Strategies for the Preparation of Bifunctional Gadolinium(III) Chelators

Frullano, Luca; Caravan, Peter

doi:10.2174/157017911796117250

Cited by 53 publications

(30 citation statements)

References 169 publications

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“…Of the methods reported for the preparation of DOTA monoamides, 25 two are well suited for large-scale synthesis. The first involves monoalkylation of 1,4,7,10-tetraazacyclododecane (cyclen, 9 ) with an α-bromoacetamide, followed by incorporation of three acetate ester arms (methyl, ethyl, or tert -butyl) and their subsequent hydrolysis or cleavage to afford the DOTA monoamide.…”

Section: Resultsmentioning

confidence: 99%

Improved Synthesis of 10-(2-Alkylamino-2-oxoethyl)-1,4,7,10-tetraazacyclododecane-1,4,7-triacetic Acid Derivatives Bearing Acid-Sensitive Linkers

Jagadish

Ozumerzifon

Roberts

et al. 2013

Synthetic Communications

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Alkylation of the hydrobromide salts of 1,4,7-tris(methoxycarbonylmethyl)-1,4,7,10-tetraazacyclododecane and 1,4,7-tris(ethoxycarbonylmethyl)-1,4,7,10-tetraazacyclododecane with appropriate α-bromoacetamides, followed by hydrolysis, provides convenient access to 10-(2-alkylamino-2-oxoethyl)-1,4,7,10-tetraazacyclododecane-1,4,7-triacetic acid derivatives that contain acid-sensitive functional groups. The utility of the method is demonstrated by improved syntheses of two known DOTA monoamides bearing acid-sensitive ω-tritylthio alkyl chains in much higher yields based on cyclen as the starting material.

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Section: Resultsmentioning

confidence: 99%

Improved Synthesis of 10-(2-Alkylamino-2-oxoethyl)-1,4,7,10-tetraazacyclododecane-1,4,7-triacetic Acid Derivatives Bearing Acid-Sensitive Linkers

Jagadish

Ozumerzifon

Roberts

et al. 2013

Synthetic Communications

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“…Such ligands contain not only the chelating unit, but also another reactive functionality suitable for the conjugation. The topic of polyaminopolycarboxylic bifunctional ligands is very broad and has been recently reviewed [407,408]. Here, we only present representative examples of the bifunctional ligands and conjugation strategies utilized in the frame of MRI research.…”

Section: Bifunctional Ligands and Their Conjugationsmentioning

confidence: 99%

Synthesis and Characterization of Ligands and their Gadolinium(III) Complexes

Kotek¹,

Kubíček²,

Hermann³

et al. 2013

The Chemistry of Contrast Agents in Medical Magnetic Resonance Imaging

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“…The first macrocyclic MRI contrast agent (CA) approved for commercial use in Europe was Gd‐DOTA under the name Dotarem ® in 1988. The rigidity and the preorganization provided by the macrocyclic ring, as well as the good correspondence between the macrocyclic cavity and the Gd(III) ionic radius are reflected in its kinetic stability ,. Furthermore, DOTA derivatives are exploited in SPECT (single photon emission computed tomography) and PET (positron emission tomography) imaging modalities by complexing radiotracers.…”

Section: Introductionmentioning

confidence: 99%

Importance of DOTA derivatives in bimodal imaging

Chilla

Henoumont

Elst

et al. 2017

Israel Journal of Chemistry

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The clinical applications of multimodal probes are numerous since a few decades. 1,4,7,10‐tetraazacyclododecane‐1,4,7,10‐tetraacetic acid (DOTA) has played an important role in diagnostic and therapeutic areas. The vast applications of DOTA as chelator have been explored in magnetic resonance imaging (MRI) and in radioisotope chemistry. Moreover, the possibility to functionalize the macrocycle with pendant arms has allowed to explore new functionalities as bimodal imaging agents. Different combinations are possible between the different possible imaging techniques like Magnetic Resonance Imaging, Positron Emission Tomography (PET), Single Photon Emission Computed Tomography (SPECT), and Optical imaging (OI). The main use of DOTA and its derivatives was for MRI as gadolinium complexes. It was then further extended to the complexation with europium or terbium for optical imaging. Although other chelates are available such as DTPA or NOTA, derivatives of DOTA were often the primary choice due to their versatility. DOTA derivatives can indeed also be complexed with radioisotopes and conjugated to peptides which leads to targeted contrast agents for PET or SPECT. Depending on the chosen imaging modality, a variety of radiometals can be complexed with DOTA, e.i. 64Cu and 68Ga for PET, or 111In and 90Y for SPECT. Conjugation of chromophores to gadolinium complexes of DOTA derivatives can also lead to bimodal agents for MRI and OI. In this review, we will provide the applications of DOTA and its derivatives in different imaging modalities and their clinical applications.

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Strategies for the Preparation of Bifunctional Gadolinium(III) Chelators

Cited by 53 publications

References 169 publications

Improved Synthesis of 10-(2-Alkylamino-2-oxoethyl)-1,4,7,10-tetraazacyclododecane-1,4,7-triacetic Acid Derivatives Bearing Acid-Sensitive Linkers

Improved Synthesis of 10-(2-Alkylamino-2-oxoethyl)-1,4,7,10-tetraazacyclododecane-1,4,7-triacetic Acid Derivatives Bearing Acid-Sensitive Linkers

Synthesis and Characterization of Ligands and their Gadolinium(III) Complexes

Importance of DOTA derivatives in bimodal imaging

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