A convenient synthesis of 6,6′-dimethyl-2,2′-bipyridine-4-ester and its application to the preparation of bifunctional lanthanide chelators

Havas, F.; Mathieu, Daniel; Galaup, Chantal; Tisnès, P.; Picard, Claude

doi:10.1016/j.tetlet.2006.12.012

Cited by 17 publications

(8 citation statements)

References 30 publications

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“…BPCA is an interesting chelator that was published in 2010, which is based on a 2,2 0 -bipyridine backbone, and provides an octadentate N 4 O 4 donor set (Table 10). 277,278 BPCA was conjugated to a novel cholecystokinin C-terminal tetrapeptide (CCK4), which targets tumors expressing the cholecystokinin receptor subtype 2 (CCK2R), and radiolabeled with 111 In in high RCY after 1 hour at room temperature. The novel peptideconjugate BPCA-(Ahx) 2 -CCK4 was evaluated in vitro by serum stability transchelation assays, and in vivo by biodistribution and planar scintigraphy experiments.…”

Section: Bpcamentioning

confidence: 99%

Matching chelators to radiometals for radiopharmaceuticals

2014

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Radiometals comprise many useful radioactive isotopes of various metallic elements. When properly harnessed, these have valuable emission properties that can be used for diagnostic imaging techniques, such as single photon emission computed tomography (SPECT, e.g.(67)Ga, (99m)Tc, (111)In, (177)Lu) and positron emission tomography (PET, e.g.(68)Ga, (64)Cu, (44)Sc, (86)Y, (89)Zr), as well as therapeutic applications (e.g.(47)Sc, (114m)In, (177)Lu, (90)Y, (212/213)Bi, (212)Pb, (225)Ac, (186/188)Re). A fundamental critical component of a radiometal-based radiopharmaceutical is the chelator, the ligand system that binds the radiometal ion in a tight stable coordination complex so that it can be properly directed to a desirable molecular target in vivo. This article is a guide for selecting the optimal match between chelator and radiometal for use in these systems. The article briefly introduces a selection of relevant and high impact radiometals, and their potential utility to the fields of radiochemistry, nuclear medicine, and molecular imaging. A description of radiometal-based radiopharmaceuticals is provided, and several key design considerations are discussed. The experimental methods by which chelators are assessed for their suitability with a variety of radiometal ions is explained, and a large selection of the most common and most promising chelators are evaluated and discussed for their potential use with a variety of radiometals. Comprehensive tables have been assembled to provide a convenient and accessible overview of the field of radiometal chelating agents.

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Section: Bpcamentioning

confidence: 99%

Matching chelators to radiometals for radiopharmaceuticals

2014

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“…113 Some single examples for the synthesis of 2,2 0 -bipyridines for different purposes utilising the Negishi cross-coupling approach have been recorded during the last couple years and should be cited here. [115][116][117][118] The use of heterogeneous catalysts and microwave heating in the Negishi coupling was investigated very recently and interestingly found to proceed within short reaction times. 119 However, the investigation of the functionalised 2,2 0 -bipyridines was limited to methyl substitution.…”

Section: General Considerationsmentioning

confidence: 99%

Versatile tools in the construction of substituted 2,2′-bipyridines—cross-coupling reactions with tin, zinc and boron compounds

2008

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2,2'-Bipyridines are among the most widely used classes of chelating ligands that have found applications in the fields of coordination chemistry, supra-, nano- and macromolecular chemistry, analytical and photochemistry, but also in asymmetric synthesis and natural product chemistry. Hence, there is a huge demand for efficient synthetic approaches to functionalized derivatives. Modern cross-coupling procedures have been proven to be particularly effective in this context. This critical review will give an overview about the advances made so far focussing mainly on cross-coupling reactions with tin, zinc and boron compounds for the achievement of interesting, versatile and unusual substitution patterns (156 references).

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“…From a chemical perspective, the macrobicyclic cryptand scaffold has been varied quite extensively by the replacement of the 2,2′-bipyridine moieties with other biaryl motifs such as isoquinolines, pyridine- N -oxide, or other common nitrogen-based heterocycles (Figure ). , …”

Section: Introductionmentioning

confidence: 99%

“…Representative examples of aromatic building blocks A – L for cryptate construction reported in the literature. , …”

Section: Introductionmentioning

confidence: 99%

Long Wavelength Excitation of Europium Luminescence in Extended, Carboline-Based Cryptates

et al. 2018

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Two new β-carboline-based tris(biaryl) europium cryptates are introduced. The extended antenna moiety incorporated into the cryptand frameworks enables the sensitization of europium emission with excitation wavelengths well above 450 nm. In aqueous solution, the cryptates show great complex stability, luminescence lifetimes around 0.5 ms, and absolute quantum yields of ca. 3%. In addition, the europium luminescence shows a well-defined pH-dependence in the physiologically interesting pH range 7-9.

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A convenient synthesis of 6,6′-dimethyl-2,2′-bipyridine-4-ester and its application to the preparation of bifunctional lanthanide chelators

Cited by 17 publications

References 30 publications

Matching chelators to radiometals for radiopharmaceuticals

Matching chelators to radiometals for radiopharmaceuticals

Versatile tools in the construction of substituted 2,2′-bipyridines—cross-coupling reactions with tin, zinc and boron compounds

Long Wavelength Excitation of Europium Luminescence in Extended, Carboline-Based Cryptates

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