Nanochain and vesicles formed by inclusion complexation of 4,4′-diaminobenzanilide with cyclodextrins

References

• Szejtli J. Introduction and general overview of cyclodextrin chemistry. Chem Rev. 1998;98:1743–1754.
   PubMed Web of Science ®Google Scholar
• Misiuk W, Zalewska M. Investigation of inclusion complex of trazdone hydrochloride with hydroxypropyl-β-cyclodextrin. Carbohydr Polymers. 2009;77:482–488.
   Web of Science ®Google Scholar
• Connors KA. The stability of cyclodextrin complexes in solution. Chem Rev. 1997;97:1325–1358.
   PubMed Web of Science ®Google Scholar
• Zhao YL, Stoddart JF. Azobenzene-based light-responsive hydrogel system. Langmuir. 2009;25:8442–8446.
   PubMed Web of Science ®Google Scholar
• Tu CW, Kuo SW, Chang FC. Supramolecular self-assembly through inclusion complex formation between poly(ethylene oxide-b-n-isopropylacrylamide) block copolymer and alpha cyclodextrins. Polymer. 2009;50:2958–2966.
   Web of Science ®Google Scholar
• Choi S, Munteanu M, Ritter HJ. Monoacrylated cyclodextrin via ‘click’ reaction and copolymerization with n-isopropylacrylamide: guest controlled solution properties. J Polymer Res. 2009;16:389–394.
   Web of Science ®Google Scholar
• Wenz G, Han B-H, Muller A. Cyclodextrin rotaxanes and polyrotaxanes. Chem Rev. 2006;106:782–817.
   PubMed Web of Science ®Google Scholar
• Osaki M, Takashima Y, Yamaguchi H, Harada A. Nanospheres with polymerization ability coated by polyrotaxane. J Org Chem. 2009;74:1858–1863.
   PubMed Web of Science ®Google Scholar
• Discher DE, Eisenberg A. Polymer vesicles. Science. 2002;297:967–973.
   PubMed Web of Science ®Google Scholar
• Voskuhl J, Ravoo BJ. Molecular recognition of bilayer vesicles. Chem Soc Rev. 2009;38:495–505.
   PubMed Web of Science ®Google Scholar
• Bugler J, Sommerdijk NAJM, Visser AJWG, van Hoek A, Nolte RJM, Engbersen JFJ, Reinhoudt DN. Interconnective host–guest complexation of β-cyclodextrin–calix[4]arene couples. J Am Chem Soc. 1998;121:28–33.
   Web of Science ®Google Scholar
• Ravoo BJ, Darcy R. Cyclodextrin bilayer vesicles. Angew Chem. 2000;112:4494–4496.
   Google Scholar
• Ravoo BJ, Darcy R, Mazzaglia A, Nolan D, Gaffney K. Supramolecular tapes formed by a catanionic cyclodextrin in water. Chem Commun. 2001;9:827–828.
   Web of Science ®Google Scholar
• Sun L, Zhang H, Hao WAA, Hao J. Vesicles were prepared by β-cyclodextrins inclusion complexes based on switching supramolecular interaction models induced by mixed solvents. J Inclusion Phenomena Macrocyclic Chem. 2010;68:277–285.
   Web of Science ®Google Scholar
• Felici M, Marza-Perez M, Hatzakis NS, Nolte RJM, Feiters MC. Beta-cyclodextrin-appended giant amphiphile: aggregation to vesicle polymersomes and immobilisation of enzymes. Chem Eur J. 2008;14:9914–9920.
   PubMed Web of Science ®Google Scholar
• Jing B, Chen X, Wang XD, Yang CJ, Xie YZ, Qiu HY. Self-assembly vesicles made from a cyclodextrin supramolecular complex. Chem Eur J. 2007;13:9137–9142.
   PubMed Web of Science ®Google Scholar
• Duchene D, Ponchel G, Wouassindjewe D. Cyclodextrins targeting. Application of nanoparticles. Adv Drug Deliv Rev. 1999;36:29–40.
   PubMed Web of Science ®Google Scholar
• Silvera A, Ponchel G, Puisieux F, Duchene D. Combined poly(isobutylcyanoacrylate) and cyclodextrins nanoparticles for enhancing the encapsulation of lipophilic drugs. Pharm Res. 1998;15:1051–1055.
   Google Scholar
• Cavalli R, Trotta F, Tumiatti W. Cyclodextrin-based nanosponges for drug delivery. J Inclusion Phenomena Macrocyclic Chem. 2006;56:209–213.
   Web of Science ®Google Scholar
• Memisoglu-Bilensoy E, Vural I, Bochot A, Renoir JM, Duchene D, Huncal A. Tamoxifen citrate loaded amphiphilic β-cyclodextrin nanoparticles: in vitro characterization and cytotoxicity. J Controlled Release. 2005;104:489–496.
   PubMed Web of Science ®Google Scholar
• Karelson M, Lobanov VS, Katrizky R. Quantum-chemical descriptors in QSAR/QSPR studies. Chem Rev. 1996;96:1027–1044.
   PubMed Web of Science ®Google Scholar
• Sandra S, Dogra SK. Spectral characteristics of 2-(2′-aminophenyl) benzimidazole in β-cyclodextrin. J Photochem Photobiol A. 1996;101:221–227.
   Web of Science ®Google Scholar
• Krishnamoorthy G, Dogra SK. Dual fluorescence of 2-(4′-N,N-dimethylaminophenyl) benzimidazole: effect of β-cyclodextrin and pH. J Photochem Photobiol A. 1999;123:109–119.
   Web of Science ®Google Scholar
• Kim TH, Cho DW, Yoon M, Kim D. Effects on twisted intramolecular charge transfer of p-(N,N-diethylamino) benzoic acid in aqueous cyclodextrin solutions. J Phys Chem. 1996;1601:5670–15676.
   Google Scholar
• Das S. Inclusion complexation of 2-(40-N; N-dimethylaminophenyl)-1H-naphth[2,3-d]imidazole by β-cyclodextrin: effect on the twisted intramolecular charge transfer emission. Chem Phys Lett. 2002;361:21–28.
   Web of Science ®Google Scholar
• Cho DW, Kim TH, Yoon M, Kim D. Cyclodextrin effects on intramolecular charge transfer of 2-biphenylcarboxylic acid: a pre-twisted molecule. J Chem Soc Faraday Trans. 1996;92:29–33.
   Google Scholar
• Benesi HA, Hildebrand JH. Spectrophotometric investigation of the interaction of iodine with aromatic hydrocarbons. J Am Chem Soc. 1949;71:2703–2707.
   Web of Science ®Google Scholar
• Antony Muthu Prabhu A, Sankaranarayanan RK, Siva S, Rajendiran N. Unusual spectral shifts on fast violet-B and benzanilide: effect of solvents, pH and β-cyclodextrin. Spectrochim Acta Part A. 2009;74:484–497.
   PubMed Web of Science ®Google Scholar
• Antony Muthu Prabhu A, Sankaranarayanan RK, Venkatesh G, Rajendiran N. Dual fluorescence of fast blue RR and fast violet B: effect of solvents, α- and β-cyclodextrins. J Phys Chem B. 2012;116:9061–9074.
   PubMed Web of Science ®Google Scholar
• Antony Muthu Prabhu A, Venkatesh G, Rajendiran N. Spectral characteristics of sulfa drugs: effect of solvents, pH and β-cyclodextrin. J Solution Chem. 2010;39:1061–1086.
   Web of Science ®Google Scholar
• Sivasankar T, Antony Muthu Prabhu A, Karthick M, Rajendiran N. Encapsulation of vanillylamine by native and modified cyclodextrins: spectral and computational studies. J Mol Struct. 2012;1028:57–67.
   Web of Science ®Google Scholar
• Venkatesh G, Sivasankar T, Karthick M, Rajendiran N. Inclusion complexes of sulphanilamide drugs and β-cyclodextrin: a theoretical approach. J Inclusion Phenomena Macrocyclic Chem. 2013;77:309–318.
   Web of Science ®Google Scholar
• Jude Jenita M, Antony Muthu Prabhu A, Rajendiran N. Theoretical study of inclusion complexation of tricylic antidepressant drugs with β-cyclodextrin. Indian J Chem Section A. 2012;51:1686–1694.
   Google Scholar
• Rajendiran N, Balasubramanian T. Dual fluorescence of syringaldazine. Spectrochim Acta Part A. 2007;68:894–904.
   PubMed Web of Science ®Google Scholar
• Hamdi H, Abderrahim R, Meganem F. Spectroscopic studies of inclusion complex of β-cyclodextrin and benzidine diammonium dipicrate. Spectrochim Acta Part A. 2010;75A:32–36.
   Web of Science ®Google Scholar
• Xing SK, Zhang C, Ai HQ, Zhao Q, Zhang Q, Sun DZ. Theoretical study of the interactions of β-cyclodextrin with 2′-hydroxyl-5′-methoxyacetophone and two of its isomers. J Mol Liquids. 2009;146:15–22.
   Web of Science ®Google Scholar
• Morokuma K. Why do molecules interact? The origin of electron donor–acceptor complexes, hydrogen bonding and proton affinity. Acc Chem Res. 1977;10:294–300.
   Web of Science ®Google Scholar
• Kuang M, Duan HW, Wang J, Chen DY, Jiang M. A novel approach to polymeric hollow nanospheres with stabilized structure. Chem Commun. 2003;4:496–497.
   PubMed Web of Science ®Google Scholar
• Kuang M, Duan HW, Wang J, Jiang M. Structural factors of rigid-coil polymer pairs influencing their self-assembly in common solvent. J Phys Chem B. 2004;108:16023–16029.
   Web of Science ®Google Scholar
• Duan HW, Kuang M, Wang J, Chen DY, Jiang M. Self-assembly of rigid and coil polymers into hollow spheres in their common solvent. J Phys Chem B. 2004;108:550–555.
   Web of Science ®Google Scholar
• Chen DY, Jiang M. Strategies for constructing polymeric micelles and hollow spheres in solution via specific intermolecular interactions. Acc Chem Res. 2005;38:494–502.
   PubMed Web of Science ®Google Scholar
• Sun T, Zhang H, Kong L, Qiao H, Li Y, Xin F, Hao A. Controlled transformation of from nanorods to vesicles induced by cyclomaltoheptoses (β-cyclodextrin). Carbohydr Res. 2011;346:285–293.
   PubMed Web of Science ®Google Scholar
• Putcharin C, Suganya S, Piamsook P. Preparation and characterization of inclusion complexes containing fixolide, a synthetic musk fragrance and cyclodextrins. J Inclusion Phenomena Macrocyclic Chem. 2007;57:69–73.
   Web of Science ®Google Scholar
• Giampiero B, Milena S, Alessandra N, Massimo S, Paola M, Fabrizio M. Interaction of naproxen with alpha-cyclodextrin and its noncyclic analog maltohexaose. Pharm Res. 1999;16:689–694.
   PubMed Web of Science ®Google Scholar