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Chemia bioortogonalna – użyteczne narzędzie badania procesów wewnątrzkomórkowych

Latos Krystian

Wiadomości Chemiczne

2022

[Z] 76, 1-2

79--95

Bioorthogonal chemistry is a rapidly developing field of science operating on the border of chemistry and biology. Its initial goal was to study metabolism and imaging using fluorescently labelled compounds. Due to recent advances, bioorthogonal chemistry can also be used to engineer therapeutic bioconjugates. By using a combination of bioconjugation and advanced omics techniques, it is possible to study and modify complex interactions inside living cells. In the relatively short time since its introduction, bioorthogonal chemistry has found many applications. In nucleic acid research, it is used for labelling, e.g. with biotin, to facilitate detection, immobilization, and purification. Additionally, thanks to the use of fluorescent nucleoside analogues, it can be used to study the interaction and dynamics of nucleic acids. For the study of proteins, bioorthogonal chemistry is an invaluable tool for studying conformation, as well as intramolecular and intermolecular interactions. Using techniques such as PET and FRET it is possible to take a closer look at the structure of proteins, which has a significant impact on their functionality. By using biarsenical dyes, interactions between proteins are tracked. This is used in the study of protein aggregation in diseases such as Alzheimer's, Huntington's, and prion diseases. Thanks to this, it becomes possible to understand the mechanism and pathology of these diseases. In biosensing, the elements of bioorthogonal chemistry have been used in a variety of tests and imaging methods. In the end, methods for testing glycan are presented. The advantage of bioorthogonal methods is that they allow labelling on the whole cell or lysate. This application in glycoproteomics is extremely important due to the fact that changes in glycosylation occur during disease states.

Chemia bioortogonalna : nowa perspektywa dla chemii organicznej

Miszczak K.

Wiadomości Chemiczne

2018

[Z] 72, 9-10

703--722

This work is about bioorthogonal chemistry as a chemistry of reactions taking place in the living, in particular human, organism environment. In the search for reactions that can occur under conditions, the focus is mainly on the reactions of molecules that do not occur naturally in the body. Then, to have any application, generally for the purpose of using this reactions to locate the accumulation spotes of the selected substance, one molekule is covalently bonded to the biomarker molecule, the second binds to the indicator molecule, which is frequently fluorescein. Among a numerous examples of reactions that were designed during the short history of bioorthogonal chemistry, there are mainly reactions involving organic azides, which are not naturalny present in the human body. An example of such a reaction is the Staudinger ligation. Subsequent modifications include mainly the 1,3-dipolar addition of azides to alkynes, catalyzed by copper(I) ions. The instability and toxicity of this catalyst has forced further innovations in bioorthogonal reactions. One of them is the use of alkynes with high angular stress, which causes a significant reduction in the activation energy of the process, that it is unnecessary to use a catalyst. Another example of the bioorthogonal reactions are Diels-Alder reactions. The interest in these reactions is not diminishing for several reasons. One of them is the fact that as a result of a simple reaction two new carbon-carbon bonds (or others, for the HDA reaction) occur. Furthermore, many of these reactions occur at standard temperature, without additional heating. Moreover, the possibility of numerous modifications of the skeleton and functional groups and the substituents of dienes and dienophils facilitates carrying out these reactions in the aquatic environment. At the end, the article presents examples of the application of cyclooaddition reactions in bioorthogonal chemistry.