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

Abstract

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.

Functional Polyion Complex Vesicles Enabled by Supramolecular Reversible Coordination Polyelectrolytes

“…[17] As such, it presents an alternative for gadoliniumbased contrast agents which have lately been under scrutiny because of increased safety concerns regarding nephrogenic systemic fibrosis (NSF) problems. [18] Thel ongitudinal relaxivity,d efined as r 1 = [(1/T 1 )À(1/T 1,0 )]/y Mn ,( where C Mn is the manganese concentration, and T 1 and T 1,0 are the longitudinal relaxation times of the vesicle solution and pure water, respectively) is about 4.3 mm À1 s À1 ,w hich is comparable with other reported Mn-based MR contrast agents [19] (Figure 4a).…”

Thiazole Moiety: An Interesting Scaffold for Developing New Antitumoral Compounds

“…Other metal complexes and applications: Manganese is a metal that plays a critical role in cell development, and it is required for mitochondrial function. As novelty, Islam et al [54] have described a new Mn-EDTA complex (compound 19 in Figure 5) incorporating a benzothiazole that has been investigated as potential agents for diagnosis of liver cancer by magnetic resonance.…”

Functional Polyion Complex Vesicles Enabled by Supramolecular Reversible Coordination Polyelectrolytes

“…As such, it presents an alternative for gadolinium‐based contrast agents which have lately been under scrutiny because of increased safety concerns regarding nephrogenic systemic fibrosis (NSF) problems . The longitudinal relaxivity, defined as r 1 =[(1/ T 1 )−(1/ T 1,0 )]/y Mn , (where C Mn is the manganese concentration, and T 1 and T 1,0 are the longitudinal relaxation times of the vesicle solution and pure water, respectively) is about 4.3 m m −1 s −1 , which is comparable with other reported Mn‐based MR contrast agents (Figure a). The in vitro MR image of the solution with Mn‐based vesicles shows a significantly enhanced contrast compared to pure water, demonstrating their potential as MR imaging contrast agents.…”