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dc.contributor.authorSaal, Wiebke
dc.contributor.authorWyttenbach, Nicole
dc.contributor.authorAlsenz, Jochem
dc.contributor.authorKuentz, Martin
dc.date.accessioned2018-01-09T12:48:20Z
dc.date.available2018-01-09T12:48:20Z
dc.date.issued2017
dc.identifier.doi10.1080/10837450.2017.1316288
dc.identifier.urihttp://hdl.handle.net/11654/25767
dc.description.abstractSelf-aggregation of drugs is since many years an important topic in the pharmaceutical sciences. Drugs can aggregate similar to surfactants and thereby exhibit a critical micelle concentration (CMC). The present work focused on amphiphilic drug bases and it was aimed to predict log(CMC) based on chemical structure alone. A dataset of 35 compounds was gathered mostly form the literature and complemented with own measurements based on ultrasonic resonator technology. The hydrophilic–lipophilic balance (HLB) values of the protonated bases were calculated and provided a range of 22.9–27.4. Based on a hypothesis from surfactant sciences, it was tried to predict log(CMC) with connectivity and shape indices as well as molecular dipole moment. A fairly good model was obtained using the Randix index (RI), 3 D Wiener number (WN) and molecular dipole moment (DM) (R2 = 0.824). Interestingly, a simple linear regression of log(CMC) with the Randic index alone, resulted in an acceptable model (R2 = 0.755). The present work should help with early identification of drug bases that exhibit surfactant-like behavior and an estimation of log(CMC) values is proposed. An improved understanding of drug aggregation and prediction of log(CMC) helps to better cope with physical consequences like, for example, “anomalous” drug solubility in drug discovery and development.
dc.language.isoen_US
dc.relation.ispartofPharmaceutical Development and Technology
dc.accessRightsAnonymous
dc.subjectSolubility
dc.subjectsurface active
dc.subjectmicelle
dc.subjectmolecular modeling
dc.subjectphysicochemical properties
dc.titleCan we estimate the critical micelle concentration of amphiphilic drug bases from molecular connectivity indices?
dc.type01 - Zeitschriftenartikel, Journalartikel oder Magazin
dc.volume23
dc.issue2
dc.audienceScience
fhnw.publicationStatePublished
fhnw.ReviewTypeAnonymous ex ante peer review of a complete publication
fhnw.InventedHereYes
fhnw.PublishedSwitzerlandYes
fhnw.pagination211-215
fhnw.IsStudentsWorkno
fhnw.publicationOnlineJa


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