Investigation on the interactions between pirarubicin and phospholipids

Biophysical Chemistry

Volumn 143, Issue 3, 2009, Pages 154-160

  Cong, Wenjuan ^a,b   Liu, Qingfei ^b   Liang, Qionglin ^c   Wang, Yiming ^b,c   Luo, Guoan ^a,b  

^a EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

^b Tsinghua University   (China)

^c TSINGHUA UNIVERSITY   (China)

Author keywords

Differential scanning calorimetry (DSC); Distearoylphosphatidylcholine (DSPC); Distearoylphosphatidylglycerol (DSPG); Fourier transform infrared (FTIR) spectroscopy; Pirarubicin; Quantum calculation

Indexed keywords

AMMONIA; ANTHRACYCLINE ANTIBIOTIC AGENT; DISTEAROYLPHOSPHATIDIC ACID; DISTEAROYLPHOSPHATIDYLCHOLINE; PHOSPHATE; PHOSPHOLIPID DERIVATIVE; PIRARUBICIN;

ARTICLE; CALCULATION; CONTROLLED STUDY; DIFFERENTIAL SCANNING CALORIMETRY; DRUG DETERMINATION; DRUG PROTEIN BINDING; DRUG STRUCTURE; INFRARED SPECTROSCOPY; MOLECULAR MODEL; PHYSICAL CHEMISTRY; PRIORITY JOURNAL; QUANTUM MECHANICS; STRUCTURE ANALYSIS;

ANTINEOPLASTIC AGENTS; CALORIMETRY, DIFFERENTIAL SCANNING; DOXORUBICIN; DRUG INTERACTIONS; MOLECULAR CONFORMATION; PHOSPHATIDYLCHOLINES; PHOSPHATIDYLGLYCEROLS; PHOSPHOLIPIDS; QUANTUM THEORY; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; THERMODYNAMICS;

EID: 67349158250     PISSN: 03014622     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bpc.2009.05.005     Document Type: Article

References (38)

1. Kawano K., Takayama K., Nagai T., and Maitani Y. Preparation and pharmacokinetics of pirarubicin loaded dehydration-rehydration vesicles. Int. J. Pharm. 252 (2003) 73-79
2. Shi Y.Y., Zhao H.M., and Wu C.X. Relative binding free energy calculations of DNA to daunomycin and its 13-dihydro analogue. Int. J. Biol. Macromol. 15 (1993) 247-251
3. Goormaghtigh E., Huart P., Brasseur R., and Ruysschaert J.M. Mechanism of inhibition of mitochondrial enzymatic complex I-III by adriamycin derivatives.spectroscopy. Biochim. Biophys. Acta 861 (1986) 83-94
4. Joachim K.S., Coats E.A., Cordes H.P., and Wiese M. Drug membrane interaction and the importance for drug transport, distribution, accumulation, efficacy and resistance. Arch. Pharm. 327 (1994) 601-610
5. Raimund M., Kubinyi H., and Folkers G. Drug-Membrane Interactions (2002), GmbH, Weinheim, Germany
6. Zhao L.Y., Feng S.S., Kocherginsky N., and Kostetski I. DSC and EPR investigations on effects of cholesterol component on molecular interactions between paclitaxel and phospholipid within lipid bilayer membrane. Int. J. Pharm. 338 (2007) 258-266
7. Constantinides P.P., Inouchi N., Tritton T.R., Sartorelli A.C., and Sturtevant J.M. A scanning calorimetric study on the interaction of anthracyclines with neutral and acidic phospholipids alone and in binary mixtures. J.Biol. Chem. 22 (1986) 10196-10203
8. Barcelo F., Escriba P.V., and Miralles F. A scanning calorimetric study of natural and DNA antitumor anthracycline antibiotic-DNA complexes. Chem-Biol. Interact. 74 (1990) 315-324
9. Seto G.W.T., Marwaha S., Kobewka D.M., Lewis R.N.A.H., Separovic F., and McElhaney R.N. Interactions of the Australian tree frog antimicrobial peptides aurein 1.2, citropin 1.1 and maculation 1.1 with lipid model membranes: differential scanning calorimetric and Fourier transform infrared spectroscopic studies. Biochim. Biophys. Acta 1768 (2007) 2787-2800
10. Toyran N., and Severcan F. Interaction between vitamin D2 and magnesium in liposomes: differential scanning calorimetry and FTIR spectroscopy studies. J. Mol. Struct. 839 (2007) 19-27
11. Heywang C., Chazalet M.S.P., Masson M., and Bolard J. Incorporation of exogenous molecules inside mono- and bilayers of phospholipids: influence of the mode of preparation revealed by SERRS and surface pressure studies. Langmuir 12 (1996) 6459-6467
12. Bensikaddour H., Snoussi K., Lins L., Bambeke F.V., Tulkens P.M., Brasseur R., Goormaghtigh E., and Mingeot- Leclercq M.P. Interactions of ciprofloxacin with DPPC and DPPG: Fluorescence anisotropy, ATR-FTIR and 31P NMR spectroscopies and conformational analysis. Biochim. Biophys. Acta 1778 (2008) 2535-2543
13. Mrzkov E., Hobza P., Bohl M., Gauger D.R., and Pohle W. Hydration-induced changes of structures and vibrational frequencies of methylphosphocholine studied as a model of biomembrane lipids. J. Phys. Chem. B 109 (2005) 15126-15134
14. Lohner K., and Prenner E.J. Differential scanning calorimetric and X-ray diffraction studies of the specificity of the interaction of antimicrobial peptides with membrane-mimetic systems. Biochim.Biophys.Acta 1462 (1999) 141-156
15. Epand R.F., Savage P.B., and Epand R.M. Bacterial lipid composition and the antimicrobial efficacy of cationic steroid compounds (Ceragenins). Biochim. Biophys. Acta 1768 (2007) 2500-2509
16. Bangham A.D., Hill M.W., and Miller N.G.A. Preparation and use of liposomes as models of biological membranes. In: Kom E.D. (Ed). Methods in Membrane Biology vol. 1 (1974), Plenum Press 1-68
17. Corvis Y., Korchowiec B., Korchowiec J., Badis M., Puchalska E.M., Fokt I., Priebe W., and Rogalska E. Complexation of metal ions in Langmuir films formed with two amphiphilic dioxadithia crown ethers. J. Phys. Chem. B 112 (2008) 10953-10963
18. Sabio M., and Topiol S. A computational study of a host-guest complex. J. Mol. Recognit. 10 (1997) 159-168
19. Rocha G.B., Freire R.O., Costa N.B.D., De S G.F., and Simas A.M. Sparkle model for AM1 calculation of lanthanide complexes: improved parameters for Europium. Inorg. Chem. 43 (2004) 2346-2354
20. Zhang Y.P., Lewis R.N., Hodges R.S., and McElhaney R.N. Interaction of a peptide model of a hydrophobic transmembrane alpha-helical segment of a membrane protein with phosphatidylethanolamine bilayers: differential scanning calorimetric and Fourier transform infrared spectroscopic studies. Biophys. J. 68 (1995) 847-857
21. Arouri A., Dathe M., and Blume A. Peptide induced demixing in PG/PE lipid mixtures: a mechanism for the specificity of antimicrobial peptides towards bacterial membrane. Biochim. Biophys. Acta 1788 (2009) 650-659
22. Inoue T., and Nibu Y. Miscibility of binary phospholipids mixtures under hydrated and non-hydrated conditions. IV. Phosphatidylglycerols with different acyl chain length. Chem. Phys. Lipids 76 (1995) 181-191
23. Inoue T., Kitahashi T., and Nibu Y. Phase behavior of hydrated bilayer of binary phospholipids mixtures composed of 1, 2-distearoylphosphatidylcholine and 1-stearoyl-2-oleoylphosphatidylcholine or 1-oleoyl-2-stearoylphosphatidylcholine. Chem. Phys. Lipids 99 (1999) 103-109
24. Ali S., Minchey S., Janoff A., and Mayhew E. A different scanning calorimetry study of phosphocholines mixed with paclitaxel and its bromoacylated taxanes. Biophys. J. 78 (2000) 246-256
25. Tamai N., Uemura M., Takeichi T., Goto M., Matsuki H., and Kaneshina S. A new interpretation of eutectic behavior for distearoylphosphatidycholine-cholesterol binary bilayer membrane. Biophys. Chem. 135 (2008) 95-101
26. Gardisks K., Hatziantoniou S., Viras K., Wangner M., and Demetzos C. A DSC and Raman spectroscopy study on the effect of PAMAM dendrimer on DPPC model lipid membranes. Int. J. Pharm. 318 (2006) 118-123
27. Klajnert B., Janiszewska J., Urbanczyk-Lipkowska Z., Bryszewska M., and Epand R.M. DSC studies on interactions between low molecular mass peptide dendrimers and model lipid membranes. Int. J. Pharm. 327 (2006) 145-152
28. Epand R.M., and Hui S.W. Effect of electrostatic repulsion on the morphology and thermotropictransitions of anionic phospholipids. FEBS Lett. 209 (1986) 257-260
29. Lewis R.N.A.H., and McElhaney R.N. FTIR spectroscopy in the study of hydrated lipids and lipid bilayer membranes. In: Mantsch H.H., and Chapman D. (Eds). Infrared Spectroscopy of Biomolecules (1996), John Wiley &Sons, New York 159-202
30. Lewis R.N.A.H., and McElhaney R.N. Vibrational spectroscopy of lipids. In: Chalmers J.M., and Griffith P.R. (Eds). Handbook of Vibrational Spectroscopy vol. 5 (2002), John Wiley and Sons, Chichester, England 3447-3464
31. Mantsch H.H., and McElhaney R.N. Phospholipid phase transitions in model and biological membranes as studied by infrared spectroscopy. Chem. Phys. Lipids 57 (1991) 213-226
32. Jackson M., and Mantsch H.H. Biomembrane structure from FT-IR spectroscopy. Spectrochim. Acta 15 (1993) 53-69
33. Blume A., Huebner W., and Messner G. Fourier transform infrared spectroscopy of 13C:O labeled phospholipids hydrogen bonding to carbonyl groups. Biochemistry 27 (1988) 8239-8249
34. Lewis R.N.A.H., Zhang Y.P., and McElhaney R.N. Calorimetric and spectroscopic studies of the phase behavior and organization of lipid bilayer model membranes composed of binary mixtures of dimyristoylphosphatidylcholine and dimyristoylphosphatidylglycerol. Biochim. Biophys. Acta 1668 (2005) 203-214
35. a of lipid carboxyl groups and the dehydration degree of the phosphate group of phospholipids. Chem. Phys. Lipids 96 (1998) 41-52
36. De Vries A.H., Mark A.E., and Marrink S.J. Molecular dynamics simulation of the spontaneous formation of a small DPPC vesicle in water in atomistic detail. J. Am. Chem. Soc. 126 (2004) 4488-4489
37. Heywang C., Chazalet M.S.P., Masson M., and Bolard J. SERR study of the interaction of anthracyclines with mono- and bilayers of charged phospholipids. Langmuir 13 (1997) 5634-5643
38. Heywang C., Chazalet M.S.P., Masson M., and Bolard J. Orientation of anthracyclines in lipid monolayers and planar asymmetric bilayers: a surface-enhanced resonance Raman scattering study. Biophys. J. 75 (1998) 2368-2381