Microcalorimetric titration of a tetra-p-sulphonated calix[4]arene with α,ω-alkyl diammonium ions in an aqueous solution

Stödeman, Magnus; Dhar, N.S.

doi:10.1016/s0040-6031(98)00429-8

Cited by 23 publications

(7 citation statements)

References 19 publications

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“…Excess ethanediamine was added to induce sufficient release of RhB. 9,26,42 As shown in Fig. 3a, an immediate release of cargo molecules was observed as a result of ethanediamine-induced opening of nanovalves.…”

Section: Resultsmentioning

confidence: 95%

Near-infrared light-responsive supramolecular nanovalve based on mesoporous silica-coated gold nanorods

et al. 2014

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We constructed a novel cancer theranostic hybrid platform, based on mesoporous silica-coated gold nanorods (AuNR@MSN) gated by sulfonatocalix[4]arene (SC[4]A) switches, for bio-friendly near-infrared (NIR) light-triggered cargo release in a remote and stepwise fashion. The advantages of supramolecular switches, mesoporous silicas, and AuNRs were combined in one drug delivery system. Mesoporous silicas coated on AuNRs guarantee a high drug payload and can be easily post-functionalized.Significantly, the plasmonic heating from the NIR light-stimulated AuNR cores can decrease the ringstalk binding affinity, leading to the dissociation of SC[4]A rings from the stalks, thus opening the nanovalves and releasing the cargos. The NIR light-responsive mechanized AuNR@MSN offers exciting prospects for non-invasive controlled drug delivery, being more effective and safer than other techniques.

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Section: Resultsmentioning

confidence: 95%

Near-infrared light-responsive supramolecular nanovalve based on mesoporous silica-coated gold nanorods

et al. 2014

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“…The desired 1:2 type V manner is prerequisite for building supramolecular polymers. To our surprise, although a lot of effort has been devoted to the binding behaviors of SC n As with various organic cations, − , the inclusion phenomena of SC n As with ditopic guests have been paid much less attention, despite some solid-state supramolecular structures . With this regard, we wish to report herein that how SC n As include ditopic guests in aqueous solution.…”

Section: Introductionmentioning

confidence: 97%

Binding Behaviors of p-Sulfonatocalix[4]arene with Gemini Guests

2013

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A dozen of homoditopic cations, possessing different spacer lengths and rigidities, as well as sizes, shapes, and charges of terminal groups, were synthesized as candidate gemini guests for the complexation of p-sulfonatocalix[4]arenes (SC4A). The 12 gemini guests are divided into five species according to the different terminal groups: imidazolium (G1-G3), pyridinium (G4-G6), quinolinium (G7), viologen (G8-G11), and 1,4-diazabicyclo[2.2.2]octane (DBO, G12). Their binding structures and stoichiometries with SC4A were examined by NMR spectroscopy, which is helpful to construct diverse highly ordered assemblies. The obtained results show that the length of the linkers, as well as the charge numbers on the end groups have a pronounced effect on the binding stoichiometry, whereas the size and shape of the terminal groups have no significant influence. Furthermore, both the stability constants and thermodynamic parameters of SC4A with the terminal subunits were determined by the isothermal titration calorimetry experiments, which are valuable to understand the binding behavior, giving quantitatively deep insight.

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“…Among these recognition processes, the molecular recognition of calixarenes in aqueous solution seems to be more important because most biological processes occur in aqueous solution. Arena, [5] Stödeman [6,7] and MorelDesrosiers [8,9] et al have successively investigated the binding behaviors of some p-sulfonatocalix [4]arenes with organic ammonium cations by NMR spectroscopy and microcalorimetry, finding that the sulfonate groups of hosts appear to serve as anchoring points for positively charged guests to give a more stable inclusion complex. Coleman et al [10] examined the binding thermodynamics of p-sulfonatocalix [n]arenes (n = 4, 6 and 8) with amino acids and polypeptides to understand the nature and manner of interactions between the synthetic receptors and glycosylaminoglycan (GAG) receptor sequences.…”

Section: Introductionmentioning

confidence: 99%

Molecular Selective Binding of Pyridinium Guest Ions by Water‐Soluble Calix[4]arenes

et al. 2005

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The complex stability constants (KS) and thermodynamic parameters (ΔG°, ΔH°, and TΔS°) for 1:1 intermolecular complexation of water‐soluble calix[4]arene tetrasulfonate (CAS) and thiacalix[4]arene tetrasulfonate (TCAS) with pyridinium guest ions 1–10 have been determined by means of titration calorimetry in an acidic buffer solution (pH = 2.0) at 298.15 K, and their binding modes have been investigated by NMR spectroscopy. Possessing a smaller cavity and a higher π electron density than TCAS, CAS affords the stronger binding abilities for all guests examined, giving an exciting molecular selectivity of up to 354 for the 2,6‐dimethylpyridine/2,6‐pyridinedicarboxylic acid pair. The high binding affinities, attributed to the favorable enthalpic gains, are comprehensively discussed from the viewpoint of π–π stacking, electronic effect and size‐fit relationship between host and guest. The thermodynamic parameters that have been obtained, together with the NMR results, jointly demonstrate that the position, number, and type of substituent groups introduced onto the guest molecule are the key factors controlling the structural‐energetics correlation for the molecular selective binding of water‐soluble calixarenes. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)

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Microcalorimetric titration of a tetra-p-sulphonated calix[4]arene with α,ω-alkyl diammonium ions in an aqueous solution

Cited by 23 publications

References 19 publications

Near-infrared light-responsive supramolecular nanovalve based on mesoporous silica-coated gold nanorods

Near-infrared light-responsive supramolecular nanovalve based on mesoporous silica-coated gold nanorods

Binding Behaviors of p-Sulfonatocalix[4]arene with Gemini Guests

Molecular Selective Binding of Pyridinium Guest Ions by Water‐Soluble Calix[4]arenes

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