the Certificate of Analysis.

Shelf Life: ≥12 months if stored properly.

Stock Solution Storage: 0 - 4 ^oC for 1 month or refer to the Certificate of Analysis.

Drug Formulation: To be determined

HS Tariff Code: 382200

How to use

In Vitro:

Glucopiericidin A has cytotoxicities against three renal carcinoma cell lines, ACHN (IC50=0.21 μM), OS-RC-2 (IC50>100 μM), and 786-O (IC50>100 μM), as well as a normal renal cell line, HK-2 (IC50>100 μM). Glucopiericidin A (25, 50 nM; 24 h) causes the upregulation of PRDX1 in ACHN cells. Glucopiericidin A (25, 50 nM; 24 h) not only raises the expression of mRNA and protein of PRDX1 but also forces it into the nucleus. Glucopiericidin A (25, 50 nM; 24 h) reduces ROS in normal ACHN cells. Neither Glucopiericidin A (GPA) nor Piericidin A (PA) alone, at concentrations up to 500 nM and 2.3 mM, respectively, shows inhibitory activity. When combined, much lower concentrations of GPA (17 nM) and PA (0.68 nM) produces inhibition of filopodia protrusion.

In Vivo:

Glucopiericidin A (0.8 mg/kg/day; IP; for three weeks) significantly reduces the final tumor weight of the mice.

References:

1. Mitsuhiro Kitagawa, et al. Metabolomic identification of the target of the filopodia protrusion inhibitor glucopiericidin A. Chem Biol. 2010 Sep 24;17(9):989-98.
2. Xuefeng Zhou, et al. Exploring the Natural Piericidins as Anti-Renal Cell Carcinoma Agents Targeting Peroxiredoxin 1. J Med Chem. 2019 Aug 8;62(15):7058-7069.

Products are for research use only. Not for human use.