Protonation of tyrosine kinase inhibitor lapatinib: A theoretical and experimental study

Ilze Grante, Rihards Kluga, Liana Orola

Research output: Chapter in Book/Report/Conference proceedingConference contributionpeer-review

Abstract

The protonation process of tyrosine kinase inhibitor lapatinib was studied by means of 1H NMR and UV/Vis spectroscopy joint with the theoretical calculations at DFT and semi-empirical levels. DFT/M06-2X geometries were used to describe and compare the different cationic forms of lapatinib, while ZINDO/S-CI method performed on those geometries allowed for the interpretation by experimental UV/Vis spectra of lapatinib at various pH. We found that at low pH two different dicationic forms (N2N1 and N1N3) of lapatinib were present in ethanol and DMSO-d6 solutions. The first protonation, however, occurred on the aliphatic N1 in DMSO-d6, while in ethanol solutions most probably the quinazoline nitrogen atom N2 was also protonated.

Original languageEnglish
Title of host publicationMaterials Science and Applied Chemistry II
EditorsMaris Turks
Place of PublicationZurich
PublisherTrans Tech Publications Ltd
Pages19-24
ISBN (Print)9783035714074
DOIs
Publication statusPublished - 2019
Externally publishedYes
Event59th International Scientific Conference of Riga Technical University (RTU) Section of Materials Science and Applied Chemistry - Riga, Latvia
Duration: 26 Oct 201826 Oct 2018
Conference number: 59

Publication series

NameKey Engineering Materials
Volume800 KEM
ISSN (Print)1013-9826
ISSN (Electronic)1662-9795

Conference

Conference59th International Scientific Conference of Riga Technical University (RTU) Section of Materials Science and Applied Chemistry
Abbreviated titleMSAC 2018
CountryLatvia
CityRiga
Period26/10/1826/10/18

Keywords

  • Lapatinib
  • NMR spectroscopy
  • Protonation
  • UV/Vis spectroscopy
  • ZINDO-CI

Field of Science

  • 3.1 Basic medicine
  • 1.4 Chemical sciences

Publication Type

  • 3.1. Articles or chapters in proceedings/scientific books indexed in Web of Science and/or Scopus database

Fingerprint Dive into the research topics of 'Protonation of tyrosine kinase inhibitor lapatinib: A theoretical and experimental study'. Together they form a unique fingerprint.

Cite this