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Chemical Compound Review:

AC1NQZQY (Z)-7-[(1S,2S,3R,5S)-3,5- dihydroxy-2-[(E...

Synonyms: SureCN64966, BSPBio_001483, CHEBI:34505, HMDB05083, BML2-B04, ...

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Disease relevance of LMFA03110001

METHODS AND RESULTS: To evaluate oxidant stress in the heart, we measured pericardial fluid levels of 8-iso-prostaglandin F2alpha (8-iso-PGF2alpha), a specific and quantitative marker of oxidant stress in vivo, in a series of 51 consecutive patients with ischemic and/or valvular heart disease referred for cardiac surgery [1].
No difference of 8-epi-PGF2alpha was observed between patients with and without previous history of thrombosis [2].
Both hyperglycemia in vitro and maternal diabetes in vivo caused embryonic dysmorphogenesis and increased embryonic levels of 8-epi-PGF2alpha, an indicator of lipid peroxidation [3].
8-epi-PGF2alpha was also increased in patients with sarcoidosis, although to a lesser extent (12.0 +/- 0.70 pg/ml, p < 0. 01) [4].
Our study shows that the level of oxidative stress is enhanced in patients with interstitial lung diseases as reflected by increased concentrations of 8-epi-PGF2alpha in BAL fluid [4].

Psychiatry related information on LMFA03110001

Interestingly, in sporadic CJD patients, high CSF levels of PGE2, but not 8-epi-PGF2alpha, correlated with short survival time, suggesting that the inflammatory response correlates with the clinical duration of disease [5].
The rabbit model of arteriogenic ED demonstrated decreased intracavernous blood flow, erectile dysfunction, loss of smooth muscle relaxation, decreased endothelial NOS and neuronal NOS, increased inducible NOS expression, diffused cavernous fibrosis and increased cavernous levels of the oxidative product isoprostane 8-epi-prostaglandin F2alpha [6].

High impact information on LMFA03110001

Lipid peroxidation, assessed by measuring the isoprostane 8-iso-PGF2alpha, was decreased in the lungs of GM-/- mice [7].
Patients with systemic lupus erythematosus had higher urinary excretion of 8-epi-PGF2alpha and IPF2alpha -I than controls; urinary excretion of the two isoprostanes was highly correlated (Rho = 0.74, P < .0001) [2].
Urinary 8-epi-PGF2alpha was highly correlated with both aCL titer (Rho = 0. 70, P < .0001) and TNF (Rho = 0.84, P < .0001), a measure of disease severity [2].
Generation of 8-epiprostaglandin F2alpha by human monocytes. Discriminate production by reactive oxygen species and prostaglandin endoperoxide synthase-2 [8].
In conclusion, human monocytes may form bioactive 8-epi-PGF2alpha either via free radical- or enzyme-catalyzed pathways [8].

Chemical compound and disease context of LMFA03110001

Similarly, PGE2 and 8-epi-PGF2alpha levels were higher in brain homogenates obtained from C57BL/6J mice infected with the ME7 scrapie strain than in brain homogenates from control animals [5].
In WG and CSS, 8-epi-PGF2alpha concentrations correlated with disease activity (r = 0.8, P = 0.01) and were higher than in patients with Behcet disease (P = 0.003) [9].
This study investigates the circulatory alpha-tocopherol levels and its relationship with 8-iso-prostaglandin F2alpha (8-iso-PGF2alpha), a non-enzymatic and, 15-keto-13,14-dihydro-PGF2alpha (15-K-DH-PGF2alpha), a cyclooxygenase catalysed oxidation product of arachidonic acid in experimental septic shock in pigs [10].
As the urinary concentration of 8-epi-PGF2alpha increased, the number of criteria for MetS were significantly met (abdominal obesity, hypertriglyceridemia, low high-density lipoprotein-cholesterol, hypertension, and high fasting glucose) [11].

Biological context of LMFA03110001

Concentrations of 8-iso-PGF2alpha, 15-keto-DH-PGF2alpha and other oxidative stress variables were measured [12].
The 8-epi-PGF2alpha was correlated with fasting glucose (r = 0.50, p < 0.001), triglycerides (r = 0.40, p < 0.001) and insulin resistance (r = 0.35, p < 0.001) [13].
The current study investigated the effects of 8-epiprostaglandin F2alpha (8-epi-PGF2alpha) on critical events of platelet activation [14].
Significant decreases in 8-iso-PGF2alpha, MCP-1, and UAE were observed with spironolactone (P = 0.0001, P = 0.0041, and P = 0.0037, respectively), and systolic blood pressure significantly decreased after both spironolactone and amlodipine therapy (P = 0.00011 and P = 0.0051, respectively) [15].
RESULTS: Our results show that physiological concentrations of 8-iso-PGF2alpha stimulated cell proliferation, DNA synthesis, and ET-1 mRNA and protein expression in bovine aortic endothelial cells (BAECs) [16].

Anatomical context of LMFA03110001

There was no difference in the amniotic fluid concentration of 8-iso-PGF2alpha between the normal and the diabetic group [12].
The antiaggregatory effects of both the NO donor NOR-3 (basal, 21.4+/-4.6%; with 8-epi-PGF2alpha, 30.8+/-6.9%; n=14, P<0.05) and endothelial cells that release NO (basal, 18.5+/-4.6%; with 8-epi-PGF2alpha, 30.7+/-5.3%; n=15, P<0.001) were also reduced [14].
Increased immunoreactivity to 15-F2t-IsoP (8-iso-PGF2alpha) or to isoketal protein adducts was found in epithelial cells 24 h after the first aerosol challenge and at 5 days in macrophages [17].
METHODS AND RESULTS: We measured the MMP activity and the level of 8-iso-prostagandin F2alpha (8-iso-PGF2alpha), a specific and quantitative maker of oxidant stress, in the pericardial fluid (PF) in 47 consecutive patients with coronary artery disease who underwent coronary artery bypass surgery [18].
In conclusion, although 8-iso-PGF2alpha production from rat brain synaptosomes is independent from aging in the basal state, aging renders neurons more vulnerable to amyloid beta-peptide-induced oxidative toxicity [19].

Associations of LMFA03110001 with other chemical compounds

Pretreatment of monocytes with the antioxidant, butylated hydroxytoluene or with superoxide dismutase, but not with L 745,337, suppressed formation of 8-epi-PGF2alpha, thiobarbituric acid-reactive substances, and lipid hydroperoxides [8].
The levels of 8-iso-PGF2alpha (a major F2-isoprostane and biomarker of oxidative stress) and 15-keto-dihydro-PGF2alpha (a major metabolite of PGF2alpha and biomarker of inflammatory response) were measured in frequently collected plasma samples before, during, and up to 24 h postsurgery in 21 patients [20].
SLE patients not taking prednisolone showed higher 8-epi-PGF2alpha concentrations than SLE patients on prednisolone (P = 0.02) [9].
A prostaglandin F2-like compound, 8-epi-PGF2alpha, formed from oxidation of arachidonate, has been proposed as an indicator of lipid peroxidation [21].
Vascular lesions and extensive vascular remodeling, coupled to increased production of 8-epi-PGF2alpha, nuclear localization of NFkappaB, and alterations in glutathione homeostasis, were observed in animals treated with allylamine for up to 20 days [22].

Gene context of LMFA03110001

CONCLUSIONS: Our data suggest that urinary MCP-1 is correlated with oxidative stress as measured by urinary 8-iso-PGF2alpha and that spironolactone can decrease urinary MCP-1 and oxidative stress [15].
Moreover, MMP-2, MMP-9 and total gelatinolysis activities were all positively correlated with pericardial level of 8-iso-PGF2alpha [18].
Based on the turnover number, cyclooxygenase-2 formed higher levels of 8-epi-PGF2alpha than cyclooxygenase-1 [23].
In monocyte adhesion assays, 8-iso-PGF2alpha (>10(-8) M) suppressed both basal and TNF-alpha-induced monocyte adhesion to quiescent or proliferating human dermal (HMEC) and rat renal microvascular endothelial cells [24].
8-Iso-PGF2alpha also had no effect on HMEC surface expression of ICAM-1 or VCAM-1 [24].

Analytical, diagnostic and therapeutic context of LMFA03110001

Increased formation of the isoprostanes IPF2alpha-I and 8-epi-prostaglandin F2alpha in acute coronary angioplasty: evidence for oxidant stress during coronary reperfusion in humans [25].
There was a slight increase in urinary 8-epi-PGF2alpha levels (64.7+/-9.5 versus 84.9+/-10.6; P=.02) after diagnostic coronary arteriography and elective PTCA (88.7+/-7.5 versus 114.3+/-16.1; P=.01) [25].
RESULTS: During reperfusion, 8-iso-PGF2alpha release increased tenfold compared with the preischemic value in all groups [26].
The level of TxB2, a stable TxA2 metabolite, increased in bronchoalveolar lavage fluid (BALF) after 8-epi-PGF2alpha instillation [27].
No correlation between 8-epi-PGF2alpha and either lung function tests or BAL cell types was observed in any group of patients [4].

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