scholarly journals Evaluation of the stability of cucurbit[8]uril-based ternary host−guest complexation in physiological environment and the fabrication of a supramolecular theranostic nanomedicine

2021 ◽  
Vol 19 (1) ◽  
Author(s):  
Han Wu ◽  
Zuobing Chen ◽  
Shaolong Qi ◽  
Bing Bai ◽  
Jiajun Ye ◽  
...  
Keyword(s):  
Molecular Recognition ◽  
Isothermal Titration Calorimetry ◽  
Disease Diagnosis ◽  
Titration Calorimetry ◽  
Resonance Spectroscopy ◽  
Diagnosis And Therapy ◽  
Vis Spectroscopy ◽  
Non Covalent Interactions ◽  
The Stability ◽  
Covalent Interactions

Abstract Background Supramolecular theranostics have exhibited promising potentials in disease diagnosis and therapy by taking advantages of the dynamic and reversible nature of non-covalent interactions. It is extremely important to figure out the stability of the driving forces in physiological environment for the preparation of theranostic systems. Methods The host−guest complexation between cucurbit[8]uril (CB[8]), 4,4′-bipyridinium, and napththyl guest was fully studied using various characterizations, including nuclear magnetic resonance spectroscopy, ultraviolet–visible (UV–vis) spectroscopy, isothermal titration calorimetry (ITC). The association constants of this ternary complex were determined using isothermal titration calorimetry. The stability of the non-covalent interactions and self-assemblies form from this molecular recognition was confirmed by UV–vis spectroscopy and dynamic light scattering (DLS). A supramolecular nanomedicine was constructed on the basis of this 1:1:1 ternary recognition, and its in vitro and in vivo anticancer efficacy were thoroughly evaluated. Positron emission tomography (PET) imaging was used to monitor the delivery and biodistribution of the supramolecular nanomedicine. Results Various experiments confirmed that the ternary complexation between 4,4′-bipyridinium, and napththyl derivative and CB[8] was stable in physiological environment, including phosphate buffered solution and cell culture medium. Supramolecular nanomedicine (SNM@DOX) encapsulating a neutral anticancer drug (doxrubincin, DOX) was prepared based on this molecular recognition that linked the hydrophobic poly(ε-caprolactone) chain and hydrophilic polyethylene glycol segment. The non-covalent interactions guaranteed the stability of SNM@DOX during blood circulation and promoted its tumor accumulation by taking advantage of the enhanced permeability and retention effect, thus greatly improving the anti-tumor efficacy as compared with the free drug. Conclusion Arising from the host-enhanced charge-transfer interactions, the CB[8]-based ternary recognition was stable enough in physiological environment, which was suitable for the fabrication of supramolecular nanotheranostics showing promising potentials in precise cancer diagnosis and therapy. Graphic Abstract

scholarly journals Evaluation of the stability of cucurbit[8]uril-based ternary host−guest complexation in physiological environment and the fabrication of a supramolecular theranostic nanomedicine

2021 ◽  
Author(s):  
Han Wu ◽  
Zuobing Chen ◽  
Shaolong Qi ◽  
Bing Bai ◽  
Jiajun Ye ◽  
...  
Keyword(s):  
Molecular Recognition ◽  
Isothermal Titration Calorimetry ◽  
Titration Calorimetry ◽  
Resonance Spectroscopy ◽  
Vis Spectroscopy ◽  
Non Covalent Interactions ◽  
The Stability ◽  
Covalent Interactions

Abstract PurposeTo evaluate the stability of cucurbit[8]uril-based 1:1:1 ternary host−guest complexation in physiological environment for the fabrication of supramolecular theranostics with promising potentials in precise cancer imaging and therapy. MethodsThe host−guest complexation between cucurbit[8]uril (CB[8]), 4,4′-bipyridinium, and napththyl guest was fully studied using various characterizations, including nuclear magnetic resonance spectroscopy ( 1 H NMR), ultraviolet-visible (UV-vis) spectroscopy, isothermal titration calorimetry (ITC). The association constants of this ternary complex were determined using isothermal titration calorimetry. The stability of the non-covalent interactions and self-assemblies form from this molecular recognition was confirmed by UV-vis spectroscopy and dynamic light scattering (DLS). A supramolecular nanomedicine was constructed on the basis of this 1:1:1 ternary recognition, and its in vitro and in vivo anticancer efficacy were thoroughly evaluated. Positron emission tomography (PET) imaging was used to monitor the delivery and biodistribution of the supramolecular nanomedicine. ResultsVarious experiments confirmed that the ternary complexation between 4,4′-bipyridinium, and napththyl derivative and CB[8] was stable in physiological environment, including phosphate buffered solution and cell culture medium. Supramolecular nanomedicine (SNM@DOX) encapsulating a neutral anticancer drug (doxrubincin, DOX) was prepared based on this molecular recognition that linked the hydrophobic poly(ε-caprolactone) chain and hydrophilic polyethylene glycol segment. The non-covalent interactions guaranteed the stability of SNM@DOX during blood circulation and promoted its tumor accumulation by taking advantage of the enhanced permeability and retention effect, thus greatly improving the anti-tumor efficacy as compared with the free drug. ConclusionArising from the host-enhanced charge-transfer interactions, the CB[8]-based ternary recognition was stable enough in physiological environment, which was suitable for the fabrication of supramolecular nanotheranostics showing promising potentials in precise cancer diagnosis and therapy.

scholarly journals Deciphering the H-Bonding Preference on Nucleoside Molecular Recognition through Model Copper(II) Compounds

2021 ◽  
Vol 14 (3) ◽  
pp. 244
Author(s):  
Inmaculada Velo-Gala ◽  
Miquel Barceló-Oliver ◽  
Diego M. Gil ◽  
Josefa M. González-Pérez ◽  
Alfonso Castiñeiras ◽  
...  
Keyword(s):  
Molecular Recognition ◽  
Magnetic Measurements ◽  
Theoretical Calculations ◽  
X Ray Diffraction ◽  
Paramagnetic Resonance ◽  
Vis Spectroscopy ◽  
Non Covalent Interactions ◽  
Electron Paramagnetic ◽  
Covalent Interactions ◽  
Coordination Plane

The synthetic nucleoside acyclovir is considered an outstanding model of the natural nucleoside guanosine. With the purpose of deepening on the influence and nature of non-covalent interactions regarding molecular recognition patterns, three novel Cu(II) complexes, involving acyclovir (acv) and the ligand receptor N-(2-hydroxyethyl)ethylenediamine (hen), have been synthesized and thoroughly characterized. The three novel compounds introduce none, one or two acyclovir molecules, respectively. Molecular recognition has been evaluated using single crystal X-ray diffraction. Furthermore, theoretical calculations and other physical methods such as thermogravimetric analysis, infrared and UV-Vis spectroscopy, electron paramagnetic resonance and magnetic measurements have been used. Theoretical calculations are in line with experimental results, supporting the relevance of the [metal-N7(acv) + H-bond] molecular recognition pattern. It was also shown that (hen)O-H group is used as preferred H-donor when it is found within the basal coordination plane, since the higher polarity of the terminal (hen)O-H versus the N-H group favours its implication. Otherwise, when (hen)O-H occupies the distal coordination site, (hen)N-H groups can take over.

Interplay between non-covalent interactions in 1D supramolecular polymers based on 1,4-bis(iodoethynyl)benzene

2021 ◽  
Vol 23 (5) ◽  
pp. 3531-3542
Author(s):  
Lucia González ◽  
Sara Graus ◽  
Blanca Gaspar ◽  
Sheila Espasa ◽  
Adrián Velázquez-Campoy ◽  
...  
Keyword(s):  
Isothermal Titration Calorimetry ◽  
Supramolecular Interactions ◽  
Supramolecular Polymers ◽  
Titration Calorimetry ◽  
Theoretical Methods ◽  
Non Covalent Interactions ◽  
Covalent Interactions

Supramolecular interactions of three halogen-bonded co-crystals of 1,4-bis(iodoethynyl)benzene (p-BIB) with organic bromide salts have been studied via isothermal titration calorimetry and theoretical methods including NCI methodology.

scholarly journals Synthesis, Characterization, and Non-Covalent Interactions of Palladium(II)-Amino Acid Complexes

Molecules ◽  
2021 ◽  
Vol 26 (14) ◽  
pp. 4331
Author(s):  
David B. Hobart ◽  
Michael A. G. Berg ◽  
Hannah M. Rogers ◽  
Joseph S. Merola
Keyword(s):  
Amino Acid ◽  
High Resolution Mass Spectrometry ◽  
Resonance Spectroscopy ◽  
Spectroscopic Techniques ◽  
X Ray Diffraction ◽  
Amino Acid Complexes ◽  
Acetone Water ◽  
Square Planar ◽  
Non Covalent Interactions ◽  
Covalent Interactions

The reaction of palladium(II) acetate with acyclic amino acids in acetone/water yields square planar bis-chelated palladium amino acid complexes that exhibit interesting non-covalent interactions. In all cases, complexes were examined by multiple spectroscopic techniques, especially HRMS (high resolution mass spectrometry), IR (infrared spectroscopy), and 1H NMR (nuclear magnetic resonance) spectroscopy. In some cases, suitable crystals for single crystal X-ray diffraction were able to be grown and the molecular structure was obtained. The molecular geometries of the products are discussed. Except for the alanine complex, all complexes incorporate water molecules into the extended lattice and exhibit N-H···O and/or O···(HOH)···O hydrogen bonding interactions. The non-covalent interactions are discussed in terms of the extended lattice structures exhibited by the structures.

scholarly journals Spectroscopic (FT-IR, FT-Raman, and 13C SS-NMR) and quantum chemical investigations to provide structural insights into nitrofurantoin–4-hydroxybenzoic acid cocrystals

2019 ◽  
Vol 43 (18) ◽  
pp. 7136-7149 ◽  
Author(s):  
Anuradha Shukla ◽  
Eram Khan ◽  
MHD. Bashir Alsirawan ◽  
Rajorshi Mandal ◽  
Poonam Tandon ◽  
...  
Keyword(s):  
Quantum Chemical ◽  
Molecular Geometry ◽  
Hydroxybenzoic Acid ◽  
Ft Ir ◽  
Non Covalent Interactions ◽  
The Stability ◽  
Covalent Interactions ◽  
Structural Insights ◽  
Ft Raman

Non-covalent interactions contribute considerably to the stability of cocrystals and have appreciable effects on their molecular geometry as well.

Computational evidence that hyperconjugative orbital interactions are responsible for the stability of intramolecular Te⋯O/Te⋯S non-covalent interactions and comparable to hydrogen bonds in quasi-cyclic systems

2016 ◽  
Vol 40 (11) ◽  
pp. 9132-9138 ◽  
Author(s):  
Mrinal Kanti Si ◽  
Bishwajit Ganguly
Keyword(s):  
Hydrogen Bonds ◽  
Bond Strength ◽  
Orbital Interactions ◽  
Non Covalent Interactions ◽  
Cyclic Systems ◽  
The Stability ◽  
Covalent Interactions ◽  
Secondary Bonding

The intramolecular secondary bonding interactions involving quasi-cyclic tellurium are comparable to H-bond strength and partially governed by orbital interactions.

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