ArticleJournal of the American Chemical Society2026
Accelerating Proton Exchange in 1,8-Bis(dialkylamino)naphthalene Proton Sponges through Intramolecular Catalysis for CEST MRI.
Article in Journal of the American Chemical Society, 2026. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.
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Abstract
Chemical exchange saturation transfer (CEST) MRI generates contrast by transferring saturation from exchangeable protons to bulk water. In diamagnetic agents, labile -NH/-OH protons typically resonate close to water (1-5 ppm), severely limiting selectivity. Thus, larger chemical shift offsets are highly desirable for in vivo applications. Efficient CEST at clinical field strengths also requires exchange rates within a narrow kinetic window. Tetraalkyl 1,8-diaminonaphthalenes (proton sponges) are attractive scaffolds for diaCEST agents because the labile proton locked in a strong hydrogen bond between the two nitrogens in the monoprotonated forms can exhibit extraordinarily large downfield chemical shift offsets from water. However, these compounds do not have CEST because the strong H-bond also results in very slow exchange with the bulk. Here, we report the design, synthesis, and evaluation of a new tetrasubstituted 1,8-diaminonaphthalene derivative in which proton exchange is accelerated by intramolecular catalysis. Detailed structural, thermodynamic, and kinetic studies of 1,8-diaminonaphthalene tetraacetic acid (DANTA) reveal that the carboxylate groups participate in intramolecular hydrogen-bonding interactions with the central N···H
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