Exploring the interactions of irbesartan and irbesartan-2-hydroxypropyl-β-cyclodextrin complex with model membranes

Αdamantia S Liossi¹, Dimitrios Ntountaniotis¹, Tahsin F Kellici², Maria V Chatziathanasiadou³, Grigorios Megariotis⁴, Maria Mania⁵, Johanna Becker-Baldus⁶, Manfred Kriechbaum⁷, Andraž Krajnc⁸, Eirini Christodoulou⁹, Clemens Glaubitz⁶, Michael Rappolt¹⁰, Heinz Amenitsch⁷, Gregor Mali⁸, Doros N Theodorou⁴, Georgia Valsami⁹, Marinos Pitsikalis¹, Hermis Iatrou¹, Andreas G Tzakos³, Thomas Mavromoustakos¹¹

Affiliations

¹ Department of Chemistry, National and Kapodistrian University of Athens, Panepistimiopolis Zografou 15771, Greece.
² Department of Chemistry, National and Kapodistrian University of Athens, Panepistimiopolis Zografou 15771, Greece; Department of Chemistry, University of Ioannina, GR-45110, Greece.
³ Department of Chemistry, University of Ioannina, GR-45110, Greece.
⁴ School of Chemical Engineering, National Technical University of Athens, Athens, Greece.
⁵ Department of Chemistry, National and Kapodistrian University of Athens, Panepistimiopolis Zografou 15771, Greece; Department of Chemistry, University of Patras, Rio 26510, Greece.
⁶ Institute of Biophysical Chemistry and Centre for Biomolecular Magnetic Resonance, Goethe-University Frankfurt, Max-von-Laue-Str. 9, 60438 Frankfurt, Germany.
⁷ Institute of Inorganic Chemistry, Graz University of Technology, Stremayrgasse 9/5, A-8010 Graz, Austria.
⁸ National Institute of Chemistry, Hajdrihova 19, SI-1001 Ljubljana, Slovenia.
⁹ Department of Pharmacy, National and Kapodistrian University of Athens, Panepistimiopolis Zografou 15771, Greece.
¹⁰ School of Food Science and Nutrition, University of Leeds, Leeds LS2 9JT, UK.
¹¹ Department of Chemistry, National and Kapodistrian University of Athens, Panepistimiopolis Zografou 15771, Greece; Department of Chemistry, York College and the Graduate Center of the City University of New York, 94-20 Guy R. Brewer Blvd., Jamaica, New York, 11451, United States. Electronic address: tmavrom@chem.uoa.gr.

PMID: 28274845
DOI: 10.1016/j.bbamem.2017.03.003

Free article

Exploring the interactions of irbesartan and irbesartan-2-hydroxypropyl-β-cyclodextrin complex with model membranes

Αdamantia S Liossi et al. Biochim Biophys Acta Biomembr. 2017 Jun.

Free article

. 2017 Jun;1859(6):1089-1098.

doi: 10.1016/j.bbamem.2017.03.003. Epub 2017 Mar 6.

Authors

Affiliations

¹ Department of Chemistry, National and Kapodistrian University of Athens, Panepistimiopolis Zografou 15771, Greece.
² Department of Chemistry, National and Kapodistrian University of Athens, Panepistimiopolis Zografou 15771, Greece; Department of Chemistry, University of Ioannina, GR-45110, Greece.
³ Department of Chemistry, University of Ioannina, GR-45110, Greece.
⁴ School of Chemical Engineering, National Technical University of Athens, Athens, Greece.
⁵ Department of Chemistry, National and Kapodistrian University of Athens, Panepistimiopolis Zografou 15771, Greece; Department of Chemistry, University of Patras, Rio 26510, Greece.
⁶ Institute of Biophysical Chemistry and Centre for Biomolecular Magnetic Resonance, Goethe-University Frankfurt, Max-von-Laue-Str. 9, 60438 Frankfurt, Germany.
⁷ Institute of Inorganic Chemistry, Graz University of Technology, Stremayrgasse 9/5, A-8010 Graz, Austria.
⁸ National Institute of Chemistry, Hajdrihova 19, SI-1001 Ljubljana, Slovenia.
⁹ Department of Pharmacy, National and Kapodistrian University of Athens, Panepistimiopolis Zografou 15771, Greece.
¹⁰ School of Food Science and Nutrition, University of Leeds, Leeds LS2 9JT, UK.
¹¹ Department of Chemistry, National and Kapodistrian University of Athens, Panepistimiopolis Zografou 15771, Greece; Department of Chemistry, York College and the Graduate Center of the City University of New York, 94-20 Guy R. Brewer Blvd., Jamaica, New York, 11451, United States. Electronic address: tmavrom@chem.uoa.gr.

PMID: 28274845
DOI: 10.1016/j.bbamem.2017.03.003

Abstract

The interactions of irbesartan (IRB) and irbesartan-2-hydroxypropyl-β-cyclodextrin (HP-β-CD) complex with dipalmitoyl phosphatidylcholine (DPPC) bilayers have been explored utilizing an array of biophysical techniques ranging from differential scanning calorimetry (DSC), small angle X-ray scattering (SAXS), ESI mass spectrometry (ESI-MS) and solid state nuclear magnetic resonance (ssNMR). Molecular dynamics (MD) calculations have been also conducted to complement the experimental results. Irbesartan was found to be embedded in the lipid membrane core and to affect the phase transition properties of the DPPC bilayers. SAXS studies revealed that irbesartan alone does not display perfect solvation since some coexisting irbesartan crystallites are present. In its complexed form IRB gets fully solvated in the membranes showing that encapsulation of IRB in HP-β-CD may have beneficial effects in the ADME properties of this drug. MD experiments revealed the topological and orientational integration of irbesartan into the phospholipid bilayer being placed at about 1nm from the membrane centre.

Keywords: DPPC; HP-β-CD; Irbesartan; Molecular dynamics; Small angle X-ray scattering.

PubMed Disclaimer

Publication types

Actions

MeSH terms

Actions
Actions
Actions
Actions
Actions
Actions
Actions
Actions
Actions
Actions
Actions
Actions
Actions
Actions
Actions

Substances

Actions
Actions
Actions
Actions
Actions
Actions
Actions
Actions
Actions

LinkOut - more resources

Full Text Sources
- Elsevier Science
- White Rose Research Online
Other Literature Sources
- scite Smart Citations
Medical
- MedlinePlus Health Information
Research Materials
- NCI CPTC Antibody Characterization Program
Miscellaneous
- NCI CPTAC Assay Portal

Save citation to file

Email citation

Add to Collections

Add to My Bibliography

Your saved search

Create a file for external citation management software

Your RSS Feed

Exploring the interactions of irbesartan and irbesartan-2-hydroxypropyl-β-cyclodextrin complex with model membranes

Affiliations

Exploring the interactions of irbesartan and irbesartan-2-hydroxypropyl-β-cyclodextrin complex with model membranes

Authors

Affiliations

Abstract

Publication types

MeSH terms

Substances

LinkOut - more resources

Full Text Sources

Other Literature Sources

Medical

Research Materials

Miscellaneous