Abstract
The potential of novel benzanthrone aminoderivatives to trace the changes in physicochemical properties of lipid bilayer has been evaluated. Binding of the dyes to the lipid bilayers composed of zwitterionic phospholipid phosphatidylcholine (PC) and its mixtures with anionic phospholipid cardiolipin (CL) and cholesterol (Chol) was followed by significant quantum yield increase with small blue shift of emission maximum. Analysis of partition coefficients of the dyes under study showed that all aminobenzanthrones possess high lipid-associating ability. The dyes A8 and AM2 proved to be sensitive to the variations in membrane chemical composition responding to the changes in bilayer hydration induced by CL and Chol.
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References
Grabchev I, Bojinov V, Moneva I (2001) The synthesis and application of fluorescent dyes based on 3-amino benzanthrone. Dye Pigment 48:143–150
Refat MS, Aqeel SM, Grabtchev IK (2004) Spectroscopic and physicochemical studies of charge-transfer complexes of some benzanthrone derivatives “Luminophore Dyes” with iodine as σ-acceptor. Canad J Analyt Sci Spectr 49:258–265
Kirilova E, Kalnina I, Kirilov G, Meirovics I (2008) Spectroscopic study of benzanthrone 3-N-derivatives as new hydrophobic fluorescent probes for biomolecules. J Fluoresc 18:645–648
Valeur B (2001) Molecular fluorescence: principles and applications. Wiley-VCH, Weinheim
Kirilova E, Kalnina I (2010) 3-isopropyloxy-6-morpholino-2-phenylphenalen-1-one as lipophilic fluorescent probe for lymphocyte investigations. Appl Biochem Biotechnol 160:1744–1751
Kalnina I, Klimkane L, Kirilova E, Toma MM, Kizane G, Meirovics I (2007) Fluorescent probe ABM for screening gastrointestinal patient’s immune state. J Fluoresc 17:619–625
Kalnina I, Bruvere R, Zvagule T, Gabruseva N, Volrate A, Feldmane G, Klimkane L, Kirilova E, Meirovics I (2006) Immune state of patients with different pathologies monitored by fluorescent probe 3-aminobenzanthrone derivative. Proc Latv Acad Sci 60:113–120
Gorbenko G, Trusova V, Kirilova E, Kirilov G, Kalnina I, Vasilev A, Kaloyanova S, Deligeorgiev T (2010) New fluorescent probes for detection and characterization of amyloid fibrils. Chem Phys Lett 495:275–279
Kirilova E, Meirovics I, Belyakov S (2002) Preparation and properties of benzanthrone derivatives with heterocyclic fragments. Chem Heterocycl Compd 7:896–899
Kirilova E, Meirovics I (2000) Reactions of 3-bromobenzanthrone with some aminoalcohols. Latv J Chem 4:64–66
Mui B, Chow L, Hope MJ (2003) Extrusion technique to generate liposomes of defined size. Meth Enzymol 367:3–14
Bartlett G (1959) Phosphorus assay in column chromatography. J Biol Chem 234:466–468
Santos N, Prieto M, Castanho M (2003) Quantifying molecular partition into model systems of biomembranes: an emphasis on optical spectroscopic methods. Biochim Biophys Acta 1612:123–135
Ivkov V, Berestovsky G (1981) Dynamic structure of lipid bilayer. Nauka, Moscow
Hutterer R, Schneider F, Sprinz H, Hof M (1996) Binding and relaxation behaviour of prodan and patman in phospholipid vesicles: a fluorescence and 1H NMR study. Biophys Chem 61:151–160
Lakowicz JR (2006) Principles of fluorescent spectroscopy, 3rd edn. Springer, New York
Ioffe V, Gorbenko G (2005) Lysozyme effect on structural state of model membranes as revealed by pyrene excimerization studies. Biophys Chem 114:199–204
Krasovitskiy B, Bolotin B (1984) Organic luminophores. Chemistry, Moscow
Demchenko A (2008) Introduction to fluorescence sensing. Springer, New York
Chattopadhyay A, Mukherjee S (1999) Red edge excitation shift of a deeply embedded membrane probe: implications in water penetration in the bilayer. J Phys Chem B 103:8180–8185
Raghuraman H, Kelkar D, Chattopadhyay A (2005) In: Geddes CD, Lakowicz JR (eds) Novel insights into protein structure and dynamics utilizing the red edge excitation shift approach in Reviews in Fluorescence 2005. Springer, New York, pp 199–222
Pasenkiewicz-Gierula M, Rog T, Kitamura K, Kusumi A (2000) Cholesterol effects on the phosphatidylcholine bilayer polar region: a molecular simulation study. Biophys J 78:1376–1389
Karolis C, Coster H, Chilcott T, Barrow K (1998) Differential effects of cholesterol and oxidised-cholesterol in egg lecithin bilayers. Biochim Biophys Acta 1368:247–255
Dahlberg M, Maliniak A (2008) Molecular dynamics simulation of cardiolipin bilayers. J Phys Chem B 112:11655–11663
Chen Q-P, Li Q-T (2001) Effect of cardiolipin on proton permeability of phospholipid liposomes: the role of hydration at the lipid-water interface. Arch Biochem Biophys 389:201–206
Shibata A, Ikawa K, Shimooka T, Terada H (1994) Significant stabilization of the phosphatidylcholine bilayer structure by incorporation of small amounts of cardiolipin. Biochim Biophys Acta 1192:71–78
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Trusova, V.M., Kirilova, E., Kalnina, I. et al. Novel Benzanthrone Aminoderivatives for Membrane Studies. J Fluoresc 22, 953–959 (2012). https://doi.org/10.1007/s10895-011-1035-8
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DOI: https://doi.org/10.1007/s10895-011-1035-8