Deciphering the host–guest chemistry of Acridine Yellow and Cucurbit[7]uril: An integrated spectroscopic and calorimetric study

Chakraborty, Brotati; Basu, Samita

doi:10.1016/j.cplett.2011.03.014

Cited by 16 publications

(76 citation statements)

References 39 publications

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“…However, in comparison with the solution of the supramolecular system, the characteristic emission peak for Azo/!-CD-RB has moved from 580 to 587 nm. The reason for this red shift may be the change of surrounding environment from dryness to aqueous, so does the polarity [43,44].…”

Section: Fabrication Of Multilayer Films Via Electrostatic Interactionmentioning

confidence: 99%

Light-controlled drug releasing polymer films combining LbL self-assembly and host-guest interactions

Li¹,

He²,

Wang³

et al. 2014

Express Polym. Lett.

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Abstract. By combining LbL (layer-by-layer) self-assembly approach and host-guest interactions, a unique multilayer film was constructed and employed for a light-controlled drug release system. The drug molecules can be loaded and released into the resulting polyelectrolyte multilayers containing azobenzene (Azo) function groups by using the irradiation of visible light and UV light alternately. The photo-sensitivity of the multilayer films was studied through UV-vis spectrum, fluorescence spectrum and confocal microscopy. The target molecules could be rapidly released from the multilayers after 300 W UV light irradiation for 20 minutes. Moreover, they could be readsorbed into the multilayers uniformly when illuminated under the 300 W visible light for 10 minutes confirmed by the observation of confocal microscopy, and the readsorption ratio exceeds 100% evidenced from UV-vis spectroscopy. After several cycles of the above-mentioned process, the multilayer films show good fatigue resistance. All these results indicate the photo-sensitivity and high-efficiency of the multilayer films, which have great potential in controlled drug delivery platform and biomedical applications. : coatings, layer-by-layer, host-guest interactions, light response, drug delivery eXPRESS Polymer Letters Vol.8, No.3 (2014) 143-153 Available online at www.expresspolymlett.com DOI: 10.3144/expresspolymlett.2014.18 * Corresponding author, e-mail: softmatter@163.com © BME-PT nating irradiation with UV and Vis light allows for reversible sliding of !-CD along the surfactant, leading to the formation of rotaxane-like vesicles. Based on this principle, light-responsive host-guest assembly and disassembly between Azo and CD hold great potential to design a reversible drug delivery profile [16,17]. Layer-by-layer (LbL) self-assembly approach is particularly well-suited for fabricating functional multilayer thin films with ultrafine nanometer-scale structure for use as drug delivery vehicles [18][19][20][21]. The traditional means of loading drugs on layers of LbL platform always uses physical adsorption or chemical bonding. However, these methods of loading drugs have a common drawback: drug loading and release is irreversible. This is a critical problem in LbL multilayers for drug delivery. Therefore, it's desired to devise a reversible LbL-based system to manipulate the drug release in a more controllable manner. In the past decade, the pioneering work on LbL assembly with supramolecular interaction has been established by Ikeda et al. [22]. Subsequently, Smith et al. [23] have reported that loading smallmolecule drugs on the layers of LbL-based system using supramolecular interaction. On another front, the light-induced drug release from a LbL-based system is the most elegant way to combine reversibly and efficiency, because light as an attractive stimulus can be applied rapidly, remotely, and locally [24,25]. While numerous well-established photoresponsive LbL-based systems are available [26,27], their applications in drug release b...

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Section: Fabrication Of Multilayer Films Via Electrostatic Interactionmentioning

confidence: 99%

Light-controlled drug releasing polymer films combining LbL self-assembly and host-guest interactions

Li¹,

He²,

Wang³

et al. 2014

Express Polym. Lett.

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“…São caracterizadas pelas colorações vermelha, roxa e azul de uma variedade de flores, frutas e folhas. A sua estabilidade é influenciada por diversos fatores como o pH local do meio, temperatura, luz ou copigmentos.A inclusão das antocianinas e análogos sintéticos, os sais de flavílio, dentro da cavidade da cucurbit [7]uril (CB [7]), sistema hóspede-hospedeiro, foi estudada a partir da espectroscopia de fluorescência. As antocianinas sintéticas utilizadas foram o cloreto de 7-hidroxi-4-metilflavílio (HMF) e o cloreto de 7-metoxi-4-metilflavílio (MMF) e as antocianinas naturais foram a cianindina-3-glicosídeo, cianidina-3,5-di-O-glicosídeo e antocianinas presentes no extrato do jambolão (Syzygium cumini).…”

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“…Essa elevada constante de incorporação é devida à interação eletrostática entre as carbonilas do CB [7] e a carga positiva do anel pírilio das antocianinas. Entretanto, a segunda constante de incorporação, K12, apresenta um valor menor por causa da repulsão entre a primeira e a segunda molécula de CB [7].A segunda constante de inclusão das antocianinas naturais apresentou um valor muito baixo em relação à segunda constante de incorporação do HMF e MMF. Essa diferença ocorreu pelo impedimento estérico provocado pelas unidades glicosídicas presentes nas antocianinas naturais.…”

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“…The stoichiometry of the inclusion and the incorporation equilibrium constants were determined from the binding isotherms by non-linear regression. For the synthetic flavylium ions, the stoichiometry was also verified using the method of continuous variations or Job plots.The first binding constant, K11, between the anthocyanins or flavylium ions and CB [7] was of the order of 10 5 -10 6 M -1 . This large equilibrium constant for incorporation reflects the electrostatic interaction between the carbonyl groups of CB [7] and the positive charge of the pyrilium ring of the anthocyanins.…”

mentioning

confidence: 99%

“…The anthocyanins, the largest group of natural plant pigments, are responsible for the red, purple and blue colors of a variety of flowers, fruit and leaves. Their stability is influenced by several factors, including the local pH of the medium, temperature, light and copigments.The inclusion of natural anthocyanins and their synthetic analogs, flavylium cations, in the cavity of cucurbit [7]uril, CB [7], to form host-guest complexes, was studied by fluorescence spectroscopy. The synthetic anthocyanin model compounds utilized were 7-hydroxy-4-methylalavylium (HMF) chloride and 7-methoxy-4-methylflavylium (MMF) chloride and the naturally-occurring anthocyanins were cyaniding-3-O-glucoside, cyaniding-3,5-di-O-glucoside and the anthocyanins extracted from jambolão (Syzygium cumini) fruit.…”

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Complexos de inclusão de antocianinas e análogos sintéticos de antocianinas

Silva¹

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São Paulo 2015 DedicatóriaDedico esse trabalho ao meu Pai (in memoriam) e a minha Mãe com todo o meu amor, afeto, gratidão por tudo que fizeram por mim, pôr os seus apoios ao longo da minha vida. Obrigado pelos seus ensinamentos, os quais me tornaram essa pessoa de bom caráter. Desejo poder ter sido merecedor de todos os seus esforços principalmente o da minha formação. AGRADECIMENTO(S)A DEUS, dando-me a oportunidade de estudar, trabalhar e crescer frente as dificuldades e desafios enfrentados durante essa jornada.Ao meu orientador, Prof. Dr. Frank Herbert Quina, pela oportunidade de realizar essa importante etapa em seu grupo de pesquisa.Ao meu grande amigo Walter Estella pela amizade, uma das pessoas mais incríveis que conheci ao longo da minha vida.À Bárbara que me auxiliou durante os experimentos iniciais.Ao Volnir que sempre me auxiliou todas às vezes que precisei dele e pelas discussões durante o cafezinho.À minha amiga Jennifer.Ao Prof. Drª. Cornélia Bohne pela disponibilização das cucurbit [7]urila.Ao pessoal do laboratório Celize, Joaquim, Jair, Letícia, Marina.Ao pessoal da minha república Lucas, Nícolas, César e Alexandre.Aos meus amigos Isis, Léo, Renan, Eliana, Evandro, Paulo, Diego, Cássio, Karla, Raquel.À Arlete uma irmã que sempre me apoiou em toda a minha vida.À minha família por todo o apoio.Ao CNPQ, pelo auxílio financeiro concedido (processo 132095/2013-0).Descobri como é bom chegar quando se tem paciência. E para se chegar, onde quer que seja, aprendi que não é preciso dominar a força, mas a razão. É preciso, antes de mais nada, querer. " Amyr Klink As antocianinas compreendem o maior conjunto de pigmentos naturais do Reino Vegetal. São caracterizadas pelas colorações vermelha, roxa e azul de uma variedade de flores, frutas e folhas. A sua estabilidade é influenciada por diversos fatores como o pH local do meio, temperatura, luz ou copigmentos.A inclusão das antocianinas e análogos sintéticos, os sais de flavílio, dentro da cavidade da cucurbit [7]uril (CB [7]), sistema hóspede-hospedeiro, foi estudada a partir da espectroscopia de fluorescência. As antocianinas sintéticas utilizadas foram o cloreto de 7-hidroxi-4-metilflavílio (HMF) e o cloreto de 7-metoxi-4-metilflavílio (MMF) e as antocianinas naturais foram a cianindina-3-glicosídeo, cianidina-3,5-di-O-glicosídeo e antocianinas presentes no extrato do jambolão (Syzygium cumini).Os complexos de inclusão das antocianinas e os análogos sintéticos dentro da cavidade do CB [7] apresentaram uma estequiometria de inclusão do tipo 1:2, uma molécula hóspede e duas moléculas hospedeiras. A estequiometria de inclusão e as constantes de incorporação foram determinadas a partir de isotermas da inclusão pelo método de regressão não-linear. Para os íons flavílios, a determinação da estequiometria também foi comprovada pelo Método da Variação Contínua (MVC) ou método Job.A primeira constante de incorporação K11 obtida para as antocianinas e os íons flavílios foi da ordem de 10 5 -10 6 M -1 . Essa elevada constante de incorporação é devida à interação el...

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Chemical Sensors Based on Cucurbit[n]uril Macrocycles

Sinn

Biedermann

2018

Israel Journal of Chemistry

147

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Cucurbit[n]urils (CBn) are glycoluril‐based macrocyclic hosts that bind many biologically, medicinally and environmentally relevant analytes with record high affinities in aqueous media. They are therefore prime candidates for the design of chemosensors that are operational in biological fluids, waste and drinking water and have promising potential to be utilized for in vitro and in vivo sensing and imaging applications. Unlike protein‐based antibodies, CBn can be prepared in multi kilogram scales, they are chemically robust and they show a desired fast analyte‐binding kinetics. Unlike protein‐based antibodies, CBn can be prepared in multi kilogram scales, are chemically robust and show a desired fast analyte‐binding kinetics Selective analyte detection and differentiation is possible owing to the charge‐ and size‐selective binding characteristics of the CBn members and due to the wide range of cyclic and acyclic CBn derivatives that differ in their analyte binding preference. Because CBn hosts are spectroscopically silent in the visible electromagnetic spectrum, optical signal transduction with CBn based chemosensing ensembles is typically performed by indicator displacement assays (IDA), which are easy to implement and applicable to both aliphatic and aromatic analytes. The extension to array‐based sensing with CBn chemosensors is straightforward. Associative binding assays (ABA), which are uniquely available with CB8‐based self‐assembled receptors offer superior analyte differentiation possibility due to emerging spectral fingerprints in the absorbance, circular dichroism (CD) and emission spectra for the receptor•analyte complexes. Direct signal generation is promising for inherently spectroscopically active analytes, for instance through absorbance, CD, emission and surface enhanced Raman spectroscopy (SERS). Sensitive NMR (19F, 129Xe) techniques, electron spin resonance (ESR), redox, and mass spectrometry are also valuable signal transduction options for specific analytes. CBn based chemosensors were successfully utilized for the monitoring of biophysical processes and enzymatic reactions with label free analytes or substrates in real time. These applications capitalize on the fast equilibration kinetics of CBn‐analyte complexes and the bio‐compatibility of CBn hosts. The tabulated large body of data extracted from reported CBn‐based binding studies is hoped to provide the reader with a valuable starting point for designing practically applicable CBn‐based sensors.

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Deciphering the host–guest chemistry of Acridine Yellow and Cucurbit[7]uril: An integrated spectroscopic and calorimetric study

Cited by 16 publications

References 39 publications

Light-controlled drug releasing polymer films combining LbL self-assembly and host-guest interactions

Light-controlled drug releasing polymer films combining LbL self-assembly and host-guest interactions

Complexos de inclusão de antocianinas e análogos sintéticos de antocianinas

Chemical Sensors Based on Cucurbit[n]uril Macrocycles

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