DataVXAdvanced SciencePaper
journal article·2025-04Open access

Chiral Switch of Gadopiclenol: New Standards in MRI Probes

Roberta Napolitano, Nicol Guidolin, Mariangela Boccalon, Alberto Fringuello Mingo, Sonia Colombo Serra, Federica Buonsanti, Roberta Fretta, Nicola Demitri, Attila Bényei, Mauro Botta, Giovanni Battista Giovenzana, Fabio Tedoldi, Zsolt Baranyai

Advanced Science· Volume 12· Issue 14
Publisher pageOpen full text
Source abstract

Abstract

Abstract Magnetic Resonance Imaging (MRI) plays a vital role in the accurate diagnosis of numerous human diseases and disorders, with Gd(III)‐based contrast agents (GBCAs) being used in ≈30%–40% of procedures, resulting in ≈30 million doses administered annually worldwide. The careful design of a rigid macrocyclic chelator featuring a highly hydrophilic periphery leads to the development of gadopiclenol, the first bis‐hydrated Gd(III)‐based MRI contrast agent, recently approved for clinical use by both the FDA and EMA. The stereochemistry of the coordinating arms is found to play a crucial role in the remarkable thermodynamic stability and inertness of the Gd(III)‐complex with the RRR/SSS ‐stereoisomer of this heptadentate chelating agent, ensuring its safety in vivo. The exceptional stability of the most effective gadopiclenol enantiomeric pair ( RRR/SSS ), coupled with a relaxivity 2 to 3 times higher than that of currently used GBCAs, has enabled the use of reduced doses while ensuring non‐inferior image contrast.
Source: crossref · Quality: baseline

Research context

OpenAlex topics: Lanthanide and Transition Metal Complexes · Advanced MRI Techniques and Applications · Radioactive element chemistry and processing

SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.

Affiliations

Bracco Research Centre Bracco Imaging SpA Via Ribes 5 Colleretto Giacosa 10010 TO Italy

CRB Trieste Bracco Imaging SpA AREA Science Park Basovizza 34149 TS Italy

XRD2 Beamline Elettra‐Sincrotrone Trieste S.C.p.A. S.S. 14 Km 163.5 in Area Science Park Basovizza 34149 TS Italy

Department of Physical Chemistry University of Debrecen Egyetem tér 1 Debrecen H‐4032 Hungary

Dipartimento di Scienze e Innovazione Tecnologica, Piattaforma di Risonanze Magnetiche (PRISMA‐UPO) Università del Piemonte Orientale “A. Avogadro” Viale Teresa Michel 11 Alessandria 15121 Italy

Dipartimento di Scienze del Farmaco (DSF) Università del Piemonte Orientale “A. Avogadro” Largo Donegani 2/3 Novara 28100 Italy

Headquarters Bracco Imaging SpA Via Egidio Folli 50 Milano 20134 MI Italy

References (51)

Show source-provided references
1. 10.1021/cr980440x10.1021/cr980440x ↗
2. 10.1021/acs.chemrev.8b0036310.1021/acs.chemrev.8b00363 ↗
3. 10.1002/9781118503652.ch210.1002/9781118503652.ch2 ↗
4. 10.1021/jacs.9b0914910.1021/jacs.9b09149 ↗
5. 10.1002/chem.20120293010.1002/chem.201202930 ↗
6. 10.1148/radiol.1313166910.1148/radiol.13131669 ↗
7. 10.1016/S1474-4422(17)30158-810.1016/S1474-4422(17)30158-8 ↗
8. 10.1148/radiol.201716285710.1148/radiol.2017162857 ↗
9. 10.1021/acs.inorgchem.0c0051010.1021/acs.inorgchem.0c00510 ↗
10. 10.4155/fmc-2018-060810.4155/fmc-2018-0608 ↗
11. 10.1097/RLI.000000000000105310.1097/RLI.0000000000001053 ↗
12. 10.1148/radiol.201717230510.1148/radiol.2017172305 ↗
13. 10.1039/D1SC02200H10.1039/D1SC02200H ↗
14. 10.1021/acs.accounts.2c0010210.1021/acs.accounts.2c00102 ↗
15. 10.1148/radiol.201717097710.1148/radiol.2017170977 ↗
16. 10.1021/ic00095a02810.1021/ic00095a028 ↗
17. 10.1021/ar800250h10.1021/ar800250h ↗
18. 10.1016/j.ccr.2021.21390810.1016/j.ccr.2021.213908 ↗
19. 10.1002/(SICI)1097-458X(199806)36:13<S200::AID-OMR324>3.0.CO;2-H10.1002/(SICI)1097-458X(199806)36:13<S200::AID-OMR324>3.0.CO;2-H ↗
20. 10.1039/b108294a10.1039/b108294a ↗
21. 10.1021/ic060875010.1021/ic0608750 ↗
22. 10.1021/ic00112a04110.1021/ic00112a041 ↗
23. 10.1021/ic00096a03610.1021/ic00096a036 ↗
24. 10.1038/s41467-018-03315-810.1038/s41467-018-03315-8 ↗
25. 10.1021/acs.inorgchem.4c0102810.1021/acs.inorgchem.4c01028 ↗
26. 10.1097/RLI.000000000000056310.1097/RLI.0000000000000563 ↗
27. 10.1021/ic960794b10.1021/ic960794b ↗
28. 10.1039/b700673j10.1039/b700673j ↗
29. 10.1016/S0020-1693(00)80228-510.1016/S0020-1693(00)80228-5 ↗
30. 10.1021/ic00253a03810.1021/ic00253a038 ↗
31. 10.1002/chem.20040000610.1002/chem.200400006 ↗
32. 10.1021/ic00130a01210.1021/ic00130a012 ↗
33. 10.1016/0020-1693(96)05094-310.1016/0020-1693(96)05094-3 ↗
34. 10.1021/ic00032a03410.1021/ic00032a034 ↗
35. 10.1021/ic402595810.1021/ic4025958 ↗
36. 10.1021/ic201282710.1021/ic2012827 ↗
37. 10.1002/mrm.191038041510.1002/mrm.1910380415 ↗
38. Helm L. · 2018 · 121
39. 10.1038/s41467-019-09342-310.1038/s41467-019-09342-3 ↗
40. 10.1002/chem.20020447510.1002/chem.200204475 ↗
41. 10.1021/ja961743g10.1021/ja961743g ↗
42. 10.1002/(SICI)1099-0682(200003)2000:3<399::AID-EJIC399>3.0.CO;2-B10.1002/(SICI)1099-0682(200003)2000:3<399::AID-EJIC399>3.0.CO;2-B ↗
43. 10.1039/b413536a10.1039/b413536a ↗
44. 10.1039/b517997a10.1039/b517997a ↗
45. 10.1021/acs.inorgchem.2c0022510.1021/acs.inorgchem.2c00225 ↗
46. 10.1016/S0003-2670(01)80616-410.1016/S0003-2670(01)80616-4 ↗
47. 10.1002/chem.20170150810.1002/chem.201701508 ↗
48. 10.1007/978-1-4684-4934-1_810.1007/978-1-4684-4934-1_8 ↗
49. 10.1140/epjp/i2015-15043-310.1140/epjp/i2015-15043-3 ↗
50. 10.1107/S090744490904733710.1107/S0907444909047337 ↗
51. I. J. Wiki ImageJ Wiki https://imagej.github.io/(accessed: February 2020).