| Revision as of 13:14, 12 May 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (no changed fields - added verified revid - updated 'UNII_Ref', 'ChemSpiderID_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref', 'ChEMBL_Ref', 'KEGG_Ref') per Chem/Drugbox validation (← Previous edit |
Latest revision as of 17:04, 30 March 2024 edit undo109.241.162.167 (talk) →Biosynthesis: more duplicated refsTag: references removed |
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{{DISPLAYTITLE:Leukotriene A<sub>4</sub>}} |
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{{chembox |
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{{Chembox |
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| verifiedrevid = 396932507 |
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|ImageFile=Leukotriene A4.svg |
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| Name = Leukotriene A<sub>4</sub> |
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|IUPACName= |
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| verifiedrevid = 428749275 |
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|OtherNames= |
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| ImageFile = Leukotriene A4.svg |
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|Section1= {{Chembox Identifiers |
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| ImageSize = |
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| CASNo= 72059-45-1 |
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| PIN = 4-<nowiki>{</nowiki>(2''S'',3''S'')-3-oxiran-2-yl}butanoic acid |
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| PubChem=5280383 |
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| OtherNames = |
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| SMILES= |
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|Section1={{Chembox Identifiers |
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| MeSHName=Leukotriene+A4 |
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| IUPHAR_ligand = 5214 |
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}} |
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| Abbreviations = LTA<sub>4</sub> |
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|Section2= {{Chembox Properties |
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| CASNo_Ref = {{cascite|correct|??}} |
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| Formula=C<sub>20</sub>H<sub>30</sub>O<sub>3</sub> |
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| CASNo = 72059-45-1 |
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| MolarMass=318.45 g/mol |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| Appearance= |
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| UNII = 7Y7MPZ6563 |
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| Density= |
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| EINECS = |
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| MeltingPt= |
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| PubChem = 5280383 |
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| BoilingPt= |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| Solubility= |
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| ChemSpiderID = 4444074 |
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}} |
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| SMILES = CCCCC/C=C\C/C=C\C=C\C=C\1(O1)CCCC(=O)O |
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|Section3= {{Chembox Hazards |
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| InChI = 1/C20H30O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-15-18-19(23-18)16-14-17-20(21)22/h6-7,9-13,15,18-19H,2-5,8,14,16-17H2,1H3,(H,21,22)/b7-6-,10-9-,12-11+,15-13+/t18-,19-/m0/s1 |
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| MainHazards= |
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| InChIKey = UFPQIRYSPUYQHK-WAQVJNLQBZ |
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| FlashPt= |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| Autoignition= |
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| StdInChI = 1S/C20H30O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-15-18-19(23-18)16-14-17-20(21)22/h6-7,9-13,15,18-19H,2-5,8,14,16-17H2,1H3,(H,21,22)/b7-6-,10-9-,12-11+,15-13+/t18-,19-/m0/s1 |
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}} |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey = UFPQIRYSPUYQHK-WAQVJNLQSA-N |
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| RTECS = |
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| MeSHName = D017572 |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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| ChEBI = 15651 |
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| KEGG_Ref = {{keggcite|changed|kegg}} |
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| KEGG = C00909 |
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}} |
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|Section2={{Chembox Properties |
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| C = 20 | H = 30 | O =3 |
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| Appearance = |
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| MeltingPt_notes = |
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|Section3={{Chembox Structure |
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|Section4={{Chembox Thermochemistry |
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|Section5={{Chembox Pharmacology |
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|Section6={{Chembox Explosive |
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| ShockSens = |
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|Section7={{Chembox Hazards |
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| ExternalSDS = |
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|Section8={{Chembox Related |
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| OtherAnions = |
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| OtherCations = |
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| OtherFunction = |
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'''Leukotriene A4''' is a ]. |
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'''Leukotriene A<sub>4</sub>''' ('''LTA<sub>4</sub>''') is a ], and is the precursor for the productions of ] (LTB<sub>4</sub>) and ] (LTC<sub>4</sub>). |
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] converts it to ]. |
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== Biosynthesis == |
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Following the biosynthesis of eicosanoid, triggered as a result of infection or inflammation, the resulting arachidonic acid substrate is released from the cell membrane phospholipid will enter the lipooxygenase pathway to produce leukotriene A<sub>4</sub>.<ref name= Abu >{{Cite journal |last1=Abu |first1=J.I. |last2=Konje |first2=J.C. |date=March 2000 |title=Leukotrienes in gynaecology: the hypothetical value of anti-leukotriene therapy in dysmenorrhoea and endometriosis |journal=Human Reproduction Update |volume=6 |issue=2 |pages=200–205 |issn=1355-4786 |pmid=10782578 |doi=10.1093/humupd/6.2.200 |doi-access=free}}</ref><ref name= Marx >{{Cite journal |last=Marx |first=J.L. |date=1982-03-12 |title=The leukotrienes in allergy and inflammation |journal=Science |volume=215 |issue=4538 |pages=1380–1383 |doi=10.1126/science.6278589 |issn=0036-8075 |pmid=6278589 |bibcode=1982Sci...215.1380M}}</ref> In this pathway, arachidonic acid is converted into ] (5-HPETE) as a result of a catalytic complex consisting of the enzyme ] (5-LO) and ] (FLAP) in the presence of ] and ].{{r|Abu|Marx}}<ref>{{Cite journal|last=Nicolls|first=Mark R.|last2=Voelkel|first2=Norbert F.|last3=Peters-Golden|first3=Marc|last4=Rajadas|first4=Jayakumar|last5=Fridlib|first5=Marina|last6=Inayathullah|first6=Mohammed|last7=Zamanian|first7=Roham T.|last8=Rabinovitch|first8=Marlene|last9=Farkas|first9=Laszlo|date=2013-08-28|title=Blocking Macrophage Leukotriene B4 Prevents Endothelial Injury and Reverses Pulmonary Hypertension|journal=Science Translational Medicine|volume=5|issue=200|pages=200ra117|doi=10.1126/scitranslmed.3006674|issn=1946-6234|pmid=23986401|pmc=4016764}}</ref> The resulting 5-HPETE yields the unstable allylic epoxide substrate LTA<sub>4</sub><ref name= Serhan >{{Cite journal |last1=Serhan |first1=C.N. |last2=Rouzer |first2=C.A. |last3=Lindgren |first3=J.A. |last4=Dahlen |first4=S.E. |last5=Samuelsson |first5=B. |date=1987-09-04 |title=Leukotrienes and lipoxins: structures, biosynthesis, and biological effects |journal=Science |volume=237 |issue=4819 |pages=1171–1176 |doi=10.1126/science.2820055 |issn=0036-8075 |pmid=2820055 |bibcode=1987Sci...237.1171S}}</ref> which is quickly hydrolyzed by the ] (LTA<sub>4</sub>H) enzyme to produce LTB<sub>4</sub>, or synthesized by ] (LTC<sub>4</sub>S) with the addition of glutathione to produce LTC<sub>4</sub> which can be further metabolized to produce ] (LTD<sub>4</sub>) and ] (LTE<sub>4</sub>).<ref>{{Cite journal|last=Nicolls|first=Mark R.|last2=Dixon|first2=J. Brandon|last3=Kitajewski|first3=Jan|last4=Peters-Golden|first4=Marc|last5=Voelkel|first5=Norbert F.|last6=Dhillon|first6=Gundeep S.|last7=Zamanian|first7=Roham T.|last8=Feroze|first8=Abdullah H.|last9=Nepiyushchikh|first9=Zhanna|date=2017-05-10|title=Leukotriene B4 antagonism ameliorates experimental lymphedema|journal=Science Translational Medicine|volume=9|issue=389|pages=eaal3920|doi=10.1126/scitranslmed.aal3920|issn=1946-6234|pmid=28490670|doi-access=free}}</ref>{{r|Serhan}} The lipooxygenase pathway is one of several possible pathways including the cyclooxygenase pathway (also PGH synthase pathway), isoprostane pathway, and cytochrome P450 epoxygenases pathway following the arachidonic acid metabolism,<ref>{{Cite journal|last=O'Connor|first=J. Patrick|last2=Lysz|first2=Thomas|date=September 2008|title=Celecoxib, NSAIDs and the skeleton|journal=Drugs of Today|volume=44|issue=9|pages=693–709|doi=10.1358/dot.2008.44.9.1251573|issn=1699-3993|pmid=19137124}}</ref> but is the only pathway in which the subsequent steps will lead to the production of leukotrienes. |
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] |
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{{Leukotrienes}} |
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==References== |
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{{Reflist|2}} |
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{{Leukotrienes}} |
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{{Leukotrienergics}} |
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] |
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] |
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{{biochemistry-stub}} |
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