PMID- 31672546
OWN - NLM
STAT- MEDLINE
DCOM- 20200424
LR  - 20200424
IS  - 1879-2642 (Electronic)
IS  - 0005-2736 (Linking)
VI  - 1862
IP  - 2
DP  - 2020 Feb 1
TI  - The influence of charge and lipophilicity of daunorubicin and idarubicin on their 
      penetration of model biological membranes - Langmuir monolayer and 
      electrochemical studies.
PG  - 183104
LID - S0005-2736(19)30250-0 [pii]
LID - 10.1016/j.bbamem.2019.183104 [doi]
AB  - The interactions of two selected anthracyclines, daunorubicin (DNR) and 
      idarubicin (IDA), with phospholipid monolayers used as simple models of cell 
      membranes, were investigated. The results of Langmuir experiments together with 
      Brewster angle microscopy showed that both drugs strongly affect cancer cell 
      membranes composed of 1,2-dimyristoyl-sn-glycero-3-phospho-l-serine (DMPS). 
      Electrostatic interactions allow positively charged DNR and IDA to interact with 
      negatively charged DMPS polar heads but increased lipophilicity of IDA allows it 
      to penetrate the layer more effectively than DNR and prevents from its expulsion 
      at higher surface pressures. The analysis of the thermodynamical functions of 
      hysteresis proves the presence of the enthalpically favorable interactions within 
      the monolayer during its compression in the presence of idarubicin, which may 
      form aggregates with DMPS molecules. The influence of the drugs was significantly 
      less pronounced for a healthy cell model composed of 
      1,2-dimyristoyl-sn-glycero-3-phosphocholine (DMPC) due to the lack of strong 
      electrostatic attractions. The interactions of drugs with pre-compressed 
      phospholipid monolayers were also examined. The physical state of the monolayer 
      and its packing determined only to some extent the penetration of anthracyclines. 
      Since drug molecules first approach the polar region of the monolayer, the 
      increase in surface pressure in time was more pronounced for negatively charged 
      DMPS monolayers than for zwitterionic DMPC. Additionally, idarubicin was able to 
      penetrate the precompressed DMPS monolayers more effectively than daunorubicin 
      due to increased lipophilicity. This property of the drug was also responsible 
      for IDA better penetration of hydrocarbon chains of supported DMPS monolayers 
      compared to DNR, as shown by electrochemical studies.
CI  - Copyright (c) 2019 The Author. Published by Elsevier B.V. All rights reserved.
FAU - Matyszewska, Dorota
AU  - Matyszewska D
AD  - Faculty of Chemistry, Biological and Chemical Research Centre, University of 
      Warsaw, ul. Zwirki i Wigury 101, 02089 Warsaw, Poland. Electronic address: 
      dorota.matyszewska@chem.uw.edu.pl.
LA  - eng
PT  - Journal Article
PT  - Research Support, Non-U.S. Gov't
DEP - 20191028
PL  - Netherlands
TA  - Biochim Biophys Acta Biomembr
JT  - Biochimica et biophysica acta. Biomembranes
JID - 101731713
RN  - 0 (Antineoplastic Agents)
RN  - 0 (Unilamellar Liposomes)
RN  - U86ZGC74V5 (Dimyristoylphosphatidylcholine)
RN  - ZRP63D75JW (Idarubicin)
RN  - ZS7284E0ZP (Daunorubicin)
SB  - IM
MH  - Antineoplastic Agents/chemistry/*pharmacology
MH  - Cell Membrane/chemistry/*drug effects
MH  - Daunorubicin/chemistry/*pharmacology
MH  - Dimyristoylphosphatidylcholine/chemistry
MH  - Hydrophobic and Hydrophilic Interactions
MH  - Idarubicin/chemistry/*pharmacology
MH  - Static Electricity
MH  - Unilamellar Liposomes/chemistry
OTO - NOTNLM
OT  - Brewster angle microscopy (BAM)
OT  - Cyclic voltammetry
OT  - Daunorubicin (DNR)
OT  - Idarubicin (IDA)
OT  - Langmuir monolayer
OT  - Model lipid membrane
EDAT- 2019/11/02 06:00
MHDA- 2020/04/25 06:00
CRDT- 2019/11/02 06:00
PHST- 2019/08/09 00:00 [received]
PHST- 2019/09/23 00:00 [revised]
PHST- 2019/10/15 00:00 [accepted]
PHST- 2019/11/02 06:00 [pubmed]
PHST- 2020/04/25 06:00 [medline]
PHST- 2019/11/02 06:00 [entrez]
AID - S0005-2736(19)30250-0 [pii]
AID - 10.1016/j.bbamem.2019.183104 [doi]
PST - ppublish
SO  - Biochim Biophys Acta Biomembr. 2020 Feb 1;1862(2):183104. doi: 
      10.1016/j.bbamem.2019.183104. Epub 2019 Oct 28.