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 language | English |
|---|---|
| Title of host publication | Materials Science and Applied Chemistry II |
| Editors | Maris Turks |
| Place of Publication | Zurich |
| Publisher | Trans Tech Publications Ltd |
| Pages | 19-24 |
| ISBN (Print) | 9783035714074 |
| DOIs | |
| Publication status | Published - 2019 |
| Externally published | Yes |
| Event | 59th International Scientific Conference of Riga Technical University (RTU): Section of Materials Science and Applied Chemistry (MSAC 2018) - Riga, Latvia Duration: 26 Oct 2018 → 26 Oct 2018 Conference number: 59 https://www.worldcat.org/title/materials-science-and-applied-chemistry-ii-59th-international-scientific-conference-of-riga-technical-university-rtu-section-of-materials-science-and-applied-chemistry-msac-2018/oclc/1100071421 https://research.ebscomedical.com/eds/detail?db=nlebk&an=2117338&isbn=9783035734072 |
Publication series
| Name | Key Engineering Materials |
|---|---|
| Volume | 800 KEM |
| ISSN (Print) | 1013-9826 |
| ISSN (Electronic) | 1662-9795 |
Conference
| Conference | 59th International Scientific Conference of Riga Technical University (RTU) |
|---|---|
| Abbreviated title | MSAC 2018 |
| Country/Territory | Latvia |
| City | Riga |
| Period | 26/10/18 → 26/10/18 |
| Internet address |
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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