The Diels-Alder reaction: A powerful tool for the design of drug delivery systems and biomaterials

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• 作者：Manuel Gregoritza ; Ferdinand P. Brandl ; ^{ferdinand.brandl@ur.de" class="auth_mail" title="E-mail the corresponding author}
• 关键词：2D ; two-dimensional ; 3D ; three-dimensional ; ATRP ; atom transfer free radical polymerization ; CPP ; cell penetrating peptide ; CuAAC ; copper(I)-catalyzed azide&ndash ; alkyne Huisgen cycloaddition ; DA ; Diels&ndash ; Alder ; DNA ; deoxyribonucleic acid ; ECM ; extracellular matrix ; HA ; hyaluronic acid ; hMSC ; human mesenchymal stem cell ; IEDDA ; inverse electron-demand Diels&ndash ; Alder ; MES ; 2-(N-morpholino)ethanesulfonic acid ; NIR ; near-infrared ; NLS ; nuclear localization sequence ; NMR ; nuclear magnetic res
• 刊名：European Journal of Pharmaceutics and Biopharmaceutics
• 出版年：2015
• 出版时间：November 2015
• 年：2015
• 卷：97
• 期：part_PB
• 页码：438-453
• 全文大小：2537 K

文摘

Click reactions have the potential to greatly facilitate the development of drug delivery systems and biomaterials. These reactions proceed under mild conditions, give high yields, and form only inoffensive by-products. The Diels–Alder cycloaddition is one of the click reactions that do not require any metal catalyst; it is one of the most useful reactions in synthetic organic chemistry and material design. Herein, we highlight possible applications of the Diels–Alder reaction in pharmaceutics and biomedical engineering. Particular focus is placed on the synthesis of polymers and dendrimers for drug delivery, the preparation of functionalized surfaces, bioconjugation techniques, and applications of the Diels–Alder reaction in nanotechnology. Moreover, applications of the reaction for the preparation of hydrogels for drug delivery and tissue engineering are reviewed. A general introduction to the Diels–Alder reaction is presented, along with a discussion of potential pitfalls and challenges. At the end of the article, we provide a set of tools that may facilitate the application of the Diels–Alder reaction to solve important pharmaceutical or biomedical problems.