Efficient Multigram Synthesis of the Bifunctional Chelating Agent (<i>S</i>)-1-<i>p</i>-Isothiocyanatobenzyl-diethylene- tetramine pentaacetic Acid

Corson, Donald T; Meares, Claude F.

doi:10.1021/bc000020q

Cited by 5 publications

(8 citation statements)

References 6 publications

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“…Isothiocyanates may not be suitable for modifying biomolecules sensitive to alkaline pH conditions. Aromatic isothiocyanates are often used to conjugate biomolecules onto DTPA and DOTA analogs [252][253][254][255]260,[277][278][279]].…”

Section: Isothiocynatesmentioning

confidence: 99%

Bifunctional coupling agents for radiolabeling of biomolecules and target-specific delivery of metallic radionuclides

Liu

2008

Advanced Drug Delivery Reviews

372

339

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Receptor-based radiopharmaceuticals are of great current interest in molecular imaging and radiotherapy of cancers, and provide a unique tool for target-specific delivery of radionuclides to the diseased tissues. In general, a target-specific radiopharmaceutical can be divided into four parts: targeting biomolecule (BM), pharmacokinetic modifying (PKM) linker, bifunctional coupling or chelating agent (BFC), and radionuclide. The targeting biomolecule serves as a "carrier" for specific delivery of the radionuclide. PKM linkers are used to modify radiotracer excretion kinetics. BFC is needed for radiolabeling of biomolecules with a metallic radionuclide. Different radiometals have significant difference in their coordination chemistry, and require BFCs with different donor atoms and chelator frameworks. Since the radiometal chelate can have a significant impact on physical and biological properties of the target-specific radiopharmaceutical, its excretion kinetics can be altered by modifying the coordination environment with various chelators or coligand, if needed. This review will focus on the design of BFCs and their coordination chemistry with technetium, copper, gallium, indium, yttrium and lanthanide radiometals.

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Section: Isothiocynatesmentioning

confidence: 99%

Bifunctional coupling agents for radiolabeling of biomolecules and target-specific delivery of metallic radionuclides

Liu

2008

Advanced Drug Delivery Reviews

372

339

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“…a) HCl, MeOH 88–97% yield; b) ethylenediamine, TEA, 88–95% yield; c) BH 3 , THF 34–96% yield; d) BrCH 2 COOH, KOH, 35% yield; e) Pd/C, H 2 pH=10, yield not given; f) CSCl 2 , yield not given; g) BrCH 2 COO t -Bu, 71–94% yield; h) Pd/C, H 2 , EtOAc, 90–99% yield, i) HCl (aq) or TFA, 95–100% yield; Refs. [195, 198–200]…”

Section: Methodsmentioning

confidence: 99%

“…The same procedure has been adapted, substituting the appropriate branched 1,2 diamine for ethylenediamine, to produce p -SCN-Bz-DTPA derivatives containing methyl substituents on the backbone in order to investigate more rigid and kinetically inert ligands (Chart 5) [195, 199]. Brechbiel’s procedure was slightly modified by Cummins et al [195] and later adapted to a multigram scale by Corson and Meares [200] (Scheme 8, path B). The main difference was that the carboxymethylation step was performed with t -Bu bromoacetate to avoid the lengthy purification of the highly polar compound 49 .…”

Section: Dtpa Derivativesmentioning

confidence: 99%

Strategies for the Preparation of Bifunctional Gadolinium(III) Chelators

Frullano

Caravan²

2011

COS

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The development of gadolinium chelators that can be easily and readily linked to various substrates is of primary importance for the development high relaxation efficiency and/or targeted magnetic resonance imaging (MRI) contrast agents. Over the last 25 years a large number of bifunctional chelators have been prepared. For the most part, these compounds are based on ligands that are already used in clinically approved contrast agents. More recently, new bifunctional chelators have been reported based on complexes that show a more potent relaxation effect, faster complexation kinetics and in some cases simpler synthetic procedures. This review provides an overview of the synthetic strategies used for the preparation of bifunctional chelators for MRI applications.

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“…Complexes 1* 25 and 5 26 were synthesized following previously published procedures. Compound 7 was converted to compound 8 by following previously published procedures.…”

Section: Methodsmentioning

confidence: 99%

Quantitative Imaging of Cell-Permeable Magnetic Resonance Contrast Agents Using X-Ray Fluorescence

et al. 2006

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The inability to transduce cellular membranes is a limitation of current magnetic resonance imaging probes used in biologic and clinical settings. This constraint confines contrast agents to extracellular and vascular regions of the body, drastically reducing their viability for investigating processes and cycles in developmental biology. Conversely, a contrast agent with the ability to permeate cell membranes could be used in visualizing cell patterning, cell fate mapping, gene therapy, and, eventually, noninvasive cancer diagnosis. Therefore, we describe the synthesis and quantitative imaging of four contrast agents with the capability to cross cell membranes in sufficient quantity for detection. Each agent is based on the conjugation of a Gd(III) chelator with a cellular transduction moiety. Specifically, we coupled Gd(III)-diethylenetriaminepentaacetic acid DTPA and Gd(III)-1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetic acid with an 8-amino acid polyarginine oligomer and an amphipathic stilbene molecule, 4-amino-49-(N,Ndimethylamino)stilbene. The imaging modality that provided the best sensitivity and spatial resolution for direct detection of the contrast agents is synchrotron radiation x-ray fluorescence (SR-XRF). Unlike optical microscopy, SR-XRF provides two-dimensional images with resolution 10 3 better than 153Gd gamma counting, without altering the agent by organic fluorophore conjugation. The transduction efficiency of the intracellular agents was evaluated by T 1 analysis and inductively coupled plasma mass spectrometry to determine the efficacy of each chelate-transporter combination.

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Efficient Multigram Synthesis of the Bifunctional Chelating Agent (S)-1-p-Isothiocyanatobenzyl-diethylene- tetramine pentaacetic Acid

Cited by 5 publications

References 6 publications

Bifunctional coupling agents for radiolabeling of biomolecules and target-specific delivery of metallic radionuclides

Bifunctional coupling agents for radiolabeling of biomolecules and target-specific delivery of metallic radionuclides

Strategies for the Preparation of Bifunctional Gadolinium(III) Chelators

Quantitative Imaging of Cell-Permeable Magnetic Resonance Contrast Agents Using X-Ray Fluorescence

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