Chemical Formula: C30H47N3O10S
Chemical Formula C30H47N3O10S
Found 13 metabolite its formula value is C30H47N3O10S
S-(9-deoxy-delta9,12-PGD2)-glutathione
The major dehydration product of prostaglandin D2, 9-deoxy-d9,d12(E)-prostaglandin D2, is a potent cytotoxic compound. Like other cytotoxic prostaglandins, this compound possesses an α,β-unsaturated ketone group to which cytotoxic activity has been attributed. This prostaglandin was found to readily conjugate with glutathione (GSH) in vitro. When 9-deoxy-d9,d12(E)-prostaglandin D2 was incubated with Chinese hamster ovary or hepatoma tissue culture cells, it was rapidly taken up and was recovered in the cell lysate primarily as a GSH conjugate in which the keto group at C-11 and the Δ12 double bond had been reduced. Identification of the GSH conjugate was accomplished by analysis by fast atom bombardment mass spectrometry following purification by high performance liquid chromatography. This GSH conjugate and its cysteinylglycinyl and cysteinyl metabolites were also identified in the cell culture medium. 9-Deoxy-d9,d12(E)-prostaglandin D2 inhibited cell proliferation of these two cell lines in a concentration dependent manner. Depletion of intracellular glutathione by treatment with diethyl maleate and buthionine sulfoximine decreased the amount of intracellular conjugated prostaglandin recovered, and significantly enhanced the antiproliferative effect of 9-deoxy-d9-d12(E)-prostaglandin D2 on the growth of these cell lines in a concentration dependent fashion. Intracellular GSH may modulate the antiproliferative activity of 9-deoxy-Δ9,Δ12(E)-prostaglandin D2 and, possibly, of other cytotoxic prostaglandins. [HMDB] The major dehydration product of prostaglandin D2, 9-deoxy-d9,d12(E)-prostaglandin D2, is a potent cytotoxic compound. Like other cytotoxic prostaglandins, this compound possesses an α,β-unsaturated ketone group to which cytotoxic activity has been attributed. This prostaglandin was found to readily conjugate with glutathione (GSH) in vitro. When 9-deoxy-d9,d12(E)-prostaglandin D2 was incubated with Chinese hamster ovary or hepatoma tissue culture cells, it was rapidly taken up and was recovered in the cell lysate primarily as a GSH conjugate in which the keto group at C-11 and the Δ12 double bond had been reduced. Identification of the GSH conjugate was accomplished by analysis by fast atom bombardment mass spectrometry following purification by high performance liquid chromatography. This GSH conjugate and its cysteinylglycinyl and cysteinyl metabolites were also identified in the cell culture medium. 9-Deoxy-d9,d12(E)-prostaglandin D2 inhibited cell proliferation of these two cell lines in a concentration dependent manner. Depletion of intracellular glutathione by treatment with diethyl maleate and buthionine sulfoximine decreased the amount of intracellular conjugated prostaglandin recovered, and significantly enhanced the antiproliferative effect of 9-deoxy-d9-d12(E)-prostaglandin D2 on the growth of these cell lines in a concentration dependent fashion. Intracellular GSH may modulate the antiproliferative activity of 9-deoxy-Δ9,Δ12(E)-prostaglandin D2 and, possibly, of other cytotoxic prostaglandins.
S-(PGA2)-glutathione
S-(PGA2)-glutathione is the glutathione conjugate of prostaglanding A2. PGA2 is converted to its glutathione conjugate by human mu-class GST M1a-a. Vertebrate alpha-, mu-, and pi-class GSTs were found to enhance PGA2 conjugation with glutathione, suggesting that the overexpression of GST forms could modulate the cytotoxic effects of cyclopentenone prostaglandins. Mammalian GSTs also have the ability to non-catalytically bind lipophilic, amphipathic ligands, including PGJ2, via noncovalent interactions, which effectively sequester these ligands in the cytosol away from their nuclear targets (i.e., peroxisomal proliferator-activated receptor, PPAR). S-(PGA2)-glutathione is the glutathione conjugate of prostaglanding A2
S-(PGJ2)-glutathione
S-(PGJ2)-glutathione is a glutathione conjugate of prostaglandin J2. By reacting with glutathione and proteins, 15-d-PGJ(2) is believed to exert potent biological activity. HepG2 cells primarily convert 15-d-PGJ(2) to a glutathione conjugate in which the carbonyl at C-11 is reduced to a hydroxyl. Subsequently, the glutathione portion of the molecule is hydrolyzed with loss of glutamic acid and glycine resulting in a cysteine conjugate. These findings confirm a general route for the metabolism of cyclopentenone eicosanoids in HepG2 cells and may pave the way for new insights regarding the formation of 15-d-PGJ(2) in vivo. S-(PGJ2)-glutathione is a glutathione conjugate of prostaglandin J2.
12-Oxo-c-LTB3
This compound belongs to the family of Leukotrienes. These are eicosanoids containing an hydroxyl group attached to the aliphati chain of an arachidonic acid.
L-gamma-glutamyl-S-[(4S,5R,6E,8E,13Z)-1-carboxy-4-hydroxy-11-oxononadeca-6,8,13-trien-5-yl]-L-cysteinylglycine
L-gamma-glutamyl-S-[(5Z,11beta,13E,15S)-1,15-dihydroxy-1,9-dioxoprosta-5,13-dien-11-yl]-L-cysteinylglycine
L-gamma-glutamyl-S-[(5Z,9beta,13E,15S)-1,15-dihydroxy-1,11-dioxoprosta-5,13-dien-9-yl]-L-cysteinylglycine
L-gamma-glutamyl-S-[(5Z,9alpha,13E,15S)-1,15-dihydroxy-1,11-dioxoprosta-5,13-dien-9-yl]-L-cysteinylglycine
L-gamma-glutamyl-S-[(5Z,11alpha,13E,15S)-1,15-dihydroxy-1,9-dioxoprosta-5,13-dien-11-yl]-L-cysteinylglycine
(5S,6R,7E,9E,14Z)-6-[(2R)-2-[[(4S)-4-amino-4-carboxybutanoyl]amino]-3-(carboxymethylamino)-3-oxopropyl]sulfanyl-5-hydroxy-12-oxoicosa-7,9,14-trienoic acid
11(S),15(S)-dihydroxy-14(R)-(S-glutathionyl)-5(Z),8(Z),12(E)-icosatrienoate(2-)
An peptide anion obtained by deprotonation of the carboxylic acid groups and protonation of the amino group of 11(S),15(S)-dihydroxy-14(R)-(S-glutathionyl)-5(Z),8(Z),12(E)-icosatrienoic acid; major species at pH 7.3.