메뉴 건너뛰기




Volumn 105, Issue 12, 2016, Pages 3615-3625

Host-Guest Complexes of Carboxylated Pillar[n]arenes With Drugs

Author keywords

biodiagnostics; drug delivery; excipient; fluorescence; host guest; molecular modeling; nanocapsule; pharmaceutics; pillar n arene

Indexed keywords

ACRIDINE ORANGE; AFALANINE; ALBENDAZOLE; CHLORHEXIDINE; HYDROGEN; MEMANTINE; NANOCAPSULE; PILLAR[N]ARENE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; PROFLAVINE; UNCLASSIFIED DRUG; DRUG; QUATERNARY AMMONIUM DERIVATIVE;

EID: 84994480412     PISSN: 00223549     EISSN: 15206017     Source Type: Journal    
DOI: 10.1016/j.xphs.2016.09.008     Document Type: Article
Times cited : (42)

References (46)
  • 1
    • 84922553980 scopus 로고    scopus 로고
    • Biomedical applications of supramolecular systems based on host-guest interactions
    • 1 Ma, X., Zhao, Y., Biomedical applications of supramolecular systems based on host-guest interactions. Chem Rev 115 (2015), 7794–7839.
    • (2015) Chem Rev , vol.115 , pp. 7794-7839
    • Ma, X.1    Zhao, Y.2
  • 2
    • 84965082424 scopus 로고    scopus 로고
    • Cucurbit[n]urils as excipients in pharmaceutical dosage forms
    • [Epub ahead of print]
    • 2 Wheate, N.J., Limantoro, C., Cucurbit[n]urils as excipients in pharmaceutical dosage forms. Supramol Chem, 2016 [Epub ahead of print].
    • (2016) Supramol Chem
    • Wheate, N.J.1    Limantoro, C.2
  • 3
    • 84904543750 scopus 로고    scopus 로고
    • Synthetic versus natural receptors: supramolecular control of chemical sensing in fish
    • 3 Da Silva, J.P., Choudhury, R., Porel, M., et al. Synthetic versus natural receptors: supramolecular control of chemical sensing in fish. ACS Chem Biol 9:7 (2014), 1432–1436.
    • (2014) ACS Chem Biol , vol.9 , Issue.7 , pp. 1432-1436
    • Da Silva, J.P.1    Choudhury, R.2    Porel, M.3
  • 5
    • 79957567058 scopus 로고    scopus 로고
    • Encapsulation of drug molecules by cucurbiturils: effects on their chemical properties in aqueous solution
    • 5 Macartney, D.H., Encapsulation of drug molecules by cucurbiturils: effects on their chemical properties in aqueous solution. Isr J Chem 51 (2011), 600–615.
    • (2011) Isr J Chem , vol.51 , pp. 600-615
    • Macartney, D.H.1
  • 6
    • 84933678296 scopus 로고    scopus 로고
    • Controlled drug delivery systems based on calixarenes
    • 6 Zhou, Y., Li, H., Yang, Y.W., Controlled drug delivery systems based on calixarenes. Chin Chem Lett 26 (2015), 825–828.
    • (2015) Chin Chem Lett , vol.26 , pp. 825-828
    • Zhou, Y.1    Li, H.2    Yang, Y.W.3
  • 8
    • 42149123240 scopus 로고    scopus 로고
    • para-Bridged symmetrical pillar[5]arenes: their Lewis acid catalyzed synthesis and host-guest property
    • 8 Ogoshi, T., Kanai, S., Fuginami, S., Yamagishi, T., Nakamoto, Y., para-Bridged symmetrical pillar[5]arenes: their Lewis acid catalyzed synthesis and host-guest property. J Am Chem Soc 130 (2008), 5022–5023.
    • (2008) J Am Chem Soc , vol.130 , pp. 5022-5023
    • Ogoshi, T.1    Kanai, S.2    Fuginami, S.3    Yamagishi, T.4    Nakamoto, Y.5
  • 9
    • 78650897518 scopus 로고    scopus 로고
    • Facile, rapid, and high yield synthesis of pillar[5]arene from commercially available reagents and its X-ray crystal structure
    • 9 Ogoshi, T., Aoki, T., Kitajima, K., Fujinami, S., Yamagishi, T., Nakamoto, Y., Facile, rapid, and high yield synthesis of pillar[5]arene from commercially available reagents and its X-ray crystal structure. J Org Chem 76 (2011), 328–331.
    • (2011) J Org Chem , vol.76 , pp. 328-331
    • Ogoshi, T.1    Aoki, T.2    Kitajima, K.3    Fujinami, S.4    Yamagishi, T.5    Nakamoto, Y.6
  • 10
    • 84937231562 scopus 로고    scopus 로고
    • A pH-responsive fluorescent [5]pseudorotaxane formed by self-assembly of cationic water-soluble pillar[5]arenes and a tetraphenylethene derivative
    • 10 Chen, R., Jiang, H., Gu, H., et al. A pH-responsive fluorescent [5]pseudorotaxane formed by self-assembly of cationic water-soluble pillar[5]arenes and a tetraphenylethene derivative. Chem Commun 51 (2015), 12220–12223.
    • (2015) Chem Commun , vol.51 , pp. 12220-12223
    • Chen, R.1    Jiang, H.2    Gu, H.3
  • 11
    • 84942428923 scopus 로고    scopus 로고
    • Enzyme-responsive pillar[5]arene-based polymer-substituted amphiphiles: synthesis, self-assembly in water, and application in controlled drug release
    • 11 Gao, L., Zheng, B., Chen, W., Schalley, C.A., Enzyme-responsive pillar[5]arene-based polymer-substituted amphiphiles: synthesis, self-assembly in water, and application in controlled drug release. Chem Commun 51 (2015), 14901–14904.
    • (2015) Chem Commun , vol.51 , pp. 14901-14904
    • Gao, L.1    Zheng, B.2    Chen, W.3    Schalley, C.A.4
  • 12
    • 84915750008 scopus 로고    scopus 로고
    • Cationic vesicles based on amphiphilic pillar[5]arene capped with ferrocenium: a redox-responsive system for drug/siRNA co-delivery
    • 12 Chang, Y., Yang, K., Wei, P., et al. Cationic vesicles based on amphiphilic pillar[5]arene capped with ferrocenium: a redox-responsive system for drug/siRNA co-delivery. Angew Chem Int Ed 53 (2014), 13126–13130.
    • (2014) Angew Chem Int Ed , vol.53 , pp. 13126-13130
    • Chang, Y.1    Yang, K.2    Wei, P.3
  • 13
    • 84923336719 scopus 로고    scopus 로고
    • A pillararene-based ternary drug-delivery system with photocontrolled anticancer drug release
    • 13 Yu, G., Yu, W., Mao, Z., Gao, C., Huang, F., A pillararene-based ternary drug-delivery system with photocontrolled anticancer drug release. Small 11:8 (2015), 919–925.
    • (2015) Small , vol.11 , Issue.8 , pp. 919-925
    • Yu, G.1    Yu, W.2    Mao, Z.3    Gao, C.4    Huang, F.5
  • 14
    • 77952415148 scopus 로고    scopus 로고
    • Synthesis, conformational and host-guest properties of water-soluble pillar[5]arene
    • 14 Ogoshi, T., Hashizume, M., Yamagishi, T-a, Nakamoto, Y., Synthesis, conformational and host-guest properties of water-soluble pillar[5]arene. Chem Commun 46 (2010), 3708–3710.
    • (2010) Chem Commun , vol.46 , pp. 3708-3710
    • Ogoshi, T.1    Hashizume, M.2    Yamagishi, T.-A.3    Nakamoto, Y.4
  • 15
    • 84961208203 scopus 로고    scopus 로고
    • Quantitative determination of the surfactant-induced split ratio of influenza virus by fluorescence spectroscopy
    • 15 Lee, K.K.H., Sahin, Y.Z., Neeleman, R., Trout, B.L., Kayser, V., Quantitative determination of the surfactant-induced split ratio of influenza virus by fluorescence spectroscopy. Hum Vaccin Immunother 12 (2016), 1757–1765.
    • (2016) Hum Vaccin Immunother , vol.12 , pp. 1757-1765
    • Lee, K.K.H.1    Sahin, Y.Z.2    Neeleman, R.3    Trout, B.L.4    Kayser, V.5
  • 16
    • 0003478714 scopus 로고
    • Data Reduction and Error Analysis for the Physical Sciences
    • McGraw-Hill New York, NY
    • 16 Bevington, P.R., Data Reduction and Error Analysis for the Physical Sciences. 1969, McGraw-Hill, New York, NY.
    • (1969)
    • Bevington, P.R.1
  • 17
    • 76149120388 scopus 로고    scopus 로고
    • AutoDock Vina: improving the speed and accuracy of docking with a new scoring function, efficient optimization, and multithreading
    • 17 Trott, O., Olson, A.J., AutoDock Vina: improving the speed and accuracy of docking with a new scoring function, efficient optimization, and multithreading. J Comput Chem 31:2 (2010), 455–461.
    • (2010) J Comput Chem , vol.31 , Issue.2 , pp. 455-461
    • Trott, O.1    Olson, A.J.2
  • 18
    • 84919808055 scopus 로고    scopus 로고
    • Solid-state assembly of carboxylic acid substituted pillar 5 arene and its host-guest complex with tetracaine
    • 18 Danylyuk, O., Sashuk, V., Solid-state assembly of carboxylic acid substituted pillar 5 arene and its host-guest complex with tetracaine. CrystEngComm 17:4 (2015), 719–722.
    • (2015) CrystEngComm , vol.17 , Issue.4 , pp. 719-722
    • Danylyuk, O.1    Sashuk, V.2
  • 19
    • 84928476077 scopus 로고    scopus 로고
    • New ways to boost molecular dynamics simulations
    • 19 Krieger, E., Vriend, G., New ways to boost molecular dynamics simulations. J Comput Chem 36:13 (2015), 996–1007.
    • (2015) J Comput Chem , vol.36 , Issue.13 , pp. 996-1007
    • Krieger, E.1    Vriend, G.2
  • 20
    • 70349932423 scopus 로고    scopus 로고
    • AutoDock4 and AutoDockTools4: automated docking with selective receptor flexibility
    • 20 Morris, G.M., Huey, R., Lindstrom, W., et al. AutoDock4 and AutoDockTools4: automated docking with selective receptor flexibility. J Comput Chem 16 (2009), 2785–2791.
    • (2009) J Comput Chem , vol.16 , pp. 2785-2791
    • Morris, G.M.1    Huey, R.2    Lindstrom, W.3
  • 21
    • 0033397980 scopus 로고    scopus 로고
    • Python: a programming language for software integration and development
    • 21 Sanner, M.F., Python: a programming language for software integration and development. J Mol Graph Model 17:1 (1999), 57–61.
    • (1999) J Mol Graph Model , vol.17 , Issue.1 , pp. 57-61
    • Sanner, M.F.1
  • 22
    • 84891419209 scopus 로고    scopus 로고
    • Host-guest properties of pillar[7]arene towards substituted adamantane ammonium cations
    • 22 Fan, J., Chen, Y., Cao, D., Yang, Y.W., Jia, X., Li, C., Host-guest properties of pillar[7]arene towards substituted adamantane ammonium cations. RSC Adv 4 (2014), 4330–4333.
    • (2014) RSC Adv , vol.4 , pp. 4330-4333
    • Fan, J.1    Chen, Y.2    Cao, D.3    Yang, Y.W.4    Jia, X.5    Li, C.6
  • 23
    • 76249095376 scopus 로고    scopus 로고
    • Solid state stabilisation of the orally delivered drugs atenolol, glibenclamide, memantine and paracetamol through their complexation with cucurbit[7]uril
    • 23 McInnes, F.J., Anthony, N.G., Kennedy, A.R., Wheate, N.J., Solid state stabilisation of the orally delivered drugs atenolol, glibenclamide, memantine and paracetamol through their complexation with cucurbit[7]uril. Org Biomol Chem 8 (2010), 765–773.
    • (2010) Org Biomol Chem , vol.8 , pp. 765-773
    • McInnes, F.J.1    Anthony, N.G.2    Kennedy, A.R.3    Wheate, N.J.4
  • 24
    • 80052333670 scopus 로고    scopus 로고
    • Cucurbit[n]uril based supramolecular assemblies: tunable physio-chemical properties and their prospects
    • 24 Bhasikuttan, A.C., Pal, H., Mohanty, J., Cucurbit[n]uril based supramolecular assemblies: tunable physio-chemical properties and their prospects. Chem Commun 47 (2011), 9959–9971.
    • (2011) Chem Commun , vol.47 , pp. 9959-9971
    • Bhasikuttan, A.C.1    Pal, H.2    Mohanty, J.3
  • 26
    • 84872496389 scopus 로고    scopus 로고
    • Host-guest complexes of cucurbit[7]uril with albendazole in solid state
    • 26 Saleh, Ni, Khaleel, A., Al-Dmour, H., Yakushenko, E., Host-guest complexes of cucurbit[7]uril with albendazole in solid state. J Therm Anal Calorim 111:1 (2013), 385–392.
    • (2013) J Therm Anal Calorim , vol.111 , Issue.1 , pp. 385-392
    • Saleh, N.1    Khaleel, A.2    Al-Dmour, H.3    Yakushenko, E.4
  • 27
    • 55749113885 scopus 로고    scopus 로고
    • Albendazole-cyclodextrin complex: enhanced cytotoxicity in ovarian cancer cells
    • 27 Pourgholami, M.H., Wangoo, K.T., Morris, D.L., Albendazole-cyclodextrin complex: enhanced cytotoxicity in ovarian cancer cells. Anticancer Res 28:5A (2008), 2775–2779.
    • (2008) Anticancer Res , vol.28 , Issue.5A , pp. 2775-2779
    • Pourgholami, M.H.1    Wangoo, K.T.2    Morris, D.L.3
  • 28
    • 84904467104 scopus 로고    scopus 로고
    • Supramolecular inhibition of amyloid fibrillation by cucurbit[7]uril
    • 28 Lee, H.H., Choi, T.S., Lee, S.J.C., et al. Supramolecular inhibition of amyloid fibrillation by cucurbit[7]uril. Angew Chem Int Ed 53 (2014), 7461–7465.
    • (2014) Angew Chem Int Ed , vol.53 , pp. 7461-7465
    • Lee, H.H.1    Choi, T.S.2    Lee, S.J.C.3
  • 29
    • 84925276278 scopus 로고    scopus 로고
    • Sequence-specific, nanomolar peptide binding via cucurbit[8]uril-induced folding and inclusion of neighboring side chains
    • 29 Smith, L., Leach, D.G., Blaylock, B.E., Ali, O.A., Urbach, A.R., Sequence-specific, nanomolar peptide binding via cucurbit[8]uril-induced folding and inclusion of neighboring side chains. J Am Chem Soc 137 (2015), 3663–3669.
    • (2015) J Am Chem Soc , vol.137 , pp. 3663-3669
    • Smith, L.1    Leach, D.G.2    Blaylock, B.E.3    Ali, O.A.4    Urbach, A.R.5
  • 30
    • 55949125880 scopus 로고    scopus 로고
    • Scope of amino acid recognition by cucurbit[8]uril
    • 30 Rajgariash, P., Urbach, A.R., Scope of amino acid recognition by cucurbit[8]uril. J Incl Phenom Macrocycl Chem 62 (2008), 251–254.
    • (2008) J Incl Phenom Macrocycl Chem , vol.62 , pp. 251-254
    • Rajgariash, P.1    Urbach, A.R.2
  • 31
    • 0000124272 scopus 로고
    • Calorimetric and diffusional behavior of the system α-cyclodextrin-L-phenylalanine in aqueous solution
    • 31 Paduano, L., Sartorio, R., Vitagliano, V., Castronuovo, G., Calorimetric and diffusional behavior of the system α-cyclodextrin-L-phenylalanine in aqueous solution. Thermochim Acta 162:1 (1990), 155–161.
    • (1990) Thermochim Acta , vol.162 , Issue.1 , pp. 155-161
    • Paduano, L.1    Sartorio, R.2    Vitagliano, V.3    Castronuovo, G.4
  • 32
    • 54449088018 scopus 로고    scopus 로고
    • A comparison between the responses of neutral red and acridine orange: acridine orange should be preferential and alternative to neutral red as a dye for the monitoring of contaminants by means of biological sensors
    • 32 Manente, S., De Pieri, S., Iero, A., Rigo, C., Bragadin, M., A comparison between the responses of neutral red and acridine orange: acridine orange should be preferential and alternative to neutral red as a dye for the monitoring of contaminants by means of biological sensors. Anal Biochem 383 (2008), 316–319.
    • (2008) Anal Biochem , vol.383 , pp. 316-319
    • Manente, S.1    De Pieri, S.2    Iero, A.3    Rigo, C.4    Bragadin, M.5
  • 33
    • 80052600643 scopus 로고    scopus 로고
    • A coumarin-based fluorescent PET sensor utilizing supramolecular pKa shifts
    • 33 Saleh, Ni, Al-Soud, Y.A., Al-Kaabi, L., Ghosh, I., Nau, W.M., A coumarin-based fluorescent PET sensor utilizing supramolecular pKa shifts. Chemistry 52 (2011), 5249–5254.
    • (2011) Chemistry , vol.52 , pp. 5249-5254
    • Saleh, N.1    Al-Soud, Y.A.2    Al-Kaabi, L.3    Ghosh, I.4    Nau, W.M.5
  • 34
    • 18444380577 scopus 로고    scopus 로고
    • A cucurbit[6]uril analogue: host properties monitored by fluorescence spectroscopy
    • 34 Wagner, B.D., Boland, P.G., Lagona, J., Isaacs, L., A cucurbit[6]uril analogue: host properties monitored by fluorescence spectroscopy. J Phys Chem B 109 (2005), 7686–7691.
    • (2005) J Phys Chem B , vol.109 , pp. 7686-7691
    • Wagner, B.D.1    Boland, P.G.2    Lagona, J.3    Isaacs, L.4
  • 35
    • 84870360757 scopus 로고    scopus 로고
    • Pillar[6]arene/paraquat molecular recognition in water: high binding strength, pH-responsiveness, and application in controllable self-assembly, controlled release, and treatment of paraquat poisoning
    • 35 Yu, G., Zhou, X., Zhang, Z., et al. Pillar[6]arene/paraquat molecular recognition in water: high binding strength, pH-responsiveness, and application in controllable self-assembly, controlled release, and treatment of paraquat poisoning. J Am Chem Soc 134 (2012), 19489–19497.
    • (2012) J Am Chem Soc , vol.134 , pp. 19489-19497
    • Yu, G.1    Zhou, X.2    Zhang, Z.3
  • 36
    • 0004040064 scopus 로고    scopus 로고
    • Principles of Fluorescence Spectroscopy
    • 2nd ed. Kluwer Academic/Plenum New York, NY
    • 36 Lakowicz, J.R., Principles of Fluorescence Spectroscopy. 2nd ed., 1999, Kluwer Academic/Plenum, New York, NY.
    • (1999)
    • Lakowicz, J.R.1
  • 37
    • 0017377391 scopus 로고
    • Fluorescence decay and quantum yield characteristics of acridine orange and proflavine bound to DNA
    • 37 Kubota, Y., Stelner, R.F., Fluorescence decay and quantum yield characteristics of acridine orange and proflavine bound to DNA. Biophys Chem 6 (1977), 279–289.
    • (1977) Biophys Chem , vol.6 , pp. 279-289
    • Kubota, Y.1    Stelner, R.F.2
  • 38
    • 0008710785 scopus 로고
    • Association and self-quenching of proflavine in water
    • 38 Haugen, G.R., Melhuish, W.H., Association and self-quenching of proflavine in water. Trans Faraday Soc 60 (1964), 386–394.
    • (1964) Trans Faraday Soc , vol.60 , pp. 386-394
    • Haugen, G.R.1    Melhuish, W.H.2
  • 39
    • 84905236679 scopus 로고    scopus 로고
    • A simple assay for quality binders to cucurbiturils
    • 39 Vazquez, J., Remon, P., Dsouza, R.N., et al. A simple assay for quality binders to cucurbiturils. Chemistry 20:32 (2014), 9897–9901.
    • (2014) Chemistry , vol.20 , Issue.32 , pp. 9897-9901
    • Vazquez, J.1    Remon, P.2    Dsouza, R.N.3
  • 40
    • 78649915732 scopus 로고    scopus 로고
    • Benzobis(imidazolium)-cucurbit[8]uril complexes for binding and sensing aromatic compounds in aqueous solution
    • 40 Biedermann, F., Rauwald, U., Cziferszky, M., et al. Benzobis(imidazolium)-cucurbit[8]uril complexes for binding and sensing aromatic compounds in aqueous solution. Chemistry 16:46 (2010), 13716–13722.
    • (2010) Chemistry , vol.16 , Issue.46 , pp. 13716-13722
    • Biedermann, F.1    Rauwald, U.2    Cziferszky, M.3
  • 41
    • 75749101746 scopus 로고    scopus 로고
    • Cooperative metal ion binding to a cucurbit[7]uril-thioflavin T complex: demonstration of a stimulus-responsive fluorescent supramolecular capsule
    • 41 Choudhury, S.D., Mohanty, J., Pal, H., Bhasikuttan, A.C., Cooperative metal ion binding to a cucurbit[7]uril-thioflavin T complex: demonstration of a stimulus-responsive fluorescent supramolecular capsule. J Am Chem Soc 132 (2010), 1395–1401.
    • (2010) J Am Chem Soc , vol.132 , pp. 1395-1401
    • Choudhury, S.D.1    Mohanty, J.2    Pal, H.3    Bhasikuttan, A.C.4
  • 42
    • 61349110662 scopus 로고    scopus 로고
    • Design of a fluorescent dye for indicator displacement from cucurbiturils: a macrocycle-responsive fluorescent switch operating through a pKa shift
    • 42 Praetorius, A., Bailey, D.M., Schwarzlose, T., Nau, W.M., Design of a fluorescent dye for indicator displacement from cucurbiturils: a macrocycle-responsive fluorescent switch operating through a pKa shift. Org Lett 18 (2008), 4089–4092.
    • (2008) Org Lett , vol.18 , pp. 4089-4092
    • Praetorius, A.1    Bailey, D.M.2    Schwarzlose, T.3    Nau, W.M.4
  • 43
    • 58149464560 scopus 로고    scopus 로고
    • A new spectrofluorometric method for the determination of nicotine base on the inclusion interaction of methylene blue and cucurbit[7]uril
    • 43 Zhou, Y., Yu, H., Zhang, L., et al. A new spectrofluorometric method for the determination of nicotine base on the inclusion interaction of methylene blue and cucurbit[7]uril. Microchim Acta 164 (2009), 63–68.
    • (2009) Microchim Acta , vol.164 , pp. 63-68
    • Zhou, Y.1    Yu, H.2    Zhang, L.3
  • 44
    • 77956403467 scopus 로고    scopus 로고
    • Toxicology and drug delivery by cucurbit[n]uril type molecular containers
    • 44 Hettiarachchi, G., Hguyen, D., Wu, J., et al. Toxicology and drug delivery by cucurbit[n]uril type molecular containers. PLoS One, 5(5), 2010, e105014.
    • (2010) PLoS One , vol.5 , Issue.5 , pp. e105014
    • Hettiarachchi, G.1    Hguyen, D.2    Wu, J.3
  • 45
    • 84907995170 scopus 로고    scopus 로고
    • The ex vivo neurotoxic, myotoxic and cardiotoxic activity of cucurbituril-based macrocyclic drug delivery vehicles
    • 45 Oun, R., Floriano, R.S., Isaacs, L., Rowan, E.G., Wheate, N.J., The ex vivo neurotoxic, myotoxic and cardiotoxic activity of cucurbituril-based macrocyclic drug delivery vehicles. Toxicol Res 3 (2014), 447–455.
    • (2014) Toxicol Res , vol.3 , pp. 447-455
    • Oun, R.1    Floriano, R.S.2    Isaacs, L.3    Rowan, E.G.4    Wheate, N.J.5
  • 46
    • 77951131840 scopus 로고    scopus 로고
    • Toxicity of cucurbit[7]uril and cucurbit[8]uril: an exploratory in vitro and in vivo study
    • 46 Uzunova, V.D., Cullinane, C., Brix, K., Nau, W.M., Day, A.I., Toxicity of cucurbit[7]uril and cucurbit[8]uril: an exploratory in vitro and in vivo study. Org Biomol Chem 8 (2010), 2037–2042.
    • (2010) Org Biomol Chem , vol.8 , pp. 2037-2042
    • Uzunova, V.D.1    Cullinane, C.2    Brix, K.3    Nau, W.M.4    Day, A.I.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.