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14-September-2008 18:02:48 - Prostaglandin E1 - Alprostadil E1 - Alprostadil I2 - Prostacyclin I2 - Prostacyclin A prostaglandin is any member of a group of lipid compounds that are derived enzymatically from fatty acids and have important functions in the animal body. Every prostaglandin contains 20 carbon atoms, including a 5-carbon ring. They are mediators and have a variety of strong physiological effects; although they are technically hormones, they are rarely classified as such. The prostaglandins together with the thromboxanes and prostacyclins form the prostanoid class of fatty acid derivatives; the prostanoid class is a subclass of eicosanoids. Contents 1 History and name 2 Biochemistry 2.1 Biosynthesis 2.2 Release of prostaglandins from the cell 2.2.1 Cyclooxygenases 2.2.2 Prostaglandin E synthase 2.2.3 Other terminal prostaglandin synthases 3 Function 4 Types 5 Role in pharmacology 5.1 Inhibition 5.2 Clinical uses 6 References 7 External links History and name The name prostaglandin derives from the prostate gland. When prostaglandin was first isolated from seminal fluid in 1935 by the Swedish physiologist Ulf von Euler,1 and independently by M.W. Goldblatt,2 it was believed to be part of the prostatic secretions in actuality prostaglandins are produced by the seminal vesicles; it was later shown that many other tissues secrete prostaglandins for various functions. In 1971, it was determined that aspirin-like drugs could inhibit the synthesis of prostaglandins. The biochemists Sune K. Bergström, Bengt I. Samuelsson and John R. Vane jointly received the 1982 Nobel Prize in Physiology or Medicine for their research on prostaglandins. Biochemistry Biosynthesis Biosynthesis of eicosanoids. series-2 Biosynthesis of eicosanoids. series-2 Prostaglandins are found in virtually all tissues and organs. These are autocrine and paracrine lipid mediators that act upon platelet, endothelium, uterine and mast cells, among others. They are synthesized in the cell from the essential fatty acids3 EFAs. An intermediate is created by phospholipase-A2, then passed into one of either the cyclooxygenase pathway or the lipoxygenase pathway to form either prostaglandin and thromboxane or leukotriene. The cyclooxygenase pathway produces thromboxane, prostacyclin and prostaglandin D, E and F. The lipoxygenase pathway is active in leukocytes and in macrophages and synthesizes leukotrienes. Name EFA Type Series Gamma-linolenic acid GLA via DGLA ω-6 series-1 Arachidonic acid AA ω-6 series-2 Eicosapentaenoic acid EPA ω-3 series-3 Release of prostaglandins from the cell Prostaglandins were originally believed to leave the cells via passive diffusion because of their high lipophilicity. The discovery of the prostaglandin transporter PGT, SLCO2A1, which mediates the cellular uptake of prostaglandin, demonstrated that diffusion cannot explain the penetration of prostaglandin through the cellular membrane. The release of prostaglandin has now also been shown to be mediated by a specific transporter, namely the multidrug resistance protein 4 MRP4, ABCC4, a member of the ATP-binding cassette transporter superfamily. Whether MRP4 is the only transporter releasing prostaglandins from the cells is still unclear. Cyclooxygenases Prostaglandins are produced following the sequential oxidation of AA, DGLA or EPA by cyclooxygenases COX-1 and COX-2 and terminal prostaglandin synthases. The classic dogma is as follows: COX-1 is responsible for the baseline levels of prostaglandins. COX-2 produces prostaglandins through stimulation. However, while COX-1 and COX-2 are both located in the blood vessels, stomach and the kidneys, prostaglandin levels are increased by COX-2 in scenarios of inflammation. A third form of COX, termed COX-3, has been identified, but its exact function is still being determined. Prostaglandin E synthase Prostaglandin E2 PGE2 is generated from the action of prostaglandin E synthases on prostaglandin H2 PGH2. Several prostaglandin E synthases have been identified. To date, microsomal prostaglandin E synthase-1 emerges as a key enzyme in the formation of PGE2. Other terminal prostaglandin synthases Terminal prostaglandin synthases have been identified that are responsible for the formation of other prostaglandins. For example, hematopoietic and lipocalin prostaglandin D synthases hPGDS and lPGDS are responsible for the formation of PGD2 from PGH2. Similarly, prostacyclin PGI2 synthase PGIS converts PGH2 into PGI2. A thromboxane synthase TxAS has also been idenfitied. Prostaglandin F synthase PGFS catalyzes the formation of 9α,11β-PGF2α,β from PGD2 and PGF2α from PGH2 in the presence of NADPH. This enzyme has recently been crystallyzed in complex with PGD24 and bimatoprost5 a synthetic analogue of PGF2α. Function There are currently nine known prostaglandin receptors on various cell types. Prostaglandins ligate a subfamily of cell surface seven-transmembrane receptors, G-protein-coupled receptors. These receptors are termed DP1-2, EP1-4, FP, IP, and TP, corresponding to the receptor that ligates the corresponding prostaglandin e.g., DP1-2 receptors bind to PGD2. These varied receptors mean that Prostaglandins thus act on a variety of cells, and have a wide variety of actions: cause constriction or dilation in vascular smooth muscle cells cause aggregation or disaggregation of platelets sensitize spinal neurons to pain decrease intraocular pressure regulate inflammatory mediation regulate calcium movement control hormone regulation control cell growth Prostaglandins are potent but have a short half-life before being inactivated and excreted. Therefore, they exert only a paracrine locally active or autocrine acting on the same cell from which it is synthesized function. Types Following is a comparison of the prostaglandin types Prostaglandin I2 PGI2, Prostaglandin E2 PGE2 and Prostaglandin F2α PGF2α. Type Receptor Function PGI2 IP vasodilatation inhibit platelet aggregation bronchodilatation PGE2 EP1 bronchoconstriction GI tract smooth muscle contraction EP2 bronchodilatation GI tract smooth muscle relaxation vasodilatation EP3 ↓ gastric acid secretion ↑ gastric mucus secretion uterus contraction when pregnant GI tract smooth muscle contraction lipolysis inhibition ↑ autonomic neurotransmitters 6 Unspecified hyperalgesia6 pyrogenic PGF2α FP uterus contraction bronchoconstriction Role in pharmacology Inhibition See also: Prostaglandin antagonist and Mechanism of action of aspirin Examples of prostaglandin antagonists are: NSAIDs inhibit cyclooxygenase Corticosteroids inhibit phospholipase A2 production COX-2 selective inhibitors or coxibs However, both NSAIDs and Coxibs can raise the risk of myocardial infarction. Clinical uses Synthetic prostaglandins are used: To induce childbirth parturition or abortion PGE2 or PGF2, with or without mifepristone, a progesterone antagonist; To prevent closure of patent ductus arteriosus in newborns with particular cyanotic heart defects PGE1 To prevent and treat peptic ulcers PGE As a vasodilator in severe Raynaud's phenomenon or ischemia of a limb In pulmonary hypertension In treatment of glaucoma as in bimatoprost ophthalmic solution, a synthetic prostamide analog with ocular hypotensive activity To treat erectile dysfunction or in penile rehabilitation following surgery PGE1 as alprostadil.7 To treat egg binding in small birds8 References ^ Von Euler US. Ãœber die spezifische blutdrucksenkende Substanz des menschlichen Prostata- und Samenblasensekrets. Klin Wochenschr 1935;14:1182-1183. ^ Goldblatt MW. Properties of human seminal plasma. J Physiol 1935;84:208-18. PMID 16994667. ^ Dorlands Medical Dictionary 1 URL reference on 10/23/05. ^ Komoto J, Yamada T, Watanabe K, Takusagawa F 2004. Crystal structure of human prostaglandin F synthase AKR1C3. Biochemistry 43 8: 2188-98. doi:10.1021/bi036046x. PMID 14979715. ^ Komoto J, Yamada T, Watanabe K, Woodward D, Takusagawa F 2006. Prostaglandin F2alpha formation from prostaglandin H2 by prostaglandin F synthase PGFS: crystal structure of PGFS containing bimatoprost. Biochemistry 45 7: 1987-96. doi:10.1021/bi051861t. PMID 16475787. ^ a b Pharmacology, Rang, Dale, Ritter Moore, ISBN 0443071454, 5:th ed., Churchill Livingstone 2003 Page 234 ^ Medscape Early Penile Rehabilitation Helps Reduce Later Intractable ED 2 URL reference on 10/23/05. ^ LaBonde, MS, DVM, Jerry. Avian Reproductive and Pediatric Disorders. Michigan Veterinary Medical Association. Retrieved on 2008-01-26. External links MeSH Prostaglandins v d e Endocrine system: hormones/endocrine glands Peptide hormones, Steroid hormones Hypothalamic-pituitary Hypothalamus: TRH, CRH , GnRH, GHRH, somatostatin, dopamine - Posterior pituitary: vasopressin, oxytocin - Anterior pituitary: α FSH, LH, TSH, GH, prolactin, POMC ACTH, MSH, endorphins, lipotropin Adrenal axis Adrenal medulla: epinephrine, norepinephrine - Adrenal cortex: aldosterone, cortisol, DHEA Thyroid axis Thyroid: thyroid hormone T3 and T4 - calcitonin - Parathyroid: PTH Gonadal axis Testis: testosterone, AMH, inhibin - Ovary: estradiol, progesterone, inhibin/activin, relaxin pregnancy Other end. glands Pancreas: glucagon, insulin, somatostatin - Pineal gland: melatonin Non-end. glands Placenta: hCG, HPL, estrogen, progesterone - Kidney: renin, EPO, calcitriol, prostaglandin - Heart atrium: ANP - Stomach: gastrin, ghrelin - Duodenum: CCK, GIP, secretin, motilin, VIP - Ileum: enteroglucagon - Adipose tissue: leptin, adiponectin, resistin - Thymus: Thymosin - Thymopoietin - Thymulin - Skeleton: Osteocalcin - Liver/other: Insulin-like growth factor IGF-1, IGF-2 Target-derived NGF, BDNF, NT-3 v d e Autacoids, unsaturated fatty acids: Eicosanoids Prostanoids Prostaglandins - Thromboxanes A2, B2 Leukotrienes A4 - B4 - Slow reacting substance of anaphylaxis C4, D4, E4 Other Arachidonic acids - Eicosapentaenoic acid - Lipoxins v d e Eicosanoids: prostaglandins Endogenous/series 2 D2 - E2 Dinoprostone - F2 Dinoprost - H2 - I2 Prostacyclin Prostaglandin analogues E: Alprostadil - Enprostil - Misoprostol F: Bimatoprost - Carboprost - Latanoprost - Travoprost I: Beraprost - Epoprostenol - Iloprost - Treprostinil Retrieved from http://en..org/wiki/Prostaglandin Categories: Prostaglandins Views Article Discussion this page History Personal tools Log in / create account Navigation Main page Contents Featured content Current events Random article Search Go Search Interaction Community portal Recent changes Contact Donate to Help Toolbox What links here Related changes Upload file Special pages Printable version Permanent link Cite this page Languages Deutsch Español Français Italiano עברית Lietuvių Nederlands 日本語 ‪Norsk bokmÃ¥l‬ ‪Norsk nynorsk‬ Polski Português РуÑ?Ñ?кий SlovenÅ¡Ä?ina Suomi Svenska Tiếng Việt Türkçe УкраїнÑ?ька ä¸æ–‡ This page was last modified on 26 August 2008, at 19:5
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