{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,4]],"date-time":"2026-10-04T23:52:35Z","timestamp":1791157955891,"version":"4.1.0"},"reference-count":46,"publisher":"Wiley","issue":"3","license":[{"start":{"date-parts":[[2009,1,29]],"date-time":"2009-01-29T00:00:00Z","timestamp":1233187200000},"content-version":"vor","delay-in-days":3650,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":["bpspubs.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["British J Pharmacology"],"published-print":{"date-parts":[[1999,2]]},"abstract":"<jats:p>\n<jats:list list-type=\"explicit-label\">\n<jats:list-item><jats:p>Previous studies show that linking acetylated glucosamine to S\u2010nitroso\u2010<jats:italic>N<\/jats:italic>\u2010acetyl\u2010<jats:sc>D<\/jats:sc>,<jats:sc>L<\/jats:sc>\u2010penicillamine (SNAP) stabilizes the molecule and causes it to elicit unusually prolonged vasodilator effects in endothelium\u2010denuded, isolated rat femoral arteries. Here we studied the propanoyl (SNPP; 3 carbon side\u2010chain), valeryl (SNVP; 5C) and heptanoyl (SNHP; 7C) N\u2010substituted analogues of SNAP (2C), to further investigate other molecular characteristics that might influence chemical stability and duration of vascular action of S\u2010nitrosothiols.<\/jats:p><\/jats:list-item>\n<jats:list-item><jats:p>Spectrophotometric analysis revealed that SNVP was the most stable analogue in solution. Decomposition of all four compounds was accelerated by Cu(II) and cysteine, and neocuproine, a specific Cu(I) chelator, slowed decomposition of SNHP. Generation of NO from the compounds was confirmed by electrochemical detection at 37\u00b0C.<\/jats:p><\/jats:list-item>\n<jats:list-item><jats:p>Bolus injections of SNAP (10\u2003\u03bcl; 10<jats:sup>\u22128<\/jats:sup>\u201310<jats:sup>\u22123<\/jats:sup>\u2003<jats:sc>M<\/jats:sc>) into the perfusate of precontracted, isolated rat femoral arteries taken from adult male Wistar rats (400\u2013500\u2003g), caused concentration\u2010dependent, transient vasodilatations irrespective of endothelial integrity. Equivalent vasodilatations induced by SNVP and SNHP were transient in endothelium\u2010intact vessels but failed to recover to pre\u2010injection pressures at moderate and high concentrations (10<jats:sup>\u22126<\/jats:sup>\u201310<jats:sup>\u22123<\/jats:sup>\u2003<jats:sc>M<\/jats:sc>) in those denuded of endothelium. This sustained effect (&gt;1\u2003h) was most prevalent with SNHP and was largely reversed by the NO scavenger, haemoglobin.<\/jats:p><\/jats:list-item>\n<jats:list-item><jats:p>We suggest that increased lipophilicity of SNAP analogues with longer sidechains facilitates their retention by endothelium\u2010denuded vessels; subsequent slow decomposition within the tissue generates sufficient NO to cause prolonged vasodilatation. This is a potentially useful characteristic for targeting NO delivery to areas of endothelial damage.<\/jats:p><\/jats:list-item>\n<\/jats:list>\n<\/jats:p><jats:p><jats:italic>British Journal of Pharmacology<\/jats:italic> (1999) <jats:bold>126<\/jats:bold>, 639\u2013648; doi:<jats:ext-link xmlns:xlink=\"http:\/\/www.w3.org\/1999\/xlink\" ext-link-type=\"doi\" xlink:href=\"10.1038\/sj.bjp.0702346\">10.1038\/sj.bjp.0702346<\/jats:ext-link><\/jats:p>","DOI":"10.1038\/sj.bjp.0702346","type":"journal-article","created":{"date-parts":[[2005,1,28]],"date-time":"2005-01-28T19:41:09Z","timestamp":1106941269000},"page":"639-648","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":46,"title":["N\u2010substituted analogues of S\u2010nitroso\u2010<scp><i>N<\/i><\/scp>\u2010acetyl\u2010<scp>D<\/scp>,<scp>L<\/scp>\u2010penicillamine: chemical stability and prolonged nitric oxide mediated vasodilatation in isolated rat femoral arteries"],"prefix":"10.1111","volume":"126","author":[{"given":"I L","family":"Megson","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"S","family":"Morton","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"I R","family":"Greig","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"F A","family":"Mazzei","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"R A","family":"Field","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"A R","family":"Butler","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"G","family":"Caron","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"A","family":"Gasco","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"R","family":"Fruttero","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"D J","family":"Webb","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2009,1,29]]},"reference":[{"key":"e_1_2_7_2_1","doi-asserted-by":"publisher","DOI":"10.1016\/0006-291X(89)92517-5"},{"key":"e_1_2_7_3_1","doi-asserted-by":"publisher","DOI":"10.1038\/sj.bjp.0701218"},{"key":"e_1_2_7_4_1","doi-asserted-by":"publisher","DOI":"10.1016\/0968-0896(94)00139-T"},{"key":"e_1_2_7_5_1","doi-asserted-by":"publisher","DOI":"10.1002\/9783527614998.ch7"},{"key":"e_1_2_7_6_1","doi-asserted-by":"publisher","DOI":"10.1002\/jps.2600820214"},{"key":"e_1_2_7_7_1","doi-asserted-by":"publisher","DOI":"10.1039\/a604148e"},{"key":"e_1_2_7_8_1","first-page":"249","article-title":"Differential hemodynamic effects and tolerance properties of nitroglycerin and an S\u2010nitrosothiol in experimental heart failure","volume":"256","author":"BAUER J.A.","year":"1991","journal-title":"J. Pharmacol. Exp. Ther."},{"key":"e_1_2_7_9_1","doi-asserted-by":"publisher","DOI":"10.1002\/hlca.19970800210"},{"key":"e_1_2_7_10_1","doi-asserted-by":"publisher","DOI":"10.1093\/cvr\/21.1.34"},{"key":"e_1_2_7_11_1","doi-asserted-by":"publisher","DOI":"10.1172\/JCI115223"},{"key":"e_1_2_7_12_1","doi-asserted-by":"publisher","DOI":"10.1161\/01.CIR.92.11.3337"},{"key":"e_1_2_7_13_1","doi-asserted-by":"publisher","DOI":"10.1093\/cvr\/28.5.691"},{"key":"e_1_2_7_14_1","doi-asserted-by":"publisher","DOI":"10.1111\/j.1476-5381.1996.tb15769.x"},{"key":"e_1_2_7_15_1","doi-asserted-by":"publisher","DOI":"10.1039\/p29960000481"},{"key":"e_1_2_7_16_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0021-9150(97)00130-5"},{"key":"e_1_2_7_17_1","doi-asserted-by":"publisher","DOI":"10.1039\/c39780000249"},{"key":"e_1_2_7_18_1","doi-asserted-by":"publisher","DOI":"10.1111\/j.1476-5381.1992.tb14534.x"},{"key":"e_1_2_7_19_1","doi-asserted-by":"publisher","DOI":"10.1161\/01.RES.62.2.185"},{"key":"e_1_2_7_20_1","doi-asserted-by":"publisher","DOI":"10.1023\/A:1011953622052"},{"key":"e_1_2_7_21_1","doi-asserted-by":"publisher","DOI":"10.1111\/j.1476-5381.1990.tb14131.x"},{"key":"e_1_2_7_22_1","doi-asserted-by":"publisher","DOI":"10.1172\/JCI114081"},{"key":"e_1_2_7_23_1","doi-asserted-by":"publisher","DOI":"10.1111\/j.1476-5381.1995.tb13317.x"},{"key":"e_1_2_7_24_1","first-page":"300","article-title":"Mechanism of abnormal endothelium\u2010dependent relaxation in atherosclerosis: implications for altered autocrine and paracrine functions of EDRF","volume":"26","author":"GUERRA R.J.","year":"1989","journal-title":"Blood Vessels"},{"key":"e_1_2_7_25_1","doi-asserted-by":"publisher","DOI":"10.1161\/01.CIR.68.6.1247"},{"key":"e_1_2_7_26_1","doi-asserted-by":"publisher","DOI":"10.1172\/JCI113276"},{"key":"e_1_2_7_27_1","doi-asserted-by":"publisher","DOI":"10.1016\/0140-6736(93)91981-Q"},{"key":"e_1_2_7_28_1","doi-asserted-by":"publisher","DOI":"10.1161\/01.STR.19.12.1550"},{"key":"e_1_2_7_29_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0140-6736(94)90287-9"},{"key":"e_1_2_7_30_1","doi-asserted-by":"publisher","DOI":"10.1161\/01.CIR.95.3.553"},{"key":"e_1_2_7_31_1","first-page":"1529","article-title":"Relative potency of nitrovasodilators on human blood vessels: an insight into the targetting of nitric oxide delivery","volume":"273","author":"MACALLISTER R.J.","year":"1995","journal-title":"J. Pharmacol. Exp. Ther."},{"key":"e_1_2_7_32_1","doi-asserted-by":"publisher","DOI":"10.1002\/jps.2600841206"},{"key":"e_1_2_7_33_1","first-page":"708","article-title":"Selective blockade of endothelium\u2010dependent and glyceryl trinitrate\u2010induced relaxation by hemoglobin, and by methylene blue in the rabbit aorta","volume":"232","author":"MARTIN W.","year":"1985","journal-title":"J. Pharmacol. Exp. Ther."},{"key":"e_1_2_7_34_1","doi-asserted-by":"publisher","DOI":"10.3109\/10623329509024657"},{"key":"e_1_2_7_35_1","doi-asserted-by":"publisher","DOI":"10.1038\/sj.bjp.0701557"},{"key":"e_1_2_7_36_1","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.88.6.2166"},{"key":"e_1_2_7_37_1","doi-asserted-by":"publisher","DOI":"10.1038\/333664a0"},{"key":"e_1_2_7_38_1","doi-asserted-by":"publisher","DOI":"10.1038\/327524a0"},{"key":"e_1_2_7_39_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0006-291X(89)80219-0"},{"key":"e_1_2_7_40_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0140-6736(87)91481-4"},{"key":"e_1_2_7_41_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0006-291X(87)80299-1"},{"key":"e_1_2_7_42_1","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.87.13.5193"},{"key":"e_1_2_7_43_1","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.86.9.3375"},{"key":"e_1_2_7_44_1","unstructured":"SWIFT H.(1989). PhD Thesis. Department of Chemistry University of Durham Durham U.K."},{"key":"e_1_2_7_45_1","doi-asserted-by":"publisher","DOI":"10.1002\/9783527614998.ch4"},{"key":"e_1_2_7_46_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0140-6736(89)91013-1"},{"key":"e_1_2_7_47_1","doi-asserted-by":"publisher","DOI":"10.1039\/cs9851400171"}],"container-title":["British Journal of Pharmacology"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1038%2Fsj.bjp.0702346","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1038%2Fsj.bjp.0702346","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/bpspubs.onlinelibrary.wiley.com\/doi\/pdf\/10.1038\/sj.bjp.0702346","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,10,28]],"date-time":"2023-10-28T16:43:46Z","timestamp":1698511426000},"score":1,"resource":{"primary":{"URL":"https:\/\/bpspubs.onlinelibrary.wiley.com\/doi\/10.1038\/sj.bjp.0702346"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[1999,2]]},"references-count":46,"journal-issue":{"issue":"3","published-print":{"date-parts":[[1999,2]]}},"alternative-id":["10.1038\/sj.bjp.0702346"],"URL":"https:\/\/doi.org\/10.1038\/sj.bjp.0702346","archive":["Portico"],"relation":{},"ISSN":["0007-1188","1476-5381"],"issn-type":[{"value":"0007-1188","type":"print"},{"value":"1476-5381","type":"electronic"}],"subject":[],"published":{"date-parts":[[1999,2]]},"assertion":[{"value":"2009-01-29","order":2,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}]}}