{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,17]],"date-time":"2026-09-17T16:49:21Z","timestamp":1789663761179,"version":"4.0.1"},"reference-count":26,"publisher":"Oxford University Press (OUP)","issue":"9","license":[{"start":{"date-parts":[[2011,9,1]],"date-time":"2011-09-01T00:00:00Z","timestamp":1314835200000},"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":[[2011,9,1]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:sec>\n                    <jats:title>Objectives<\/jats:title>\n                    <jats:p>The purpose of this work was to study the chemical stability of the new antitumoral \u03b2-lapachone (\u03b2LAP) to determine the degradation pathway\/s of the molecule and the degradation kinetics in addition to identifying several degradation products.<\/jats:p>\n                    <jats:p>Method\u2002 Samples of \u03b2LAP in solution were stored under conditions of darkness and illumination at 40\u00b0C at which the pseudo-first order rate constants for the \u03b2LAP degradation were determined. Furthermore, drug degraded solutions were concentrated and purified using Sephadex LH-20 and preparative thin-layer chromatography and degradation products were identified by nuclear magnetic resonance spectroscopy.<\/jats:p>\n                  <\/jats:sec>\n                  <jats:sec>\n                    <jats:title>Key findings<\/jats:title>\n                    <jats:p>The results revealed that \u03b2LAP shows two different degradation routes: hydrolysis in the dark and photolysis under the light. The \u03b2LAP exposure to light accelerated the drug degradation about 140 fold, compared with the samples stored in the absence of light. The hydrolysis produced hydroxylapachol as the main degradation product. The photolysis yielded phthalic acid, 6-hydroxy-3methylene-3H-isobenzofuran-1-one and a benzomacrolactone together with a complex mixture of other phthalate-derivatives such as 2-(2-carboxy-acetyl)-benzoic acid.<\/jats:p>\n                  <\/jats:sec>\n                  <jats:sec>\n                    <jats:title>Conclusions<\/jats:title>\n                    <jats:p>This study provides useful information for the development of \u03b2LAP dosage forms, their storage, manipulation and quality control.<\/jats:p>\n                  <\/jats:sec>","DOI":"10.1111\/j.2042-7158.2011.01323.x","type":"journal-article","created":{"date-parts":[[2011,6,30]],"date-time":"2011-06-30T07:50:35Z","timestamp":1309420235000},"page":"1156-1160","source":"Crossref","is-referenced-by-count":16,"title":["Light effect on the stability of\n                    <i>\u03b2<\/i>\n                    -lapachone in solution: pathways and kinetics of degradation"],"prefix":"10.1093","volume":"63","author":[{"given":"Marc\u00edlio S S","family":"Cunha-Filho","sequence":"first","affiliation":[{"name":"Instituto de Ci\u00eancias da Sa\u00fade, Campus Universit\u00e1rio de Sinop, Universidade Federal de Mato Grosso (UFMT) , Avenida Alexandre Ferronato, Sinop, MT,","place":["Brazil"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ana","family":"Est\u00e9vez-Braun","sequence":"additional","affiliation":[{"name":"Instituto Universitario de Bio-Org\u00e1nica \u2018Antonio Gonz\u00e1lez\u2019, Universidad de La Laguna , La Laguna, Tenerife,","place":["Spain"]},{"name":"Instituto Canario de Investigaci\u00f3n del C\u00e1ncer ( http:\/\/www.icic.es ), La Laguna, Tenerife,","place":["Spain"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Elisa","family":"P\u00e9rez-Sacau","sequence":"additional","affiliation":[{"name":"Instituto Universitario de Bio-Org\u00e1nica \u2018Antonio Gonz\u00e1lez\u2019, Universidad de La Laguna , La Laguna, Tenerife,","place":["Spain"]},{"name":"Instituto Canario de Investigaci\u00f3n del C\u00e1ncer ( http:\/\/www.icic.es ), La Laguna, Tenerife,","place":["Spain"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ma Magdalena","family":"Echezarreta-L\u00f3pez","sequence":"additional","affiliation":[{"name":"Departamento de Farmacia y Tecnolog\u00eda Farmac\u00e9utica, Facultad de Farmacia, Universidad de Santiago de Compostela , Santiago de Compostela,","place":["Spain"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ram\u00f3n","family":"Mart\u00ednez-Pacheco","sequence":"additional","affiliation":[{"name":"Departamento de Farmacia y Tecnolog\u00eda Farmac\u00e9utica, Facultad de Farmacia, Universidad de Santiago de Compostela , Santiago de Compostela,","place":["Spain"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Mariana","family":"Land\u00edn","sequence":"additional","affiliation":[{"name":"Departamento de Farmacia y Tecnolog\u00eda Farmac\u00e9utica, Facultad de Farmacia, Universidad de Santiago de Compostela , Santiago de Compostela,","place":["Spain"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"286","published-online":{"date-parts":[[2011,9,1]]},"reference":[{"key":"2024103013285474400_cit1","doi-asserted-by":"crossref","first-page":"850","DOI":"10.1039\/j39680000850","article-title":"Naturally occurring quinones. 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