A multimeric MRI contrast agent based on a closo-borane scaffold bearing modified AAZTA chelates on the periphery

Shatadru Chakravarty; Saurav J Sarma; Lalit N Goswami; Quan-Yu Cai; Erik M Shapiro; M Frederick Hawthorne; Lixin Ma

doi:10.1039/c9cc05383b

A multimeric MRI contrast agent based on a closo-borane scaffold bearing modified AAZTA chelates on the periphery

Chem Commun (Camb). 2019 Oct 10;55(82):12348-12351. doi: 10.1039/c9cc05383b.

Authors

Shatadru Chakravarty¹, Saurav J Sarma², Lalit N Goswami³, Quan-Yu Cai⁴, Erik M Shapiro⁵, M Frederick Hawthorne³, Lixin Ma⁴

Affiliations

¹ International Institute of Nano and Molecular Medicine and Department of Radiology, University of Missouri, Columbia, MO 65212, USA. mal@health.missouri.edu and Molecular and Cellular Imaging Laboratory, Department of Radiology, Michigan State University, East Lansing, MI 48823, USA and Institute for Quantitative Health Science and Engineering, Michigan State University, East Lansing, MI 48823, USA.
² International Institute of Nano and Molecular Medicine and Department of Radiology, University of Missouri, Columbia, MO 65212, USA. mal@health.missouri.edu and Bond Life Sciences Centre, University of Missouri, Columbia, MO 65201, USA and MU Metabolomics Centre, University of Missouri, Columbia, MO 65201, USA.
³ International Institute of Nano and Molecular Medicine and Department of Radiology, University of Missouri, Columbia, MO 65212, USA. mal@health.missouri.edu.
⁴ International Institute of Nano and Molecular Medicine and Department of Radiology, University of Missouri, Columbia, MO 65212, USA. mal@health.missouri.edu and Harry S. Truman Memorial Veterans' Hospital, Columbia, MO 65201, USA.
⁵ Molecular and Cellular Imaging Laboratory, Department of Radiology, Michigan State University, East Lansing, MI 48823, USA and Institute for Quantitative Health Science and Engineering, Michigan State University, East Lansing, MI 48823, USA.

PMID: 31559401
DOI: 10.1039/c9cc05383b

Abstract

A multimeric MRI contrast agent based on the closo-borane motif is reported. Twelve copies of a modified AAZTA chelate with an alkyne end group are appended on an azide-functionalized closo-borane motif using Cu(i) catalyzed click chemistry. The presence of two water molecules on the Gd-bound AAZTA chelate results in high relaxivity for the closomer in vitro/in vivo.

MeSH terms

Acetates / chemical synthesis
Acetates / chemistry*
Azepines / chemical synthesis
Azepines / chemistry*
Boranes / chemical synthesis
Boranes / chemistry*
Chelating Agents / chemical synthesis
Chelating Agents / chemistry*
Contrast Media / chemical synthesis
Contrast Media / chemistry*
Coordination Complexes / chemical synthesis
Coordination Complexes / chemistry*
Magnetic Resonance Imaging*
Molecular Structure

Substances

1,4-bis(hydroxycarbonylmethyl)-6-(bis(hydroxycarbonylmethyl))amino-6-methylperhydro-1,4-diazepine
Acetates
Azepines
Boranes
Chelating Agents
Contrast Media
Coordination Complexes