Enhancement of solubility of albendazole by complexation with β-cyclodextrin
A high dosage of albendazole (ABZ) is required for treating systemic helminthe infections because of its low solubility. Aiming at increasing ABZ solubility, complexation with beta-cyclodextrin (β-CD) using aqueous and acetic acid solutions as ABZ solubilizer was studied. In aqueous β-CD, complexati...
Gespeichert in:
Veröffentlicht in: | Brazilian journal of chemical engineering 2008-06, Vol.25 (2), p.255-267 |
---|---|
Hauptverfasser: | , , , , , , |
Format: | Artikel |
Sprache: | eng |
Schlagworte: | |
Online-Zugang: | Volltext |
Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
container_end_page | 267 |
---|---|
container_issue | 2 |
container_start_page | 255 |
container_title | Brazilian journal of chemical engineering |
container_volume | 25 |
creator | Moriwaki, C. Costa, G. L. Ferracini, C. N. Moraes, F. F. de Zanin, G. M. Pineda, E. A. G. Matioli, G. |
description | A high dosage of albendazole (ABZ) is required for treating systemic helminthe infections because of its low solubility. Aiming at increasing ABZ solubility, complexation with beta-cyclodextrin (β-CD) using aqueous and acetic acid solutions as ABZ solubilizer was studied. In aqueous β-CD, complexation increased solubility 53.4 times, giving a complex equilibrium constant of 1266 L mol-1 with a maximum ABZ concentration of 276 µmol L-1 for 16.3 mmol L-1 β-CD. For complexation in 1.05 mol L-1 acetic acid, UV absorbance spectra and ¹H-NMR analysis confirmed complex formation. The UV absorbance of ABZ/acid acetic/β-CD solutions was modeled by the formation of two complexes with molar ratios 1:1 and 1:2 ABZ:β-CD. When neutralized with NaOH these solutions did not form precipitates only for the ABZ:β-CD molar ratios of 1:8 and 1:10, showing that ABZ solubility could be increased 306 times. Results show that high β-CD molar ratios hold ABZ in solution by complexation enhanced by the acetate anion. |
doi_str_mv | 10.1590/S0104-66322008000200005 |
format | Article |
fullrecord | <record><control><sourceid>scielo_cross</sourceid><recordid>TN_cdi_scielo_journals_S0104_66322008000200005</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><scielo_id>S0104_66322008000200005</scielo_id><sourcerecordid>S0104_66322008000200005</sourcerecordid><originalsourceid>FETCH-LOGICAL-c345t-998e371182f4e8e2827f15cd5e04590811e24e365bfebf4f433fdd9de98f47673</originalsourceid><addsrcrecordid>eNp1kE1OwzAQhS0EEqVwBnKBlHFsJ84SVeVHKmIBrKPEGauuHLuKXdFwLA7CmUgpQkiI1ZvRzDdP8wi5pDCjooSrJ6DA0zxnWQYgAWAUAHFEJj-D41_1KTkLYT1uCWDlhDws3Kp2Cjt0MfE6Cd5uG2NNHPZdbRt0bf3mLSbNkCjfbSzu6mi8S15NXCUf76kalPUt7mJv3Dk50bUNePGtU_Jys3ie36XLx9v7-fUyVYyLmJalRFZQKjPNUWIms0JToVqBwMeXJKWYcWS5aDQ2mmvOmG7bssVSal7kBZuS2eFuUAatr9Z-27vRsPoKo_oTxggUB0D1PoQedbXpTVf3Q0Wh2sf4L_kJa4ZkLg</addsrcrecordid><sourcetype>Open Access Repository</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype></control><display><type>article</type><title>Enhancement of solubility of albendazole by complexation with β-cyclodextrin</title><source>Elektronische Zeitschriftenbibliothek - Frei zugängliche E-Journals</source><source>Free Full-Text Journals in Chemistry</source><creator>Moriwaki, C. ; Costa, G. L. ; Ferracini, C. N. ; Moraes, F. F. de ; Zanin, G. M. ; Pineda, E. A. G. ; Matioli, G.</creator><creatorcontrib>Moriwaki, C. ; Costa, G. L. ; Ferracini, C. N. ; Moraes, F. F. de ; Zanin, G. M. ; Pineda, E. A. G. ; Matioli, G.</creatorcontrib><description>A high dosage of albendazole (ABZ) is required for treating systemic helminthe infections because of its low solubility. Aiming at increasing ABZ solubility, complexation with beta-cyclodextrin (β-CD) using aqueous and acetic acid solutions as ABZ solubilizer was studied. In aqueous β-CD, complexation increased solubility 53.4 times, giving a complex equilibrium constant of 1266 L mol-1 with a maximum ABZ concentration of 276 µmol L-1 for 16.3 mmol L-1 β-CD. For complexation in 1.05 mol L-1 acetic acid, UV absorbance spectra and ¹H-NMR analysis confirmed complex formation. The UV absorbance of ABZ/acid acetic/β-CD solutions was modeled by the formation of two complexes with molar ratios 1:1 and 1:2 ABZ:β-CD. When neutralized with NaOH these solutions did not form precipitates only for the ABZ:β-CD molar ratios of 1:8 and 1:10, showing that ABZ solubility could be increased 306 times. Results show that high β-CD molar ratios hold ABZ in solution by complexation enhanced by the acetate anion.</description><identifier>ISSN: 0104-6632</identifier><identifier>ISSN: 1678-4383</identifier><identifier>EISSN: 0104-6632</identifier><identifier>DOI: 10.1590/S0104-66322008000200005</identifier><language>eng</language><publisher>Brazilian Society of Chemical Engineering</publisher><subject>ENGINEERING, CHEMICAL</subject><ispartof>Brazilian journal of chemical engineering, 2008-06, Vol.25 (2), p.255-267</ispartof><rights>This work is licensed under a Creative Commons Attribution-NonCommercial 4.0 International License.</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c345t-998e371182f4e8e2827f15cd5e04590811e24e365bfebf4f433fdd9de98f47673</citedby><cites>FETCH-LOGICAL-c345t-998e371182f4e8e2827f15cd5e04590811e24e365bfebf4f433fdd9de98f47673</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>230,314,780,784,885,27924,27925</link.rule.ids></links><search><creatorcontrib>Moriwaki, C.</creatorcontrib><creatorcontrib>Costa, G. L.</creatorcontrib><creatorcontrib>Ferracini, C. N.</creatorcontrib><creatorcontrib>Moraes, F. F. de</creatorcontrib><creatorcontrib>Zanin, G. M.</creatorcontrib><creatorcontrib>Pineda, E. A. G.</creatorcontrib><creatorcontrib>Matioli, G.</creatorcontrib><title>Enhancement of solubility of albendazole by complexation with β-cyclodextrin</title><title>Brazilian journal of chemical engineering</title><addtitle>Braz. J. Chem. Eng</addtitle><description>A high dosage of albendazole (ABZ) is required for treating systemic helminthe infections because of its low solubility. Aiming at increasing ABZ solubility, complexation with beta-cyclodextrin (β-CD) using aqueous and acetic acid solutions as ABZ solubilizer was studied. In aqueous β-CD, complexation increased solubility 53.4 times, giving a complex equilibrium constant of 1266 L mol-1 with a maximum ABZ concentration of 276 µmol L-1 for 16.3 mmol L-1 β-CD. For complexation in 1.05 mol L-1 acetic acid, UV absorbance spectra and ¹H-NMR analysis confirmed complex formation. The UV absorbance of ABZ/acid acetic/β-CD solutions was modeled by the formation of two complexes with molar ratios 1:1 and 1:2 ABZ:β-CD. When neutralized with NaOH these solutions did not form precipitates only for the ABZ:β-CD molar ratios of 1:8 and 1:10, showing that ABZ solubility could be increased 306 times. Results show that high β-CD molar ratios hold ABZ in solution by complexation enhanced by the acetate anion.</description><subject>ENGINEERING, CHEMICAL</subject><issn>0104-6632</issn><issn>1678-4383</issn><issn>0104-6632</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2008</creationdate><recordtype>article</recordtype><recordid>eNp1kE1OwzAQhS0EEqVwBnKBlHFsJ84SVeVHKmIBrKPEGauuHLuKXdFwLA7CmUgpQkiI1ZvRzDdP8wi5pDCjooSrJ6DA0zxnWQYgAWAUAHFEJj-D41_1KTkLYT1uCWDlhDws3Kp2Cjt0MfE6Cd5uG2NNHPZdbRt0bf3mLSbNkCjfbSzu6mi8S15NXCUf76kalPUt7mJv3Dk50bUNePGtU_Jys3ie36XLx9v7-fUyVYyLmJalRFZQKjPNUWIms0JToVqBwMeXJKWYcWS5aDQ2mmvOmG7bssVSal7kBZuS2eFuUAatr9Z-27vRsPoKo_oTxggUB0D1PoQedbXpTVf3Q0Wh2sf4L_kJa4ZkLg</recordid><startdate>20080601</startdate><enddate>20080601</enddate><creator>Moriwaki, C.</creator><creator>Costa, G. L.</creator><creator>Ferracini, C. N.</creator><creator>Moraes, F. F. de</creator><creator>Zanin, G. M.</creator><creator>Pineda, E. A. G.</creator><creator>Matioli, G.</creator><general>Brazilian Society of Chemical Engineering</general><scope>AAYXX</scope><scope>CITATION</scope><scope>GPN</scope></search><sort><creationdate>20080601</creationdate><title>Enhancement of solubility of albendazole by complexation with β-cyclodextrin</title><author>Moriwaki, C. ; Costa, G. L. ; Ferracini, C. N. ; Moraes, F. F. de ; Zanin, G. M. ; Pineda, E. A. G. ; Matioli, G.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c345t-998e371182f4e8e2827f15cd5e04590811e24e365bfebf4f433fdd9de98f47673</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2008</creationdate><topic>ENGINEERING, CHEMICAL</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Moriwaki, C.</creatorcontrib><creatorcontrib>Costa, G. L.</creatorcontrib><creatorcontrib>Ferracini, C. N.</creatorcontrib><creatorcontrib>Moraes, F. F. de</creatorcontrib><creatorcontrib>Zanin, G. M.</creatorcontrib><creatorcontrib>Pineda, E. A. G.</creatorcontrib><creatorcontrib>Matioli, G.</creatorcontrib><collection>CrossRef</collection><collection>SciELO</collection><jtitle>Brazilian journal of chemical engineering</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Moriwaki, C.</au><au>Costa, G. L.</au><au>Ferracini, C. N.</au><au>Moraes, F. F. de</au><au>Zanin, G. M.</au><au>Pineda, E. A. G.</au><au>Matioli, G.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Enhancement of solubility of albendazole by complexation with β-cyclodextrin</atitle><jtitle>Brazilian journal of chemical engineering</jtitle><addtitle>Braz. J. Chem. Eng</addtitle><date>2008-06-01</date><risdate>2008</risdate><volume>25</volume><issue>2</issue><spage>255</spage><epage>267</epage><pages>255-267</pages><issn>0104-6632</issn><issn>1678-4383</issn><eissn>0104-6632</eissn><abstract>A high dosage of albendazole (ABZ) is required for treating systemic helminthe infections because of its low solubility. Aiming at increasing ABZ solubility, complexation with beta-cyclodextrin (β-CD) using aqueous and acetic acid solutions as ABZ solubilizer was studied. In aqueous β-CD, complexation increased solubility 53.4 times, giving a complex equilibrium constant of 1266 L mol-1 with a maximum ABZ concentration of 276 µmol L-1 for 16.3 mmol L-1 β-CD. For complexation in 1.05 mol L-1 acetic acid, UV absorbance spectra and ¹H-NMR analysis confirmed complex formation. The UV absorbance of ABZ/acid acetic/β-CD solutions was modeled by the formation of two complexes with molar ratios 1:1 and 1:2 ABZ:β-CD. When neutralized with NaOH these solutions did not form precipitates only for the ABZ:β-CD molar ratios of 1:8 and 1:10, showing that ABZ solubility could be increased 306 times. Results show that high β-CD molar ratios hold ABZ in solution by complexation enhanced by the acetate anion.</abstract><pub>Brazilian Society of Chemical Engineering</pub><doi>10.1590/S0104-66322008000200005</doi><tpages>13</tpages><oa>free_for_read</oa></addata></record> |
fulltext | fulltext |
identifier | ISSN: 0104-6632 |
ispartof | Brazilian journal of chemical engineering, 2008-06, Vol.25 (2), p.255-267 |
issn | 0104-6632 1678-4383 0104-6632 |
language | eng |
recordid | cdi_scielo_journals_S0104_66322008000200005 |
source | Elektronische Zeitschriftenbibliothek - Frei zugängliche E-Journals; Free Full-Text Journals in Chemistry |
subjects | ENGINEERING, CHEMICAL |
title | Enhancement of solubility of albendazole by complexation with β-cyclodextrin |
url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-05T19%3A05%3A55IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-scielo_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Enhancement%20of%20solubility%20of%20albendazole%20by%20complexation%20with%20%CE%B2-cyclodextrin&rft.jtitle=Brazilian%20journal%20of%20chemical%20engineering&rft.au=Moriwaki,%20C.&rft.date=2008-06-01&rft.volume=25&rft.issue=2&rft.spage=255&rft.epage=267&rft.pages=255-267&rft.issn=0104-6632&rft.eissn=0104-6632&rft_id=info:doi/10.1590/S0104-66322008000200005&rft_dat=%3Cscielo_cross%3ES0104_66322008000200005%3C/scielo_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_id=info:pmid/&rft_scielo_id=S0104_66322008000200005&rfr_iscdi=true |