Potential use of the Diels-Alder reaction in biomedical and nanomedicine applications

被引:23
作者
Oluwasanmi, Adeolu [1 ]
Hoskins, Clare [1 ]
机构
[1] Univ Strathclyde, Dept Pure & Appl Chem, Glasgow G1 1RD, Lanark, Scotland
关键词
Diels-Alder; Drug delivery; Drug release; Intelligent delivery; Triggered release; GOLD NANOPARTICLES; HYDROGELS; MALEIMIDE; CATALYST; POLYMER; CANCER; ACID; CELL; PRESSURE; DESIGN;
D O I
10.1016/j.ijpharm.2021.120727
中图分类号
R9 [药学];
学科分类号
1007 ;
摘要
The Diels-Alder reaction and its retro breakdown has garnered increasing research focus due to several of its advantageous properties including, atomic conservation, reversibility, and substituent retention. This is especially true in biomedical application and nanomedicine development which display a preference for rapid, efficient, and clean "click" chemistry reactions allowing for delivery of active ingredients and subsequent release upon temperature elevation. There are multiple variations on the Diels-Alder reaction based around substitution position and materials being coupled which can affect the temperature threshold for and rate of the retro reaction reversal. Hence, the Diels-Alder reaction offers a simple coupling reaction for active ingredients with tailorable release. In this review the incorporation of the Diels-Alder chemistries and linkers within the biomedical and nanomedicine field will be discussed, as well as its use in future potential technologies.
引用
收藏
页数:12
相关论文
共 87 条
[61]   Immuno-polymeric nanoparticles by Diels-Alder chemistry [J].
Shi, Meng ;
Wosnick, Jordan H. ;
Ho, Karyn ;
Keating, Armand ;
Shoichet, Molly S. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (32) :6126-6131
[62]   Spontaneous formation of functionalized dendrimer-stabilized gold nanoparticles [J].
Shi, Xiangyang ;
Sun, Kai ;
Baker, James R., Jr. .
JOURNAL OF PHYSICAL CHEMISTRY C, 2008, 112 (22) :8251-8258
[63]   Computational Design of an Enzyme Catalyst for a Stereoselective Bimolecular Diels-Alder Reaction [J].
Siegel, Justin B. ;
Zanghellini, Alexandre ;
Lovick, Helena M. ;
Kiss, Gert ;
Lambert, Abigail R. ;
Clair, Jennifer L. St. ;
Gallaher, Jasmine L. ;
Hilvert, Donald ;
Gelb, Michael H. ;
Stoddard, Barry L. ;
Houk, Kendall N. ;
Michael, Forrest E. ;
Baker, David .
SCIENCE, 2010, 329 (5989) :309-313
[64]   Injectable hydrogels with high fixed charge density and swelling. pressure for nucleus pulposus repair: Biomimetic glycosaminoglycan analogues [J].
Sivan, S. S. ;
Roberts, S. ;
Urban, J. P. G. ;
Menage, J. ;
Bramhill, J. ;
Campbell, D. ;
Franklin, V. J. ;
Lydon, F. ;
Merkher, Y. ;
Maroudas, A. ;
Tighe, B. J. .
ACTA BIOMATERIALIA, 2014, 10 (03) :1124-1133
[65]   Diels-Alder "click" reactions: recent applications in polymer and material science [J].
Tasdelen, Mehmet Atilla .
POLYMER CHEMISTRY, 2011, 2 (10) :2133-2145
[66]   Properties of Reversible Diels-Alder Furan/Maleimide Polymer Networks as Function of Crosslink Density [J].
Toncelli, Claudio ;
De Reus, Dennis C. ;
Picchioni, Francesco ;
Broekhuis, Antonius A. .
MACROMOLECULAR CHEMISTRY AND PHYSICS, 2012, 213 (02) :157-165
[67]   Revisiting the Stability of endo/exo Diels-Alder Adducts between Cyclopentadiene and 1,4-benzoquinone [J].
Tormena, Claudio F. ;
Lacerda, Valdemar, Jr. ;
de Oliveira, Kleber T. .
JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY, 2010, 21 (01) :112-118
[68]   Influence of process parameters on surface plasmon resonance characteristics of densely packed gold nanoparticle films grown by pulsed laser deposition [J].
Verma, Shweta ;
Rao, B. Tirumala ;
Rai, Sanjay ;
Ganesan, V. ;
Kukreja, L. M. .
APPLIED SURFACE SCIENCE, 2012, 258 (11) :4898-4905
[69]   How Lewis Acids Catalyze Diels-Alder Reactions [J].
Vermeeren, Pascal ;
Hamlin, Trevor A. ;
Fernandez, Israel ;
Bickelhaupt, F. Matthias .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (15) :6201-6206
[70]   Hydrogels for Protein Delivery [J].
Vermonden, Tina ;
Censi, Roberta ;
Hennink, Wim E. .
CHEMICAL REVIEWS, 2012, 112 (05) :2853-2888