Protein Information

Name glutathione S transferase P
Synonyms DFN 7; PI; DFN7; FAEES 3; FAEES3; GST class pi; GST3; GSTP 1…

Compound Information

Name acrolein
CAS 2-propenal

Reference List

PubMed Abstract RScore(About this table)
9463521 van Iersel ML, Ploemen JP, Lo Bello M, Federici G, van Bladeren PJ: Interactions of alpha, beta-unsaturated aldehydes and ketones with human glutathione S-transferase P1-1. Chem Biol Interact. 1997 Dec 12;108(1-2):67-78.

When GSTP1-1 was incubated with a 50-fold molar excess of the aldehydes acrolein (ACR) and 4-hydroxy-2-nonenal (HNE) and the ketones curcumin (CUR) and ethacrynic acid (EA) at 22 degrees C, all of them inactivated GSTP1-1.
85(1,1,1,5) Details
10799737 Pal A, Hu X, Zimniak P, Singh SV: Catalytic efficiencies of allelic variants of human glutathione S-transferase Pi in the glutathione conjugation of alpha, beta-unsaturated aldehydes. Cancer Lett. 2000 Jun 1;154(1):39-43.

The catalytic efficiencies of the allelic variants of human glutathione (GSH) S-transferase Pi (hGSTP1-1), which differ in their primary structures by the amino acids in positions 104 (isoleucine or valine) and/or 113 (alanine or valine), in the GSH conjugation (detoxification) of acrolein and crotonaldehyde have been determined.
32(0,1,1,2) Details
12718659 Satoh K: Increase Intake of Water for Prevention of Cancer: an Enzymological Lesson?. Asian Pac J Cancer Prev. 2001;2(1):75-80.

However, the species of glutathione S-transferases (GSTP1-1) linked to neoplasia of rat and human were recently shown to be selective for hydrophilic carcinogens such as acrolein and hydroxyalkenals (Satoh, 1998; Satoh et al., 1999) in accord with the finding of a water-network in the active site of the human GSTP1-1 by X-ray analysis (Hu et al.; Ji et al., 1997).
31(0,1,1,1) Details
19696094 Conklin DJ, Haberzettl P, Lesgards JF, Prough RA, Srivastava S, Bhatnagar A: Increased sensitivity of glutathione S-transferase P-null mice to cyclophosphamide-induced urinary bladder toxicity. J Pharmacol Exp Ther. 2009 Nov;331(2):456-69. Epub 2009 Aug 20.

Herein, we tested the hypothesis that glutathione S-transferase P (GSTP), the GST isoform that displays high catalytic efficiency with acrolein, protects against CY-induced urotoxicity by detoxifying acrolein.
7(0,0,1,2) Details
9771939 Satoh K: Weak electrophile selective characteristics of the rat preneoplastic marker enzyme glutathione S-transferase P-form, GST-P (7-7): a theory of linear free energy relationships for evaluation of the active site hydrophobicity of isoenzymes. Carcinogenesis. 1998 Sep;19(9):1665-71.

As these thermodynamic parameters, deltadeltaG degrees and deltadeltaH degrees, may be considered as indirect and direct measures of GST hydrophobicity respectively, the H-site hydrophobicity of GST-P is thus very low as compared with those of other forms, clearly indicating that the pi class GST-P selectively targets for weak electrophiles, i.e. water-soluble carcinogens such as acrolein and hydroxyalkenals.
2(0,0,0,2) Details
19270193 Conklin DJ, Haberzettl P, Prough RA, Bhatnagar A: Glutathione-S-transferase P protects against endothelial dysfunction induced by exposure to tobacco smoke. Am J Physiol Heart Circ Physiol. 2009 May;296(5):H1586-97. Epub 2009 Mar 6.

The P isoform of GST (GSTP), which catalyzes the conjugation of electrophilic molecules in cigarette smoke such as acrolein, was expressed in high abundance in the mouse lung and aorta.
1(0,0,0,1) Details
9240470 Fukuda A, Nakamura Y, Ohigashi H, Osawa T, Uchida K: Cellular response to the redox active lipid peroxidation products: induction of glutathione S-transferase P by 4-hydroxy-2-nonenal. Biochem Biophys Res Commun. 1997 Jul 18;236(2):505-9.

We found that the GST activity in RL34 cells was induced by alpha,beta-unsaturated aldehydes, such as acrolein (1.3-fold), crotonaldehyde (1.3-fold), 4-hydroxy-2-hexenal (HHE) (1.4-fold), and 4-hydroxy-2-nonenal (HNE) (1.7-fold).
1(0,0,0,1) Details
8950226 Iersel ML, Ploemen JP, Struik I, van Amersfoort C, Keyzer AE, Schefferlie JG, van Bladeren PJ: Inhibition of glutathione S-transferase activity in human melanoma cells by alpha,beta-unsaturated carbonyl derivatives. Chem Biol Interact. 1996 Oct 21;102(2):117-32.

Reversible inhibition of GST was the major mechanism of inhibition of DNPSG-excretion in melanoma cells, except in the cases of curcumin and ethacrynic acid, which compounds also inactivated GSTP1-1 by covalent modification.
Effects of acrolein, cinnamaldehyde, citral, crotonaldehyde, curcumin, ethacrynic acid, and trans-2-hexenal..
1(0,0,0,1) Details
11600134 Satoh K, Hayakari M, Ookawa K, Satou M, Aizawa S, Tanaka M, Hatayama I, Tsuchida S, Uchida K: Lipid peroxidation end products-responded induction of a preneoplastic marker enzyme glutathione S-transferase P-form (GST-P) in rat liver on admistration via the portal vein. Mutat Res. 2001 Nov 1;483(1-2):65-72.

Unsaturated aldehydes, 4-hydroxynonenal, crotonaldehyde and acrolein, given by the same route induced putatively preneoplastic single cells positive for GST-P.
2(0,0,0,2) Details
7728969 Satoh K: The high non-enzymatic conjugation rates of some glutathione S-transferase (GST) substrates at high glutathione concentrations. Carcinogenesis. 1995 Apr;16(4):869-74.

GSTP1-1 showed a broad substrate specificity with both low and high GSH (10 mM) concentrations at pH 7.0, and the inhibitor insensitivity was then prominent.
The half-time for acrolein estimated by extrapolation was approximately 0.5 s.
1(0,0,0,1) Details
9882456 Satoh K, Sato R, Takahata T, Suzuki S, Hayakari M, Tsuchida S, Hatayama I: Quantitative differences in the active-site hydrophobicity of five human glutathione S-transferase isoenzymes: water-soluble carcinogen-selective properties of the neoplastic GSTP1-1 species. Arch Biochem Biophys. 1999 Jan 15;361(2):271-6.

In contrast to the Alpha and Mu classes being selective for strongly electrophilic compounds, the neoplastic P1-1 species was indicated to be selective for weakly electrophilic and water-soluble carcinogens such as acrolein and hydroxyalkenals.
1(0,0,0,1) Details