| 20-hydroxyeicosatetraenoic acid (20-HETE): structural determinants for renal vasoconstriction. | |
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MedLine Citation:
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PMID: 12788354 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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The effects of natural and synthetic eicosanoids on the diameter of rat interlobular arteries studied in vitro were compared to that of the potent, endogenous vasoconstrictor 20-HETE. Vasoconstrictor activity was optimum for chain lengths of 20-22 carbons with at least one olefin or epoxide between located between C(13)-C(15) and an oxygen substituent at C(20)-C(22). The presence of delta (Zou et al. Am. J. Physiol. 1996, 270, R228; Gebremedhin, D. et al. Am. J. Physiol. 1998, 507, 771)-, delta (Carroll et al. Am. J. Physiol. 1996, 271, R863; Vazquez et al. Life Sci. 1995, 56, 1455)-, or delta (Imig et al. Hypertension 2000, 35, 307; Lopez et al. Amer. J. Physiol. 2001, 281, F420)-olefins had no influence on the vasoconstrictor response whereas the introduction of a C(7)-thiomethylene enhanced potency. A sulfonamide or alcohol, but not a lactone, could replace the C(1)-carboxylate. These data were used to construct a putative binding domain map of the 20-HETE receptor consisting of: (i) a comparatively open, hydrophilic binding site accommodating the C(1)-functionality; (ii) a hydrophobic trough spanning the olefins; (iii) a shallow pocket containing a critical pi-pi binding site in the vicinity of the pi (Ito et al. Am. J. Physiol. 1998, 274, F395; Quigley, R.; Baum, M.; Reddy, K. M.; Griener, J. C.; Falck, J. R. Am. J. Physiol. 2000, 278, F949)-olefin; and (iv) an oxyphilic binding site proximate to the omega-terminus. |
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Authors:
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Ming Yu; Magdalena Alonso-Galicia; Cheng-Wen Sun; Richard J Roman; Naoya Ono; Hitomi Hirano; Tsuyoshi Ishimoto; Y Krishna Reddy; Kishta Reddy Katipally; Komandla Malla Reddy; V Raj Gopal; Ji Yu; Mohamed Takhi; J R Falck |
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Publication Detail:
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Type: Journal Article; Research Support, Non-U.S. Gov't; Research Support, U.S. Gov't, P.H.S. |
Journal Detail:
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Title: Bioorganic & medicinal chemistry Volume: 11 ISSN: 0968-0896 ISO Abbreviation: Bioorg. Med. Chem. Publication Date: 2003 Jul |
Date Detail:
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Created Date: 2003-06-05 Completed Date: 2004-04-06 Revised Date: 2007-11-14 |
Medline Journal Info:
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Nlm Unique ID: 9413298 Medline TA: Bioorg Med Chem Country: England |
Other Details:
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Languages: eng Pagination: 2803-21 Citation Subset: IM |
Affiliation:
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Department of Physiology, Medical College of Wisconsin, Milwaukee, WI 53226, USA. |
Export Citation:
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APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
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Animals Binding Sites Hydroxyeicosatetraenoic Acids / chemical synthesis*, pharmacology* Kidney / blood supply Magnetic Resonance Spectroscopy Rats Receptors, Eicosanoid / chemistry Structure-Activity Relationship Vasoconstriction / drug effects* |
| Grant Support | |
ID/Acronym/Agency:
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DK38226/DK/NIDDK NIH HHS; GM 31287/GM/NIGMS NIH HHS; HL29587/HL/NHLBI NIH HHS; HL36279/HL/NHLBI NIH HHS; HL59996/HL/NHLBI NIH HHS |
| Chemical | |
Reg. No./Substance:
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0/Hydroxyeicosatetraenoic Acids; 0/Receptors, Eicosanoid; 79551-86-3/20-hydroxy-5,8,11,14-eicosatetraenoic acid |
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