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| Hauptseite > Publikationsdatenbank > Novel CDTA-based, Bifunctional Chelators for Stable and Inert Mn II Complexation: Synthesis and Physicochemical Characterization > print |
| Hauptseite > Publikationsdatenbank > Novel CDTA-based, Bifunctional Chelators for Stable and Inert Mn II Complexation: Synthesis and Physicochemical Characterization > print |
| 001 | 836077 | ||
| 005 | 20210129230856.0 | ||
| 024 | 7 | _ | |a 10.1021/acs.inorgchem.7b00460 |2 doi |
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| 100 | 1 | _ | |a Vanasschen, Christian |0 P:(DE-Juel1)157902 |b 0 |e Corresponding author |u fzj |
| 245 | _ | _ | |a Novel CDTA-based, Bifunctional Chelators for Stable and Inert Mn II Complexation: Synthesis and Physicochemical Characterization |
| 260 | _ | _ | |a Washington, DC |c 2017 |b American Chemical Society |
| 336 | 7 | _ | |a article |2 DRIVER |
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| 520 | _ | _ | |a In the search for MnIIMR and PET/MR imaging agents with optimal balance between thermodynamic stability, kinetic inertness, and relaxivity, two novel bifunctional MnII chelators (BFMnCs) based on CDTA (trans-1,2-diaminocyclohexane-N,N,N′,N′-tetraacetic acid) weresynthesized. A six-step synthesis, involving the buildup of a functionalized trans -1,2-diaminocyclohexane core, provided CuAAC-reactive 6a and 6b bearing an alkyne or azide substituent on the cyclohexane ring, respectively (CuAAC = CuI-catalyzed azide−alkyne 1,3-dipolar cyclo-addition). Thermodynamic, kinetic, and relaxometric studies were performed with 4-HET-CDTA (8a)as a model chelator, synthesized in two steps from6a. The protonation constants revealed that8a is slightly less basic than CDTA and forms a Mn II complex of marginally lower thermodynamic stability (log KMnL= 13.80 vs 14.32, respectively), while the conditional stability constant is almost identical for both chelates (pMn = 8.62 vs 8.68, respectively). Kinetic assessment of the CuII-mediated transmetalation of [Mn(4-HET-CDTA)]2−showed that proton-assisted complex dissociation is slightly slower than for [Mn(CDTA)]2−(k1= 297 vs 400 M−1s−1, respectively). portantly, the dissociation half-life near physiologicalitions (pH 7.4, 25°C) underlined that [Mn(4-HET-CDTA)]2−is∼35% more inert (t1/2= 16.2 vs 12.1 h, respectively).Thosefindings may be accounted for by a combination of reduced basicity and increased rigidity of the ligand. Analysis of the17O NMR and1H NMRD data attributed the high relaxivity of [Mn(4-HET-CDTA)]2−(r1= 4.56 mM−1s−1vs 3.65 mM−1s−1for [Mn(CDTA)]2−; 20 MHz, 25°C) to slower rotational dynamics (τR298= 105 ps). Additionally, the fast water exchange of thecomplex correlates well with the value reported for [Mn(CDTA)]2−(kex298= 17.6×107vs 14.0×107s−1, respectively). Giventhe exquisite compromise between thermodynamic stability, kinetic inertness, and relaxivity achieved by [Mn(4-HET-CDTA)]2−,appropriately designed CuAAC-conjugates of6a/6bare promising precursors for the preparation of targeted, bioresponsive, orhigh relaxivity manganese-based PET/MR tracers (52g/55MnII) and MR contrast agents (MnII). |
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| 773 | _ | _ | |a 10.1021/acs.inorgchem.7b00460 |g Vol. 56, no. 14, p. 7746 - 7760 |0 PERI:(DE-600)1484438-2 |n 14 |p 7746 - 7760 |t Inorganic chemistry |v 56 |y 2017 |x 1520-510X |
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