{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,6]],"date-time":"2026-10-06T09:56:17Z","timestamp":1791280577018,"version":"4.1.0"},"reference-count":28,"publisher":"Oxford University Press (OUP)","issue":"6","license":[{"start":{"date-parts":[[2004,6,1]],"date-time":"2004-06-01T00:00:00Z","timestamp":1086048000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/academic.oup.com\/journals\/pages\/open_access\/funder_policies\/chorus\/standard_publication_model"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2004,6,1]]},"abstract":"<jats:title>Abstract<\/jats:title>\n               <jats:p>The solubilization of the practically water insoluble drug furosemide by guest:host inclusion complexation with 4-sulphonic calix[n]arenes has been reported. The 4-sulphonic calix[n]arenes are water-soluble phenolic cyclooligomers that form inclusion complexes with neutral molecules. The solubility of furosemide in acidic (pH &amp;lt; 4) aqueous solutions containing increasing concentrations of the calixarenes was determined at 30\u00b0C and the concentration of furosemide in solution was determined by HPLC. Results showed that the molecular size of the 4-sulphonic calix[n]arenes and the concentration of the calix[n]arenes significantly influenced the increase in the solubility of furosemide. 4-Sulphonic calix[6]arene improved the solubility of furosemide the most (\u00b1 104%) followed by 4-sulphonic calix[8]-arene (\u00b184\u2013102%), while 4-sulphonic calix[4]arene increased the solubility of furosemide the least (\u00b173\u201381%). The increase in furosemide solubility afforded by the calixarenes was most probably the result of the incorporation of the non-polar portions of the furosemide molecule into the non-polar cavities of the calixarenes similar to furosemide:cyclodextrin complexes. The driving force for this interaction was the reduction in the non-polar-water interfacial surface area when the furosemide (guest) molecules were inserted into the 4-sulphonic calix[n]arenes (host).<\/jats:p>","DOI":"10.1211\/0022357023439","type":"journal-article","created":{"date-parts":[[2004,6,28]],"date-time":"2004-06-28T22:02:27Z","timestamp":1088460147000},"page":"703-708","source":"Crossref","is-referenced-by-count":66,"title":["Aqueous solubilization of furosemide by supramolecular complexation with 4-sulphonic calix[n]arenes"],"prefix":"10.1093","volume":"56","author":[{"given":"Wenzhan","family":"Yang","sequence":"first","affiliation":[{"name":"School of Pharmacy, The University of Louisiana at Monroe , 700 University Avenue, Monroe, LA 71209,","place":["USA"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Melgardt M","family":"de Villiers","sequence":"additional","affiliation":[{"name":"School of Pharmacy, The University of Louisiana at Monroe , 700 University Avenue, Monroe, LA 71209,","place":["USA"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"286","published-online":{"date-parts":[[2004,6,1]]},"reference":[{"key":"2024103109402502000_cit1","first-page":"153","article-title":"Analytical profile of furosemide","volume-title":"Analytical profiles of drug substances","author":"Al-Obaid","year":"1989"},{"key":"2024103109402502000_cit2","first-page":"142","article-title":"Inclusion complexation of furosemide in cyclodextrins","volume":"54","author":"Ammar","year":"1999","journal-title":"Die Pharm."},{"key":"2024103109402502000_cit3","doi-asserted-by":"crossref","first-page":"19","DOI":"10.1080\/10610279208027437","article-title":"Water-soluble calix[4]arenes. A thermodynamic investigation of proton complex formation","volume":"1","author":"Arena","year":"1992","journal-title":"Supramol. Chem."},{"key":"2024103109402502000_cit4","doi-asserted-by":"crossref","first-page":"9327","DOI":"10.1016\/S0040-4039(00)01687-7","article-title":"Complexation of small neutral organic molecules by water soluble calix[4]arenes","volume":"41","author":"Arena","year":"2000","journal-title":"Tetrahedron Lett."},{"key":"2024103109402502000_cit5","doi-asserted-by":"crossref","first-page":"27","DOI":"10.1016\/0378-5173(79)90095-4","article-title":"Gastrointestinal sites of furosemide absorption in rats","volume":"4","author":"Chungi","year":"1979","journal-title":"Int. J. Pharm."},{"key":"2024103109402502000_cit6","doi-asserted-by":"crossref","first-page":"5410","DOI":"10.1021\/ja00014a037","article-title":"Cyclophane-arene inclusion complexation in protic solvents: solvent effects versus electron donor-acceptor interactions","volume":"113","author":"Ferguson","year":"1991","journal-title":"J. Am. Chem. Soc."},{"key":"2024103109402502000_cit7","volume-title":"Calixarenes","author":"Gutsche","year":"1989"},{"key":"2024103109402502000_cit8","doi-asserted-by":"crossref","DOI":"10.1039\/9781847550293","volume-title":"Calixarenes Revisited","author":"Gutsche","year":"1998"},{"key":"2024103109402502000_cit9","doi-asserted-by":"crossref","first-page":"197","DOI":"10.1007\/BF00630286","article-title":"Pharmacokinetics of furosemide in man after intravenous and oral administration. Application of moment analysis","volume":"26","author":"Hammarlund","year":"1984","journal-title":"Eur. J. Clin. Pharmacol."},{"key":"2024103109402502000_cit10","doi-asserted-by":"crossref","first-page":"644","DOI":"10.1002\/jps.2600530615","article-title":"Complexation of organic substances in aqueous solution by hydroxyaromatic acids and their salts. II. Influences of halogen, nitro, and other substituents and correlation of binding tendencies toward prednisolone, theophylline, and phenacetin","volume":"53","author":"Higuchi","year":"1964","journal-title":"J. Pharm. Sci."},{"key":"2024103109402502000_cit11","first-page":"117","article-title":"Phase-solubility techniques","volume-title":"Advances in analytical chemistry and instrumentation","author":"Higuchi","year":"1965"},{"key":"2024103109402502000_cit12","doi-asserted-by":"crossref","first-page":"327","DOI":"10.1023\/A:1011196217714","article-title":"A preliminary investigation of the solution complexation of 4-sulphonic calix[n]arenes with testosterone","volume":"39","author":"Millership","year":"2001","journal-title":"J. Inclusion Phenom. Macro. Chem."},{"key":"2024103109402502000_cit13","doi-asserted-by":"crossref","first-page":"19","DOI":"10.3109\/03639049809082348","article-title":"Improvement of dissolution properties of furosemide by complexation with \u03b2-cyclodextrin","volume":"24","author":"\u00d6zdemir","year":"1998","journal-title":"Drug Dev. Ind. Pharm."},{"key":"2024103109402502000_cit14","first-page":"987","volume-title":"Martindale: The Extra Pharmacopoeia","author":"Reynolds","year":"1989","edition":"29th edn."},{"issue":"11","key":"2024103109402502000_cit15","doi-asserted-by":"crossref","first-page":"1523","DOI":"10.1351\/pac198658111523","article-title":"Calixarenes as new functionalized host molecules","volume":"58","author":"Shinkai","year":"1986","journal-title":"Pure Appl. Chem."},{"key":"2024103109402502000_cit16","doi-asserted-by":"crossref","first-page":"2409","DOI":"10.1021\/ja00269a045","article-title":"Hexasulfonated calix[6]arene derivatives: a new class of catalysts, surfactants, and host molecules","volume":"108","author":"Shinkai","year":"1986","journal-title":"J. Am. Chem. Soc."},{"key":"2024103109402502000_cit17","doi-asserted-by":"crossref","first-page":"187","DOI":"10.1039\/C39880000187","article-title":"Does the calixarene cavity recognize the size of guest molecules? On the \u2018hole-size selectivity\u2019 in water-soluble calixarenes","volume":"3","author":"Shinkai","year":"1988","journal-title":"J. Chem. Soc. Chem. Commun."},{"key":"2024103109402502000_cit18","doi-asserted-by":"crossref","first-page":"5309","DOI":"10.1021\/j100192a025","article-title":"Cyclodextrin-induced asymmetry of achiral nitrogen heterocycles","volume":"96","author":"Shuette","year":"1992","journal-title":"J. Phys. Chem."},{"key":"2024103109402502000_cit19","doi-asserted-by":"crossref","first-page":"247","DOI":"10.1016\/S0928-0987(02)00107-0","article-title":"Characterization of the complexes of furosemide with 2-hydroxypropyl-\u03b2-cyclodextrin and sulfobutyl ether-7-\u03b2-cyclodextrin","volume":"16","author":"Spamer","year":"2002","journal-title":"Eur. J. Pharm. Sci."},{"key":"2024103109402502000_cit20","volume-title":"Cyclodextrins and their inclusion complexes","author":"Szejtli","year":"1982"},{"key":"2024103109402502000_cit21","doi-asserted-by":"crossref","first-page":"1957","DOI":"10.1039\/a802841i","article-title":"Thermodynamic study of p-sulfonated calixarene complexes in aqueous solution","volume":"9","author":"Tao","year":"1998","journal-title":"J. Chem. Soc. Perkin Trans. 2."},{"key":"2024103109402502000_cit22","volume-title":"The United States Pharmacopeial Convention","author":"The United State Pharmacopeia XXIV","year":"2000"},{"key":"2024103109402502000_cit23","volume-title":"Calixarenes: a versatile class of macrocyclic compounds","author":"Vicens","year":"1991"},{"key":"2024103109402502000_cit24","doi-asserted-by":"crossref","first-page":"197","DOI":"10.1177\/0885328203017003557","article-title":"Preparation and characterization of the inclusion complex of furosemide with hydroxypropyl-\u03b2-cyclodextrin","volume":"17","author":"Vlachou","year":"2003","journal-title":"J. Biomat. 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