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Termoczułe poli(metakrylany glikoli oligoetylenowych) i ich biokoniugaty – synteza i zachowanie w roztworze

Szweda D., Szweda R., Dworak A., Trzebicka B.

Polimery

2017

T. 62, nr 4

298--310

Growing interest for polymers containing oligoethylene side groups was observed within last years. Amongst these polymers the poly[oligo(ethylene glycol) methacrylate]s (POEGMAs) became most important. These polymers are biocompatible. Many of these polymers are thermoresponsive, when dissolved in water or physiological media, exhibit a narrow phase transition range and show only a small hysteresis. This review describes the synthesis and self-organization of homo- and copolymers of POEGMAs of different macromolecular topology. Data about the synthesis of thermoresponsive conjugates of POEGMAs with biologically active species and the possibility to use such conjugates for the synthesis of nanocarriers are discussed.

W ciągu ostatnich kilkunastu lat znacząco wzrosło zainteresowanie polimerami zawierającymi boczne łańcuchy glikolu oligoetylenowego. Wśród polimerów tego typu największe znaczenie uzyskały poli(metakrylany glikoli oligoetylenowych) (POEGMA). Polimery te są biokompatybilne. Wiele z polimerów POEGMA wykazuje termoczułość w roztworach wodnych i wpłynie fizjologicznym, a ich przejście fazowe jest wąskie i charakteryzuje się nieznaczną histerezą. Przegląd obejmuje syntezę i samoorganizację homo- i kopolimerów POEGMA o różnej topologii makrocząsteczek. Zawiera także dane o otrzymywaniu termoczułych koniugatów POEGMA z substancjami aktywnymi biologicznie i możliwość wykorzystania takich biokoniugatów do otrzymywania nanonośników.

Wykorzystanie reakcji 1,3-dipolarnej cykloaddycji Huisgena do modyfikacji nukleozydów i ligonukleotydów

Radzikowska E.

Wiadomości Chemiczne

2011

[Z] 65, 3-4

207-234

The 1,3-dipolar cycloaddition reaction between azides and terminal alkynes, known as the Huisgen reaction, constitutes a powerful tool for the synthesis of versatile molecules containing carbon – heteroatom bond. The use of a copper(I) salt in this reaction allowed Sharpless to develop the concept of „click chemistry” [1]. This strategy is based on reactions between small units characterized by mild reaction conditions, versatility, high yields and stereospecificity. The chemistry of nucleic acids and nucleoside analogues is undergoing rapid developments and numerous compounds from these classes of compounds are used in medicinal treatment. Analogues of nucleoside constitute a class of drugs that possesses either anticancer or/and antiviral activity (against HIV, HSV, VZV or HCV viruses) [3]. Many modified oligonucleotides show biological activity. As potential drugs oligonucleotides are employed in antisense, antigen and aptamer strategies. An antisense therapeutic agent acts on the pathogenic mRNA causing inactivation of the target whereas an antigen agent acts on DNA and aptamer on unwanted protein. It is not surprising that number of research groups are trying to join the concept of click chemistry with nucleic acids chemistry. In this way, it is possible to obtain new molecules like base- or sugar-modified nucleosides, nucleosides, bioconjugates and olignucleotides. The copper-catalyzed 1,3-dipolar cycloaddition CuAAC allows to functionalize DNA, for example by labelling it through attaching small molecules to DNA. Two general strategies have been developed for this purpose: presynthetic and postsynthetic labelling. In the presynthetic method nucleotide monomers are labelled before DNA synthesis and purification. In the postsynthetic strategy DNA containing small reactive groups is synthesized first and then it is conjugated with the desired molecules. CuAAC is also a convenient method for the synthesis of modified oligonucleotides in which phosphodiester linkage is replaced by 1,2,3- -triazole or for a solid phase synthesis. Such molecules appear to be useful in medicine, molecular diagnostic (e.g. fluorescent dyes) or mechanistic molecular model in the future.