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1.
Chem Commun (Camb) ; 55(81): 12200-12203, 2019 Oct 08.
Artigo em Inglês | MEDLINE | ID: mdl-31549132

RESUMO

ß-Cyclodextrin (CD)-grafted graphene oxide (GO) is an emerging drug carrier for human diseases therapy. Herein, we report two-dimensional nano-supramolecular assemblies to specifically target and disrupt tumor cell mitochondria in a photocontrollable manner. Moreover, the nanoassemblies displayed extremely high near-infrared-induced photothermal efficiency.

2.
Chem Commun (Camb) ; 55(56): 8138-8141, 2019 Jul 09.
Artigo em Inglês | MEDLINE | ID: mdl-31240296

RESUMO

A 2D polypseudorotaxane-type assembly was constructed using cucurbit[8]uril and styrylpyridinium-bearing triphenylamine. In addition, tunable non-covalent to covalent transition was achieved by [2+2] photodimerization of styrylpyridinium units. Thus, a more stable 2D polyrotaxane-type nanoarchitecture was obtained, which could capture [60]fullerene and further exhibit an excellent photodynamic therapy effect.

3.
Angew Chem Int Ed Engl ; 58(31): 10553-10557, 2019 Jul 29.
Artigo em Inglês | MEDLINE | ID: mdl-31165539

RESUMO

Tunable protein assemblies not only hold a dominant position in vital biological events but are also a significant theme in supramolecular chemistry. Herein, we demonstrated that the intertubular aggregation of microtubules (MTs) could be efficiently regulated by a synergistic polypeptide-tubulin interaction and host-guest complexation. The benzylimidazolium-modified antimitotic peptide (BP) could recognize the MTs and concurrently form stable inclusion complexes with avirulent cucurbit[7]uril (CB[7]) and cucurbit[8]uril (CB[8]) in different binding stoichiometries. The self-assembling morphology of MTs was converted from fibrous to nanoparticulate aggregates via extensive BP⊂CB[8] cross-linkage, leading to significant cell apoptosis and tumor ablation in vivo. The targeted (BP⊂CB[8])@MT ternary assembly provides a facile supramolecular method to enhance the protein-protein interactions, which may be developed as a therapy for degenerative diseases, such as cancer.

4.
iScience ; 15: 223-233, 2019 Apr 26.
Artigo em Inglês | MEDLINE | ID: mdl-31079026

RESUMO

Biofunctional supramolecular assemblies that combine macrocyclic receptors and amphiphiles are potent drug delivery systems, but optimization and implementation challenges remain. We herein describe a cooperative drug displacement strategy exemplified by the use of cyclodextrin-liposome supramolecular nanoassemblies as a therapy for acute liver injury. The hepatoprotective drug silibinin was solubilized in phosphotyramine-modified ß-cyclodextrin, and subsequent encapsulation of the silibinin-cyclodextrin complex in phosphatidylcholine liposomes gave uniformly sized and stable nanoassemblies that accumulated preferentially in the liver of mice. Enzymatic cleavage of the phosphate ester of the ß-cyclodextrin resulted in rapid release of the encapsulated silibinin. Significantly, silibinin could be readily displaced by cytotoxic bile acids, thus leading to the removal of excess bile acids from the bodies of mice and the recovery of liver function. Our results demonstrate that cyclodextrin-based nanoassemblies with a dual role of solubilizing a drug and removing toxins constitute a promising therapy for hepatic injury.

5.
Adv Mater ; : e1806158, 2019 Feb 18.
Artigo em Inglês | MEDLINE | ID: mdl-30773709

RESUMO

Cyclodextrins (CDs), which are a class of cyclic oligosaccharides extracted from the enzymatic degradation of starch, are often utilized in molecular recognition and assembly constructs, primarily via host-guest interactions in water. In this review, recent progress in CD-based supramolecular nanoassemblies that are sensitive to chemical, biological, and physical stimuli is updated and reviewed, and intriguing examples of the biological functions of these nanoassemblies are presented, including pH- and redox-responsive drug and gene delivery, enzyme-activated specific cargo release, photoswitchable morphological interconversion, microtubular aggregation, and cell-cell communication, as well as a geomagnetism-controlled nanosystem for the suppression of tumor invasion and metastasis. Moreover, future perspectives and challenges in the fabrication of intelligent CD-based biofunctional materials are also discussed at the end of this review, which is expected to promote the translational development of these nanomaterials in the biomedical field.

6.
Chem Commun (Camb) ; 55(8): 1164-1167, 2019 Jan 25.
Artigo em Inglês | MEDLINE | ID: mdl-30632564

RESUMO

A pH-responsive and targeted polysaccharide conjugate was fabricated from the boronate linkage of N-(2-aminoethyl)-gluconamide-grafted hyaluronic acid with anticancer drug bortezomib, which could exhibit targeted drug release behaviors at acidic pH and possess lower cytotoxicity and a higher inhibition effect toward cancer cells.


Assuntos
Antineoplásicos/farmacologia , Ácidos Borônicos/química , Bortezomib/farmacologia , Reagentes para Ligações Cruzadas/química , Sistemas de Liberação de Medicamentos , Polissacarídeos/química , Animais , Antineoplásicos/química , Bortezomib/química , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Sobrevivência Celular/efeitos dos fármacos , Portadores de Fármacos/química , Ensaios de Seleção de Medicamentos Antitumorais , Gluconatos/química , Humanos , Ácido Hialurônico/química , Concentração de Íons de Hidrogênio , Células MCF-7 , Camundongos , Células NIH 3T3
7.
Chem Commun (Camb) ; 54(96): 13591-13594, 2018 Dec 14.
Artigo em Inglês | MEDLINE | ID: mdl-30444508

RESUMO

Lamellar and helical supramolecular assemblies were constructed using cucurbiturils and a naphthalenediimide derivative. More interestingly, the formation of the lamellar assembly could be reversibly photocontrolled via competitive binding with α-cyclodextrin and water-soluble azobenzene.

8.
Sci Adv ; 4(9): eaat2297, 2018 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-30255143

RESUMO

Supramolecular nanoassemblies that respond to multiple stimuli exhibit high therapeutic efficacy against malignant tumors. We report a new type of supramolecular nanofiber that integrates targeting peptide-coated magnetic nanoparticles with ß-cyclodextrin-bearing polysaccharides in a complex held together by multivalent interactions. The nanofibers not only exhibited reversible photo-triggered association and disassociation depending on irradiation wavelength but also underwent magnetic field-controlled directional aggregation, even in the rather weak geomagnetic field. The nanofibers markedly suppressed invasion by and metastasis of cancer cells both in vitro and in vivo. Furthermore, compared with control mice, tumor-burdened mice treated with the nanofibers showed a lower rate of mortality from the metastatic spread of tumor cells. Our results suggest that these geomagnetism- and photo-controlled nanofibers may facilitate the rapid development of efficacious anticancer therapies.

9.
Chem Commun (Camb) ; 54(63): 8713-8716, 2018 Aug 02.
Artigo em Inglês | MEDLINE | ID: mdl-30023992

RESUMO

Supramolecular nanoparticles composed of doubly positively charged adamantane (ADA2+) and ß-CD modified hyaluronic acid (HACD) were constructed. When the ester group in ADA2+ was hydrolyzed to a carboxyl group, the quaternary ammonium chain with a positive charge in ADA2+ converted to a "zwitterionic" structure, and the controlled binding and release of pDNA was realized.


Assuntos
DNA/química , Ácido Hialurônico/química , Nanopartículas/química , beta-Ciclodextrinas/química , Adamantano/química , Substâncias Macromoleculares/química , Conformação Molecular
10.
Angew Chem Int Ed Engl ; 57(28): 8649-8653, 2018 Jul 09.
Artigo em Inglês | MEDLINE | ID: mdl-29781242

RESUMO

The design and construction of multi-stimuli-responsive supramolecular nanoassemblies that can mimic and regulate the fundamental biological processes have become a focus of interest in supramolecular chemistry. In this work, a perfect combination has been achieved between naturally occurring microtubules and artificially macrocyclic receptors. The self-assembling morphology of microtubules can be photo-tuned by the host-guest interaction of paclitaxel-modified ß-cyclodextrin (PTX-CD) and photochromic arylazopyrazole (PTX-AAP). Moreover, the supramolecularly aggregated microtubules in a cellular environment can induce a pronounced cell morphological change and cell death. This supramolecular approach based on the secondary PTX-AAP⊂PTX-CD complexation provides us a facile method to reversibly control the intertubular aggregation behaviors of microtubules, which may bring new perspectives in the treatment of diseases related to improper protein aggregation.

11.
ACS Appl Mater Interfaces ; 10(15): 12135-12140, 2018 Apr 18.
Artigo em Inglês | MEDLINE | ID: mdl-29048153

RESUMO

The precise control of molecular interaction and motion is a powerful strategy in the creation and development of intelligent materials. We demonstrate here a simple concept and approach to integrate intramolecular photochromic property with intermolecular aggregation-induced emission behaviors, with the aim to construct a new type of photoswitchable luminescent materials. This strategy is realized by the dithienylethene-bridged bispyridinium salt as photochromic molecular turnstile, and their subsequent fabrication into optically functional materials is reported. By restricting the rotation of central chemical bonds, the obtained molecular turnstile not only exhibits photocontrolled fluorescence emission through solvent exchange but is also capable of transforming into photowritable and photoerasable films in polymeric matrix with good recyclability. This functional molecular turnstile provides convenient routes to construct photochromic nanomaterials with controlled photophysical behaviors.

12.
J Thorac Dis ; 9(9): E815-E826, 2017 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-29221350

RESUMO

Glomus tumors (GTs) of the trachea are very rare neoplasms that usually arise from the distal portion of the respiratory tree. The origin of these tumors is modified smooth muscle cells of glomus bodies. In this study, we describe two cases of GT of the trachea, as well as the histologic features of these tumors and their treatments. One tumor was diagnosed via bronchoscopic biopsy, and the other tumor was diagnosed via surgery. Clinical follow-up showed that the two patients are alive and well after 8 and 15 months post-treatment, respectively. We also review the literature regarding GTs and discuss the clinical presentation, histologic features, differential diagnosis, treatment and prognosis of these tumors.

13.
Chemistry ; 23(58): 14425-14429, 2017 Oct 17.
Artigo em Inglês | MEDLINE | ID: mdl-28880426

RESUMO

Research on photochromic molecules switched by visible light is of particular interest for their application in bioimaging and stimuli-responsive materials. Here, a photoswitchable supramolecular assembly comprised of monocharged bispyridinium-modified diarylethenes (DAEs) and cucurbit[8]uril (CB[8]) has been constructed, which exhibits reversible photochromic behaviour with visible light in both directions. The transformation of CB[8] not only prompts the DAEs to form charge-transfer complexes, but also restricts its intramolecular rotation to enhance fluorescence emission. In this CB[8]-containing supramolecular system, the π-conjugation is extended and its absorption is bathochromically shifted for visible light-driven cyclization of DAEs. Meanwhile, the fluorescence of the supramolecular assembly can also be reversibly modulated by visible light. These findings may furnish a new strategy for the development of visible light-driven fluorescent biomaterials and molecular machines.

14.
J Med Chem ; 60(8): 3266-3274, 2017 Apr 27.
Artigo em Inglês | MEDLINE | ID: mdl-28398754

RESUMO

Supramolecular encapsulation has been developed into a powerful tool in clearance of toxic substances and hazardous waste from living body and external environments. Herein we tested the special efficacy of tyramine-modified ß-cyclodextrin (1) in inhibiting and reversing of the inherent cytotoxicity of deoxycholic acid (DCA). The decarboxylation from tyrosine to tyramine in 1 is crucial to the mutual electrostatic communication, ultimately leading to great enhancement in binding affinity and molecular selectivity toward bile acids. As a result, the DCA-mediated cytotoxicity could be largely eliminated by the biocompatible 1. Meanwhile, the excess DCA could be rapidly excreted by 1 via rat urinary clearance, thus facilitating the decrease of DCA concentration in blood. This study presents a proof of principle that the supramolecular encapsulation with functional cyclodextrin derivatives can efficiently modulate the cell progression and remove the cytotoxic DCA, which provides a practical approach to prevent or treat bile acid-involved diseases.


Assuntos
Sobrevivência Celular/efeitos dos fármacos , Ácido Desoxicólico/farmacologia , Animais , Linhagem Celular Tumoral , Ácido Desoxicólico/sangue , Ácido Desoxicólico/química , Ácido Desoxicólico/urina , Feminino , Humanos , Interações Hidrofóbicas e Hidrofílicas , Camundongos , Camundongos Endogâmicos BALB C , Ratos
15.
Chem Commun (Camb) ; 53(26): 3717-3720, 2017 Mar 28.
Artigo em Inglês | MEDLINE | ID: mdl-28300240

RESUMO

A novel supramolecular assembly was constructed by the noncovalent complexation of hexa-cata-hexabenzocoronene modified permethyl-ß-cyclodextrins with tetrasodium tetraphenylporphyrintetrasulfonate in water, exhibiting highly efficient excited energy transfer behaviors and a promising DNA photocleavage ability.


Assuntos
Clivagem do DNA/efeitos da radiação , Transferência de Energia , Luz , Fármacos Fotossensibilizantes/química , Compostos Policíclicos/química , Porfirinas/química , beta-Ciclodextrinas/química
16.
Onco Targets Ther ; 10: 447-452, 2017.
Artigo em Inglês | MEDLINE | ID: mdl-28176910

RESUMO

In the absence of a driver mutation, chemotherapy is the standard treatment option as first- and second-line therapy for advanced non-small-cell lung cancer (NSCLC). Though a large number of patients are suitable for post second-line therapies, the quality and quantity of the available drugs in this setting is poor. Apatinib, a small molecule vascular endothelial growth factor receptor-2 (VEGFR-2) tyrosine kinase inhibitor, is a first-generation oral antiangiogenesis drug approved in the People's Republic of China for use as a subsequent line of treatment for advanced gastric cancer. Herein, we report three cases of advanced NSCLC with epidermal growth factor receptor wild-type and anaplastic lymphoma kinase-negative status, wherein the patients showed partial response to apatinib. Moreover, the three patients have achieved a progression-free survival of 2.8, 5.8, and 6 months, respectively. The main toxicities were hypertension, proteinuria, and hand-foot syndrome. Apatinib may provide an additional option for the treatment of advanced NSCLC, especially for advanced lung adenocarcinoma without a driver mutation.

17.
Bioconjug Chem ; 27(12): 2834-2838, 2016 Dec 21.
Artigo em Inglês | MEDLINE | ID: mdl-27998070

RESUMO

ß-Cyclodextrin modified camptothecin (CPT-CD) was synthesized through esterification reaction and "click chemistry" to greatly improve the solubility of CPT in aqueous solution, and then, a supramolecular nanoparticle was constructed by strong noncovalent interaction between ß-cyclodextrin and adamantane and amphiphilic interaction by simply mixing CPT-CD and adamantane modified hyaluronic acid (HA-ADA) together. The obtained nanoparticle had a hydrophilic HA shell, which could target and recognize HA receptors overexpressed on the surface of cancer cells, and a hydrophobic CPT core, which could protect CPT from hydrolyzation. The results of cytotoxicity experiments showed that the nanoparticle we have designed in this work exhibited similar anticancer activities to, but with much lower side effects than, the commercial chemotherapeutic drug CPT in vitro. We believe that this work might provide a strategy for improving the treatment performance of CPT in laboratory and clinical settings.


Assuntos
Antineoplásicos Fitogênicos/administração & dosagem , Camptotecina/administração & dosagem , Preparações de Ação Retardada/química , beta-Ciclodextrinas/química , Adamantano/química , Animais , Antineoplásicos Fitogênicos/química , Camptotecina/química , Preparações de Ação Retardada/farmacocinética , Portadores de Fármacos/administração & dosagem , Portadores de Fármacos/química , Ensaios de Seleção de Medicamentos Antitumorais , Difusão Dinâmica da Luz , Células HCT116/efeitos dos fármacos , Humanos , Ácido Hialurônico/química , Camundongos , Microscopia de Força Atômica , Microscopia Eletrônica de Transmissão , Células NIH 3T3/efeitos dos fármacos , Nanopartículas/administração & dosagem , Nanopartículas/química , Solubilidade
18.
Angew Chem Int Ed Engl ; 55(38): 11452-6, 2016 09 12.
Artigo em Inglês | MEDLINE | ID: mdl-27527684

RESUMO

Nanosupramolecular assemblies with controlled topological features have inventive applications in fundamental studies and material manufacturing. Herein, a variety of morphologically interesting aggregates have been constructed using the supramolecular modulation with bipyridinium-modified diphenylalanine derivative (BP-FF). Benefiting from the high binding affinity of bipyridinium group with four different macrocyclic receptors, namely cucurbit[7]uril, cucurbit[8]uril, pillar[5]arene, and tetrasulfonated crown ether, we have succeeded in tuning the topological aggregates of BP-FF from fine nanofibers to nanorods, octahedron-like nanostructure, helical nanowires, and rectangular nanosheets without any tedious chemical modification. This supramolecular approach may provide us a powerful method to construct well-defined nanostructures with different morphologies that can be conveniently controlled by facile host-guest interactions.

19.
Sci Rep ; 6: 28848, 2016 07 01.
Artigo em Inglês | MEDLINE | ID: mdl-27363811

RESUMO

Biomacromolecular pKa shifting is considered as one of the most ubiquitous processes in biochemical events, e.g., the enzyme-catalyzed reaction and protein conformational stabilization. In this paper, we report on the construction of biocompatible polysaccharide nanoparticle with targeting ability and lower toxicity by supramolecular pKa shift strategy. This was realized through a ternary assembly constructed by the dual host‒guest interactions of an adamantane-bis(diamine) conjugate (ADA) with cucurbit[6]uril (CB[6]) and a polysaccharide. The potential application of such biocompatible nanostructure was further implemented by the selective transportation of small interfering RNA (siRNA) in a controlled manner. It is demonstrated that the strong encapsulation of the ADA's diammonium tail by CB[6] not only reduced the cytotoxicity of the nano-scaled vehicle but also dramatically enhanced cation density through an obvious positive macrocycle-induced pKa shift, which eventually facilitated the subsequent siRNA binding. With a targeted polysaccharide shell containing a cyclodextrin‒hyaluronic acid conjugate, macrocycle-incorporated siRNA polyplexes were specifically delivered into malignant human prostate PC-3 cells. The supramolecular polysaccharide nanoparticles, the formation of which was enabled and promoted by the complexation-assisted pKa shift, may be used as a versatile tool for controlled capture and release of biofunctional substrates.


Assuntos
Nanopartículas/química , Polissacarídeos/química , Neoplasias da Próstata/genética , RNA Interferente Pequeno/genética , Animais , Linhagem Celular Tumoral , Sobrevivência Celular/genética , Ciclodextrinas/química , Sistemas de Liberação de Medicamentos/métodos , Proteínas de Fluorescência Verde/genética , Proteínas de Fluorescência Verde/metabolismo , Humanos , Ácido Hialurônico/química , Concentração de Íons de Hidrogênio , Masculino , Camundongos , Microscopia de Fluorescência , Células NIH 3T3 , Neoplasias da Próstata/metabolismo , Neoplasias da Próstata/terapia , RNA Interferente Pequeno/administração & dosagem , RNA Interferente Pequeno/química
20.
J Phys Chem B ; 120(16): 3932-40, 2016 04 28.
Artigo em Inglês | MEDLINE | ID: mdl-27046098

RESUMO

The push-pull molecules with an intramolecular charge transfer from donor to acceptor sides upon excitation exhibit a wide variety of biological and electronic activities, as exemplified by the in vivo fluorescence imaging probes for amyloid fibrils in the diagnosis and treatment of amyloid diseases. Interestingly, the structurally much simpler bis(4,8-disulfonato-1,5-naphtho)-32-crown-8 (DNC), in keen contrast to the conventional macrocyclic receptors, was found to dramatically enhance the fluorescence of twisted intramolecular charge-transfer molecules possessing various benzothiazolium and stilbazolium fluorophores upon complexation. Spectroscopic and microcalorimetric titrations jointly demonstrated the complex structures and the interactions that promote the extremely strong complexation, revealing that the binding affinity in these artificial host-guest pairs could reach up to a nearly 10(7) M(-1) order of magnitude in water, and the sandwich-type complexation is driven by electrostatic, hydrophobic, π-stacking, and hydrogen-bonding interactions. Quantum chemical calculations on free molecules and their DNC-bound species in both the ground and excited states elucidated that the encapsulation by DNC could greatly deter the central single and double chemical bonds from free intramolecular rotation in the singlet excited state, thus leading to the unique and unprecedented fluorescence enhancement upon sandwich-type complexation. This complexation-induced structural reorganization mechanism may also apply to the binding of other small-molecule ligands by functional receptors and contribute to the molecular-level understanding of the receptor-ligand interactions in many biology-related systems.


Assuntos
Amiloide/química , Fluorescência , Receptores Artificiais/química , Tiazóis/química , Corantes Fluorescentes/química , Ligantes , Conformação Molecular , Teoria Quântica
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