Manganese Complex of Ethylenediaminetetraacetic Acid (EDTA)-Benzothiazole Aniline (BTA) Conjugate as a Potential Liver-Targeting MRI Contrast Agent

A novel manganese(II) complex based on an ethylenediaminetetraacetic acid (EDTA) coordination cage bearing a benzothiazole aniline (BTA) moiety (Mn-EDTA-BTA) was designed and synthesized for use as a liver-specific MRI contrast agent with high chelation stability. In addition to forming a hydrophili...

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Bibliographic Details
Published in:Journal of medicinal chemistry 2017-04, Vol.60 (7), p.2993-3001
Main Authors: Islam, Md Kamrul, Kim, Soyeon, Kim, Hee-Kyung, Park, Subin, Lee, Gang-Ho, Kang, Hyo Jeung, Jung, Jae-Chang, Park, Joon-Suk, Kim, Tae-Jeong, Chang, Yongmin
Format: Article
Language:English
Subjects:
Aniline Compounds - chemistry
Aniline Compounds - pharmacokinetics
Animals
Benzothiazoles - chemistry
Benzothiazoles - pharmacokinetics
Cell Line, Tumor
Chelating Agents - chemistry
Chelating Agents - pharmacokinetics
Contrast Media - chemistry
Contrast Media - pharmacokinetics
Coordination Complexes - analogs & derivatives
Coordination Complexes - pharmacokinetics
Edetic Acid - chemistry
Hepatocytes - pathology
Humans
Liver - cytology
Liver - diagnostic imaging
Liver - pathology
Liver Neoplasms - diagnostic imaging
Liver Neoplasms - pathology
Magnetic Resonance Imaging - methods
Male
Manganese - chemistry
Manganese - pharmacokinetics
Mice, Inbred BALB C
Mice, Nude
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Summary:A novel manganese(II) complex based on an ethylenediaminetetraacetic acid (EDTA) coordination cage bearing a benzothiazole aniline (BTA) moiety (Mn-EDTA-BTA) was designed and synthesized for use as a liver-specific MRI contrast agent with high chelation stability. In addition to forming a hydrophilic, stable complex with Mn , this new Mn chelate was rapidly taken up by liver hepatocytes and excreted by the kidneys and biliary system. The kinetic inertness and R relaxivity of the complex were much higher than those of mangafodipir trisodium (MnDPDP), a clinically approved liver-specific MRI contrast agent. The diagnostic utility of this new Mn complex in MRI was demonstrated by high-sensitivity tumor detection in an animal model of liver cancer.
ISSN:0022-2623
1520-4804
DOI:10.1021/acs.jmedchem.6b01799