Can we estimate the critical micelle concentration of amphiphilic drug bases from molecular connectivity indices?
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Autor:innen
Autor:in (Körperschaft)
Publikationsdatum
2017
Typ der Arbeit
Studiengang
Sammlung
Typ
01A - Beitrag in wissenschaftlicher Zeitschrift
Herausgeber:innen
Herausgeber:in (Körperschaft)
Betreuer:in
Übergeordnetes Werk
Pharmaceutical Development and Technology
Themenheft
DOI der Originalpublikation
Link
Reihe / Serie
Reihennummer
Jahrgang / Band
23
Ausgabe / Nummer
2
Seiten / Dauer
211-215
Patentnummer
Verlag / Herausgebende Institution
Informa
Verlagsort / Veranstaltungsort
Auflage
Version
Programmiersprache
Abtretungsempfänger:in
Praxispartner:in/Auftraggeber:in
Zusammenfassung
Self-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.
Schlagwörter
Solubility, surface active, micelle, molecular modeling, physicochemical properties
Fachgebiet (DDC)
Veranstaltung
Startdatum der Ausstellung
Enddatum der Ausstellung
Startdatum der Konferenz
Enddatum der Konferenz
Datum der letzten Prüfung
ISBN
ISSN
1083-7450
1097-9867
1097-9867
Sprache
Englisch
Während FHNW Zugehörigkeit erstellt
Ja
Publikationsstatus
Veröffentlicht
Begutachtung
Peer-Review der ganzen Publikation
Open Access-Status
Lizenz
Zitation
SAAL, Wiebke, Nicole WYTTENBACH, Jochem ALSENZ und Martin KUENTZ, 2017. Can we estimate the critical micelle concentration of amphiphilic drug bases from molecular connectivity indices? Pharmaceutical Development and Technology. 2017. Bd. 23, Nr. 2, S. 211–215. DOI 10.1080/10837450.2017.1316288. Verfügbar unter: http://hdl.handle.net/11654/25767