Toward Expanded Diversity of Host–Guest Interactions via Synthesis and Characterization of Cyclodextrin Derivatives

Kellett, Kathryn; Kantonen, Samuel A.; Duggan, Brendan M.; Gilson, Michael K.

doi:10.1007/s10953-018-0769-1

Cited by 20 publications

(22 citation statements)

References 94 publications

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“…While the guest-water interactions can effectively be assessed by comparing experimental and calculated free energies of hydration, a quantity often used as target in force field optimization [51,97], the host-water and host-guest interactions usually rely on parameter transferability arguments and combining rules for cross-terms. To further localize the most appropriate degrees of freedom for force field refinement, it might be useful to consider quantities such as the osmotic pressure or activity coefficients that may help to improve the balance between the various force field terms [98], but also to expand the diver-sity of experimentally studied systems including modifications of the host molecules [99] as well as considering more complex solvent environments [100].…”

Section: Benchmark Studies On Host-guest Systemsmentioning

confidence: 99%

Insights into Noncovalent Binding Obtained from Molecular Dynamics Simulations

Baz

Gebhardt

Kraus

et al. 2018

Chemie Ingenieur Technik

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The key to nanoscale control of physical, chemical, and biological processes lies in well‐founded models of noncovalent binding. Atomistic simulations probe the free‐energy surface underlying molecular assembly processes in solution. Two examples of noncovalent binding studied by molecular dynamics simulations are discussed, the dimerization of a water‐soluble perylene bisimide derivative in aqueous solution with a focus on the influence of solvent composition on the aggregation strength and the binding of 1‐butanol to α‐cyclodextrin at infinite dilution with the focus on the determination of method‐independent binding free energies.

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Section: Benchmark Studies On Host-guest Systemsmentioning

confidence: 99%

Insights into Noncovalent Binding Obtained from Molecular Dynamics Simulations

Baz

Gebhardt

Kraus

et al. 2018

Chemie Ingenieur Technik

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“…By varying the size of the cavity (α‐, β‐, γ‐CD), altering the physicochemical interactions between guest and host through synthetic modification of CD, or by pretreating the sensor with an agent with a chosen association constant, selectively blocking the sensor for analytes with lower association constants (as we demonstrated with adamantanecarboxylic acid).…”

Section: Discussionmentioning

confidence: 99%

One‐Step Covalent Immobilization of β‐Cyclodextrin on sp² Carbon Surfaces for Selective Trace Amount Probing of Guests

Guyse

Rosa

et al. 2019

Adv Funct Materials

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The modification of solid surfaces with supramolecular hosts is a powerful method to tailor interfacial properties and confer chemical selectivity, but often involves multistep protocols that hinder facile upscaling. Here, the one-step covalent modification of highly oriented pyrolytic graphite (HOPG) with a β-cyclodextrin (β-CD) derivative, which efficiently forms inclusion complexes with hydrophobic guests of suitable size, is demonstrated. The grafted β-CD-HOPG surface is investigated toward electrochemical detection of ferrocene and dopamine. The enrichment of the analytes at the electrode surface, through inclusion in β-CD, leads to an enhanced electrochemical response and an improved detection limit. Furthermore, the modified β-CD-HOPG electrode discriminates analytes that form host-guest complexes with β-CD against a 100-fold higher background of electroactive substances that do not. Atomic force microscopy, scanning tunneling microscopy, and Raman spectroscopy confirm the covalent nature of the modification and reveal high stability toward solvent rinsing, ultrasonication, and temperatures up to 140 °C. The one-step covalent modification therefore holds substantial promise for the routine production of inexpensive, yet robust and highly performant electrochemical sensors. Beyond electrochemical sensor development, our strategy is valuable to prepare materials where accurate spatial positioning of functional units and efficient current collection are crucial, e.g. in photoelectrodes or electrocatalysts.

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“…The CD host derivatives are aimed to have a truncated cone shape ( Figure 4) with a hydrophobic cavity and a hydrophilic surface, while the substituents are intended to alter the host's chemical and physical properties. The new host substituents introduce new host-guest interactions, while retaining some of the same binding characteristics [76].…”

Section: Cyclodextrins (Cds) and Cyclodextrin Derivativesmentioning

confidence: 99%

“…Previous studies on CDs ( -CD, -CD, and mono-3-carboxyproponamido-CD) report two distinct bound states for each hostguest pair. The first bound state, called the "primary orientation", has the guest polar group (i.e., alcohol, ammonium, carboxylate) towards the glucose subunits primary alcohols, while the "secondary orientation" has the guest polar group towards the secondary alcohol [76,77] (Figure 4). Though a possible third "surface orientation"/binding mode has been speculated to exist, it may be this is a transition needed for the guest to flip from primary to secondary phase orientation or vice-versa [43].…”

Section: Cyclodextrins (Cds) and Cyclodextrin Derivativesmentioning

confidence: 99%

“…The guests studied here have been reported to bind native -CD, mono-3-carboxyproponamido--CD, and -CD substituted with an amine at the 3 position (secondary face). Rimantadine (Figure 3) binds beta-CD and mono-3-carboxyproponamido-CD with its cationic ammonium group projecting out from the secondary face [76,78]. On the other hand rimantadine prefers the primary orientation when binding -CD with an amine at the 3 position.…”

Section: Cyclodextrins (Cds) and Cyclodextrin Derivativesmentioning

confidence: 99%

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SAMPL7 Host-Guest Challenge Overview: Assessing the reliability of polarizable and non-polarizable methods for binding free energy calculations

Amezcua¹,

Khoury²,

Mobley

2020

Preprint

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The SAMPL challenges focus on testing and driving progress of computational methods to help guide pharmaceutical drug discovery. However, assessment of methods for predicting binding affinities is often hampered by computational challenges such as conformational sampling, protonation state uncertainties, variation in test sets selected, and even lack of high quality experimental data. SAMPL blind challenges have thus frequently included a component focusing on host-guest binding, which removes some of these challenges while still focusing on molecular recognition. Here, we report on the results of the SAMPL7 blind prediction challenge for host-guest affinity prediction. In this study, we focused on three different host-guest categories -- a familiar deep cavity cavitand series which has been featured in several prior challenges (where we examine binding of a series of guests to two hosts), a new series of cyclodextrin derivatives which are monofunctionalized around the rim to add amino acid-like functionality (where we examine binding of a two guests to a series of hosts), and binding of a series of guests to a new acyclic TrimerTrip host which is related to previous cucurbituril hosts. Many predictions used methods based on molecular simulations, and overall success was mixed, though several methods stood out. As in SAMPL6, we find that one strategy for achieving reasonable accuracy here was to make empirical corrections to binding predictions based on previous data for host categories which have been studied well before, though this can be of limited value when new systems are included. Additionally, we found that methods using the AMOEBA polarizable force field had considerable success for the two host categories in which they participated. The new TrimerTrip system was also found to introduce some sampling problems, because multiple conformations may be relevant to binding and interconvert only slowly. Overall, results in this challenge tentatively suggest that further investigation of polarizable force fields for these challenges may be warranted.

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Toward Expanded Diversity of Host–Guest Interactions via Synthesis and Characterization of Cyclodextrin Derivatives

Cited by 20 publications

References 94 publications

Insights into Noncovalent Binding Obtained from Molecular Dynamics Simulations

Insights into Noncovalent Binding Obtained from Molecular Dynamics Simulations

One‐Step Covalent Immobilization of β‐Cyclodextrin on sp² Carbon Surfaces for Selective Trace Amount Probing of Guests

SAMPL7 Host-Guest Challenge Overview: Assessing the reliability of polarizable and non-polarizable methods for binding free energy calculations

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Toward Expanded Diversity of Host–Guest Interactions via Synthesis and Characterization of Cyclodextrin Derivatives

Cited by 20 publications

References 94 publications

Insights into Noncovalent Binding Obtained from Molecular Dynamics Simulations

Insights into Noncovalent Binding Obtained from Molecular Dynamics Simulations

One‐Step Covalent Immobilization of β‐Cyclodextrin on sp2 Carbon Surfaces for Selective Trace Amount Probing of Guests

SAMPL7 Host-Guest Challenge Overview: Assessing the reliability of polarizable and non-polarizable methods for binding free energy calculations

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One‐Step Covalent Immobilization of β‐Cyclodextrin on sp² Carbon Surfaces for Selective Trace Amount Probing of Guests