메뉴 건너뛰기




Volumn 74, Issue 1-4, 2012, Pages 415-423

Solubilizing effect of the p-phosphonate calix[n]arenes towards poorly soluble drug molecules such as nifedipine, niclosamide and furosemide

Author keywords

Calixarene; Drug; Furosemide; Niclosamide; Nifedipine

Indexed keywords


EID: 84864440406     PISSN: 09230750     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10847-012-0135-7     Document Type: Article
Times cited : (22)

References (45)
  • 2
    • 33748539998 scopus 로고
    • Calixarenes, macrocycles with (almost) unlimited possibilities
    • 10.1002/anie.199507131
    • V Böhmer 1995 Calixarenes, macrocycles with (almost) unlimited possibilities Angew. Chem. Int. Ed. Engl 34 713 745 10.1002/anie.199507131
    • (1995) Angew. Chem. Int. Ed. Engl , vol.34 , pp. 713-745
    • Böhmer, V.1
  • 6
    • 49049122645 scopus 로고
    • Calixarenes 9: Conformational isomers of the ethers and esters of calix[4]arenes
    • 10.1016/S0040-4020(01)88541-0 1:CAS:528:DyaL3sXhvFOhtbY%3D
    • CD Gutsche B Dhawan JA Levine KH No LJ Bauer 1983 Calixarenes 9: conformational isomers of the ethers and esters of calix[4]arenes Tetrahedron 39 409 426 10.1016/S0040-4020(01)88541-0 1:CAS:528:DyaL3sXhvFOhtbY%3D
    • (1983) Tetrahedron , vol.39 , pp. 409-426
    • Gutsche, C.D.1    Dhawan, B.2    Levine, J.A.3    No, K.H.4    Bauer, L.J.5
  • 7
    • 34249836381 scopus 로고
    • Synthesis and complexing properties of a double-calix[4]arene crown ether
    • 10.1007/BF01053640 1:CAS:528:DyaK38XltVaqt7g%3D
    • Z Asfari R Abidi F Arnaud-Neu J Vicens 1992 Synthesis and complexing properties of a double-calix[4]arene crown ether J. Inclusion Phenom. 13 163 169 10.1007/BF01053640 1:CAS:528:DyaK38XltVaqt7g%3D
    • (1992) J. Inclusion Phenom. , vol.13 , pp. 163-169
    • Asfari, Z.1    Abidi, R.2    Arnaud-Neu, F.3    Vicens, J.4
  • 9
    • 0000275429 scopus 로고    scopus 로고
    • Azacalixarene: Synthesis, conformational analysis, and recognition behavior toward anions
    • K Niikura E Anslyn 1999 Azacalixarene: synthesis, conformational analysis, and recognition behavior toward anions J. Chem. Soc. Perkin Trans. 2 2769 2775 (Pubitemid 129561071)
    • (1999) Journal of the Chemical Society. Perkin Transactions 2 , Issue.12 , pp. 2769-2775
    • Niikura, K.1    Anslyn, E.V.2
  • 10
    • 0000285995 scopus 로고
    • Chloromethylation of calixarenes and synthesis of new water-soluble macrocyclic hosts
    • 10.1016/S0040-4020(01)80077-6 1:CAS:528:DyaK3cXntFSl
    • M Almi A Arduini A Casnati A Pochini R Ungaro 1989 Chloromethylation of calixarenes and synthesis of new water-soluble macrocyclic hosts Tetrahedron 45 2177 2182 10.1016/S0040-4020(01)80077-6 1:CAS:528:DyaK3cXntFSl
    • (1989) Tetrahedron , vol.45 , pp. 2177-2182
    • Almi, M.1    Arduini, A.2    Casnati, A.3    Pochini, A.4    Ungaro, R.5
  • 11
    • 0000402993 scopus 로고
    • Calixarenes.23. the complexation and catalytic properties of water-soluble calixarenes
    • 10.1016/S0040-4020(01)86171-8 1:CAS:528:DyaL1MXhsFertr0%3D
    • CD Gutsche I Alam 1988 Calixarenes.23. The complexation and catalytic properties of water-soluble calixarenes Tetrahedron 44 4689 4694 10.1016/S0040-4020(01)86171-8 1:CAS:528:DyaL1MXhsFertr0%3D
    • (1988) Tetrahedron , vol.44 , pp. 4689-4694
    • Gutsche, C.D.1    Alam, I.2
  • 14
    • 21844502288 scopus 로고
    • Host-guest interactions in aqueous media with p-tert-butylcalix[4]arene bearing polyoxyethylene chains
    • 10.1007/BF00705817 1:CAS:528:DyaK2MXjtVajtro%3D
    • Y Shi Z Zhang 1994 Host-guest interactions in aqueous media with p-tert-butylcalix[4]arene bearing polyoxyethylene chains J. Inclusion Phenom. Macrocycl. Chem. 18 137 147 10.1007/BF00705817 1:CAS:528:DyaK2MXjtVajtro%3D
    • (1994) J. Inclusion Phenom. Macrocycl. Chem. , vol.18 , pp. 137-147
    • Shi, Y.1    Zhang, Z.2
  • 15
    • 0037426692 scopus 로고    scopus 로고
    • Nano-encapsulation of furosemide microcrystals for controlled drug release
    • DOI 10.1016/S0168-3659(02)00322-X, PII S016836590200322X
    • H Ai SA Jones MM de Villiers YM Lvov 2003 Nano-encapsulation of furosemide microcrystals for controlled drug release J. Control Release 86 59 68 10.1016/S0168-3659(02)00322-X 1:CAS:528:DC%2BD38XpsFSjsrY%3D (Pubitemid 35461974)
    • (2003) Journal of Controlled Release , vol.86 , Issue.1 , pp. 59-68
    • Ai, H.1    Jones, S.A.2    De Villiers, M.M.3    Lvov, Y.M.4
  • 16
    • 26444488204 scopus 로고    scopus 로고
    • Comparison of the aqueous solubilization of practically insoluble niclosamide by polyamidoamine (PAMAM) dendrimers and cyclodextrins
    • DOI 10.1016/j.ijpharm.2005.07.023, PII S0378517305005338
    • B Devarakonda RA Hill W Liebenberg M Brits MM de Villiers 2005 Comparison of the aqueous solubilization of practically insoluble niclosamide by polyamidoamine (PAMAM) dendrimers and cyclodextrins Int. J. Pharm. 304 193 209 10.1016/j.ijpharm.2005.07.023 1:CAS:528:DC%2BD2MXhtFSitLnP (Pubitemid 41427662)
    • (2005) International Journal of Pharmaceutics , vol.304 , Issue.1-2 , pp. 193-209
    • Devarakonda, B.1    Hill, R.A.2    Liebenberg, W.3    Brits, M.4    De Villiers, M.M.5
  • 17
    • 0023698052 scopus 로고    scopus 로고
    • Complexation of nifedipine with substituted phenolic ligands
    • 10.1023/A:1015979021590
    • KM Boje M Sak HL Fung 1998 Complexation of nifedipine with substituted phenolic ligands Pharm. Res. 5 655 659 10.1023/A:1015979021590
    • (1998) Pharm. Res. , vol.5 , pp. 655-659
    • Boje, K.M.1    Sak, M.2    Fung, H.L.3
  • 18
    • 0033583495 scopus 로고    scopus 로고
    • Complexation study and anticellular activity enhancement by doxorubicin- cyclodextrin complexes on a multidrug-resistant adenocarcinoma cell line
    • DOI 10.1016/S0960-894X(99)00150-X, PII S0960894X9900150X
    • A Al-Omar S Abdou L De Robertis A Marsura C Finance 1999 Complexation study and anticellular activity enhancement by doxorubicin-cyclodextrin complexes on a multidrugresistant adenocarcinoma cell line Bioorg. Med. Chem. Lett. 9 1115 1120 10.1016/S0960-894X(99)00150-X 1:CAS:528:DyaK1MXjtVKls7o%3D (Pubitemid 29204668)
    • (1999) Bioorganic and Medicinal Chemistry Letters , vol.9 , Issue.8 , pp. 1115-1120
    • Al-Omar, A.1    Abdou, S.2    De Robertis, L.3    Marsura, A.4    Finance, C.5
  • 19
    • 0035379090 scopus 로고    scopus 로고
    • Improving bioavailability and anthelmintic activity of albendazole by preparing albendazole-cyclodextrin complexes
    • JJ Garcia-Rodriguez J Torrado F Bolas 2001 Improving bioavailability and anthelmintic activity of albendazole by preparing albendazole-cyclodextrin complexes Parasite 8 188 190
    • (2001) Parasite , vol.8 , pp. 188-190
    • Garcia-Rodriguez, J.J.1    Torrado, J.2    Bolas, F.3
  • 22
    • 37049086202 scopus 로고
    • Does the calixarene cavity recognize the size of guest molecules? on the hole-size selectivity in watersoluble calixarenes
    • 10.1039/c39880000187
    • S Shinkai K Araki O Manabe 1988 Does the calixarene cavity recognize the size of guest molecules? On the hole-size selectivity in watersoluble calixarenes J. Chem. Soc. Chem. Commun. 3 187 189 10.1039/c39880000187
    • (1988) J. Chem. Soc. Chem. Commun. , vol.3 , pp. 187-189
    • Shinkai, S.1    Araki, K.2    Manabe, O.3
  • 23
    • 0000108789 scopus 로고
    • Cyclodextrin-induced symmetry of achiral nitrogen heterocycles
    • 10.1021/j100192a025
    • JM Shuette TT Ndou IM Warner 1992 Cyclodextrin-induced symmetry of achiral nitrogen heterocycles J. Phys. Chem. 96 5309 5314 10.1021/j100192a025
    • (1992) J. Phys. Chem. , vol.96 , pp. 5309-5314
    • Shuette, J.M.1    Ndou, T.T.2    Warner, I.M.3
  • 24
    • 67650215632 scopus 로고    scopus 로고
    • Calixarenes in bio-medical researches
    • 10.2174/092986709788186219 1:CAS:528:DC%2BD1MXmsFWgsbo%3D
    • RV Rodik VI Boyko VI Kalchenko 2009 Calixarenes in bio-medical researches Curr. Med. Chem. 16 1630 1655 10.2174/092986709788186219 1:CAS:528: DC%2BD1MXmsFWgsbo%3D
    • (2009) Curr. Med. Chem. , vol.16 , pp. 1630-1655
    • Rodik, R.V.1    Boyko, V.I.2    Kalchenko, V.I.3
  • 25
    • 1542335326 scopus 로고    scopus 로고
    • A first approach to the study of calixarene Solid Lipid Nanoparticle (SLN) toxicity
    • DOI 10.1023/A:1026301906487
    • P Shahgaldian E Da Silva AW Coleman 2003 A first approach to the study of calixarene solid lipid nanoparticle (SLN) toxicity J. Incl. Phenom. 46 175 177 10.1023/A:1026301906487 1:CAS:528:DC%2BD3sXosFCmsL8%3D (Pubitemid 39011188)
    • (2003) Journal of Inclusion Phenomena , vol.46 , Issue.3-4 , pp. 175-177
    • Shahgaldian, P.1    Da Silva, E.2    Coleman, A.W.3
  • 26
    • 0037258407 scopus 로고    scopus 로고
    • Direct formation of nanospheres from amphiphilic β-cyclodextrin inclusion complexes
    • DOI 10.1023/A:1022263111961
    • E Memişoglu A Bochot M Özalp M Şen D Duchene AA Hincal 2003 Direct formation of nanospheres from amphiphilic β-cyclodextrin inclusion complexes Pharm. Res. 20 117 125 10.1023/A:1022263111961 (Pubitemid 36152926)
    • (2003) Pharmaceutical Research , vol.20 , Issue.1 , pp. 117-125
    • Memisoglu, E.1    Bochot, A.2    Ozalp, M.3    Sen, M.4    Duchene, D.5    Hincal, A.A.6
  • 27
    • 63049134146 scopus 로고    scopus 로고
    • Synthesis of two new p-tert-butylcalix[4]arene b-ketoimin derivatives for extraction of dichromate anion
    • 10.1007/s10847-008-9513-6 1:CAS:528:DC%2BD1MXjsFKmsb4%3D
    • M Bayrakci S Ertul O Sahin M Yilmaz 2009 Synthesis of two new p-tert-butylcalix[4]arene b-ketoimin derivatives for extraction of dichromate anion J. Inclusion Phenom. Macrocycl. Chem. 63 241 247 10.1007/s10847-008-9513-6 1:CAS:528:DC%2BD1MXjsFKmsb4%3D
    • (2009) J. Inclusion Phenom. Macrocycl. Chem. , vol.63 , pp. 241-247
    • Bayrakci, M.1    Ertul, S.2    Sahin, O.3    Yilmaz, M.4
  • 28
    • 77954565054 scopus 로고    scopus 로고
    • Removal of chromate and phosphate anion from aqueous solutions using calix[4]arene receptors containing proton switchable units
    • 10.1016/j.jhazmat.2010.05.121 1:CAS:528:DC%2BC3cXosF2gs74%3D
    • Ş Ertul M BayrakcI M Yilmaz 2010 Removal of chromate and phosphate anion from aqueous solutions using calix[4]arene receptors containing proton switchable units J. Hazard. Mater. 181 1059 1065 10.1016/j.jhazmat.2010.05.121 1:CAS:528:DC%2BC3cXosF2gs74%3D
    • (2010) J. Hazard. Mater. , vol.181 , pp. 1059-1065
    • Ertul, Ş.1    Bayrakci, M.2    Yilmaz, M.3
  • 29
    • 68549109521 scopus 로고    scopus 로고
    • Synthesis of di-substituted calix[4]arene-based receptors for extraction of chromate and arsenate anions
    • 10.1016/j.tet.2009.07.062 1:CAS:528:DC%2BD1MXhtVSlsL3E
    • M Bayrakci S Ertul M Yilmaz 2009 Synthesis of di-substituted calix[4]arene-based receptors for extraction of chromate and arsenate anions Tetrahedron 65 7963 7968 10.1016/j.tet.2009.07.062 1:CAS:528:DC%2BD1MXhtVSlsL3E
    • (2009) Tetrahedron , vol.65 , pp. 7963-7968
    • Bayrakci, M.1    Ertul, S.2    Yilmaz, M.3
  • 30
    • 4644231741 scopus 로고    scopus 로고
    • The solubilization of the poorly water soluble drug nifedipine by water soluble 4-sulphonic calix[n]arenes
    • DOI 10.1016/j.ejpb.2004.04.010, PII S0939641104001225
    • W Yang MM de Villiers 2004 The solubilization of the poorly water soluble drug nifedipine by water soluble 4-sulphonic calix[n]arenes E. J. Pharm. Biopharm 58 629 636 10.1016/j.ejpb.2004.04.010 1:CAS:528:DC%2BD2cXnvFagur0%3D (Pubitemid 39297110)
    • (2004) European Journal of Pharmaceutics and Biopharmaceutics , vol.58 , Issue.3 , pp. 629-636
    • Yang, W.1    De Villiers, M.M.2
  • 31
    • 27644507355 scopus 로고    scopus 로고
    • Effect of 4-Sulphonato-Calix[n]Arenes and cyclodextrins on the solubilization of niclosamide, a poorly water soluble anthelmintic
    • DOI 10.1208/aapsj070123, 23
    • W Yang MM de Villiers 2005 Effect of 4-sulphonato-calix[n]arenes and cyclodextrins on the solubilization of niclosamide, a poorly water soluble anthelmintic AAPS J. 7 241 248 10.1208/aapsj070123 (Pubitemid 41554284)
    • (2005) AAPS Journal , vol.7 , Issue.1
    • Yang, W.1    De Villiers, M.M.2
  • 32
    • 3042695167 scopus 로고    scopus 로고
    • Aqueous solubilization of furosemide by supramolecular complexation with 4-sulphonic calix[n]arenes
    • DOI 10.1211/0022357023439
    • W Yang MM de Villiers 2004 Aqueous solubilization of furosemide by supramolecular complexation with 4-sulphonic calix[n]arenes J. Pharm. Pharmacol. 56 703 708 10.1211/0022357023439 1:CAS:528:DC%2BD2cXmtFSks7o%3D (Pubitemid 38801685)
    • (2004) Journal of Pharmacy and Pharmacology , vol.56 , Issue.6 , pp. 703-708
    • Yang, W.1    De Villiers, M.M.2
  • 33
    • 83455218258 scopus 로고    scopus 로고
    • Transportation of poorly soluble drug molecules from the organic phase to the aqueous phase by using phosphorylated calixarenes
    • doi: 10.1021/je2004319
    • BayrakcI, M.; Ertul, S.; Yilmaz, M.: Transportation of poorly soluble drug molecules from the organic phase to the aqueous phase by using phosphorylated calixarenes. J. Chem. Eng. Data. doi: 10.1021/je2004319
    • J. Chem. Eng. Data.
    • Bayrakci, M.1    Ertul, S.2    Yilmaz, M.3
  • 34
    • 0031938330 scopus 로고    scopus 로고
    • Improvement of dissolution properties of furosemide by complexation with β-cyclodextrin
    • N Özdemir S Ordu 1998 Improvement of dissolution properties of furosemide by complexation with β-cyclodextrin Drug Dev. Ind. Pharm. 24 19 25 10.3109/03639049809082348 (Pubitemid 28080834)
    • (1998) Drug Development and Industrial Pharmacy , vol.24 , Issue.1 , pp. 19-25
    • Ozdemir, N.1    Ordu, S.2
  • 35
    • 0033066167 scopus 로고    scopus 로고
    • Inclusion complexation of furosemide in cyclodextrins
    • 1:CAS:528:DyaK1MXhsVyjtb8%3D
    • HO Ammar M Ghorab SA El-Nahhas LH Emara TS Makram 1999 Inclusion complexation of furosemide in cyclodextrins Die Pharm. 54 142 144 1:CAS:528:DyaK1MXhsVyjtb8%3D
    • (1999) Die Pharm. , vol.54 , pp. 142-144
    • Ammar, H.O.1    Ghorab, M.2    El-Nahhas, S.A.3    Emara, L.H.4    Makram, T.S.5
  • 36
    • 0036942430 scopus 로고    scopus 로고
    • Effect of upper rim para-alkyl substituents on extraction of alkali and alkaline earth metal cations by di-ionizable calix[4]arenes
    • GG Talanova VS Talanov MG Gorbunova H-S Hwang RA Bartsch 2002 Effect of upper rim para-alkyl substituents on extraction of alkali and alkaline earth metal cations by di-ionizable calix[4]arenes J. Chem. Soc. Perkin Trans. 2 2072 2077
    • (2002) J. Chem. Soc. Perkin Trans. , vol.2 , pp. 2072-2077
    • Talanova, G.G.1    Talanov, V.S.2    Gorbunova, M.G.3    Hwang, H.-S.4    Bartsch, R.A.5
  • 37
    • 33846072916 scopus 로고    scopus 로고
    • Effect of para-substituents on alkaline earth metal ion extraction by proton di-ionizable calix[4]arene-crown-6 ligands in cone, partial-cone and 1,3-alternate conformations
    • DOI 10.1039/b611570e
    • H Zhou D Liu J Gega K Surowiec DW Purkiss RA Bartsch 2007 Effect of para-substituents on alkaline earth metal ion extraction by proton di-ionizable calix[4]arene-crown-6 ligands in cone, partial-cone and 1,3-alternate conformations Org. Biomol. Chem. 5 324 332 10.1039/b611570e 1:CAS:528: DC%2BD2sXhtlShtA%3D%3D (Pubitemid 46058482)
    • (2007) Organic and Biomolecular Chemistry , vol.5 , Issue.2 , pp. 324-332
    • Zhou, H.1    Liu, D.2    Gega, J.3    Surowiec, K.4    Purkiss, D.W.5    Bartsch, R.A.6
  • 39
    • 58149234269 scopus 로고    scopus 로고
    • Cyclodextrins as drug carrier molecule: A review
    • 10.3797/scipharm.0808-05
    • R Arun CK Ashok Kumar VVNSS Sravanthi 2008 Cyclodextrins as drug carrier molecule: a review Sci. Pharm. 76 567 598 10.3797/scipharm.0808-05
    • (2008) Sci. Pharm. , vol.76 , pp. 567-598
    • Arun, R.1    Ashok Kumar, C.K.2    Vvnss, S.3
  • 41
    • 0008988686 scopus 로고    scopus 로고
    • The influence of β-cyclodextrins on the solubility of furosemide
    • 10.1023/A:1007909715459
    • RM Amin Kreaz GY Dombi M Kata 1998 The influence of β-cyclodextrins on the solubility of furosemide J. Inclusion Phenom. Mol. Recognit. Chem. 31 189 196 10.1023/A:1007909715459
    • (1998) J. Inclusion Phenom. Mol. Recognit. Chem. , vol.31 , pp. 189-196
    • Amin Kreaz, R.M.1    Dombi, G.Y.2    Kata, M.3
  • 45
    • 0004144140 scopus 로고
    • Martindale (ed.) 29th ed. The pharmaceutical press, London
    • Reynolds, J.E.F.: In: Martindale (ed.) The Extra Pharmacopoeia, 29th ed. The pharmaceutical press, London (1989)
    • (1989) The Extra Pharmacopoeia
    • Reynolds, E.J.F.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.