Effect of Hydroxypropyl-β-cyclodextrin on the Solubility of an Antibacterial Isoxazolyl-naphthoquinone
The complexation of 2-hydroxy-N-(3,4-dimethyl-5-isoxazolyl)-1,4-naphthoquinone-4-imine (I) with a highly soluble cyclodextrin, hydroxypropyl-β-cyclodextrin (HP-β-CD) was studied in aqueous media by solubility methods. I is an antibacterial and trypanocidal agent that is undergoing preclinical testin...
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| Veröffentlicht in: | Drug development and industrial pharmacy 2000-01, Vol.26 (9), p.1003-1006 |
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| container_title | Drug development and industrial pharmacy |
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| creator | Linares, M. S. de Bertorello, M. M. Longhi, M. R. |
| description | The complexation of 2-hydroxy-N-(3,4-dimethyl-5-isoxazolyl)-1,4-naphthoquinone-4-imine (I) with a highly soluble cyclodextrin, hydroxypropyl-β-cyclodextrin (HP-β-CD) was studied in aqueous media by solubility methods. I is an antibacterial and trypanocidal agent that is undergoing preclinical testing. Unfortunately, I exhibits low water solubility, and it is therefore difficult to prepare the solutions for biological tests. I inclusion took place with 1:1 stoichiometry. The stability constants of the I complexes calculated from the slope and the intercept of the phase solubility diagrams are larger in the less ionized form, whereas greater overall solubility is obtained in basic media. |
| doi_str_mv | 10.1081/DDC-100101329 |
| format | Article |
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The stability constants of the I complexes calculated from the slope and the intercept of the phase solubility diagrams are larger in the less ionized form, whereas greater overall solubility is obtained in basic media.</description><identifier>ISSN: 0363-9045</identifier><identifier>EISSN: 1520-5762</identifier><identifier>DOI: 10.1081/DDC-100101329</identifier><identifier>PMID: 10914326</identifier><language>eng</language><publisher>Colchester: Informa UK Ltd</publisher><subject>2-Hydroxypropyl-beta-cyclodextrin ; Anti-Infective Agents - chemistry ; Antibacterial agents ; Antibiotics. Antiinfectious agents. Antiparasitic agents ; beta-Cyclodextrins ; Biological and medical sciences ; Complexation ; Cyclodextrins - chemistry ; Excipients - chemistry ; General pharmacology ; Hydrogen-Ion Concentration ; Hydroxypropyl-β-cyclodextrin ; Isoxazoles - chemistry ; Medical sciences ; Naphthols - chemistry ; Naphthoquinones ; Pharmaceutical technology. Pharmaceutical industry ; Pharmacology. Drug treatments ; Solubility ; Trypanocidal Agents - chemistry ; Water - chemistry</subject><ispartof>Drug development and industrial pharmacy, 2000-01, Vol.26 (9), p.1003-1006</ispartof><rights>2000 Informa UK Ltd All rights reserved: reproduction in whole or part not permitted 2000</rights><rights>2000 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c415t-e15df14ff50fab6e82bd6b126da551a14a202e76c6ce8687839269626744567b3</citedby><cites>FETCH-LOGICAL-c415t-e15df14ff50fab6e82bd6b126da551a14a202e76c6ce8687839269626744567b3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.tandfonline.com/doi/pdf/10.1081/DDC-100101329$$EPDF$$P50$$Ginformaworld$$H</linktopdf><linktohtml>$$Uhttps://www.tandfonline.com/doi/full/10.1081/DDC-100101329$$EHTML$$P50$$Ginformaworld$$H</linktohtml><link.rule.ids>314,780,784,27924,27925,59647,59753,60436,60542,61221,61256,61402,61437</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=1413226$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/10914326$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Linares, M. S.</creatorcontrib><creatorcontrib>de Bertorello, M. M.</creatorcontrib><creatorcontrib>Longhi, M. R.</creatorcontrib><title>Effect of Hydroxypropyl-β-cyclodextrin on the Solubility of an Antibacterial Isoxazolyl-naphthoquinone</title><title>Drug development and industrial pharmacy</title><addtitle>Drug Dev Ind Pharm</addtitle><description>The complexation of 2-hydroxy-N-(3,4-dimethyl-5-isoxazolyl)-1,4-naphthoquinone-4-imine (I) with a highly soluble cyclodextrin, hydroxypropyl-β-cyclodextrin (HP-β-CD) was studied in aqueous media by solubility methods. I is an antibacterial and trypanocidal agent that is undergoing preclinical testing. Unfortunately, I exhibits low water solubility, and it is therefore difficult to prepare the solutions for biological tests. I inclusion took place with 1:1 stoichiometry. The stability constants of the I complexes calculated from the slope and the intercept of the phase solubility diagrams are larger in the less ionized form, whereas greater overall solubility is obtained in basic media.</description><subject>2-Hydroxypropyl-beta-cyclodextrin</subject><subject>Anti-Infective Agents - chemistry</subject><subject>Antibacterial agents</subject><subject>Antibiotics. Antiinfectious agents. Antiparasitic agents</subject><subject>beta-Cyclodextrins</subject><subject>Biological and medical sciences</subject><subject>Complexation</subject><subject>Cyclodextrins - chemistry</subject><subject>Excipients - chemistry</subject><subject>General pharmacology</subject><subject>Hydrogen-Ion Concentration</subject><subject>Hydroxypropyl-β-cyclodextrin</subject><subject>Isoxazoles - chemistry</subject><subject>Medical sciences</subject><subject>Naphthols - chemistry</subject><subject>Naphthoquinones</subject><subject>Pharmaceutical technology. Pharmaceutical industry</subject><subject>Pharmacology. Drug treatments</subject><subject>Solubility</subject><subject>Trypanocidal Agents - chemistry</subject><subject>Water - chemistry</subject><issn>0363-9045</issn><issn>1520-5762</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2000</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp10M1u1DAUBWALgehQWLJFWSB2prYTO8mymhZaqVIXtGvrxrGJK489tR11wmPxIDwTLjP8Lbry5jtH1weht5R8pKSjJ2dna0wJoYTWrH-GVpQzgnkr2HO0IrWocU8afoRepXRXFOs5f4mOKOlpUzOxQl_PjdEqV8FUF8sYw27ZxrBdHP7xHatFuTDqXY7WV8FXedLVl-DmwTqbl8cI-OrUZzuAyjpacNVlCjv4Flwp8LCd8hTuZ-uD16_RCwMu6TeH9xjdfjq_WV_gq-vPl-vTK6wayjPWlI-GNsZwYmAQumPDKAbKxAicU6ANMMJ0K5RQuhNd29U9E71gom0aLtqhPkYf9r3lG_ezTllubFLaOfA6zEm2lHEhBC0Q76GKIaWojdxGu4G4SErk47KyLCv_LFv8u0PxPGz0-I_eT1nA-wOApMCZCF7Z9Nc1peYX6_bMehPiBh5CdKPMsLgQf2fqp05o_4tOGlyeFEQt78Icfdn1ieN_AtibpmU</recordid><startdate>20000101</startdate><enddate>20000101</enddate><creator>Linares, M. S.</creator><creator>de Bertorello, M. M.</creator><creator>Longhi, M. R.</creator><general>Informa UK Ltd</general><general>Taylor & Francis</general><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20000101</creationdate><title>Effect of Hydroxypropyl-β-cyclodextrin on the Solubility of an Antibacterial Isoxazolyl-naphthoquinone</title><author>Linares, M. S. ; de Bertorello, M. M. ; Longhi, M. R.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c415t-e15df14ff50fab6e82bd6b126da551a14a202e76c6ce8687839269626744567b3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2000</creationdate><topic>2-Hydroxypropyl-beta-cyclodextrin</topic><topic>Anti-Infective Agents - chemistry</topic><topic>Antibacterial agents</topic><topic>Antibiotics. Antiinfectious agents. Antiparasitic agents</topic><topic>beta-Cyclodextrins</topic><topic>Biological and medical sciences</topic><topic>Complexation</topic><topic>Cyclodextrins - chemistry</topic><topic>Excipients - chemistry</topic><topic>General pharmacology</topic><topic>Hydrogen-Ion Concentration</topic><topic>Hydroxypropyl-β-cyclodextrin</topic><topic>Isoxazoles - chemistry</topic><topic>Medical sciences</topic><topic>Naphthols - chemistry</topic><topic>Naphthoquinones</topic><topic>Pharmaceutical technology. Pharmaceutical industry</topic><topic>Pharmacology. Drug treatments</topic><topic>Solubility</topic><topic>Trypanocidal Agents - chemistry</topic><topic>Water - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Linares, M. S.</creatorcontrib><creatorcontrib>de Bertorello, M. M.</creatorcontrib><creatorcontrib>Longhi, M. R.</creatorcontrib><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Drug development and industrial pharmacy</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Linares, M. S.</au><au>de Bertorello, M. M.</au><au>Longhi, M. R.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Effect of Hydroxypropyl-β-cyclodextrin on the Solubility of an Antibacterial Isoxazolyl-naphthoquinone</atitle><jtitle>Drug development and industrial pharmacy</jtitle><addtitle>Drug Dev Ind Pharm</addtitle><date>2000-01-01</date><risdate>2000</risdate><volume>26</volume><issue>9</issue><spage>1003</spage><epage>1006</epage><pages>1003-1006</pages><issn>0363-9045</issn><eissn>1520-5762</eissn><abstract>The complexation of 2-hydroxy-N-(3,4-dimethyl-5-isoxazolyl)-1,4-naphthoquinone-4-imine (I) with a highly soluble cyclodextrin, hydroxypropyl-β-cyclodextrin (HP-β-CD) was studied in aqueous media by solubility methods. I is an antibacterial and trypanocidal agent that is undergoing preclinical testing. Unfortunately, I exhibits low water solubility, and it is therefore difficult to prepare the solutions for biological tests. I inclusion took place with 1:1 stoichiometry. The stability constants of the I complexes calculated from the slope and the intercept of the phase solubility diagrams are larger in the less ionized form, whereas greater overall solubility is obtained in basic media.</abstract><cop>Colchester</cop><pub>Informa UK Ltd</pub><pmid>10914326</pmid><doi>10.1081/DDC-100101329</doi><tpages>4</tpages></addata></record> |
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| ispartof | Drug development and industrial pharmacy, 2000-01, Vol.26 (9), p.1003-1006 |
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| language | eng |
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| source | MEDLINE; EBSCOhost Business Source Complete; Taylor & Francis Medical Library - CRKN; Taylor & Francis Journals Complete |
| subjects | 2-Hydroxypropyl-beta-cyclodextrin Anti-Infective Agents - chemistry Antibacterial agents Antibiotics. Antiinfectious agents. Antiparasitic agents beta-Cyclodextrins Biological and medical sciences Complexation Cyclodextrins - chemistry Excipients - chemistry General pharmacology Hydrogen-Ion Concentration Hydroxypropyl-β-cyclodextrin Isoxazoles - chemistry Medical sciences Naphthols - chemistry Naphthoquinones Pharmaceutical technology. Pharmaceutical industry Pharmacology. Drug treatments Solubility Trypanocidal Agents - chemistry Water - chemistry |
| title | Effect of Hydroxypropyl-β-cyclodextrin on the Solubility of an Antibacterial Isoxazolyl-naphthoquinone |
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