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Synthesis of novel modified β-cyclodextrins and their fluorescence studies of inclusion complexation with Rhodamine B

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Chinese Journal of Chemistry 2000年第3期18卷 432-434页

作者：靳兰刘育 Department of Chemistry Nankai University Tianjin 300071 China

Three novel β-cyclodextrin derivatives have been synthesized and their inclusion complexation behavior with Rhodamine B (RhB) was investigated by the fluorescence spectroscopy.

关键词： β-Cyclodextrin derivatives Rhodamine B inclusion complexation

Synthesis of a Novel Aromatic Diamino-bridged Bis(β-cyclodextrin) and its inclusion complexation with Dyes Molecules

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Chinese Chemical Letters 2006年第12期17卷 1543-1546页

作者： Yah ZHAO Xiao Qing LIU Hong You ZHU Zi Ming YANG Rong HUANG College of Chemistry and Chemical Engineering Yunnan Normal University Kunming 650092 School of Chemical Science and Technology Yunnan University Kunming 650091 Experimental Center Yunnan University Kunming 650091

A novel brideed bis（β-cvclodextrin）, 4, 4＇-diaminodiphenyl ether-bfiged-bis （6-aimino-6-deoxv-β-cyclodextrin） 3, has been synthesized and its inclusion complexation behavior with three linear＇guest dyes （AR, NR and MB ） has been investigated by. means of fluorescence spectrometry. The-result obtained demonstrated that the novel bridged bis（β-cyclodextnn） showed much higher affinities towards guest dyes than native β-cyclodextrin.

关键词： Bridged bis(β-cyclodextrin)s cooperative binding inclusion complexation dye.

Spectrofluorometric Study of the inclusion complexation of Fluorescent Whitening Agents and β-Cyclodextrins

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International Journal of Organic Chemistry 2016年第4期6卷 192-206页

作者： Carlos Alberto Ramírez Barragán Ezequiel Delgado Fornué Jesús Angel Andrade Ortega Guillermo Toríz González Héctor Jesús Contreras Quiñones Centro de Investigación en Biomateriales Departamento de Madera Celulosa y Papel Centro Universitario de Ciencias Exactas e Ingenierías Universidad de Guadalajara Guadalajara Jalisco México

The inclusion complexation behavior of 2,5-Bis(5-tert-butyl-benzoxazol-2yl)-thiophene (UVOB) with native β-cyclodextrin (βCD) and βCD-monochlorotriazinyl (βCD-MCT) was evaluated by fluorescence spectroscopy. The association constant (Ks), stoichiometry, , and were evaluated at 25℃ ± 0.1℃ in phosphate buffer solution (pH = 10.5, 0.1 mo•dm–3) in order to find out the complex formation ability and stability. Fluorescence enhancement for UVOB and UVBNB with both CDs has been observed as a result of the complex formation. A stoichiometry 1:1 for UVOB in both CDs was observed;a stoichiometry 3:1 for UVBNB in both CDs has been observed. The Ksvalues for UVOB were 4916 ± 137 M–1 and 655 ± 19 M–1 (acetone: water 90/10, v/v) with βCD and βCD-MCT, respectively. The value obtained indicates a spontaneous and stable complex formation, but the complex βCD-UVOB showed high Ks value as an indicative of a high concentration of complex formed. Additionally, Ks and thermodynamic parameters and were evaluated in a commercial product UVBNB (UVOB, 13%, v/v). In aqueous solution, the values obtained were 2552 ± 115 and 1787 ± 75 M–1 respectively. complexation of UVOB with CDs is an interesting approach for utilization of UVOB in aqueous systems without the need of solvents and or surfactants used in commercial product (UVBNB).

关键词： Spectrofluorometry β-Cyclodextrin Monochlorotriazinyl Fluorescent Whitening Agents inclusion complexation

Modification of polyfluorene nanoparticles via inclusion complexa- tion based on cyclodextrin for lectin sensing and cell imaging

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Science China Chemistry 2016年第12期59卷 1616-1620页

作者： PengfeiSun Mingchang Lin Guosong Chen Ming Jiang Key Laboratory for Organic Electronics and Information Displays&Institute of Advanced Materials(IAM) Jiangsu National Synergetic Innovation Center for Advanced Materials(SICAM)Nanjing University of Posts&TelecommunicationsNanjing 210023China State Key Laboratory of Molecular Engineering of Polymers Department of Macromolecular ScienceFudan UniversityShanghai 200433China

Currently, conjugated polymer nanoparticles are widely used with many biological applications, especially bio-imaging and labeling. Thus their modification with different biomacromolecules becomes a crucial step before various applications. In literature,this modification was normally performed via covalent bonds. To our best knowledge, modification based on inclusion complexation has not been reported. Herein, via host-guest interaction between cyclodextrin and adamantane, supramolecular modification to conjugated polyfluorene nanoparticles has been successfully achieved. The glycopolymer-modified conjugated polymer nanoparticles showed excellent binding ability to lectins, such as Galectin-3 and selective imaging behavior to Hep G2 cells.

关键词： inclusion complexation conjugated polymer nanoparticles polyfluorene glycopolymer Galectin-3

Molecular Recognition of Bridged Bis(β-cyclodextrin)s Linked by Phenylenediseleno Tether on the Primary or Secondary Side with Fluorescent Dyes

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Chinese Journal of Chemistry 2003年第7期21卷 964-969页

作者：李莉何松刘育 Department of Chemistry State Key Laboratory of Elemento-Organic Chemistry Nankai University Tianjin 300071 China

A Novel β-cyclodextrin dimer,2,2′-o-phenylenediseleno-bridgedbis（β-cyclodextrin）（2）,has been synthesized by reaction ofmono-[2-O-（p-tolylsulfonyl）]-β-cyclodextrin and poly（o-phenylenediselenide）.The complexation stability constants（Ks）and Gibbs free energy changes（-ΔG°）of dimer 2 with fourfluorescence dyes,that is,ammonium 8-anilino-1-naphthalene-sulfonate（ANS）,sodium 6-（p-toluidino）-2-naphthalenesul-fonate（TNS）,Acridine Red（AR）and Rhodamine B（RhB）have been determined in aqueous phosphate buffer solution(pH=7.2,0.1 mol·L-1at 25℃ by means of fluorescence spec-

关键词： oganoselenium-bridged bis(β-cyclodextrin) molecular recognition inclusion complexation binding mode

Insoluble drug delivery strategies: review of recent advances and business prospects

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Acta Pharmaceutica Sinica B 2015年第5期5卷 442-453页

作者： Sandeep Kalepu Vijaykumar Nekkanti Department of Pharmaceutical Technology Shri Vishnu College of Pharmacy College of Pharmaceutical Sciences Western University of Health Sciences

The emerging trends in the combinatorial chemistry and drug design have led to the development of drug candidates with greater lipophilicity, high molecular weight and poor water solubility. Majority of the failures in new drug development have been attributed to poor water solubility of the drug. Issues associated with poor solubility can lead to low bioavailability resulting in suboptimal drug delivery. About 40% of drugs with market approval and nearly 90% of molecules in the discovery pipeline are poorly water-soluble. With the advent of various insoluble drug delivery technologies, the challenge to formulate poorly water soluble drugs could be achieved. Numerous drugs associated with poor solubility and low bioavailabilities have been formulated into successful drug products. Several marketed drugs were reformulated to improve ef fi cacy, safety and patient compliance. In order to gain marketing exclusivity and patent protection for such products, revitalization of poorly soluble drugs using insoluble drug delivery technologies have been successfully adopted by many pharmaceutical *** review covers the recent advances in the fi eld of insoluble drug delivery and business prospects.

关键词： Bioavailability Cocrystals Solubility inclusion complexation Nanoparticles Self-emulsifying formulations Proliposomes

Synthesis of A Novel Bridged Bis(β-cyclodextrin)s Possessing Phenan- throline Tether and Its Molecular Binding Ability with Dyes

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Chinese Chemical Letters 2003年第1期14卷 9-12页

作者： Li Peng LIANG 等 DepartmentofChemistry StateKeyLaboratoryofElemento-OrganicChemistryNankaiUniversityTianjin300071 DepartmentofChemistry StateKeyLaboratoryofElemento-OrganicChemistryNankaiUniversit

A novel b-cyclodextrin dimer bearing 2, 9-diformyl-1, 10-phenanthroline tether 4 has been synthesized and its inclusion complexation behavior with two triangular model substrates (RhB and BG) has been investigated through fluorescence and ultraviolet spectrometry. The result obtained indicated that novel bridged bis(b-cyclodextrin)s could significantly enhance the original molecular binding ability of native b-cyclodextrin by cooperative binding of two hydrophobic cavities.

关键词： Bis(β-cyclodextrin)s inclusion complexation dye binding ability.

A Theoretical Study on the Stereoisomerism in the Complex of Cucurbit[8]uril with 2,6-Bis(4,5-dihydro-1H-imidazol-2-yl)naphthalene

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Chinese Chemical Letters 2001年第9期12卷 783-786页

作者： Ting Wei MU Lei LIU Ke Chun ZHANG Qing Xiang GUO Department of Chemistry University of Science and Technology of ChinaHefei 230026

Semiempirical PM3 and density function theory B3LYP/3-21g* calculations in vacuum and in water indicated that the 'syn' orientation was preferred in the 1:2 complex of cucurbit[8]uril with protonated 2, 6-bis(4, 5-dihydro-1H-imidazol-2-yl)naphthalene. The pi-pi stacking interaction between the two substrate molecules was proposed as the physical origin of such a behavior.

关键词： Cucurbiturils inclusion complexation PM3 B3LYP pi-pi stacking

A Study on the Driving Force for Binding of Benzene Derivatives by α-and β-Cyclodextrin

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Chinese Chemical Letters 1998年第5期9卷 463-464页

作者： Shuang Hui LUO Hui Ming JMNG You Cheng LIU(National Laboratory of Applied organic Chemistry, Lanzhou University, Lanzhou 730000)Qing Xiang GUO (Department of Chemistry, University of Science and Technology of China, Hefei 230026) Lanzhou Univ Natl Lab Appl Organ Chem Lanzhou 730000 Peoples R China Univ Sci & Technol China Dept Chem Hefei 230026 Peoples R China

A three-dimensional diagram shows that the association constants (Ka) for the inclusionof a- and 6-CD with substitUted benzene are mainly correIated with the molar refraction (R.) andhydrophobic constant (%) of the substitUents of guest compounds. It reveals that the inclusion ofcyclodextrin with the substitUted benzene is dondnantly driYen by van der Waals forces andhydrophobic interactions.

关键词： benzene derivatives cyclodextrin driving force inclusion complexation