4.8 Article

An Interlocked Figure-of-Eight Molecular Shuttle

Related references

Note: Only part of the references are listed.
Article Chemistry, Applied

Single-molecule characterization of a bright and photostable deep-red fluorescent squaraine-figure-eight (SF8) dye

Kirill Kniazev et al.

Summary: Squaraine Figure Eight (SF8) dyes are deep-red fluorescent dyes with unique self-threaded molecular architecture, providing structural rigidity and protection for the fluorochrome. Studies have shown that SF8 dyes have significantly higher photostability and improved emission quantum yields, longer times to photobleaching, and enhanced total photon yields at the single molecule level compared to conventional dyes. SF8-based dye SF8(D4)2 exhibits three-fold larger emission quantum yield, order of magnitude longer average times before photobleaching, and twenty times larger photon yields compared to Cy5. These features, along with water solubility, fluorochrome encapsulation, and biomarker targeting capability, make SF8-based dyes promising for biological labeling, microscopy, and single molecule tracking applications.

DYES AND PIGMENTS (2023)

Article Biochemistry & Molecular Biology

Structural Engineering of Fluorescent Self-Threaded Peptide Probes for Targeted Cell Imaging(dagger)

Cynthia L. Schreiber et al.

Summary: The new class of deep-red fluorescent probes SF8 exhibit high fluorescence brightness and stability, making them suitable for fluorescence cell microscopy research. By synthesizing and evaluating different SF8 probes for probe uptake by cancer cells, it was found that the probe with the RGD motif permeated the cells through receptor-mediated endocytosis, while the other two homologous SF8 probes showed negligible cell uptake, indicating differences in targeting capability. Additionally, the synthetic method allows for easy alteration of the peptide sequence, enabling the development of new peptidyl SF8 probes targeting other cancer biomarkers.

PHOTOCHEMISTRY AND PHOTOBIOLOGY (2022)

Article Chemistry, Multidisciplinary

[3]Foldarotaxane-mediated synthesis of an improbable [2]rotaxane

Victor Koehler et al.

Summary: This study investigates the wrapping of an aromatic oligoamide helix around an active ester-containing [2]rotaxane, which enforces the sliding and sequestration of the surrounding macrocycle around a part of the axle without any formal affinity. The foldamer-mediated compartmentalization of the [2]rotaxane shuttle was subsequently used to prepare an improbable rotaxane.

CHEMICAL COMMUNICATIONS (2022)

Review Chemistry, Multidisciplinary

Challenges and Opportunities in the Post-Synthetic Modification of Interlocked Molecules

Philip Waeles et al.

Summary: The synthesis of interlocked molecules often involves the challenging post-synthetic modifications while conserving the mechanical bond. To overcome synthetic problems, a strategy of synthesizing isolable and storable interlocked building blocks before modification is appealing. The reactivity of functional groups and preservation of the interlocked architecture are closely linked to the fundamental role of the mechanical bond in the strategy employed.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Review Chemistry, Multidisciplinary

The Rise and Promise of Molecular Nanotopology

Qing-Hui Guo et al.

Summary: Molecular nanotopology, a rapidly developing field emerging from the confluence of chemical topology and mechanical bond, is on its way to becoming a recognized discipline. The article reviews the historical development of chemical topology, the design and synthesis of molecular links and knots, and the challenges and future directions of molecular nanotopology. Representative examples are highlighted to provide an extensive overview of ongoing research in the field.

CCS CHEMISTRY (2021)

Article Chemistry, Multidisciplinary

Interplay between a Foldamer Helix and a Macrocycle in a Foldarotaxane Architecture

Maxime Gauthier et al.

Summary: A novel rotaxane/foldaxane hybrid architecture was designed and synthesized, with the winding of an aromatic oligoamide helix host around a dumbbell-shaped thread-like guest already surrounded by a macrocycle evidenced by NMR spectroscopy and X-ray crystallography. The position of the macrocycle along the axle and the associated steric hindrance were found to affect this process, with the macrocycle acting as a switchable shield modulating the affinity of the helix for the axle. Conversely, the foldamer helix acted as a supramolecular auxiliary compartmentalizing the axle.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2021)

Article Chemistry, Medicinal

Absolute configuration of a [1]rotaxane determined from vibrational and electronic circular dichroism spectra

Andrew R. Puente et al.

Summary: The absolute configuration of [1]rotaxane 1 was definitively assigned through comparisons between experimental and predicted vibrational circular dichroism (VCD) and electronic circular dichroism (ECD) spectra.

CHIRALITY (2021)

Review Chemistry, Multidisciplinary

Chiroptical Properties of Mechanically Interlocked Molecules

Arthur H. G. David et al.

Summary: Mechanically Interlocked Molecules (MIMs) are a class of molecules possessing mechanical bonds, with unique chiroptical properties that can be applied in various fields. In-depth studies on the chiroptical properties of these molecules can lead to breakthroughs in materials science and catalysis.

ISRAEL JOURNAL OF CHEMISTRY (2021)

Review Chemistry, Multidisciplinary

The role of chemical synthesis in developing RiPP antibiotics

Sam M. Rowe et al.

Summary: RiPPs are recognized as a potential source of antimicrobial drugs due to their potent activity and high stability, but issues such as low solubility and poor bioavailability often hinder their clinical development. Chemical synthesis can help overcome some of these challenges, and the structural complexity of RiPPs makes them interesting synthetic targets.

CHEMICAL SOCIETY REVIEWS (2021)

Article Chemistry, Organic

Chiral figure-eight molecular scaffold for fluorescent probe development†

Cynthia L. Schreiber et al.

Summary: Fluorescent molecular probes are essential for cellular microscopy, diagnostics, and biological imaging. This study evaluated a new probe scaffold called SF8 and found that subtle structural changes can lead to significant differences in intracellular targeting, especially in terms of mitochondrial accumulation. The research results point to the development of a bright, photostable fluorescent probe for mitochondrial imaging and as a molecular tool for identifying mitochondrial biomarkers for selective targeting. Expanding the SF8 probe chemical space can lead to structurally diverse probe libraries with high potential for selective targeting of various biomarkers.

ORGANIC & BIOMOLECULAR CHEMISTRY (2021)

Article Chemistry, Multidisciplinary

Diastereoselective synthesis of [1]rotaxanes via an active metal template strategy

Noel Pairault et al.

Summary: This study presents the first diastereoselective synthesis of mechanically planar chiral [1]rotaxanes using the active template Cu-mediated alkyne-azide cycloaddition reaction. This synthetic method allows for the preparation of a variety of mechanically planar chiral [1]rotaxanes, paving the way for the study of their properties and potential applications.

CHEMICAL SCIENCE (2021)

Review Chemistry, Multidisciplinary

Coordination-Directed Construction of Molecular Links

Wen-Xi Gao et al.

CHEMICAL REVIEWS (2020)

Article Chemistry, Multidisciplinary

Fluorescent Self-Threaded Peptide Probes for Biological Imaging

Canjia Zhai et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2020)

Review Chemistry, Inorganic & Nuclear

The flowering of Mechanically Interlocked Molecules: Novel approaches to the synthesis of rotaxanes and catenanes

Bahareh Taghavi Shahraki et al.

COORDINATION CHEMISTRY REVIEWS (2020)

Article Chemistry, Multidisciplinary

Synthesis of a new solvent-responsive pillar[5]arene-based [1]rotaxane molecular machine

Huasheng Tian et al.

NEW JOURNAL OF CHEMISTRY (2020)

Article Chemistry, Organic

Synthesis and properties of a redox-switchable calix[6]arene-based molecular lasso

Guido Orlandini et al.

ORGANIC CHEMISTRY FRONTIERS (2020)

Review Chemistry, Multidisciplinary

The Burgeoning of Mechanically Interlocked Molecules in Chemistry

Damien Sluysmans et al.

TRENDS IN CHEMISTRY (2019)

Article Chemistry, Inorganic & Nuclear

Strategies To Assemble Catenanes with Multiple Interlocked Macrocycles

Ho Yu Au-Yeung et al.

INORGANIC CHEMISTRY (2018)

Review Chemistry, Organic

Lasso peptides: chemical approaches and structural elucidation

Helena Martin-Gomez et al.

ORGANIC & BIOMOLECULAR CHEMISTRY (2018)

News Item Chemistry, Multidisciplinary

Moving into another dimension

Karine Fournel-Marotte et al.

NATURE CHEMISTRY (2017)

Article Chemistry, Multidisciplinary

Mechanically interlocked daisy-chain-like structures as multidimensional molecular muscles

Jia-Cheng Chang et al.

NATURE CHEMISTRY (2017)

Article Chemistry, Multidisciplinary

Synthesis and stabilities of peptide-based [1]rotaxanes: molecular grafting onto lasso peptide scaffolds

Fumito Saito et al.

CHEMICAL SCIENCE (2017)

Review Chemistry, Multidisciplinary

Molecular Knots

Stephen D. P. Fielden et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2017)

Article Chemistry, Multidisciplinary

Synthesis of a pH-Sensitive Hetero[4]Rotaxane Molecular Machine that Combines [c2]Daisy and [2]Rotaxane Arrangements

Philip Waeles et al.

CHEMISTRY-A EUROPEAN JOURNAL (2016)

Review Chemistry, Multidisciplinary

Catenanes: Fifty Years of Molecular Links

Guzman Gil-Ramirez et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2015)

Proceedings Paper Nanoscience & Nanotechnology

Recent Advances in the Chemical Synthesis of Lasso Molecular Switches

Frederic Coutrot

SINGLE MOLECULAR MACHINES AND MOTORS (2015)

Review Chemistry, Multidisciplinary

Rotaxane-Based Molecular Muscles

Carson J. Bruns et al.

ACCOUNTS OF CHEMICAL RESEARCH (2014)

Review Chemistry, Multidisciplinary

Progress in the synthesis and exploitation of catenanes since the Millennium

Nicholas H. Evans et al.

CHEMICAL SOCIETY REVIEWS (2014)

Review Chemistry, Multidisciplinary

Functional interlocked systems

Stijn F. M. van Dongen et al.

CHEMICAL SOCIETY REVIEWS (2014)

Review Chemistry, Multidisciplinary

Molecular Muscles: From Species in Solution to Materials and Devices

Frederic Niess et al.

CHEMISTRY LETTERS (2014)

Review Chemistry, Multidisciplinary

Molecular daisy chains

Juergen Rotzler et al.

CHEMICAL SOCIETY REVIEWS (2013)

Article Chemistry, Multidisciplinary

A pH-Sensitive Lasso-Based Rotaxane Molecular Switch

Caroline Clavel et al.

CHEMISTRY-A EUROPEAN JOURNAL (2013)

Article Biochemistry & Molecular Biology

A pH-Sensitive Peptide-Containing Lasso Molecular Switch

Caroline Clavel et al.

MOLECULES (2013)

Article Chemistry, Organic

Straightforward Synthesis of a Double-Lasso Macrocycle from a Nonsymmetrical [c2]Daisy Chain

Camille Romuald et al.

ORGANIC LETTERS (2013)

Review Chemistry, Multidisciplinary

Stereochemistry of Molecular Figures-of-Eight

Megan M. Boyle et al.

CHEMISTRY-A EUROPEAN JOURNAL (2012)

Article Chemistry, Organic

A Switchable Ferrocene-Based [1]Rotaxane with an Electrochemical Signal Output

Hong Li et al.

ORGANIC LETTERS (2012)

Review Chemistry, Multidisciplinary

Strategies and Tactics for the Metal-Directed Synthesis of Rotaxanes, Knots, Catenanes, and Higher Order Links

Jonathon E. Beves et al.

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION (2011)

Article Chemistry, Multidisciplinary

Donor-acceptor molecular figures-of-eight

Megan M. Boyle et al.

CHEMICAL COMMUNICATIONS (2011)

Review Chemistry, Multidisciplinary

Mechanically bonded macromolecules

Lei Fang et al.

CHEMICAL SOCIETY REVIEWS (2010)

Article Chemistry, Multidisciplinary

The foundation of a light driven molecular muscle based on stilbene and α-cyclodextrin

Ryan E. Dawson et al.

CHEMICAL COMMUNICATIONS (2008)

Article Chemistry, Multidisciplinary

A new glycorotaxane molecular machine based on an anilinium and a triazolium station

Frederic Coutrot et al.

CHEMISTRY-A EUROPEAN JOURNAL (2008)

Article Chemistry, Organic

A new pH-switchable dimannosyl[c2]daisy chain molecular machine

Frederic Coutrot et al.

ORGANIC LETTERS (2008)

Review Chemistry, Multidisciplinary

Anion templated assembly of mechanically interlocked structures

Matthew S. Vickers et al.

CHEMICAL SOCIETY REVIEWS (2007)

Review Chemistry, Multidisciplinary

Recent progress on switchable rotaxanes

H Tian et al.

CHEMICAL SOCIETY REVIEWS (2006)