rotaxanes

Summary

Summary: Complex compounds in which a dumbbell shaped molecule is encircled by a macrocycle. They are named after rota (wheel) and axis (axle). Notation with a prefix is used to indicate the number of interlocked components. They have potential use in NANOTECHNOLOGY. Rotaxanes have been made with CYCLODEXTRINS and CYCLIC ETHERS.

Top Publications

  1. Li J, Loh X. Cyclodextrin-based supramolecular architectures: syntheses, structures, and applications for drug and gene delivery. Adv Drug Deliv Rev. 2008;60:1000-17 pubmed publisher
  2. Smukste I, Smithrud D. Structure-function relationship of amino acid-[2]rotaxanes. J Org Chem. 2003;68:2547-58 pubmed
    Synthetic methodology was developed to construct amino acid-[2]rotaxanes that have phenylalanine and 3,5-di-tert-butylbenzene as blocking groups and dibenzo-24-crown-8, derivatized with either N-acetylargininyl or a carboxylic group, as ..
  3. Ugajin K, Takahashi E, Yamasaki R, Mutoh Y, Kasama T, Saito S. Synthesis of [2]rotaxanes by the copper-mediated threading reactions of aryl iodides with alkynes. Org Lett. 2013;15:2684-7 pubmed publisher
    ..the macrocyclic phenanthroline-copper(I) complex is utilized for the Sonogashira-type reaction to synthesize [2]rotaxanes. Thus, [2]rotaxanes were prepared by reactions between terminal alkynes and aryl iodides in the presence of the ..
  4. Movsisyan L, Kondratuk D, Franz M, Thompson A, Tykwinski R, Anderson H. Synthesis of polyyne rotaxanes. Org Lett. 2012;14:3424-6 pubmed publisher
    Active-metal templating has been used to synthesize rotaxanes consisting of a phenanthroline-based macrocycle threaded around a C8, C12, or C20 polyyne chain. The crystal structure of the C12 rotaxane has been determined...
  5. Choudhary U, Northrop B. Rotaxanes and biofunctionalized pseudorotaxanes via thiol-maleimide click chemistry. Org Lett. 2012;14:2082-5 pubmed publisher
    Base-catalyzed thiol-maleimide click chemistry has been applied to the synthesis of neutral donor-acceptor [2]rotaxanes in good yield...
  6. Berná J, Alajarin M, Orenes R. Azodicarboxamides as template binding motifs for the building of hydrogen-bonded molecular shuttles. J Am Chem Soc. 2010;132:10741-7 pubmed publisher
    ..shown to act as new templates for the assembly of unprecedented azo-functionalized hydrogen-bond-assembled [2]rotaxanes. Moreover, these binding sites can be reversibly and efficiently interconverted with their hydrazo forms through ..
  7. Cooke G, Garety J, Jordan B, Kryvokhyzha N, Parkin A, Rabani G, et al. Flavin-based [2]rotaxanes. Org Lett. 2006;8:2297-300 pubmed
    reaction: see text] We report the synthesis of flavin-stoppered hydrogen bonded [2]rotaxanes 1 and 2...
  8. Li J, Ni X, Zhou Z, Leong K. Preparation and characterization of polypseudorotaxanes based on block-selected inclusion complexation between poly(propylene oxide)-poly(ethylene oxide)-poly(propylene oxide) triblock copolymers and alpha-cyclodextrin. J Am Chem Soc. 2003;125:1788-95 pubmed
    ..The findings reported in this article suggested interesting possibilities in designing other cyclodextrin ICs and polypseudorotaxanes with block structures. ..
  9. Maniam S, Cieslinski M, Lincoln S, Onagi H, Steel P, Willis A, et al. Molecular fibers and wires in solid-state and solution self-assemblies of cyclodextrin [2]rotaxanes. Org Lett. 2008;10:1885-8 pubmed publisher
    Cyclodextrin [2]rotaxanes have been prepared by coupling dimethylanilines with dicarboxylic acids using DMT-MM, in aqueous solutions of alpha-cyclodextrin, and the example illustrated shows unusual fluorescence emission and other ..

More Information

Publications100

  1. Sanchez Quesada J, Saghatelian A, Cheley S, Bayley H, Ghadiri M. Single DNA rotaxanes of a transmembrane pore protein. Angew Chem Int Ed Engl. 2004;43:3063-7 pubmed
  2. Tamura A, Yui N. Cellular internalization and gene silencing of siRNA polyplexes by cytocleavable cationic polyrotaxanes with tailored rigid backbones. Biomaterials. 2013;34:2480-91 pubmed publisher
    ..Thus, the cytocleavable cationic PRXs are suggested to be attractive supermolecules for the delivery of therapeutic siRNAs. ..
  3. Lohmann F, Ackermann D, Famulok M. Reversible light switch for macrocycle mobility in a DNA rotaxane. J Am Chem Soc. 2012;134:11884-7 pubmed publisher
    ..The ability to reversibly operate mechanical motion in an interlocked DNA nanostructure opens exciting new avenues in DNA nanotechnology. ..
  4. Crowley J, Hänni K, Leigh D, Slawin A. Diels-Alder active-template synthesis of rotaxanes and metal-ion-switchable molecular shuttles. J Am Chem Soc. 2010;132:5309-14 pubmed publisher
    A synthesis of [2]rotaxanes in which Zn(II) or Cu(II) Lewis acids catalyze a Diels-Alder cycloaddition to form the axle while simultaneously acting as the template for the assembly of the interlocked molecules is described...
  5. Yamashita A, Kanda D, Katoono R, Yui N, Ooya T, Maruyama A, et al. Supramolecular control of polyplex dissociation and cell transfection: efficacy of amino groups and threading cyclodextrins in biocleavable polyrotaxanes. J Control Release. 2008;131:137-44 pubmed publisher
    ..Therefore, transfection activity seems to be related to an appropriate timing of pDNA release. ..
  6. Jakob M, Berg A, Rubin R, Levanon H, Li K, Schuster D. Photoinduced electron transfer in porphyrin- and fullerene/porphyrin-based rotaxanes as studied by time-resolved EPR spectroscopy. J Phys Chem A. 2009;113:5846-54 pubmed publisher
    Photoinduced intramolecular electron-transfer (ET) and energy-transfer (EnT) processes in two rotaxanes, one containing both zinc porphyrin and C(60) fullerene moieties incorporated around the Cu(I) bisphenanthroline core [(ZnP)(2)-Cu(I)(..
  7. Ackermann D, Schmidt T, Hannam J, Purohit C, Heckel A, Famulok M. A double-stranded DNA rotaxane. Nat Nanotechnol. 2010;5:436-42 pubmed publisher
    Mechanically interlocked molecules such as rotaxanes and catenanes have potential as components of molecular machinery...
  8. Wenz G, Han B, Muller A. Cyclodextrin rotaxanes and polyrotaxanes. Chem Rev. 2006;106:782-817 pubmed
  9. Lussis P, Svaldo Lanero T, Bertocco A, Fustin C, Leigh D, Duwez A. A single synthetic small molecule that generates force against a load. Nat Nanotechnol. 2011;6:553-7 pubmed publisher
    ..The results show that individual rotaxanes can generate directional forces of similar magnitude to those generated by natural molecular machines.
  10. Ooya T, Choi H, Yamashita A, Yui N, Sugaya Y, Kano A, et al. Biocleavable polyrotaxane-plasmid DNA polyplex for enhanced gene delivery. J Am Chem Soc. 2006;128:3852-3 pubmed
    ..Those properties played a key role for delivery of pDNA clusters to the nucleus. Therefore, the polyplex nature and the supramolecular dissociation of the polyrotaxane contributed to the enhanced gene delivery. ..
  11. Yamada Y, Nomura T, Harashima H, Yamashita A, Katoono R, Yui N. Intranuclear DNA release is a determinant of transfection activity for a non-viral vector: biocleavable polyrotaxane as a supramolecularly dissociative condenser for efficient intranuclear DNA release. Biol Pharm Bull. 2010;33:1218-22 pubmed
    ..Moreover, this system provides a strong support for our hypothesis that intranuclear DNA disposition plays a critical role in gene expression for non-viral vectors. ..
  12. Yamashita A, Yui N, Ooya T, Kano A, Maruyama A, Akita H, et al. Synthesis of a biocleavable polyrotaxane-plasmid DNA (pDNA) polyplex and its use for the rapid nonviral delivery of pDNA to cell nuclei. Nat Protoc. 2006;1:2861-9 pubmed
    ..Significant amounts of pDNA delivered to the nucleus can be expected as well as high transfection activity of the polyplex. This protocol can be completed in 23-32 d. ..
  13. Arunkumar E, Forbes C, Noll B, Smith B. Squaraine-derived rotaxanes: sterically protected fluorescent near-IR dyes. J Am Chem Soc. 2005;127:3288-9 pubmed
    A squaraine dye with bulky end groups is employed as the thread component in two Leigh-type amide rotaxanes. The rotaxanes are synthesized in a simple two-step process...
  14. Deligkiozi I, Papadakis R, Tsolomitis A. Photoconductive properties of a ?-conjugated ?-cyclodextrin containing [2]rotaxane and its corresponding molecular dumbbell. Phys Chem Chem Phys. 2013;15:3497-503 pubmed publisher
    ..The photoresponsive behavior of the title [2]rotaxane was proved to be more intense than that of its analogue lacking the ?-cyclodextrin (?-CyD) macrocycle. A mechanism of the photoinduced charge transport in both cases is proposed. ..
  15. Li L, Zhang H, Zhao J, Li N, Liu Y. Self-sorting of four organic molecules into a heterowheel polypseudorotaxane. Chemistry. 2013;19:6498-506 pubmed publisher
  16. Gao C, Zhao L, Wang M. Designed synthesis of metal cluster-centered pseudo-rotaxane supramolecular architectures. J Am Chem Soc. 2011;133:8448-51 pubmed publisher
    ..The tetrasilver cluster centered [2]- and [3]-pseudo-rotaxane structures are obtained and fully characterized by X-ray crystallography, ESI mass spectrometry, and (1)H NMR spectroscopy. ..
  17. Li J, Zhao F, Li J. Polyrotaxanes for applications in life science and biotechnology. Appl Microbiol Biotechnol. 2011;90:427-43 pubmed publisher
    ..Finally, hydrolyzable polyrotaxane hydrogels with cross-linked ?-CDs could be a desirable scaffold for cartilage and bone tissue engineering. ..
  18. Zhang K, Wang G, Zhao X, Jiang X, Li Z. Vesicle self-assembly by tetrathiafulvalene derivatives in both polar and nonpolar solvents and pseudo-rotaxane mediated vesicle-to-microtube transformation. Langmuir. 2010;26:6878-82 pubmed publisher
    ..This process can be reversed by introducing pristine TTF into the solution of microtubes, due to release of T2 from the pseudo[2]rotaxane through the formation of a more stable complex between pristine TTF and tetracation cyclophane. ..
  19. Masai H, Terao J, Fujihara T, Tsuji Y. Rational Design for Rotaxane Synthesis through Intramolecular Slippage: Control of Activation Energy by Rigid Axle Length. Chemistry. 2016;22:6624-30 pubmed publisher
    ..Through hydrophilic-hydrophobic interactions and flipping of PM ?-CDs, successful quantitative conversion into rotaxanes was achieved without covalent bond formation...
  20. Zanichelli V, Ragazzon G, Orlandini G, Venturi M, Credi A, Silvi S, et al. Efficient active-template synthesis of calix[6]arene-based oriented pseudorotaxanes and rotaxanes. Org Biomol Chem. 2017;15:6753-6763 pubmed publisher
    ..We found that the alkylation of complexed substrates leads to the formation of pseudorotaxanes and rotaxanes with faster kinetics and higher yields with respect to the standard procedures exploited so far...
  21. Coutrot F, Romuald C, Busseron E. A new pH-switchable dimannosyl[c2]daisy chain molecular machine. Org Lett. 2008;10:3741-4 pubmed publisher
    ..The both stretched and contracted states of the molecular machine can be obtained by variation of the pH, thus localizing the mannosyl stoppers closer or farther away. ..
  22. Ho W, Lee S, Wong C, Zhu X, Kwan C, Chak C, et al. Type III-B rotaxane dendrimers. Chem Commun (Camb). 2013;49:10781-3 pubmed publisher
    ..The dendron does not reveal obvious cytotoxicities in L929 fibroblast cells. The rotaxane dendrimers can capture ammonia and are switchable both in solution and on surfaces. ..
  23. Wilson H, Byrne S, Bampos N, Mullen K. 'Click' functionalised polymer resins: a new approach to the synthesis of surface attached bipyridinium and naphthalene diimide [2]rotaxanes. Org Biomol Chem. 2013;11:2105-15 pubmed publisher
    Herein we describe the design and synthesis of a series of solid-tethered [2]rotaxanes utilising crown ether-naphthalene diimide or crown ether-bipyridinium host guest interactions...
  24. Xia B, Xue M. Design and efficient synthesis of a pillar[5]arene-based [1]rotaxane. Chem Commun (Camb). 2014;50:1021-3 pubmed publisher
    ..A pillar[5]arene-based [1]rotaxane was simply prepared in a high yield of 73%. Its stucture was confirmed by (1)H NMR, 2D NMR spectra, mass spectra and theoretical calculation. ..
  25. Farahani N, Zhu K, Loeb S. Rigid, Bistable Molecular Shuttles Combining T-shaped Benzimidazolium and Y-shaped Imidazolium Recognition Sites. Chemphyschem. 2016;17:1875-80 pubmed publisher
    ..Molecular shuttling in both the neutral and dicationic versions were studied. ..
  26. Liu Y, Yang Z, Chen Y, Song Y, Shao N. Construction of a long cyclodextrin-based bis(molecular tube) from bis(polypseudorotaxane) and its capture of C60. ACS Nano. 2008;2:554-60 pubmed publisher
    ..Further investigations demonstrate that this bis(molecular tube) can capture C(60) through interaction with its many pi-electron-rich biquinolino groups. ..
  27. Basu S, Coskun A, Friedman D, Olson M, Benitez D, Tkatchouk E, et al. Donor-acceptor oligorotaxanes made to order. Chemistry. 2011;17:2107-19 pubmed publisher
    ..The secondary structures of a foldamer-like nature have received further support from a solid-state superstructure of a related [3]pseudorotaxane and density functional calculations performed thereon. ..
  28. Pierro T, Gaeta C, Talotta C, Casapullo A, Neri P. Fixed or invertible calixarene-based directional shuttles. Org Lett. 2011;13:2650-3 pubmed publisher
    The first examples of rotaxanes based on calixarenes threaded by dialkylammonium ions, which also represent the first examples of calixarene-based molecular shuttles, are reported...
  29. Higashi T, Tanaka H, Yoshimatsu A, Ikeda H, Arima K, Honjo M, et al. Improvement of Pharmaceutical Properties of Isoprenoid Compounds through the Formation of Cyclodextrin Pseudorotaxane-Like Supramolecules. Chem Pharm Bull (Tokyo). 2016;64:340-5 pubmed publisher
    ..In conclusion, pharmaceutical properties such as photostability and dispersion rates of isoprenoid compounds were improved by the formation of pseudorotaxane-like supramolecular complexes with ?-CyD and/or ?-CyD. ..
  30. Wang Y, Sun J, Liu Z, Nassar M, Botros Y, Stoddart J. Symbiotic Control in Mechanical Bond Formation. Angew Chem Int Ed Engl. 2016;55:12387-92 pubmed publisher
    ..also an attractive source of templation because of the unique properties residing in the resulting catenanes and rotaxanes. Herein, we report a copper-mediated procedure that enables the generation, in the MIM-precursors, of BIPY(...
  31. Schuster D, Li K, Guldi D, Ramey J. Novel porphyrin-fullerene assemblies: from rotaxanes to catenanes. Org Lett. 2004;6:1919-22 pubmed
    reaction: see text] Titration of porphyrin-fullerene rotaxanes with DABCO or 4,4'-bipyridine led to photo- and redoxactive catenanic architectures, which upon photoexcitation undergo a sequence of short-range energy and electron ..
  32. Dai X, Dong C, Fa H, Yan D, Wei Y. Supramolecular Polypseudorotaxanes composed of star-shaped porphyrin-cored poly(epsilon-caprolactone) and alpha-cyclodextrin. Biomacromolecules. 2006;7:3527-33 pubmed
  33. Pan T, Liu J. Catalysts Encapsulated in Molecular Machines. Chemphyschem. 2016;17:1752-8 pubmed publisher
    ..In recent years, scientists have made efforts to utilize molecular machines (molecular switches, rotaxanes, motors, etc.) as scaffolds to develop smart catalysts...
  34. Lin C, Lai C, Liu Y, Peng S, Chiu S. Use of anions to allow translational isomerism of a [2]rotaxane. Chemistry. 2007;13:4350-5 pubmed
  35. Hardouin Lerouge M, Hudhomme P, Salle M. Molecular clips and tweezers hosting neutral guests. Chem Soc Rev. 2011;40:30-43 pubmed publisher
    ..Porphyrin-based systems will not be covered here as this very active field has been recently reviewed. ..
  36. Baggi G, Loeb S. Rotationally Active Ligands: Dialing-Up the Co-conformations of a [2]Rotaxane for Metal Ion Binding. Angew Chem Int Ed Engl. 2016;55:12533-7 pubmed publisher
    ..This concept of rotationally active ligands should be possible with a wide variety of donor sets and could find broad application in areas of coordination chemistry, such as catalysis and metal sequestration. ..
  37. Katz E, Sheeney Haj Ichia L, Willner I. Electrical contacting of glucose oxidase in a redox-active rotaxane configuration. Angew Chem Int Ed Engl. 2004;43:3292-300 pubmed
  38. Megiatto J, Schuster D. Alternative demetalation method for Cu(I)-phenanthroline-based catenanes and rotaxanes. Org Lett. 2011;13:1808-11 pubmed publisher
    ..The conditions are compatible with materials containing nucleophile-sensitive appended groups such as C(60), and coordinating moieties such as zinc(II)-porphyrins. ..
  39. Ooya T, Utsunomiya H, Eguchi M, Yui N. Rapid binding of concanavalin A and maltose-polyrotaxane conjugates due to mobile motion of alpha-cyclodextrins threaded onto a poly(ethylene glycol). Bioconjug Chem. 2005;16:62-9 pubmed
    ..Therefore, we concluded that both highly molecular motion due to the mobile motion of maltose-conjugated alpha-CDs and multivalency of the Mal-PRXs contributes to inducing rapid Con A binding. ..
  40. Higashi T, Tajima A, Motoyama K, Arima H. Cyclodextrin/poly(ethylene glycol) polypseudorotaxane hydrogels as a promising sustained-release system for lysozyme. J Pharm Sci. 2012;101:2891-9 pubmed publisher
    ..In conclusion, these results suggest that ?- and ?-CyD PPRX hydrogels possess the potential as a sustained-release system for lysozyme. ..
  41. Seo J, Yui N. The effect of molecular mobility of supramolecular polymer surfaces on fibroblast adhesion. Biomaterials. 2013;34:55-63 pubmed publisher
    ..These results indicate that molecular mobility on polymer surfaces is one of the significant considerations for regulating cellular responses. ..
  42. Qiao B, Liu Y, Lee S, Pink M, Flood A. A high-yield synthesis and acid-base response of phosphate-templated [3]rotaxanes. Chem Commun (Camb). 2016;52:13675-13678 pubmed
    Anion-templated rotaxanes are a rare class of functional organic molecules capable of novel switching and mechanical behaviors. Yet, investigations of these properties are limited by existing synthetic strategies...
  43. Yamada Y, Nomura T, Harashima H, Yamashita A, Yui N. Post-nuclear gene delivery events for transgene expression by biocleavable polyrotaxanes. Biomaterials. 2012;33:3952-8 pubmed publisher
    ..Such information provides a new viewpoint for the development of cationic polymer-based vectors. ..
  44. Chen Z, Aoki D, Uchida S, Marubayashi H, Nojima S, Takata T. Effect of Component Mobility on the Properties of Macromolecular [2]Rotaxanes. Angew Chem Int Ed Engl. 2016;55:2778-81 pubmed publisher
    Macromolecular [2]rotaxanes comprising a polymer axle and crown ether wheel were synthesized to evaluate the effect of component mobility on the properties of the axle polymer, especially its crystallinity...
  45. Valero M, Grillo I, Dreiss C. Rupture of pluronic micelles by di-methylated ?-cyclodextrin is not due to polypseudorotaxane formation. J Phys Chem B. 2012;116:1273-81 pubmed publisher
    ..In the latter case, after micellar rupture, lamellar structures are seen to form over a longer period of time, thus suggesting that after the instantaneous micellar disruption, further, longer-scale rearrangements are not excluded. ..
  46. Lai C, Lai L, Zhao J, Chen J. [Synthesis of polyrotaxane-camptothecin conjugates and evaluation of its anti-tumor effect]. Yao Xue Xue Bao. 2010;45:920-5 pubmed
    ..The result indicated anti-tumor mechanism may be through affect the angiogenesis and reduced blood supply to tumor cells and then leading to necrosis. ..
  47. Moon C, Kwon Y, Lee W, Park Y, Yang V. In vitro assessment of a novel polyrotaxane-based drug delivery system integrated with a cell-penetrating peptide. J Control Release. 2007;124:43-50 pubmed
    ..Intracellular uptake of these conjugates by A2780 human ovarian cancer cells and regulation of such uptake by heparin and protamine were confirmed by using the MTT assay and also the confocal microscopy method. ..
  48. Kuwahara S, Chamura R, Tsuchiya S, Ikeda M, Habata Y. Chirality transcription and amplification by [2]pseudorotaxanes. Chem Commun (Camb). 2013;49:2186-8 pubmed publisher
    ..It was revealed that the absolute configurations of the chiral sec-ammonium ions can be detected directly from the CD spectra of the chiral [2]pseudorotaxanes. ..
  49. Kilah N, Wise M, Serpell C, Thompson A, White N, Christensen K, et al. Enhancement of anion recognition exhibited by a halogen-bonding rotaxane host system. J Am Chem Soc. 2010;132:11893-5 pubmed publisher
    ..The incorporation of a halogen atom into the rotaxane host cavity dramatically improves the anion-recognition capabilities of the interlocked receptor, giving unusual iodide selectivity in a competitive aqueous medium. ..
  50. Akae Y, Koyama Y, Sogawa H, Hayashi Y, Kawauchi S, Kuwata S, et al. Structural Analysis and Inclusion Mechanism of Native and Permethylated α-Cyclodextrin-Based Rotaxanes Containing Alkylene Axles. Chemistry. 2016;22:5335-41 pubmed publisher
    Native α-cyclodextrin- (α-CD) and permethylated α-CD (PMeCD)-based rotaxanes with various short alkylene chains as axles can be synthesized through a urea end-capping method...
  51. Pikulska A, Kauch M, Pecul M. Theoretical prediction of the spin-spin coupling constants between an axis and macrocycle of a rotaxane. J Phys Chem A. 2011;115:10795-800 pubmed publisher
    ..coupling constants between nuclei belonging to the axis and to the macrocycle of three structurally related rotaxanes have been calculated by means of density functional theory...
  52. Bodis P, Panman M, Bakker B, Mateo Alonso A, Prato M, Buma W, et al. Two-dimensional vibrational spectroscopy of rotaxane-based molecular machines. Acc Chem Res. 2009;42:1462-9 pubmed publisher
    ..In this Account, we use 2D vibrational spectroscopy to study molecular machines based on rotaxanes. These devices consist of a linear thread and a macrocycle that is noncovalently locked onto the thread...
  53. Dam H, Caruso F. Formation and degradation of layer-by-layer-assembled polyelectrolyte polyrotaxane capsules. Langmuir. 2013;29:7203-8 pubmed publisher
    ..Given the supramolecular noncovalent structure of PRXs and their adjustable properties, it is expected that PRXs will be used as building blocks for assembling advanced capsules with unique and tailored properties. ..
  54. Brown A, Mullen K, Ryu J, Chmielewski M, Santos S, Felix V, et al. Interlocked host anion recognition by an indolocarbazole-containing [2]rotaxane. J Am Chem Soc. 2009;131:4937-52 pubmed publisher
  55. Wilson C, Gualandi A, Cozzi P. A rotaxane turing machine for peptides. Chembiochem. 2013;14:1185-7 pubmed publisher
    ..By molecular movements, the rotaxane-based machine progressively introduces amino acids to form a short peptide chain. The journey towards an artificial ribosome is still quite long, but a conceivable future can be envisaged. ..
  56. Bonnet S, Collin J. Ruthenium-based light-driven molecular machine prototypes: synthesis and properties. Chem Soc Rev. 2008;37:1207-17 pubmed publisher
    ..review, we will highlight recent advances in the design and synthesis of various ruthenium(II) complexed rotaxanes, catenanes, scorpionates or macrocycles...
  57. Ashcroft B, Spadola Q, Qamar S, Zhang P, Kada G, Bension R, et al. An AFM/rotaxane molecular reading head for sequence-dependent DNA structures. Small. 2008;4:1468-75 pubmed publisher
    ..Kinetic analysis shows that much less strain is required to destabilize the double helix in this geometry. Consequently, much more force is required to provide the free energy needed for opening. ..
  58. Busseron E, Romuald C, Coutrot F. Bistable or oscillating state depending on station and temperature in three-station glycorotaxane molecular machines. Chemistry. 2010;16:10062-73 pubmed publisher
    ..It is suggested that the macrocycle acts as a molecular brake for the rotation of the pyridinium-amide bond when it interacts by hydrogen bonding with both the amide NH and the pyridinium hydrogen atoms at the same time. ..
  59. Yu G, Suzaki Y, Abe T, Osakada K. Organometallic rotaxanes with a triazole group in the axle component and their behavior as ligands of PtII complexes. Chem Asian J. 2012;7:207-13 pubmed publisher
    ..underwent a Cu-catalyzed Huisgen coupling reaction (click reaction) with an alkyl azide to afford cationic [2]rotaxanes with a triazole group in the axle molecule...
  60. Mateo Alonso A, Aminur Rahman G, Ehli C, Guldi D, Fioravanti G, Marcaccio M, et al. Photophysical and electrochemical properties of a fullerene-stoppered rotaxane. Photochem Photobiol Sci. 2006;5:1173-6 pubmed
    ..The results evidenced the strong binding interactions between the template and the macrocycle, which are also supported by molecular modelling. ..
  61. Lee S, Chen C, Flood A. A pentagonal cyanostar macrocycle with cyanostilbene CH donors binds anions and forms dialkylphosphate [3]rotaxanes. Nat Chem. 2013;5:704-10 pubmed publisher
    ..The cyanostar's size preference allowed formation of an unprecedented [3]rotaxane templated around a dialkylphosphate. ..
  62. Brovelli S, Cacialli F. Optical and electroluminescent properties of conjugated polyrotaxanes. Small. 2010;6:2796-820 pubmed publisher
    ..CD-threaded rotaxanes thus provide a class of model compounds with reduced interchain interactions which enable us to explore the ..
  63. Yang C, Li H, Wang X, Li J. Cationic supramolecules consisting of oligoethylenimine-grafted alpha-cyclodextrins threaded on poly(ethylene oxide) for gene delivery. J Biomed Mater Res A. 2009;89:13-23 pubmed publisher
    ..Moreover, the cationic polyrotaxanes showed much lower cytotoxicity than branched PEI (25 kDa). Hence, these cationic poly rotaxanes have high potentials as new carriers for gene delivery.
  64. Ghosh K, Hu J, Yang H, Northrop B, White H, Stang P. Introduction of heterofunctional groups onto molecular hexagons via coordination-driven self-assembly. J Org Chem. 2009;74:4828-33 pubmed publisher
    ..The functional moieties are shown to operate orthogonally, resulting in discrete supramolecular hexagons that are capable of carrying out a variety of functions both simultaneously and independently. ..
  65. Angelo J, Sohlberg K. Decomposition of the factors that govern binding site preference in a multiple rotaxane. J Phys Chem A. 2009;113:6724-9 pubmed publisher
    A particularly interesting class of multiple rotaxanes consists of complexes where one long shaft threads two rings. If the shaft contains three or more potential binding sites for the rings, multiple co-conformations are possible...
  66. Abu Hashim I, Higashi T, Anno T, Motoyama K, Abd ElGawad A, El Shabouri M, et al. Potential use of gamma-cyclodextrin polypseudorotaxane hydrogels as an injectable sustained release system for insulin. Int J Pharm. 2010;392:83-91 pubmed publisher
    ..In conclusion, these results suggest the potential use of gamma-CyD PPRX hydrogel as an injectable sustained release system for insulin. ..
  67. Winn J, Pinczewska A, Goldup S. Synthesis of a rotaxane Cu(I) triazolide under aqueous conditions. J Am Chem Soc. 2013;135:13318-21 pubmed publisher
    ..The isolation of this remarkably stable Cu(I) organometallic points toward potential applications of mechanical bonding in the study of reactive intermediates. ..
  68. Okada M, Harada A. Preparation of beta-cyclodextrin polyrotaxane: photodimerization of pseudo-polyrotaxane with 2-anthryl and triphenylmethyl groups at the ends of poly(propylene glycol). Org Lett. 2004;6:361-4 pubmed
  69. Franchi P, Fanì M, Mezzina E, Lucarini M. Increasing the persistency of stable free-radicals: synthesis and characterization of a nitroxide based [1]rotaxane. Org Lett. 2008;10:1901-4 pubmed publisher
    ..A persistent paramagnetic [1]rotaxane based on beta-cyclodextrin showing an increased persistency under reductive conditions has been prepared and characterized for the first time. ..
  70. Ciao R, Talotta C, Gaeta C, Margarucci L, Casapullo A, Neri P. An oriented handcuff rotaxane. Org Lett. 2013;15:5694-7 pubmed publisher
    ..The relative orientation of the two calix-wheels can be predefined by exploiting the "endo-alkyl rule" which controls the directionality of the threading of alkylbenzylammonium axles with calixarene macrocycles. ..
  71. Thibeault D, Morin J. Recent advances in the synthesis of ammonium-based rotaxanes. Molecules. 2010;15:3709-30 pubmed publisher
    The number of synthetic methods enabling the preparation of ammonium-based rotaxanes has increased very rapidly in the past ten years...
  72. Hein C, Liu X, Chen F, Cullen D, Wang D. The synthesis of a multiblock osteotropic polyrotaxane by copper(I)-catalyzed huisgen 1,3-dipolar cycloaddition. Macromol Biosci. 2010;10:1544-56 pubmed publisher
    ..Overall bone affinity of this novel polymer conjugate can be easily controlled by changing the number of ALN-?-CD incorporated. The osteotropicity of the delivery system was also confirmed in vivo. ..
  73. Momčilović N, Clark P, Boydston A, Grubbs R. One-pot synthesis of polyrotaxanes via acyclic diene metathesis polymerization of supramolecular monomers. J Am Chem Soc. 2011;133:19087-9 pubmed publisher
    ..Ultimately, highly efficient complexation, polymerization, and end-capping were accomplished in a single operation to yield polyrotaxanes with M(w) up to 19.3 kDa and >80% of the repeat units being complexed. ..
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    Four pyridine N-oxide axle containing [2]rotaxanes have been synthesised via an anion templated threading-followed-by-stoppering strategy and shown to be the first examples of neutral interlocked host systems capable of recognising ..
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    ..In one case, squaraine rotaxanes are produced in near-quantitative yields and with intense near-IR fluorescence...
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    ..30. Heterodimers 1.2 and 1.3 represent a novel class of pseudo[2]rotaxanes constructed by two different noncovalent interactions.
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    ..Significantly, a "ladder"-release pattern is obtained to balance maximal therapeutic efficacy and minimal dose frequency in the development of "pulsed" drug therapy. ..
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    ..A spacer optimized for strong binding is suboptimal for fast pseudorotaxane formation. ..
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    ..Photoisomerization of the stilbene moiety of the CD derivative affects threading due to complexation between the axle and trans- or cis-6-StiNH-?-CD. ..
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    ..In the latter case, the polymer/nanoparticle aggregates precipitate from solution such that the polymer acts as a selective 'sponge' for the capture/release of the nanoparticles of different types. ..
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    Poly-pseudo-rotaxanes CDs contains as a subset 1 (CDs; cyclodextrins, 1; poly(delta-valerolactone) having single beta-CD at the end of the polymer chain) initiate polymerization of delta-valerolactone (delta-VL) in the solid state when ..
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    ..Therefore, we concluded that the high mobility of maltose groups along the polyrotaxane structure contributes to enhanced Con A recognition. ..
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    Two rotaxanes incorporating a 3,5-bis(triazole)-pyridinium axle component have been prepared using either an anion templated amide condensation or ring closing metathesis (RCM) clipping strategy...
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    ..Mixing six components in one pot affords a hetero[4]rotaxane in one minute in quantitative yield. ..
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    ..In principle the same concept could be used for mechanically switching virtually any property that can be influenced by functional group proximity effects. ..
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  88. Chi X, Yu G, Shao L, Chen J, Huang F. A Dual-Thermoresponsive Gemini-Type Supra-amphiphilic Macromolecular [3]Pseudorotaxane Based on Pillar[10]arene/Paraquat Cooperative Complexation. J Am Chem Soc. 2016;138:3168-74 pubmed publisher
    ..Furthermore, it can self-assemble into polymeric vesicles at 37 °C in water. These vesicles can be further used in the controlled release of small molecules induced by cooling to 25 °C or heating to 60 °C. ..
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    ..is, native and modified cyclodextrins, inclusion complexes and their aggregates of cyclodextrins, cyclodextrin rotaxanes and polyrotaxanes, cyclodextrin nanotubes and their secondary assembly, and other high-order aggregates of ..
  91. Dvornikovs V, House B, Kaetzel M, Dedman J, Smithrud D. Host-[2]rotaxanes as cellular transport agents. J Am Chem Soc. 2003;125:8290-301 pubmed
    Host-[2]rotaxanes, containing a diarginine-derivatized dibenzo-24-crown-8 (DB24C8) ether as the ring and a cyclophane pocket or an aromatic cleft as one blocking group, are cell transport agents...