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2.B.60. The Interlocked Catenane/Rotaxane/Polyrotaxane (ICRP) Family

Due to their low cytotoxicity, controllable size, and unique architecture, cyclodextrin (CD)-based polyrotaxanes and polypseudorotaxanes have been considered for functions such as drug delivery, gene delivery, and tissue engineering (Li et al. 2011). CD-based biodegradable polypseudorotaxane hydrogels have been used as injectable drug delivery systems for sustained and controlled drug release. Polyrotaxanes with drug or ligand-conjugated CDs threaded on a polymer chain with biodegradable end groups may be useful for controlled, multivalent targeting delivery. Cationic polyrotaxanes consisting of multiple oligoethylenimine-grafted CDs threaded on a block copolymer chain are attractive non-viral gene carries due to the strong DNA-binding ability, low cytotoxicity, and high gene transfection efficiency. Cytocleavable end caps have been introduced in the polyrotaxane systems in order to ensure efficient endosomal escape for intracellular trafficking of DNA (Li et al. 2011).

DNA-based machines include transporters and interlocked cyclic DNA structures acting as reconfigurable catenanes, rotaxanes, and rotors (Wang et al. 2014). Interlocked circular DNA nanostructures, e.g., catenanes or rotaxanes, have been used for these and other functions (Lu et al. 2016). Naphthalene diimides (NDIs) have applications as biological sensors, molecular switching devices such as catenanes and rotaxanes and ligand-gated ion-channels (Kobaisi et al. 2016). Photoinduced electron transfer can occur in multiporphyrinic interlocked structures (Flamigni et al. 2004), and charge transfer through switchable interlinked molecules such as catenanes and rotaxanes can also occur (Jan van der Molen and Liljeroth 2010; Yang et al. 2012). Transition metal-complexed catenanes and rotaxanes are dynamic systems that can function as molecular machines (Durot et al. 2014), and interlocked cyclic DNA structures can act as reconfigurable catenanes and rotaxanes (Wang et al. 2014). Interlocked systems, rotaxanes and catenanes, have been incorporated into nanomedicine chemical platforms (Ornelas-Megiatto et al. 2015), and used as drug transporters (Wang et al. 2014; Casas-Hinestroza et al. 2019). Rotaxanes, pseudorotaxanes, and catenanes are supramolecular complexes with potential use in nanomachinery, molecular computing, and single-molecule studies and have been used to translocate proteins across ClyA nanopores (Biesemans et al. 2015). The rotaxanes described here may be structurally related to those in TC family 2.B.32.

 

References associated with 2.B.60 family:

Biesemans, A., M. Soskine, and G. Maglia. (2015). A Protein Rotaxane Controls the Translocation of Proteins Across a ClyA Nanopore. Nano Lett 15: 6076-6081. 26243210
Casas-Hinestroza, J.L., M. Bueno, E. Ibáñez, and A. Cifuentes. (2019). Recent advances in mass spectrometry studies of non-covalent complexes of macrocycles - A review. Anal Chim Acta 1081: 32-50. 31446962
Durot, S., V. Heitz, A. Sour, and J.P. Sauvage. (2014). Transition-metal-complexed catenanes and rotaxanes: from dynamic systems to functional molecular machines. Top Curr Chem 354: 35-70. 24563013
Flamigni, L., A.M. Talarico, J.C. Chambron, V. Heitz, M. Linke, N. Fujita, and J.P. Sauvage. (2004). Photoinduced electron transfer in multiporphyrinic interlocked structures: the effect of copper(I) coordination in the central site. Chemistry 10: 2689-2699. 15195300
Jan van der Molen, S. and P. Liljeroth. (2010). Charge transport through molecular switches. J Phys Condens Matter 22: 133001. 21389503
Kobaisi, M.A., S.V. Bhosale, K. Latham, A.M. Raynor, and S.V. Bhosale. (2016). Functional Naphthalene Diimides: Synthesis, Properties, and Applications. Chem Rev 116: 11685-11796. 27564253
Li, J.J., F. Zhao, and J. Li. (2011). Polyrotaxanes for applications in life science and biotechnology. Appl. Microbiol. Biotechnol. 90: 427-443. 21360153
Lu, C.H., A. Cecconello, and I. Willner. (2016). Recent Advances in the Synthesis and Functions of Reconfigurable Interlocked DNA Nanostructures. J. Am. Chem. Soc. 138: 5172-5185. 27019201
Ornelas-Megiatto, C., T.B. Becher, and J.D. Megiatto, Jr. (2015). Interlocked systems in nanomedicine. Curr Top Med Chem 15: 1236-1256. 25858133
Wang, F., B. Willner, and I. Willner. (2014). DNA-based machines. Top Curr Chem 354: 279-338. 24647836
Yang, W., Y. Li, H. Liu, L. Chi, and Y. Li. (2012). Design and assembly of rotaxane-based molecular switches and machines. Small 8: 504-516. 22267051