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Thiourea Modified Doxorubicin: A Perspective pH-Sensitive Prodrug

dc.contributor.authorKRASNOVSKAYA, Olga
dc.contributor.authorMALINNIKOV, Vladislav
dc.contributor.authorDASHKOVA, Natalia
dc.contributor.authorGERASIMOV, Vasily
dc.contributor.authorGRISHINA, Irina
hal.structure.identifierLaboratoire de Biologie cellulaire et Microscopie Electronique
dc.contributor.authorKIREEV, Igor
dc.contributor.authorLAVRUSHKINA, Svetlana
dc.contributor.authorPANCHENKO, Pavel
dc.contributor.authorZAKHARKO, Marina
dc.contributor.authorIGNATOV, Pavel
hal.structure.identifierDepartment of Chemistry
dc.contributor.authorFEDOROVA, Olga
hal.structure.identifierLaboratoire Ondes et Matière d'Aquitaine [LOMA]
dc.contributor.authorJONUSAUSKAS, Gediminas
dc.contributor.authorSKVORTSOV, Dmitry
hal.structure.identifierDépartement Décision en Entreprise : Modélisation, Optimisation [DEMO-ENSMSE]
dc.contributor.authorKOVALEV, Sergey
dc.contributor.authorBELOGLAZKINA, Elena
dc.contributor.authorZYK, Nikolay
dc.contributor.authorMAJOUGA, Alexander
dc.date.issued2019-02-11
dc.identifier.issn1043-1802
dc.description.abstractEnA novel approach to the synthesis of pH-sensitive prodrugs has been proposed: thiourea drug modification. Resulting prodrugs can release the cytotoxic agent and the biologically active 2-thiohydantoin in the acidic environment of tumor cells. The concept of acid-catalyzed cyclization of thioureas to 2-thiohydantoins has been proven using a FRET model. Dual prodrugs of model azidothymidine, cytotoxic doxorubicin, and 2-thiohydantoin albutoin were obtained, which release the corresponding drugs in the acidic environment. The resulting doxorubicin prodrug was tested on prostate cancer cells and showed that the thiourea-modified prodrug is less cytotoxic (average IC50 ranging from 0.5584 to 0.9885 μM) than doxorubicin (IC50 ranging from 0.01258 to 0.02559 μM) in neutral pH 7.6 and has similar toxicity (average IC50 ranging from 0.4970 to 0.7994 μM) to doxorubicin (IC50 ranging from 0.2303 to 0.8110 μM) under mildly acidic conditions of cancer cells. Cellular and nuclear accumulation in PC3 tumor cells of Dox prodrug is much higher than accumulation of free doxorubicin.
dc.language.isoen
dc.publisherAmerican Chemical Society
dc.title.enThiourea Modified Doxorubicin: A Perspective pH-Sensitive Prodrug
dc.typeArticle de revue
dc.identifier.doi10.1021/acs.bioconjchem.8b00885
dc.subject.halPhysique [physics]/Physique [physics]/Chimie-Physique [physics.chem-ph]
dc.subject.halPhysique [physics]/Physique [physics]/Optique [physics.optics]
bordeaux.journalBioconjugate Chemistry
bordeaux.page741-750
bordeaux.volume30
bordeaux.issue3
bordeaux.peerReviewedoui
hal.identifierhal-02404558
hal.version1
hal.origin.linkhttps://hal.archives-ouvertes.fr//hal-02404558v1
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