Lanthanide(III) complexes of pyridine–tetraacetic acid-glycoconjugates: Synthesis and luminescence studies of mono and divalent derivatives

Gouin, Sébastien G.; Roger, Mélissa; Leygue, Nadine; Deniaud, David; Julienne, Karine; Benoist, Éric; Picard, Claude; Kovensky, José; Galaup, Chantal

doi:10.1016/j.bmcl.2012.03.003

Cited by 8 publications

(5 citation statements)

References 33 publications

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“…A bifunctional chelate, 776, was clicked with azido-functionalized carbohydrate cores to afford ligands 777 (Scheme 177). 703 Likewise, Mukhopadhyay and co-workers synthesized sugarbased triazolyl compounds using the "click" methodology and exploited the developed molecules in different carbohydrate− lectin binding studies through fluoresence analysis (Figure 71). The authors found that mannose-containing compounds 781b and 781d gave a positive response with ConA.…”

Section: Carbohydrate Click-to-chelationmentioning

confidence: 99%

Cu-Catalyzed Click Reaction in Carbohydrate Chemistry

et al. 2016

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Cu(I)-catalyzed azide-alkyne 1,3-dipolar cycloaddition (CuAAC), popularly known as the "click reaction", serves as the most potent and highly dependable tool for facile construction of simple to complex architectures at the molecular level. Click-knitted threads of two exclusively different molecular entities have created some really interesting structures for more than 15 years with a broad spectrum of applicability, including in the fascinating fields of synthetic chemistry, medicinal science, biochemistry, pharmacology, material science, and catalysis. The unique properties of the carbohydrate moiety and the advantages of highly chemo- and regioselective click chemistry, such as mild reaction conditions, efficient performance with a wide range of solvents, and compatibility with different functionalities, together produce miraculous neoglycoconjugates and neoglycopolymers with various synthetic, biological, and pharmaceutical applications. In this review we highlight the successful advancement of Cu(I)-catalyzed click chemistry in glycoscience and its applications as well as future scope in different streams of applied sciences.

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Section: Carbohydrate Click-to-chelationmentioning

confidence: 99%

Cu-Catalyzed Click Reaction in Carbohydrate Chemistry

et al. 2016

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“…The synthesis of macrocycles 1 and 2 followed similar procedures to those described previously for the synthesis of MSQs (Scheme 1). 34 Briey, basic hydrolysis of methyl 2,6-bis(azido) isonicotinate 36,37 was followed immediately by reaction of the resulting carboxylic acid with either dioctylamine or dioctadecylamine in the presence of carbodiimide (CDI) to give diazides 4 and 5, respectively. Staudinger reduction of 4 and 5 to form the corresponding diamines 6 and 7 was followed by reaction with two equivalents of diethyl squarate to give disquarates 8 and 9, respectively.…”

Section: Synthesismentioning

confidence: 99%

Extraction and transport of sulfate using macrocyclic squaramide receptors

et al. 2020

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“…The bimetallic dianionic complex 33 (Ln 3+ =Eu 3+ or Tb 3+ ) was designed to accommodate two lanthanide ions, and it showed a fluorescence 2–3 times greater than that of its monovalent glycoconjugates. This finding reveals that labelling glycoconjugates with multivalent lanthanide(III) ions can increase the detection threshold of specifically‐targeted biomolecules, [51] although further biological studies are required to confirm it.…”

Section: Metal Complexes As Cancer Diagnostic Agentsmentioning

confidence: 84%

Glycoconjugated Metal Complexes as Cancer Diagnostic and Therapeutic Agents

et al. 2020

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The possibility of selectively delivering metal complexes to a defined cohort of cells on the basis of their metabolic features is a highly challenging goal, which may be extremely useful for a series of purposes, including diagnosis and therapy of pathological states, such as cancer. Tumor cells display augmented requests for carbohydrates and, in particular, for glucose in order to sustain their high proliferation rate, which causes an increased glycolytic process (Warburg effect). Since several metal complexes display diagnostic and/or therapeutic properties, their conjugation to carbohydrate portions often induce their preferential accumulation in cancer cells, similarly to what is observed with fluorodeoxyglucose (FDG). In this review we have considered the latest developments of glycoconjugates containing metal complexes in their structures. These compounds are classified as diagnostic or therapeutic agents and are further systematically discussed on the basis of the metal atom they contain. Several diagnostic techniques are possible with these probes, since, depending on the metal species included in their structures, they may be employed in nuclear medicine (PET, SPECT), magnetic resonance imaging, luminescence and phosphorescence. At the same time, the lack of selective cytotoxicity displayed by several metal‐based chemotherapeutic agents, may also be solved by the conjugation of these agents to carbohydrate portions. Overall, data so far available reveal the great potential of this chemical class in the early detection and in the cure of severe neoplastic diseases, which still needs to be fully explored in the clinic.

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Lanthanide(III) complexes of pyridine–tetraacetic acid-glycoconjugates: Synthesis and luminescence studies of mono and divalent derivatives

Cited by 8 publications

References 33 publications

Cu-Catalyzed Click Reaction in Carbohydrate Chemistry

Cu-Catalyzed Click Reaction in Carbohydrate Chemistry

Extraction and transport of sulfate using macrocyclic squaramide receptors

Glycoconjugated Metal Complexes as Cancer Diagnostic and Therapeutic Agents

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