{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,15]],"date-time":"2026-09-15T12:04:52Z","timestamp":1789473892902,"version":"build-2803163510"},"reference-count":67,"publisher":"American Chemical Society (ACS)","issue":"16","license":[{"start":{"date-parts":[[2007,7,11]],"date-time":"2007-07-11T00:00:00Z","timestamp":1184112000000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-029"},{"start":{"date-parts":[[2007,7,11]],"date-time":"2007-07-11T00:00:00Z","timestamp":1184112000000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-037"},{"start":{"date-parts":[[2007,7,11]],"date-time":"2007-07-11T00:00:00Z","timestamp":1184112000000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-045"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2007,8,6]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>The amphiphilic gadolinium complex MS-325 ((trisodium-{(2-(R)-[(4,4-diphenylcyclohexyl) phosphonooxymethyl] diethylenetriaminepentaacetato) (aquo)gadolinium(III)}) is a contrast agent for magnetic resonance angiography (MRA). MS-325 comprises a GdDTPA core with an appended phosphodiester moiety linked to a diphenylcyclohexyl group to facilitate noncovalent binding to serum albumin and extension of the plasma half-life in vivo. The chiral DTPA ligand (R) was derived from l-serine, and upon complexation with gadolinium, forms two interconvertible diastereomers, denoted herein as isomers A and B. X-ray crystallography of the tris(ethylenediamine)cobalt(III) salt derivative of isomer A revealed a structure in the polar acentric space group P32. The structure consisted of three independent molecules of the gadolinium complex in the asymmetric unit along with three \u0394-[Co(en)3]3+ cations, and it represents an unusual example of spontaneous Pasteur resolution of the cobalt cation. The geometry of the coordination core was best described as a distorted trigonal prism, and the final R factor was 5.6%. The configuration of the chiral central nitrogen of the DTPA core was S. The Gd\u2212water (2.47\u22122.48 \u00c5), the Gd\u2212acetate oxygens (2.34\u22122.42 \u00c5), and the Gd\u2212N bond distances (central N, 2.59\u22122.63 \u00c5; terminal N, 2.74\u22122.80 \u00c5) were similar to other reported GdDTPA structures. The structurally characterized single crystal was one of two interconvertable diastereomers (isomers A and B) that equilibrated to a ratio of 1.81 to 1 at pH 7.4 and were separable at elevated pH by ion-exchange chromatography. The rate of isomerization was highly pH dependent:\u2009 k1 = (1.45 \u00b1 0.08) \u00d7 102[H+] + (4.16 \u00b1 0.30) \u00d7 105[H+]2; k-1 = (2.57 \u00b1 0.17) \u00d7 102[H+] + (7.54 \u00b1 0.60) \u00d7 105[H+]2.<\/jats:p>","DOI":"10.1021\/ic7006843","type":"journal-article","created":{"date-parts":[[2007,7,11]],"date-time":"2007-07-11T09:00:27Z","timestamp":1184144427000},"page":"6621-6631","source":"Crossref","is-referenced-by-count":28,"title":["Structural, Kinetic, and Thermodynamic Characterization of the\nInterconverting Isomers of MS-325, a Gadolinium(III)-Based Magnetic\nResonance Angiography Contrast Agent"],"prefix":"10.1021","volume":"46","author":[{"given":"Zolt\u00e1n","family":"Tyekl\u00e1r","sequence":"first","affiliation":[{"name":"EPIX Pharmaceuticals, Inc., 67 Rogers Street, Cambridge, Massachusetts 02142"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Stephen U.","family":"Dunham","sequence":"additional","affiliation":[{"name":"EPIX Pharmaceuticals, Inc., 67 Rogers Street, Cambridge, Massachusetts 02142"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Katarina","family":"Midelfort","sequence":"additional","affiliation":[{"name":"EPIX Pharmaceuticals, Inc., 67 Rogers Street, Cambridge, Massachusetts 02142"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Daniel M.","family":"Scott","sequence":"additional","affiliation":[{"name":"EPIX Pharmaceuticals, Inc., 67 Rogers Street, Cambridge, Massachusetts 02142"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Hirano","family":"Sajiki","sequence":"additional","affiliation":[{"name":"EPIX Pharmaceuticals, Inc., 67 Rogers Street, Cambridge, Massachusetts 02142"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Karen","family":"Ong","sequence":"additional","affiliation":[{"name":"EPIX Pharmaceuticals, Inc., 67 Rogers Street, Cambridge, Massachusetts 02142"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Randall B.","family":"Lauffer","sequence":"additional","affiliation":[{"name":"EPIX Pharmaceuticals, Inc., 67 Rogers Street, Cambridge, Massachusetts 02142"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Peter","family":"Caravan","sequence":"additional","affiliation":[{"name":"EPIX Pharmaceuticals, Inc., 67 Rogers Street, Cambridge, Massachusetts 02142"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Thomas J.","family":"McMurry","sequence":"additional","affiliation":[{"name":"EPIX Pharmaceuticals, Inc., 67 Rogers Street, Cambridge, Massachusetts 02142"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2007,7,11]]},"reference":[{"key":"2026091506565596600_elcit1","doi-asserted-by":"publisher","first-page":"751","DOI":"10.2174\/0929867053507379","volume":"12","author":"Zhang","year":"2005","journal-title":"J. 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