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Chemical Compound Review

Ageflex PGE     2-(phenoxymethyl)oxirane

Synonyms: NSC-635, CCRIS 738, ARONIS24212, NSC635, LS-668, ...
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Disease relevance of PGE

  • Synthesis of PGE preceded and was necessary for the bone resorption caused by the lymphokine preparation [1].
  • Our earlier work revealed that PGE-mediated inactivation of NK cells in tumor-bearing mice by host macrophages promoted spontaneous lung metastasis that could be prevented or ameliorated by chronic indomethacin therapy [2].
  • In the 28 patients with benign gastric ulcer the ulcer edge contained 2.33 (0.48-7.67) ng PGE/mg protein which was more than the antrum with 1.06 (0.30-4.17) or the body with 0.97 (0.20-7.67), p less than 0.01 respectively [3].
  • Accumulation of PGE 2 in 24-hr cultures of rectal mucosa specimens obtained from patients with ulcerative colitis was 112% higher than that observed in cultures from control subjects [4].
  • PGE synthase was expressed in Escherichia coli, and both cytosolic and membrane fractions were prepared [5].

Psychiatry related information on PGE

  • Previous studies demonstrated that cultured smooth muscle cells from corpus cavernosum display significantly altered K+ channel function, PGE-induced cAMP accumulation, and endothelin-1 induced Ca2+ mobilization that are consistent with the pathophysiology of erectile dysfunction [6].

High impact information on PGE

  • This concentration of PGE produced a similar level of cAMP to that found with PDGF, suggesting that the PDGF-induced increase in cAMP is mediated by E-type prostaglandins released in the culture medium [7].
  • Here we show that although Langerhans cells express all four PGE receptor subtypes, their migration to regional lymph nodes was decreased only in EP4-deficient (Ptger4-/-) mice and in wild-type mice treated with an EP4 antagonist [8].
  • Freed NF-kappaB dimers translocate to the nucleus and induce target genes, including the one for cyclo-oxygenase 2 (COX2), which catalyses the synthesis of pro-inflammatory prostaglandins, in particular PGE [9].
  • PGE-like activity was first demonstrated in macrophage-rich peritoneal exudate cell preparations from guinea pigs; later, other kinds of PGs were also found to be released by mouse peritoneal macrophages in response to inflammatory stimuli [10].
  • Human synovium releases a factor which stimulates chondrocyte production of PGE and plasminogen activator [11].

Chemical compound and disease context of PGE


Biological context of PGE

  • Calcium-dependent stimulation of platelet aggregation by PGE [17].
  • The 50% inhibitory concentration is approximately 10(-7) M, and this is reduced to approximately 10(-8) M when endogenous PGE production is blocked [18].
  • A detailed examination of PGE synthesis indicated the PGE levels rise in parallel with phagocytosis during a continuous exposure of macrophages to zymosan [19].
  • Effects of interferons (IFN) and E-series prostaglandins (PGE) were evaluated on subpopulations of human peripheral blood mononuclear lymphocytes (PBL) that mediate natural killer (NK) activity, antibody-dependent cell-mediated cytotoxicity (ADCC), or lectin-induced cellular cytotoxicity (LICC) [20].
  • RESULTS: Application of PGE 2 to ischemia-injured ileal mucosa stimulated increases in Isc, an indicator of Cl - secretion, that was followed by marked increases in TER, an indicator of barrier function recovery [21].

Anatomical context of PGE

  • Small amounts of PGE inhibit mitogen-induced [3H]thymidine incorporation in human peripheral lymphocytes [18].
  • PGE inhibits PHA- and Con A-stimulated cultures much better than PWM cultures, suggesting a differential effect of PGE on T-cell vs. B-cell function [18].
  • PGE is produced endogenously in PHA cultures by glass adherent suppressor cells [18].
  • In this study, we have established a primary culture system of human gastric fibroblasts and clearly demonstrated that PGs strongly induce the expression of hepatocyte growth factor (HGF) in the fibroblasts, which is mediated by PGE specific receptor, EP2 or EP4 [22].
  • In vitro studies revealed that although PGE 2 induced Cl - secretion via at least 3 distinct secretory pathways, recovery of barrier function was initiated by Cl - secretion via ClC-2 Cl - channels co-expressed with occludin and localized to tight junctions within restituting epithelium [21].

Associations of PGE with other chemical compounds

  • CONCLUSIONS: PGE stimulates HCO3- secretion via different EP-receptor subtypes in the stomach and duodenum: in the stomach, EP1 receptors are linked to Ca2+; in the duodenum, EP3 receptors are coupled with both adenosine 3', 5'-cyclic monophosphate and Ca2+ [23].
  • We conclude that myoblasts possess at least three, independent pathways, each of which can initiate myoblast fusion and that the PGE-activated pathway and the acetylcholine receptor-activated pathway act synergistically [24].
  • By infusing PGE2 to mice lacking each of four PGE receptor (EP) subtypes, we have identified EP4 as the receptor that mediates bone formation in response to this agent [25].
  • The increase in contractility in response to overload in the first group was paralleled by an increase in the content of PGE and PGF 2 alpha in the left ventricle, whereas, in rabbits with heart failure, the prostaglandin level did not rise above that of the control hearts [26].
  • Following indomethacin (5 mg/kg), the same dose of BK produced a 151 +/- 18% increase in RBF (P less than 0.001 compared to the preindomethacin increase) and the concentration of "PGE" remained largely below the threshold of sensitivity of the bioassay system [27].

Gene context of PGE

  • The up-regulation of COX-2 by IL-1beta was accompanied by specific up-regulation of PGI synthase and PGE synthase, but not TX synthase [28].
  • In addition, TNF interacted in a synergistic fashion with both IL 1 peptides to augment fibroblast PGE elaboration further [29].
  • The apparent PGI(2) and PGE(2) linkage with COX-2 activity may be explained by a temporal increase in total COX activity, together with selective up-regulation of PGI synthase and PGE synthase, and different kinetic characteristics of the terminal synthases [28].
  • Cyclooxygenase-2 (COX-2) and microsomal PGE synthase levels markedly increased upon exposure of RPM to LPS, with the most rapid increases in protein expression occurring 2-6 h after addition of the stimulus [30].
  • Administration of 6 mg/kg LPS to rats i.p. resulted 6 h later in induction of NOS2 and the membrane-associated PGE synthase (mPGES) expression, and decreased constitutive COX (COX-1) expression [31].

Analytical, diagnostic and therapeutic context of PGE

  • Addition of PDGF increased (at least 25-fold) the production of E-type prostaglandins; PGE reached a concentration in the medium of 26 ng/ml 1 hr after treatment with human PDGF [7].
  • Also, 20-mM graduated reductions in [NaCl]L between 80 and 0 mM caused step-by-step increases in HEK/EP1 [Ca2+]i. Low-salt diet greatly increased the expression of both COX-2 and microsome-associated PGE synthase (mPGES) in the MD [32].
  • The prostaglandins (PGs) released from the heart have generally been characterized as resembling PGE by bioassay techniques [33].
  • Here, we identify mPGES1 as the PGE synthase that contributes to the pathogenesis of collagen-induced arthritis, a disease model of human rheumatoid arthritis [34].
  • If A549 cells were grown in the presence of IL-1beta, a significant induction of the PGE synthase was observed by Western blot analysis [5].


  1. Lymphokine-mediated bone resorption requires endogenous prostaglandin synthesis. Bockman, R.S., Repo, M.A. J. Exp. Med. (1981) [Pubmed]
  2. Amelioration of B16F10 melanoma lung metastasis in mice by a combination therapy with indomethacin and interleukin 2. Parhar, R.S., Lala, P.K. J. Exp. Med. (1987) [Pubmed]
  3. Gastric mucosal prostaglandin E levels in patients with gastric ulcer disease and carcinoma. Wright, J.P., Young, G.O., Klaff, L.J., Weers, L.A., Price, S.K., Marks, I.N. Gastroenterology (1982) [Pubmed]
  4. Role of prostaglandins in ulcerative colitis. Enhanced production during active disease and inhibition by sulfasalazine. Sharon, P., Ligumsky, M., Rachmilewitz, D., Zor, U. Gastroenterology (1978) [Pubmed]
  5. Identification of human prostaglandin E synthase: a microsomal, glutathione-dependent, inducible enzyme, constituting a potential novel drug target. Jakobsson, P.J., Thorén, S., Morgenstern, R., Samuelsson, B. Proc. Natl. Acad. Sci. U.S.A. (1999) [Pubmed]
  6. Identification of a down-regulated mRNA transcript in corpus cavernosum from diabetic patients with erectile dysfunction. Autieri, M.V., Melman, A., Christ, G.J. Int. J. Impot. Res. (1996) [Pubmed]
  7. Platelet-derived growth factor elicits cyclic AMP accumulation in Swiss 3T3 cells: role of prostaglandin production. Rozengurt, E., Stroobant, P., Waterfield, M.D., Deuel, T.F., Keehan, M. Cell (1983) [Pubmed]
  8. Prostaglandin E2-EP4 signaling initiates skin immune responses by promoting migration and maturation of Langerhans cells. Kabashima, K., Sakata, D., Nagamachi, M., Miyachi, Y., Inaba, K., Narumiya, S. Nat. Med. (2003) [Pubmed]
  9. Anti-inflammatory cyclopentenone prostaglandins are direct inhibitors of IkappaB kinase. Rossi, A., Kapahi, P., Natoli, G., Takahashi, T., Chen, Y., Karin, M., Santoro, M.G. Nature (2000) [Pubmed]
  10. Prostaglandin synthesis in different phases of phagocytosis in lung macrophages. Hsueh, W., Gonzalez-Crussi, F., Hanneman, E. Nature (1980) [Pubmed]
  11. Human synovium releases a factor which stimulates chondrocyte production of PGE and plasminogen activator. Meats, J.E., McGuire, M.B., Russell, R.G. Nature (1980) [Pubmed]
  12. Developmental aspects of the renal response to hypoxemia in the lamb fetus. Robillard, J.E., Weitzman, R.E., Burmeister, L., Smith, F.G. Circ. Res. (1981) [Pubmed]
  13. Regulation of agonist-induced prostaglandin E1 versus prostaglandin E2 production. A mass analysis. Rubin, D., Laposata, M. J. Biol. Chem. (1991) [Pubmed]
  14. A prostaglandin E receptor coupled to a pertussis toxin-sensitive guanine nucleotide regulatory protein in rabbit cortical collecting tubule cells. Sonnenburg, W.K., Zhu, J.H., Smith, W.L. J. Biol. Chem. (1990) [Pubmed]
  15. Decreased adrenergic responses in lymphocytes and granulocytes in atopic eczema. Busse, W.W., Lee, T.P. J. Allergy Clin. Immunol. (1976) [Pubmed]
  16. Stimulated gastric prostaglandin output, and the effect of inhibition of prostaglandin synthetase, in the conscious cat. Baker, R., Jaffe, B.M., Shaw, B., Venables, C.W. J. Physiol. (Lond.) (1981) [Pubmed]
  17. Calcium-dependent stimulation of platelet aggregation by PGE. MacIntyre, D.E., Gordon, J.L. Nature (1975) [Pubmed]
  18. Suppression of human T-cell mitogenesis by prostaglandin. Existence of a prostaglandin-producing suppressor cell. Goodwin, J.S., Bankhurst, A.D., Messner, R.P. J. Exp. Med. (1977) [Pubmed]
  19. Regulation of arachidonic acid metabolites in macrophages. Scott, W.A., Zrike, J.M., Hamill, A.L., Kempe, J., Cohn, Z.A. J. Exp. Med. (1980) [Pubmed]
  20. Interferon and prostaglandins: effects on human natural and lectin-induced cytotoxicity. Lang, N.P., Ortaldo, J.R., Bonnard, G.D., Herberman, R.B. J. Natl. Cancer Inst. (1982) [Pubmed]
  21. ClC-2 chloride secretion mediates prostaglandin-induced recovery of barrier function in ischemia-injured porcine ileum. Moeser, A.J., Haskell, M.M., Shifflett, D.E., Little, D., Schultz, B.D., Blikslager, A.T. Gastroenterology (2004) [Pubmed]
  22. Hepatocyte growth factor as a key to modulate anti-ulcer action of prostaglandins in stomach. Takahashi, M., Ota, S., Hata, Y., Mikami, Y., Azuma, N., Nakamura, T., Terano, A., Omata, M. J. Clin. Invest. (1996) [Pubmed]
  23. Roles of prostaglandin E-receptor subtypes in gastric and duodenal bicarbonate secretion in rats. Takeuchi, K., Yagi, K., Kato, S., Ukawa, H. Gastroenterology (1997) [Pubmed]
  24. The control of chick myoblast fusion by ion channels operated by prostaglandins and acetylcholine. Entwistle, A., Zalin, R.J., Bevan, S., Warner, A.E. J. Cell Biol. (1988) [Pubmed]
  25. Stimulation of bone formation and prevention of bone loss by prostaglandin E EP4 receptor activation. Yoshida, K., Oida, H., Kobayashi, T., Maruyama, T., Tanaka, M., Katayama, T., Yamaguchi, K., Segi, E., Tsuboyama, T., Matsushita, M., Ito, K., Ito, Y., Sugimoto, Y., Ushikubi, F., Ohuchida, S., Kondo, K., Nakamura, T., Narumiya, S. Proc. Natl. Acad. Sci. U.S.A. (2002) [Pubmed]
  26. Heart adaptation to acute pressure overload: an involvement of endogenous prostaglandins. Chazov, E.I., Pomoinetsky, V.D., Geling, N.G., Orlova, T.R., Nekrasova, A.A., Smirnov, V.N. Circ. Res. (1979) [Pubmed]
  27. Inhibition of prostaglandin synthesis by indomethacin augments the renal vasodilator response to bradykinin in the anesthetized dog. Lonigro, A.J., Hagemann, M.H., Stephenson, A.H., Fry, C.L. Circ. Res. (1978) [Pubmed]
  28. Roles of cyclooxygenase (COX)-1 and COX-2 in prostanoid production by human endothelial cells: selective up-regulation of prostacyclin synthesis by COX-2. Caughey, G.E., Cleland, L.G., Penglis, P.S., Gamble, J.R., James, M.J. J. Immunol. (2001) [Pubmed]
  29. Synergistic stimulation of fibroblast prostaglandin production by recombinant interleukin 1 and tumor necrosis factor. Elias, J.A., Gustilo, K., Baeder, W., Freundlich, B. J. Immunol. (1987) [Pubmed]
  30. Cyclooxygenase-1-dependent prostaglandin synthesis modulates tumor necrosis factor-alpha secretion in lipopolysaccharide-challenged murine resident peritoneal macrophages. Rouzer, C.A., Kingsley, P.J., Wang, H., Zhang, H., Morrow, J.D., Dey, S.K., Marnett, L.J. J. Biol. Chem. (2004) [Pubmed]
  31. Lipopolysaccharide-induced increase of prostaglandin E(2) is mediated by inducible nitric oxide synthase activation of the constitutive cyclooxygenase and induction of membrane-associated prostaglandin E synthase. Devaux, Y., Seguin, C., Grosjean, S., de Talancé, N., Camaeti, V., Burlet, A., Zannad, F., Meistelman, C., Mertes, P.M., Longrois, D. J. Immunol. (2001) [Pubmed]
  32. Luminal NaCl delivery regulates basolateral PGE2 release from macula densa cells. Peti-Peterdi, J., Komlosi, P., Fuson, A.L., Guan, Y., Schneider, A., Qi, Z., Redha, R., Rosivall, L., Breyer, M.D., Bell, P.D. J. Clin. Invest. (2003) [Pubmed]
  33. A novel prostaglandin is the major product of arachidonic acid metabolism in rabbit heart. Isakson, P.C., Raz, A., Denny, S.E., Pure, E., Needleman, P. Proc. Natl. Acad. Sci. U.S.A. (1977) [Pubmed]
  34. Impaired inflammatory and pain responses in mice lacking an inducible prostaglandin E synthase. Trebino, C.E., Stock, J.L., Gibbons, C.P., Naiman, B.M., Wachtmann, T.S., Umland, J.P., Pandher, K., Lapointe, J.M., Saha, S., Roach, M.L., Carter, D., Thomas, N.A., Durtschi, B.A., McNeish, J.D., Hambor, J.E., Jakobsson, P.J., Carty, T.J., Perez, J.R., Audoly, L.P. Proc. Natl. Acad. Sci. U.S.A. (2003) [Pubmed]
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