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Prostaglandin

January 20, 2023

The prostaglandins (PG) are a group of physiologically active lipid compounds called eicosanoids[1] having diverse hormone-like effects in animals. Prostaglandins have been found in almost every tissue in humans and other animals. They are derived enzymatically from the fatty acid arachidonic acid.[2] Every prostaglandin contains 20 carbon atoms, including a 5-carbon ring. They are a subclass of eicosanoids and of the prostanoid class of fatty acid derivatives.

The structural differences between prostaglandins account for their different biological activities. A given prostaglandin may have different and even opposite effects in different tissues in some cases. The ability of the same prostaglandin to stimulate a reaction in one tissue and inhibit the same reaction in another tissue is determined by the type of receptor to which the prostaglandin binds. They act as autocrine or paracrine factors with their target cells present in the immediate vicinity of the site of their secretion. Prostaglandins differ from endocrine hormones in that they are not produced at a specific site but in many places throughout the human body.

Prostaglandins are powerful, locally-acting vasodilators and inhibit the aggregation of blood platelets. Through their role in vasodilation, prostaglandins are also involved in inflammation. They are synthesized in the walls of blood vessels and serve the physiological function of preventing needless clot formation, as well as regulating the contraction of smooth muscle tissue.[3] Conversely, thromboxanes (produced by platelet cells) are vasoconstrictors and facilitate platelet aggregation. Their name comes from their role in clot formation (thrombosis).

Specific prostaglandins are named with a letter (which indicates the type of ring structure) followed by a number (which indicates the number of double bonds in the hydrocarbon structure). For example, prostaglandin E1 is abbreviated PGE1, and prostaglandin I2 is abbreviated PGI2.

History and name

Systematic studies of prostaglandins began in 1930, when Kurzrock and Lieb found that human seminal fluid caused either stimulation or relaxation of strips of isolated human uterus. They noted the curious finding that uteri from patients who had gone through successful pregnancies responded to the fluid with relaxation, while uteri from sterile women responded with contraction upon addition of this seminal fluid.[4] The name prostaglandin derives from the prostate gland, chosen when prostaglandin was first isolated from seminal fluid in 1935 by the Swedish physiologist Ulf von Euler,[5] and independently by the Irish-English physiologist Maurice Walter Goldblatt (1895–1967).[6][7][8] Prostaglandins were believed to be part of the prostatic secretions, and eventually were discovered to be produced by the seminal vesicles. Later, it was shown that many other tissues secrete prostaglandins and that they perform a variety of functions. The first total syntheses of prostaglandin F2α and prostaglandin E2 were reported by E. J. Corey in 1969,[9] an achievement for which he was awarded the Japan Prize in 1989.

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

Prostaglandins are found in most tissues and organs. They are produced by almost all nucleated cells. They are autocrine and paracrine lipid mediators that act upon platelets, endothelium, uterine and mast cells. They are synthesized in the cell from the fatty acid arachidonic acid.[2]

Arachidonic acid is created from diacylglycerol via phospholipase-A2, then brought to either the cyclooxygenase pathway or the lipoxygenase pathway. The cyclooxygenase pathway produces thromboxane, prostacyclin and prostaglandin D, E and F. Alternatively, the lipoxygenase enzyme pathway is active in leukocytes and in macrophages and synthesizes leukotrienes.

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 alone 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 oxygenation of arachidonic acid, 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 and growth.

Prostaglandin E synthase

Prostaglandin E2 (PGE2) — the most abundant prostaglandin[10] — is generated from the action of prostaglandin E synthases on prostaglandin H2 (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 identified. 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 crystallized in complex with PGD2[11] and bimatoprost[12] (a synthetic analogue of PGF2α).

Functions

There are currently ten known prostaglandin receptors on various cell types. Prostaglandins ligate a sub-family of cell surface seven-transmembrane receptors, G-protein-coupled receptors. These receptors are termed DP1-2, EP1-4, FP, IP1-2, and TP, corresponding to the receptor that ligates the corresponding prostaglandin (e.g., DP1-2 receptors bind to PGD2).

The diversity of receptors means that prostaglandins act on an array of cells and have a wide variety of effects such as:

Types

The following is a comparison of different types of prostaglandin, including prostaglandin I2 (prostacyclin; PGI2), prostaglandin D2 (PGD2), prostaglandin E2 (PGE2), and prostaglandin F2α (PGF2α).[18]

Type Receptor Receptor type Function
PGI2 IP Gs
PGD2 PTGDR (DP1) and CRTH2 (DP2) GPCR
  • produced by mast cells; recruits Th2 cells, eosinophils, and basophils
  • In mammalian organs, large amounts of PGD2 are found only in the brain and in mast cells
  • Critical to development of allergic diseases such as asthma
PGE2 EP1 Gq
EP2 Gs
EP3 Gi
Unspecified
PGF2α FP Gq

Role in pharmacology

Inhibition

See also: Prostaglandin antagonist and Mechanism of action of aspirin

Examples of prostaglandin antagonists are:

Clinical uses

Synthetic prostaglandins are used:

Synthesis

The original synthesis of prostaglandins F2α and E2 is shown below. It involves a Diels–Alder reaction which establishes the relative stereochemistry of three contiguous stereocenters on the prostaglandin cyclopentane core.[28]

 

Prostaglandin stimulants

Cold exposure and IUDs may increase prostaglandin production.[29]

See also

  • Prostamides, a chemically related class of physiologically active substances

References

  1. ^ "Eicosanoid Synthesis and Metabolism: Prostaglandins, Thromboxanes, Leukotrienes, Lipoxins". themedicalbiochemistrypage.org. Retrieved 2018-09-21.
  2. ^ a b Ricciotti E, FitzGerald GA (May 2011). "Prostaglandins and inflammation". Arteriosclerosis, Thrombosis, and Vascular Biology. 31 (5): 986–1000. doi:10.1161/ATVBAHA.110.207449. PMC 3081099. PMID 21508345.
  3. ^ Nelson RF (2005). An introduction to behavioral endocrinology (3rd ed.). Sunderland, Mass: Sinauer Associates. p. 100. ISBN 0-87893-617-3.
  4. ^ Kurzrock, Raphael; Lieb, Charles C. (1930). "Biochemical Studies of Human Semen. II. The Action of Semen on the Human Uterus". Proceedings of the Society for Experimental Biology and Medicine. 28 (3): 268. doi:10.3181/00379727-28-5265. S2CID 85374636.
  5. ^ Von Euler US (1935). "Über die spezifische blutdrucksenkende Substanz des menschlichen Prostata- und Samenblasensekrets" [On the specific blood-pressure-reducing substance of human prostate and seminal vesicle secretions]. Wiener Klinische Wochenschrift. 14 (33): 1182–1183. doi:10.1007/BF01778029. S2CID 38622866.
  6. ^ Goldblatt MW (May 1935). "Properties of human seminal plasma". The Journal of Physiology. 84 (2): 208–18. doi:10.1113/jphysiol.1935.sp003269. PMC 1394818. PMID 16994667.
  7. ^ Rubinstein, William D.; Jolles, Michael A.; Rubinstein, Hillary L., eds. (2011). "Goldblatt, Maurice Walter". The Palgrave Dictionary of Anglo-Jewish History. Basingstoke, England: Palgrave Macmillan. p. 333. ISBN 9780230304666.
  8. ^ R.S.F.S. (3 June 1967). "Obituary Notices: M. W. Goldblatt". British Medical Journal. 2 (5552): 644. doi:10.1136/bmj.2.5552.644. S2CID 220151673.
  9. ^ Nicolaou KC, Sorensen EJ (1996). Classics in Total Synthesis. Weinheim, Germany: VCH. p. 65. ISBN 3-527-29284-5.
  10. ^ Ke J, Yang Y, Che Q, Jiang F, Wang H, Chen Z, Zhu M, Tong H, Zhang H, Yan X, Wang X, Wang F, Liu Y, Dai C, Wan X (September 2016). "Prostaglandin E2 (PGE2) promotes proliferation and invasion by enhancing SUMO-1 activity via EP4 receptor in endometrial cancer". Tumour Biology. 37 (9): 12203–12211. doi:10.1007/s13277-016-5087-x. PMC 5080328. PMID 27230680. Prostaglandin E2 (PGE2) is the most abundant prostanoid in the human body
  11. ^ Komoto J, Yamada T, Watanabe K, Takusagawa F (March 2004). "Crystal structure of human prostaglandin F synthase (AKR1C3)". Biochemistry. 43 (8): 2188–98. doi:10.1021/bi036046x. PMID 14979715.
  12. ^ Komoto J, Yamada T, Watanabe K, Woodward DF, Takusagawa F (February 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.
  13. ^ "Hormonal and pheromonal control of spawning in goldfish (PDF Download Available)". ResearchGate. Retrieved 2017-02-04.
  14. ^ Lethaby A, Duckitt K, Farquhar C (January 2013). "Non-steroidal anti-inflammatory drugs for heavy menstrual bleeding". The Cochrane Database of Systematic Reviews (1): CD000400. doi:10.1002/14651858.CD000400.pub3. PMID 23440779.
  15. ^ Wright, Jason and Solange Wyatt. The Washington Manual Obstetrics and Gynecology Survival Guide. Lippincott Williams & Wilkins, 2003. ISBN 0-7817-4363-X[page needed]
  16. ^ Harel Z (December 2006). "Dysmenorrhea in adolescents and young adults: etiology and management". Journal of Pediatric and Adolescent Gynecology. 19 (6): 363–71. doi:10.1016/j.jpag.2006.09.001. PMID 17174824.
  17. ^ Bofill Rodriguez, M; Lethaby, A; Farquhar, C (19 September 2019). "Non-steroidal anti-inflammatory drugs for heavy menstrual bleeding". The Cochrane Database of Systematic Reviews. 2019 (9): CD000400. doi:10.1002/14651858.CD000400.pub4. PMC 6751587. PMID 31535715.
  18. ^ Moreno JJ (February 2017). "Eicosanoid receptors: Targets for the treatment of disrupted intestinal epithelial homeostasis". European Journal of Pharmacology. 796: 7–19. doi:10.1016/j.ejphar.2016.12.004. PMID 27940058. S2CID 1513449.
  19. ^ a b Rang HP (2003). Pharmacology (5th ed.). Edinburgh: Churchill Livingstone. p. 234. ISBN 0-443-07145-4.
  20. ^ Fabre JE, Nguyen M, Athirakul K, Coggins K, McNeish JD, Austin S, Parise LK, FitzGerald GA, Coffman TM, Koller BH (March 2001). "Activation of the murine EP3 receptor for PGE2 inhibits cAMP production and promotes platelet aggregation". The Journal of Clinical Investigation. 107 (5): 603–10. doi:10.1172/JCI10881. PMC 199422. PMID 11238561.
  21. ^ Gross S, Tilly P, Hentsch D, Vonesch JL, Fabre JE (February 2007). "Vascular wall-produced prostaglandin E2 exacerbates arterial thrombosis and atherothrombosis through platelet EP3 receptors". The Journal of Experimental Medicine. 204 (2): 311–20. doi:10.1084/jem.20061617. PMC 2118736. PMID 17242161.
  22. ^ Stromberga, Zane; Chess-Williams, Russ; Moro, Christian (23 June 2020). "Prostaglandin E2 and F2alpha Modulate Urinary Bladder Urothelium, Lamina Propria and Detrusor Contractility via the FP Receptor". Frontiers in Physiology. 11: 705. doi:10.3389/fphys.2020.00705. PMC 7344237. PMID 32714206.
  23. ^ Joshi, Shailendra; Ornstein, Eugene; Young, William L. (2010). "Cerebral and Spinal Cord Blood Flow". Cottrell and Young's Neuroanesthesia. pp. 17–59. doi:10.1016/B978-0-323-05908-4.10007-7. ISBN 9780323059084.
  24. ^ "WHO Recommendations for Induction of Labour". NCBI Bookshelf. Retrieved 2020-07-15. Induction of labour is defined as the process of artificially stimulating the uterus to start labour (1). It is usually performed by administering oxytocin or prostaglandins to the pregnant woman or by manually rupturing the amniotic membranes.
  25. ^ Medscape Early Penile Rehabilitation Helps Reduce Later Intractable ED
  26. ^ Veale, David; Miles, Sarah; Bramley, Sally; Muir, Gordon; Hodsoll, John (2015). "Am I normal? A systematic review and construction of nomograms for flaccid and erect penis length and circumference in up to 15 521 men". BJU International. 115 (6): 978–986. doi:10.1111/bju.13010. PMID 25487360.
  27. ^ LaBonde, MS, DVM, Jerry. (PDF). Michigan Veterinary Medical Association. Archived from the original (PDF) on 2008-02-27. Retrieved 2008-01-26.{{cite web}}: CS1 maint: multiple names: authors list (link)
  28. ^ Corey, E. J.; Weinshenker, N. M.; Schaaf, T. K.; Huber, W. (1969). "Stereo-controlled synthesis of prostaglandins F-2a and E-2 (dl)". Journal of the American Chemical Society. 91 (20): 5675–7. doi:10.1021/ja01048a062. PMID 5808505.
  29. ^ Mary Anne Koda-Kimble (2007). Handbook of Applied Therapeutics (8th ed.). Lippincott Williams & Wilkins. p. 1104. ISBN 9780781790260.{{cite book}}: CS1 maint: uses authors parameter (link)

External links

January 20, 2023
prostaglandin, prostaglandins, group, physiologically, active, lipid, compounds, called, eicosanoids, having, diverse, hormone, like, effects, animals, have, been, found, almost, every, tissue, humans, other, animals, they, derived, enzymatically, from, fatty,. The prostaglandins PG are a group of physiologically active lipid compounds called eicosanoids 1 having diverse hormone like effects in animals Prostaglandins have been found in almost every tissue in humans and other animals They are derived enzymatically from the fatty acid arachidonic acid 2 Every prostaglandin contains 20 carbon atoms including a 5 carbon ring They are a subclass of eicosanoids and of the prostanoid class of fatty acid derivatives E1 Alprostadil I2 Prostacyclin The structural differences between prostaglandins account for their different biological activities A given prostaglandin may have different and even opposite effects in different tissues in some cases The ability of the same prostaglandin to stimulate a reaction in one tissue and inhibit the same reaction in another tissue is determined by the type of receptor to which the prostaglandin binds They act as autocrine or paracrine factors with their target cells present in the immediate vicinity of the site of their secretion Prostaglandins differ from endocrine hormones in that they are not produced at a specific site but in many places throughout the human body Prostaglandins are powerful locally acting vasodilators and inhibit the aggregation of blood platelets Through their role in vasodilation prostaglandins are also involved in inflammation They are synthesized in the walls of blood vessels and serve the physiological function of preventing needless clot formation as well as regulating the contraction of smooth muscle tissue 3 Conversely thromboxanes produced by platelet cells are vasoconstrictors and facilitate platelet aggregation Their name comes from their role in clot formation thrombosis Specific prostaglandins are named with a letter which indicates the type of ring structure followed by a number which indicates the number of double bonds in the hydrocarbon structure For example prostaglandin E1 is abbreviated PGE1 and prostaglandin I2 is abbreviated PGI2 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 Functions 4 Types 5 Role in pharmacology 5 1 Inhibition 5 2 Clinical uses 6 Synthesis 7 Prostaglandin stimulants 8 See also 9 References 10 External linksHistory and name EditSystematic studies of prostaglandins began in 1930 when Kurzrock and Lieb found that human seminal fluid caused either stimulation or relaxation of strips of isolated human uterus They noted the curious finding that uteri from patients who had gone through successful pregnancies responded to the fluid with relaxation while uteri from sterile women responded with contraction upon addition of this seminal fluid 4 The name prostaglandin derives from the prostate gland chosen when prostaglandin was first isolated from seminal fluid in 1935 by the Swedish physiologist Ulf von Euler 5 and independently by the Irish English physiologist Maurice Walter Goldblatt 1895 1967 6 7 8 Prostaglandins were believed to be part of the prostatic secretions and eventually were discovered to be produced by the seminal vesicles Later it was shown that many other tissues secrete prostaglandins and that they perform a variety of functions The first total syntheses of prostaglandin F2a and prostaglandin E2 were reported by E J Corey in 1969 9 an achievement for which he was awarded the Japan Prize in 1989 In 1971 it was determined that aspirin like drugs could inhibit the synthesis of prostaglandins The biochemists Sune K Bergstrom Bengt I Samuelsson and John R Vane jointly received the 1982 Nobel Prize in Physiology or Medicine for their research on prostaglandins Biochemistry EditBiosynthesis Edit Biosynthesis of eicosanoids Prostaglandins are found in most tissues and organs They are produced by almost all nucleated cells They are autocrine and paracrine lipid mediators that act upon platelets endothelium uterine and mast cells They are synthesized in the cell from the fatty acid arachidonic acid 2 Arachidonic acid is created from diacylglycerol via phospholipase A2 then brought to either the cyclooxygenase pathway or the lipoxygenase pathway The cyclooxygenase pathway produces thromboxane prostacyclin and prostaglandin D E and F Alternatively the lipoxygenase enzyme pathway is active in leukocytes and in macrophages and synthesizes leukotrienes Release of prostaglandins from the cell Edit 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 alone 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 Edit Prostaglandins are produced following the sequential oxygenation of arachidonic acid 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 and growth Prostaglandin E synthase Edit Prostaglandin E2 PGE2 the most abundant prostaglandin 10 is generated from the action of prostaglandin E synthases on prostaglandin H2 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 Edit 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 identified Prostaglandin F synthase PGFS catalyzes the formation of 9a 11b PGF2a b from PGD2 and PGF2a from PGH2 in the presence of NADPH This enzyme has recently been crystallized in complex with PGD2 11 and bimatoprost 12 a synthetic analogue of PGF2a Functions EditThere are currently ten known prostaglandin receptors on various cell types Prostaglandins ligate a sub family of cell surface seven transmembrane receptors G protein coupled receptors These receptors are termed DP1 2 EP1 4 FP IP1 2 and TP corresponding to the receptor that ligates the corresponding prostaglandin e g DP1 2 receptors bind to PGD2 The diversity of receptors means that prostaglandins act on an array of cells and have a wide variety of effects such as create eicosanoids hormones acts on thermoregulatory center of hypothalamus to produce fever increases mating behaviors in goldfish 13 Prostaglandins are released during menstruation due to the destruction of the endometrial cells and the resultant release of their contents 14 needs update Release of prostaglandins and other inflammatory mediators in the uterus cause the uterus to contract These substances are thought to be a major factor in primary dysmenorrhea 15 16 17 Types EditThe following is a comparison of different types of prostaglandin including prostaglandin I2 prostacyclin PGI2 prostaglandin D2 PGD2 prostaglandin E2 PGE2 and prostaglandin F2a PGF2a 18 Type Receptor Receptor type FunctionPGI2 IP Gs vasodilation inhibit platelet aggregation bronchodilationPGD2 PTGDR DP1 and CRTH2 DP2 GPCR produced by mast cells recruits Th2 cells eosinophils and basophils In mammalian organs large amounts of PGD2 are found only in the brain and in mast cells Critical to development of allergic diseases such as asthmaPGE2 EP1 Gq bronchoconstriction GI tract smooth muscle contractionEP2 Gs bronchodilation GI tract smooth muscle relaxation vasodilationEP3 Gi gastric acid secretion gastric mucus secretion uterus contraction when pregnant GI tract smooth muscle contraction lipolysis inhibition autonomic neurotransmitters 19 platelet response to their agonists 20 and atherothrombosis in vivo 21 Unspecified hyperalgesia 19 pyrogenicPGF2a FP Gq uterus contraction bronchoconstriction urinary bladder contractions 22 vasoconstriction in cerebral circulation 23 Role in pharmacology EditInhibition Edit See also Prostaglandin antagonist and Mechanism of action of aspirin Examples of prostaglandin antagonists are NSAIDs inhibit cyclooxygenase and COX 2 selective inhibitors or coxibs Corticosteroids inhibit phospholipase A2 production Cyclopentenone prostaglandins may play a role in inhibiting inflammationClinical uses Edit Synthetic prostaglandins are used To induce childbirth parturition or abortion PGE2 or PGF2 with or without mifepristone a progesterone antagonist Induction of labour 24 To prevent closure of ductus arteriosus in newborns with particular cyanotic heart defects PGE1 As a vasodilator in severe Raynaud syndrome 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 PGF2a To treat erectile dysfunction or in penile rehabilitation following surgery PGE1 as alprostadil 25 To measure erect penis size in a clinical environment 26 To treat egg binding in small birds 27 Synthesis EditThe original synthesis of prostaglandins F2a and E2 is shown below It involves a Diels Alder reaction which establishes the relative stereochemistry of three contiguous stereocenters on the prostaglandin cyclopentane core 28 Prostaglandin stimulants EditCold exposure and IUDs may increase prostaglandin production 29 See also EditProstamides a chemically related class of physiologically active substancesReferences Edit Eicosanoid Synthesis and Metabolism Prostaglandins Thromboxanes Leukotrienes Lipoxins themedicalbiochemistrypage org Retrieved 2018 09 21 a b Ricciotti E FitzGerald GA May 2011 Prostaglandins and inflammation Arteriosclerosis Thrombosis and Vascular Biology 31 5 986 1000 doi 10 1161 ATVBAHA 110 207449 PMC 3081099 PMID 21508345 Nelson RF 2005 An introduction to behavioral endocrinology 3rd ed Sunderland Mass Sinauer Associates p 100 ISBN 0 87893 617 3 Kurzrock Raphael Lieb Charles C 1930 Biochemical Studies of Human Semen II The Action of Semen on the Human Uterus Proceedings of the Society for Experimental Biology and Medicine 28 3 268 doi 10 3181 00379727 28 5265 S2CID 85374636 Von Euler US 1935 Uber die spezifische blutdrucksenkende Substanz des menschlichen Prostata und Samenblasensekrets On the specific blood pressure reducing substance of human prostate and seminal vesicle secretions Wiener Klinische Wochenschrift 14 33 1182 1183 doi 10 1007 BF01778029 S2CID 38622866 Goldblatt MW May 1935 Properties of human seminal plasma The Journal of Physiology 84 2 208 18 doi 10 1113 jphysiol 1935 sp003269 PMC 1394818 PMID 16994667 Rubinstein William D Jolles Michael A Rubinstein Hillary L eds 2011 Goldblatt Maurice Walter The Palgrave Dictionary of Anglo Jewish History Basingstoke England Palgrave Macmillan p 333 ISBN 9780230304666 R S F S 3 June 1967 Obituary Notices M W Goldblatt British Medical Journal 2 5552 644 doi 10 1136 bmj 2 5552 644 S2CID 220151673 Nicolaou KC Sorensen EJ 1996 Classics in Total Synthesis Weinheim Germany VCH p 65 ISBN 3 527 29284 5 Ke J Yang Y Che Q Jiang F Wang H Chen Z Zhu M Tong H Zhang H Yan X Wang X Wang F Liu Y Dai C Wan X September 2016 Prostaglandin E2 PGE2 promotes proliferation and invasion by enhancing SUMO 1 activity via EP4 receptor in endometrial cancer Tumour Biology 37 9 12203 12211 doi 10 1007 s13277 016 5087 x PMC 5080328 PMID 27230680 Prostaglandin E2 PGE2 is the most abundant prostanoid in the human body Komoto J Yamada T Watanabe K Takusagawa F March 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 DF Takusagawa F February 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 Hormonal and pheromonal control of spawning in goldfish PDF Download Available ResearchGate Retrieved 2017 02 04 Lethaby A Duckitt K Farquhar C January 2013 Non steroidal anti inflammatory drugs for heavy menstrual bleeding The Cochrane Database of Systematic Reviews 1 CD000400 doi 10 1002 14651858 CD000400 pub3 PMID 23440779 Wright Jason and Solange Wyatt The Washington Manual Obstetrics and Gynecology Survival Guide Lippincott Williams amp Wilkins 2003 ISBN 0 7817 4363 X page needed Harel Z December 2006 Dysmenorrhea in adolescents and young adults etiology and management Journal of Pediatric and Adolescent Gynecology 19 6 363 71 doi 10 1016 j jpag 2006 09 001 PMID 17174824 Bofill Rodriguez M Lethaby A Farquhar C 19 September 2019 Non steroidal anti inflammatory drugs for heavy menstrual bleeding The Cochrane Database of Systematic Reviews 2019 9 CD000400 doi 10 1002 14651858 CD000400 pub4 PMC 6751587 PMID 31535715 Moreno JJ February 2017 Eicosanoid receptors Targets for the treatment of disrupted intestinal epithelial homeostasis European Journal of Pharmacology 796 7 19 doi 10 1016 j ejphar 2016 12 004 PMID 27940058 S2CID 1513449 a b Rang HP 2003 Pharmacology 5th ed Edinburgh Churchill Livingstone p 234 ISBN 0 443 07145 4 Fabre JE Nguyen M Athirakul K Coggins K McNeish JD Austin S Parise LK FitzGerald GA Coffman TM Koller BH March 2001 Activation of the murine EP3 receptor for PGE2 inhibits cAMP production and promotes platelet aggregation The Journal of Clinical Investigation 107 5 603 10 doi 10 1172 JCI10881 PMC 199422 PMID 11238561 Gross S Tilly P Hentsch D Vonesch JL Fabre JE February 2007 Vascular wall produced prostaglandin E2 exacerbates arterial thrombosis and atherothrombosis through platelet EP3 receptors The Journal of Experimental Medicine 204 2 311 20 doi 10 1084 jem 20061617 PMC 2118736 PMID 17242161 Stromberga Zane Chess Williams Russ Moro Christian 23 June 2020 Prostaglandin E2 and F2alpha Modulate Urinary Bladder Urothelium Lamina Propria and Detrusor Contractility via the FP Receptor Frontiers in Physiology 11 705 doi 10 3389 fphys 2020 00705 PMC 7344237 PMID 32714206 Joshi Shailendra Ornstein Eugene Young William L 2010 Cerebral and Spinal Cord Blood Flow Cottrell and Young s Neuroanesthesia pp 17 59 doi 10 1016 B978 0 323 05908 4 10007 7 ISBN 9780323059084 WHO Recommendations for Induction of Labour NCBI Bookshelf Retrieved 2020 07 15 Induction of labour is defined as the process of artificially stimulating the uterus to start labour 1 It is usually performed by administering oxytocin or prostaglandins to the pregnant woman or by manually rupturing the amniotic membranes Medscape Early Penile Rehabilitation Helps Reduce Later Intractable ED Veale David Miles Sarah Bramley Sally Muir Gordon Hodsoll John 2015 Am I normal A systematic review and construction of nomograms for flaccid and erect penis length and circumference in up to 15 521 men BJU International 115 6 978 986 doi 10 1111 bju 13010 PMID 25487360 LaBonde MS DVM Jerry Avian Reproductive and Pediatric Disorders PDF Michigan Veterinary Medical Association Archived from the original PDF on 2008 02 27 Retrieved 2008 01 26 a href Template Cite web html title Template Cite web cite web a CS1 maint multiple names authors list link Corey E J Weinshenker N M Schaaf T K Huber W 1969 Stereo controlled synthesis of prostaglandins F 2a and E 2 dl Journal of the American Chemical Society 91 20 5675 7 doi 10 1021 ja01048a062 PMID 5808505 Mary Anne Koda Kimble 2007 Handbook of Applied Therapeutics 8th ed Lippincott Williams amp Wilkins p 1104 ISBN 9780781790260 a href Template Cite book html title Template Cite book cite book a CS1 maint uses authors parameter link External links EditProstaglandins at the US National Library of Medicine Medical Subject Headings MeSH Retrieved from https en wikipedia org w index php title Prostaglandin amp oldid 1120106171, wikipedia, wiki, book, books, library,

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