Synthesis of aminooxy-functionalized lanthanide(III) chelates for carbonyl-group conjugation.
The syntheses of three new aminooxy-tethered lanthanide(III) chelates, compounds 1-3, incorporating DOTA (= 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetic acid), DTPA (= diethylenetriaminepentaacetic acid), or a substituted terpyridine (2,2',2'',2'''-[2,2': 6',2''-terpyridine-6,6''-diylbis(methylenenitrilo)]tetraacetic acid), respectively, are described. Reagents 1-3 can be used for carbonyl 'labeling', as shown by the formation of the corresponding oxime-ether bioconjugates of naltrexone (16) and 2-deoxy-beta-D-glucose (17) (Scheme 4).
Hovinen
Jari
J
PerkinElmer Life and Analytical Sciences, Turku Site, P. O. Box 10, FIN-20101 Turku, Finland. jari.hovinen@perkinelmer.com
D017554:Carbon Compounds, Inorganic / Q000138:chemical synthesis*; D002614:Chelating Agents / Q000138:chemical synthesis*; D006573:Heterocyclic Compounds, 1-Ring / Q000138:chemical synthesis; D028581:Lanthanoid Series Elements / Q000138:chemical synthesis*; D010091:Oximes / Q000138:chemical synthesis*
D017554:Carbon Compounds, Inorganic; D002614:Chelating Agents; D006573:Heterocyclic Compounds, 1-Ring; D028581:Lanthanoid Series Elements; D010091:Oximes; C071349:1,4,7,10-tetraazacyclododecane- 1,4,7,10-tetraacetic acid