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1.
Top Curr Chem (Cham) ; 382(1): 2, 2023 Dec 16.
Article in English | MEDLINE | ID: mdl-38103067

ABSTRACT

While bioorthogonal reactions are routinely employed in living cells and organisms, their application within individual organelles remains limited. In this review, we highlight diverse examples of bioorthogonal reactions used to investigate the roles of biomolecules and biological processes as well as advanced imaging techniques within cellular organelles. These innovations hold great promise for therapeutic interventions in personalized medicine and precision therapies. We also address existing challenges related to the selectivity and trafficking of subcellular dynamics. Organelle-targeted bioorthogonal reactions have the potential to significantly advance our understanding of cellular organization and function, provide new pathways for basic research and clinical applications, and shape the direction of cell biology and medical research.


Subject(s)
Organelles , Organelles/chemistry , Cell Biology
2.
Chemistry ; 27(41): 10488, 2021 Jul 21.
Article in English | MEDLINE | ID: mdl-34180093

ABSTRACT

Invited for the cover of this issue is Kamil Parkan and co-workers at University of Chemistry and Technology and Institute of Organic Chemistry and Biochemistry, Prague. The cover graphic depicts a schematic representation of the assembly of aryl-C-glycosides based on a protecting-group-free Hiyama reaction. Read the full text of the article at 10.1002/chem.202101052.


Subject(s)
Benzhydryl Compounds , Glucosides , Chemistry, Organic , Glycosides , Humans
3.
Chemistry ; 27(41): 10583-10588, 2021 Jul 21.
Article in English | MEDLINE | ID: mdl-34048112

ABSTRACT

Access to unprotected (hetero)aryl pseudo-C-glucosides via a mild Pd-catalysed Hiyama cross-coupling reaction of protecting-group-free 1-diisopropylsilyl-d-glucal with various (hetero)aryl halides has been developed. In addition, selected unprotected pseudo-C-glucosides were stereoselectively converted into the corresponding α- and ß-C-glucosides, as well as 2-deoxy-ß-C-glucosides. This methodology was applied to the efficient and high-yielding synthesis of dapagliflozin, a medicament used to treat type 2 diabetes mellitus. Finally, the versatility of our methodology was proved by the synthesis of other analogues of dapagliflozin.


Subject(s)
Diabetes Mellitus, Type 2 , Benzhydryl Compounds , Catalysis , Diabetes Mellitus, Type 2/drug therapy , Glucosides , Humans
4.
Chempluschem ; 85(8): 1669-1675, 2020 08.
Article in English | MEDLINE | ID: mdl-32757364

ABSTRACT

Bioorthogonal cleavage reactions are gaining popularity in chemically inducible prodrug activation and in the control of biomolecular functions. Despite similar applications, these reactions were developed and optimized on different substrates and under different experimental conditions. Reported herein is a side-by-side comparison of palladium-, ruthenium- and tetrazine-triggered release reactions, which aims at comparing the reaction kinetics, efficiency and overall advantages and limitations of the methods. In addition, we disclose the possibility of mutual combination of the cleavage reactions. Finally, we compare the efficiency of the bioorthogonal deprotections in cellular experiments, which revealed that among the three methods investigated, the palladium- and the tetrazine-promoted reaction can be used for efficient prodrug activation, but only the tetrazine-triggered reactions proceed efficiently inside cells.


Subject(s)
Heterocyclic Compounds/chemistry , Metals/chemistry , Transition Elements/chemistry , Cell Line, Tumor , Fluorescent Dyes/chemistry , Humans , Inhibitory Concentration 50
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