Genomes and Genes
Summary: (13E,15S)-15-Hydroxy-9-oxoprosta-10,13-dien-1-oic acid (PGA(1)); (5Z,13E,15S)-15-hydroxy-9-oxoprosta-5,10,13-trien-1-oic acid (PGA(2)); (5Z,13E,15S,17Z)-15-hydroxy-9-oxoprosta-5,10,13,17-tetraen-1-oic acid (PGA(3)). A group of naturally occurring secondary prostaglandins derived from PGE; PGA(1) and PGA(2) as well as their 19-hydroxy derivatives are found in many organs and tissues.
- Ko F, Lau C, Leung T, Wong G, Lam C, Hui D. Exhaled breath condensate levels of 8-isoprostane, growth related oncogene alpha and monocyte chemoattractant protein-1 in patients with chronic obstructive pulmonary disease. Respir Med. 2006;100:630-8 pubmed..8-isoprostane level, but not GROalpha and MCP-1, in EBC was increased in COPD patients with poorer lung function. This suggests an increased oxidative stress in the airway in patients with more severe COPD. ..
- Elia G, Polla B, Rossi A, Santoro M. Induction of ferritin and heat shock proteins by prostaglandin A1 in human monocytes. Evidence for transcriptional and post-transcriptional regulation. Eur J Biochem. 1999;264:736-45 pubmed..As ferritin, together with hsp70 and HO, plays a key role in protection from oxidant damage, these results suggest that PGA1 may have cytoprotective activity also during oxidative injury. ..
- Fulton A, Hanchin C, Butler W. Heterogeneity of prostaglandin E2 binding in murine mammary tumor cells differing in metastatic potential. Invasion Metastasis. 1988;8:17-30 pubmed..3H-PGE binding to line 410 cells is comparatively nonspecific as PGD2 is nearly as effective as PGE1, PGE2 and an analogue of PGE2 in competing with 3H-PGE2 and PGA2 also inhibits 3H-PGE2 binding. ..
- Zhang H, Gu Z, Savitz S, Han F, Fukunaga K, Qin Z. Neuroprotective effects of prostaglandin A(1) in rat models of permanent focal cerebral ischemia are associated with nuclear factor-kappaB inhibition and peroxisome proliferator-activated receptor-gamma up-regulation. J Neurosci Res. 2008;86:1132-41 pubmed..These findings suggest that PGA(1)-mediated neuroprotective effect against ischemia appears to be associated with blocking NF-kappaB activation and likely with up-regulating PPAR-gamma expression. ..
- Gayarre J, Stamatakis K, Renedo M, Perez Sala D. Differential selectivity of protein modification by the cyclopentenone prostaglandins PGA1 and 15-deoxy-Delta12,14-PGJ2: role of glutathione. FEBS Lett. 2005;579:5803-8 pubmed..Therefore GSH levels may influence not only the intensity but also the specificity of cyPG action. ..
- Schroder O, Yudina Y, Sabirsh A, Zahn N, Haeggstrom J, Stein J. 15-deoxy-Delta12,14-prostaglandin J2 inhibits the expression of microsomal prostaglandin E synthase type 2 in colon cancer cells. J Lipid Res. 2006;47:1071-80 pubmed..Our data suggest that there is a feedback mechanism between PGE(2) and CyPGs that implicates mPGES-2 as a new potential target for pharmacological intervention in CRC. ..
- Ratnayake A, Bugni T, Veltri C, Skalicky J, Ireland C. Chemical transformation of prostaglandin-A2: a novel series of C-10 halogenated, C-12 hydroxylated prostaglandin-A2 analogues. Org Lett. 2006;8:2171-4 pubmed..15S)-Prostaglandin-A(2) (1), from the gorgonian Plexaura homomalla, served as the starting material for the synthesis. The absolute configuration was determined using NMR. ..
- Xu X, Hua Y, Zhang H, Wu J, Miao Y, Han R, et al. Greater stress protein expression enhanced by combined prostaglandin A1 and lithium in a rat model of focal ischemia. Acta Pharmacol Sin. 2007;28:1097-104 pubmed..Our studies suggest that combined PGA1 and Li may have potential clinical value for the treatment of stroke. ..
- Wong Y, Gruber J, Jenner A, Ng M, Ruan R, Tay F. Elevation of oxidative-damage biomarkers during aging in F2 hybrid mice: protection by chronic oral intake of resveratrol. Free Radic Biol Med. 2009;46:799-809 pubmed publisher..Our studies demonstrate that RSV treatment consistently attenuated oxidative damage in tissues where age-related oxidative damage accumulation was prominent, but also suggested that chronic RSV treatment may induce nephrotoxicity. ..
- Rubin D, Drab E, Stone A, Walden T, Hanson W. The influence of exogenous eicosanoids on the radiation response of cultured bovine aortic endothelial cells. Radiat Res. 1991;125:41-7 pubmed..These investigations suggest that an elevated cAMP level alone does not lead to eicosanoid-induced radioprotection of bovine aortic endothelial cell monolayers in vitro. ..
- Song W, Brash A. Investigation of the allene oxide pathway in the coral Plexaura homomalla: formation of novel ketols and isomers of prostaglandin A2 from 15-hydroxyeicosatetraenoic acid. Arch Biochem Biophys. 1991;290:427-35 pubmed..homomalla. Unexpectedly, the major end products of the pathway are trihydroxy ketols and the single diastereomer of a stable epoxyalcohol. ..
- Portis T, Harding J, Ratner L. The contribution of NF-kappa B activity to spontaneous proliferation and resistance to apoptosis in human T-cell leukemia virus type 1 Tax-induced tumors. Blood. 2001;98:1200-8 pubmed..These results strongly suggest that Tax-mediated induction of NF-kappa B activity contributes to tumorigenesis in vivo. (Blood. 2001;98:1200-1208) ..
- Amici C, Belardo G, Rozera C, Bernasconi D, Santoro M. Inhibition of herpesvirus-induced HIV-1 replication by cyclopentenone prostaglandins: role of IkappaB kinase (IKK). AIDS. 2004;18:1271-80 pubmed..The results indicate that IKK is a key factor in triggering HSV-1-induced HIV-1 transcription in chronically-infected cells and identify cyclopentenone prostanoids as potent inhibitors of HSV-1-induced HIV-1 reactivation. ..
- Li Z, Melandri F, Berdo I, Jansen M, Hunter L, Wright S, et al. Delta12-Prostaglandin J2 inhibits the ubiquitin hydrolase UCH-L1 and elicits ubiquitin-protein aggregation without proteasome inhibition. Biochem Biophys Res Commun. 2004;319:1171-80 pubmed..In conclusion, impairment of ubiquitin hydrolase activity, such as triggered by Delta12-PGJ2, may be an important contributor to neurodegeneration associated with accumulation of ubiquitinated proteins and inflammation. ..
- Rossi A, Kapahi P, Natoli G, Takahashi T, Chen Y, Karin M, et al. Anti-inflammatory cyclopentenone prostaglandins are direct inhibitors of IkappaB kinase. Nature. 2000;403:103-8 pubmed..As IKKbeta is responsible for the activation of NF-kappaB by pro-inflammatory stimuli, our findings explain how cyclopentenone prostaglandins function and can be used to improve the utility of COX2 inhibitors. ..
- Zernecke A, Erl W, Fraemohs L, Lietz M, Weber C. Suppression of endothelial adhesion molecule up-regulation with cyclopentenone prostaglandins is dissociated from IkappaB-alpha kinase inhibition and cell death induction. FASEB J. 2003;17:1099-101 pubmed..Our findings define distinct mechanisms for anti-inflammatory and proapoptotic effects of cPG in endothelial cells. ..
- Mangelus M, Galron R, Naor Z, Sokolovsky M. Involvement of nuclear factor-kappaB in endothelin-A-receptor-induced proliferation and inhibition of apoptosis. Cell Mol Neurobiol. 2001;21:657-74 pubmed..These findings indicate that the regulation of cell proliferation and apoptosis by ET(A)R is mediated by the ET(A)R-activated NF-kappaB. ..
- Levine L. Stimulated release of arachidonic acid by agonists of the peroxisome proliferator-activated receptor and retinoic acid receptors. Prostaglandins Leukot Essent Fatty Acids. 2001;65:229-32 pubmed..The mechanisms involved may differ in the cases of 15-deoxy-Delta(12,14) PGJ2 and celecoxib. ..
- Lahoua Z, Astruc M, Crastes de Paulet A. Serum-induced arachidonic acid release and prostaglandin biosynthesis are potentiated by oxygenated sterols in NRK 49F cells. Biochim Biophys Acta. 1988;958:396-404 pubmed..Cholesterol and 7-ketocholesterol were unable to activate phospholipase activity. The mechanism of this activation by oxysterols is still unknown. ..
- Hirayama E, Hattori M, Kim J. Specific binding of heat shock protein 70 with HN-protein inhibits the HN-protein assembly in Sendai virus-infected Vero cells. Virus Res. 2006;120:199-207 pubmed..The results suggest that HN protein is necessary for viral morphogenesis. ..
- Pombo Jiménez M, Escribano Subias P, Tello de Meneses R, Gómez Sánchez M, Delgado Jimenez J, Dalmau González Gallarza R, et al. [Ten years' experience in continuous intravenous epoprostenol therapy in severe pulmonary arterial hypertension]. Rev Esp Cardiol. 2003;56:230-5 pubmed..Continuous intravenous epoprostenol therapy improves survival and exercise capacity in patients with severe pulmonary arterial hypertension despite potentially serious complications attributable to the delivery system. ..
- Bureau F, Desmet C, Mélotte D, Jaspar F, Volanti C, Vanderplasschen A, et al. A proinflammatory role for the cyclopentenone prostaglandins at low micromolar concentrations: oxidative stress-induced extracellular signal-regulated kinase activation without NF-kappa B inhibition. J Immunol. 2002;168:5318-25 pubmed
- Freitas T, Caldas L, Rebello M. Effect of prostaglandin A1 in porcine cells persistently infected with classical swine fever virus. J Basic Microbiol. 2003;43:468-72 pubmed..However when PGA1 was removed from persistently infected cells, the inhibition of virus replication was partially reverted. ..
- Erl W, Weber C, Zernecke A, Neuzil J, Vosseler C, Kim H, et al. Cyclopentenone prostaglandins induce endothelial cell apoptosis independent of the peroxisome proliferator-activated receptor-gamma. Eur J Immunol. 2004;34:241-50 pubmed..Our findings show that PGA1 and PGJ2 induce apoptosis in endothelial cells independent of PPARgamma. As the synthesis of PGJ2 is increased at sites of inflammation, our results may suggest a possible mechanism for endothelial damage. ..
- Stotz H, Mueller S, Zoeller M, Mueller M, Berger S. TGA transcription factors and jasmonate-independent COI1 signalling regulate specific plant responses to reactive oxylipins. J Exp Bot. 2013;64:963-75 pubmed publisher..Identification of molecular components in cyclopentenone signalling provides an insight into novel oxylipin signal transduction pathways. ..
- Satoh T, Furuta K, Tomokiyo K, Nakatsuka D, Tanikawa M, Nakanishi M, et al. Facilitatory roles of novel compounds designed from cyclopentenone prostaglandins on neurite outgrowth-promoting activities of nerve growth factor. J Neurochem. 2000;75:1092-102 pubmed
- Kikuta Y, Kusunose E, Okumoto T, Kubota I, Kusunose M. Purification and characterization of two forms of cytochrome P-450 with omega-hydroxylase activities toward prostaglandin A and fatty acids from rabbit liver microsomes. J Biochem. 1990;107:280-6 pubmed..The intensity of the immunoblot was significantly increased in liver microsomes from rabbits treated with DEHP, but not with phenobarbital or 3-methylcholanthrene.(ABSTRACT TRUNCATED AT 250 WORDS) ..
- Antoun J, Goulitquer S, Amet Y, Dreano Y, Salaun J, Corcos L, et al. CYP4F3B is induced by PGA1 in human liver cells: a regulation of the 20-HETE synthesis. J Lipid Res. 2008;49:2135-41 pubmed publisher..Since 20-HETE is a potent activator of PPARalpha and an important inflammatory mediator, CYP4F3B may exert important functions in lipid homeostasis and in inflammatory diseases. ..
- Wales N. Hormone studies in Myxine glutinosa: effects of the eicosanoids arachidonic acid, prostaglandin E1, E2, A2, F2 alpha, thromboxane B2 and of indomethacin on plasma cortisol, blood pressure, urine flow and electrolyte balance. J Comp Physiol B. 1988;158:621-6 pubmed..abstract truncated at 250 words)..
- ElAttar T, Virji A. Inhibition of growth in oral squamous carcinoma cells by cyclopentenone prostaglandins: comparison with chemotherapeutic agents. Prostaglandins Leukot Essent Fatty Acids. 1997;56:461-5 pubmed..e. cell proliferation). Combining vitamin E succinate with lower concentrations of CPPGs enhanced significantly their inhibitory effect on nuclear DNA synthesis of cancer cells. ..
- Thomas S, Ryan M, Shanley T, Wong H. Induction of the stress response with prostaglandin A1 increases I-kappaBalpha gene expression. FASEB J. 1998;12:1371-8 pubmed..The functional consequences of stress response-mediated I-kappaBalpha gene expression may involve attenuation of cellular proinflammatory responses. ..
- Milne G, Musiek E, Morrow J. The cyclopentenone (A2/J2) isoprostanes--unique, highly reactive products of arachidonate peroxidation. Antioxid Redox Signal. 2005;7:210-20 pubmed..Finally, the formation of cyclopentenone IsoP-like compounds from other fatty acids such as linolenic acid and docosahexaenoic acid will be detailed. ..
- Stark M, Rothem L, Jansen G, Scheffer G, Goldman I, Assaraf Y. Antifolate resistance associated with loss of MRP1 expression and function in Chinese hamster ovary cells with markedly impaired export of folate and cholate. Mol Pharmacol. 2003;64:220-7 pubmed..The data also suggest that MRP1, and possibly other MRPs that transport folates, can play a role in the maintenance of cellular folate homeostasis. ..
- Reid G, Wielinga P, Zelcer N, van der Heijden I, Kuil A, de Haas M, et al. The human multidrug resistance protein MRP4 functions as a prostaglandin efflux transporter and is inhibited by nonsteroidal antiinflammatory drugs. Proc Natl Acad Sci U S A. 2003;100:9244-9 pubmed..Together, these data suggest that MRP4 can release prostaglandins from cells, and that, in addition to inhibiting prostaglandin synthesis, some nonsteroidal antiinflammatory drugs might also act by inhibiting this release. ..
- Büyükgüzel K, Tunaz H, Putnam S, Stanley D. Prostaglandin biosynthesis by midgut tissue isolated from the tobacco hornworm, Manduca sexta. Insect Biochem Mol Biol. 2002;32:435-43 pubmed..We infer that insect midguts are competent to biosynthesize PGs, and speculate they exert important, albeit unrevealed, actions in midgut physiology. ..
- Amici C, Rossi A, Costanzo A, Ciafrè S, Marinari B, Balsamo M, et al. Herpes simplex virus disrupts NF-kappaB regulation by blocking its recruitment on the IkappaBalpha promoter and directing the factor on viral genes. J Biol Chem. 2006;281:7110-7 pubmed
- Amici C, Belardo G, Rossi A, Santoro M. Activation of I kappa b kinase by herpes simplex virus type 1. A novel target for anti-herpetic therapy. J Biol Chem. 2001;276:28759-66 pubmed..The results identify IKK as a potential target for anti-herpetic drugs and suggest that cyclopentenone prostaglandins or their derivatives could be used in the treatment of HSV infection. ..
- Musiek E, Breeding R, Milne G, Zanoni G, Morrow J, McLaughlin B. Cyclopentenone isoprostanes are novel bioactive products of lipid oxidation which enhance neurodegeneration. J Neurochem. 2006;97:1301-13 pubmed..Together these findings suggest that cyclopentenone IsoPs may contribute to neuronal death caused by oxidative insults, and that their activity should perhaps be addressed when designing neuroprotective therapies. ..
- Guagnano M, Ferroni P, Santilli F, Paoletti V, Manigrasso M, Pescara L, et al. Determinants of platelet activation in hypertensives with microalbuminuria. Free Radic Biol Med. 2009;46:922-7 pubmed..We conclude that lipid peroxidation is a major determinant of persistent platelet activation in hypertensive patients with microalbuminuria. ..
- Chiang P, Kung F, Huang D, Li T, Fan J, Pan S, et al. Induction of Fas clustering and apoptosis by coral prostanoid in human hormone-resistant prostate cancer cells. Eur J Pharmacol. 2006;542:22-30 pubmed..Subsequently, the Fas event causes the activation and interaction of caspase-8/Bid/caspase-9 signaling cascades, and the activation of executor caspase-3. ..
- Gaquerel E, Herve C, Labriere C, Boyen C, Potin P, Salaun J. Evidence for oxylipin synthesis and induction of a new polyunsaturated fatty acid hydroxylase activity in Chondrus crispus in response to methyljasmonate. Biochim Biophys Acta. 2007;1771:565-75 pubmed..The enzyme specificity for the fatty acid recognition was not dependent of the position of double bonds but at least requires a methylene interrupted double bond 1,4-pentadiene motif involving the omega-7 carbon...
- Ishioka C, Kanamaru R, Sato T, Dei T, Konishi Y, Asamura M, et al. Inhibitory effects of prostaglandin A2 on c-myc expression and cell cycle progression in human leukemia cell line HL-60. Cancer Res. 1988;48:2813-8 pubmed..This recovery may be due to the loss of activity of PGA2 in culture medium. This study clearly showed that PGA2 treatment arrested HL-60 cells in the G0-G1 phase of the cell cycle and was associated with the reduction of c-myc mRNA. ..
- Valmsen K, Jarving I, Boeglin W, Varvas K, Koljak R, Pehk T, et al. The origin of 15R-prostaglandins in the Caribbean coral Plexaura homomalla: molecular cloning and expression of a novel cyclooxygenase. Proc Natl Acad Sci U S A. 2001;98:7700-5 pubmed..Evaluation of the structural differences of this 15R-COX isozyme should provide new insights into the substrate binding and stereospecificity of the dioxygenation reaction of arachidonic acid in the cyclooxygenase active site. ..
- Thurnher M, Putz T, Gander H, Rahm A, Bartsch G, Ramoner R. The cyclopentenone prostaglandin PGA2 costimulates the maturation of human dendritic cells. Exp Hematol. 2005;33:144-50 pubmed..This work also demonstrates that cyclopentenone PGs may have pro-inflammatory properties and that both PGE2 and PGA2 can contribute to the development of Th1-type immune responses. ..
- Ahn S, Kim H, Jeong S, Kim B, Rhim H, Shim J, et al. Sox-4 is a positive regulator of Hep3B and HepG2 cells' apoptosis induced by prostaglandin (PG)A(2) and delta(12)-PGJ(2). Exp Mol Med. 2002;34:243-9 pubmed..These results indicate that Sox-4 is involved in Hep3B and HepG2 cells apoptosis as an important apoptotic mediator. ..
- Tonge D, Chan K, Zhu N, Panjwani A, Arno M, Lynham S, et al. Enhancement of axonal regeneration by in vitro conditioning and its inhibition by cyclopentenone prostaglandins. J Cell Sci. 2008;121:2565-77 pubmed publisher..Consistent with this hypothesis, morpholino-induced suppression of Trx expression in dissociated DRG neurons was associated with reduced neurite outgrowth. ..
- Nencioni A, Lauber K, Grunebach F, Brugger W, Denzlinger C, Wesselborg S, et al. Cyclopentenone prostaglandins induce caspase activation and apoptosis in dendritic cells by a PPAR-gamma-independent mechanism: regulation by inflammatory and T cell-derived stimuli. Exp Hematol. 2002;30:1020-8 pubmed..Since these compounds are released during an inflammatory event and show anti-inflammatory properties, they may contribute to the downregulation of DC function through apoptotic cell death. ..
- Pavithra L, Rampalli S, Sinha S, Sreenath K, Pestell R, Chattopadhyay S. Stabilization of SMAR1 mRNA by PGA2 involves a stem loop structure in the 5' UTR. Nucleic Acids Res. 2007;35:6004-16 pubmed..Our studies provide a mechanistic insight into the regulation of tumor suppressor protein SMAR1 by a cancer therapeutic PGA2, that leads to repression of Cyclin D1 gene. ..
- Hitomi M, Shu J, Strom D, Hiebert S, Harter M, Stacey D. Prostaglandin A2 blocks the activation of G1 phase cyclin-dependent kinase without altering mitogen-activated protein kinase stimulation. J Biol Chem. 1996;271:9376-83 pubmed..PGA2 treatment elevated the p21Waf1/Cip1/Sdi1 protein expression level. These data indicate that PGA2 may arrest the cell cycle in G1 by interfering with the activation of G1 phase CDKs. ..
- Conti G, Portincasa P, Visalli S, Chezzi C. Inhibition by prostaglandin PGA1 on the multiplication of influenza virus is a dose-dependent effect. Virus Res. 2001;75:43-57 pubmed..These results suggest that HSP 70 could play a role in the antiviral activity of cyclopentenone PGA1 in LLC-MK2 cells. ..
- Joubert A, Panzer A, Bianchi P, Lottering M. The effects of prostaglandin A2 on cell growth, cell cycle status and apoptosis induction in HeLa and MCF-7 cells. Cancer Lett. 2003;191:203-9 pubmed..Cell cycle progression analysis of HeLa and MCF-7 cells, showed an increase in DNA content preceding the G(0)/G(1) peak after 48 h of exposure, which is indicative of apoptotic body formation. ..
- Kolberg A, Rosa T, Puhl M, Scola G, da Rocha Janner D, Maslinkiewicz A, et al. Low expression of MRP1/GS-X pump ATPase in lymphocytes of Walker 256 tumour-bearing rats is associated with cyclopentenone prostaglandin accumulation and cancer immunodeficiency. Cell Biochem Funct. 2006;24:23-39 pubmed..Clinical approaches for overexpressing MRP1/GS-X pump in lymphocytes could then play a role as a tool for the management of cancer therapeutics. ..
- Still K, Scutt A. Stimulation of CFU-f formation by prostaglandin E2 is mediated in part by its degradation product, prostaglandin A2. Prostaglandins Other Lipid Mediat. 2001;65:21-31 pubmed