A novel squarylium dye for monitoring oxidative processes in lipid membranes

Journal of Fluorescence

Volumn 19, Issue 6, 2009, Pages 1017-1023

  Trusova, Valeriya M ^a,c   Gorbenko, Galyna P ^a   Deligeorgiev, Todor ^b   Gadjev, Nikolai ^b   Vasilev, Aleksey ^b  

^a V N KARAZIN KHARKIV NATIONAL UNIVERSITY   (Ukraine)

^b UNIVERSITY OF SOFIA   (Bulgaria)

^c NONE   (Ukraine)

Author keywords

Cytochrome c; Lipid peroxidation; Methemoglobin; Squarylium dye

Indexed keywords

DYES; OXIDATION; PHOSPHOLIPIDS;

BUTYLATED HYDROXYTOLUENE; CYTOCHROME C; FREE RADICAL SCAVENGERS; LIPID PEROXIDATION; METHEMOGLOBIN; PEROXIDATION PROCESS; PROTEIN ASSOCIATIONS; SQUARYLIUM DYES;

FREE RADICALS;

EID: 72149094563     PISSN: 10530509     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10895-009-0501-z     Document Type: Article

References (29)

1. D Keil H Hartmann T Moschny 1991 Synthesis and characterization of 1, 3-bis-(2-dialkylamino-5-thienyl)-substituted squaraines-a novel class of intensively coloured panchromatic dyes Dyes Pigments 17 19 27 10.1016/0143-7208(91)85025-4 10.1016/0143-7208(91)85025-4 1:CAS:528: DyaK3MXmtlCltLw%3D (Pubitemid 21712516)
2. D Ramaiah I Eckert KT Arun L Weidenfeller B Epe 2004 Squaraine dyes for photodynamic therapy: mechanism of cytotoxicity and DNA damage induced by halogenated squaraine dyes plus light (>600 nm) Photochem. Photobiol. 79 99 104 10.1562/0031-8655(2004) 79<99:SDFPTM>2.0.CO;2 10.1562/0031-8655(2004)79<99:SDFPTM>2.0.CO;2 1:CAS:528: DC%2BD2cXnslyjtw%3D%3D 14974721
3. KY Law FC Bailey 1987 Squaraine chemistry: effect of synthesis on the morphological and xerographic properties of photoconductive squaraines J. Imag. Sci. 31 172 175 1:CAS:528:DyaL2sXmt1Gkurw%3D
4. Polaroid Corporation: US Patent 5795981.
5. VY Merritt HJ Hovel 1976 Organic solar cells of hydroxysquarylium Appl. Phys. Lett. 29 414 416 10.1063/1.89101 10.1063/1.89101 1:CAS:528: DyaE2sXlsl2ntw%3D%3D
6. Lakowicz JR (1999) Principles of fluorescent spectroscopy, 2nd edn. Kluwer Academic/Plenum, New York
7. VM Ioffe GP Gorbenko T Deligeorgiev N Gadjev A Vasilev 2007 Fluorescence study of protein-lipid complexes with a new symmetric squarylium probe Biophys. Chem. 128 75 86 10.1016/j.bpc.2007.03.007 10.1016/j.bpc.2007.03.007 1:CAS:528:DC%2BD2sXkvFGku7s%3D 17383795 (Pubitemid 46678604)
8. K Setsukinai Y Urano K Kakinuma HJ Majima T Nagano 2003 Development of novel fluorescence probes that can reliably detect reactive oxygen species and distinguish specific species J. Biol. Chem. 278 3170 3175 10.1074/jbc.M209264200 10.1074/jbc.M209264200 1:CAS:528:DC%2BD3sXmt1GrsQ%3D%3D 12419811 (Pubitemid 36801227)
9. TD Henry SL Archer D Nelson EK Weir AH From 1990 Enhanced chemiluminescence as a measure of oxygen-derived free radical generation during ischemia and reperfusion Circ. Res. 67 1453 1461 1:CAS:528:DyaK3MXitVCrsrc%3D 2245505
10. AE Dikalova MB Kadiiska RP Mason 2001 An in vivo ESR spin-trapping study: Free radical generation in rats from formate intoxication-role of the Fenton reaction Proc. Natl. Acad. Sci. USA 98 13549 13553 10.1073/pnas.251091098 10.1073/pnas.251091098 1:CAS:528:DC%2BD3MXovVyns70%3D 11717423 (Pubitemid 33115935)
11. VV Khramtsov VA Reznikov LJ Berliner AK Litkin IA Grigorev TL Clanton 2001 NMR spin trapping: detection of free radical reactions with a new fluorinated DMPO analog Free Radic. Biol. Med. 30 1099 1107 10.1016/S0891- 5849(01)00505-6 10.1016/S0891-5849(01)00505-6 1:CAS:528:DC%2BD3MXjsFegsL4%3D 11369499 (Pubitemid 32441834)
12. SL Hempel GR Buettner YQ O'Malley DA Wessels DM Flaherty 1999 Dihydrofluorescein diacetate is superior for detecting intracellular oxidants: comparison with 2′, 7′-dichlorodihydrofluorescein diacetate, 5(and 6)-carboxy-2′, 7′-dichlorodihydrofluorescein diacetate, and dihydrorhodamine 123 Free Radic. Biol. Med. 27 146 159 10.1016/S0891-5849(99) 00061-1 10.1016/S0891-5849(99)00061-1 1:CAS:528:DyaK1MXkvVKqsbo%3D 10443931 (Pubitemid 29353095)
13. K Akasaka 1995 Development of phosphine reagents for fluorometric determination of lipid hydroperoxides Tohoku J. Agricul. Res. 45 111 119 1:CAS:528:DyaK28XmsVOq
14. OS Wolfbeis A Durkop M Wu Z Lin 2002 A europium-ion-based luminescent sensing probe for hydrogen peroxide Angew. Chem. 41 4495 4498 10.1002/1521-3773(20021202)41:23<4495::AID-ANIE4495>3.0.CO;2-I 10.1002/1521-3773(20021202)41:23<4495::AID-ANIE4495>3.0.CO;2-I 1:CAS:528:DC%2BD38Xpslels7k%3D
15. B Mui L Chow MJ Hope 2003 Extrusion technique to generate liposomes of defined size Methods Enzymol. 367 3 14 10.1016/S0076-6879(03)67001-1 10.1016/S0076-6879(03)67001-1 1:CAS:528:DC%2BD3sXhtVSjtrnP 14611054 (Pubitemid 37337825)
16. G Bartlett 1959 Phosphorus assay in column chromatography J. Biol. Chem. 234 466 468 1:CAS:528:DyaG1MXmtlWjtg%3D%3D 13641241
17. KT Arun D Ramaiah 2005 Near-infrared fluorescent probes: synthesis and spectroscopic investigations of a few amphiphilic squaraine dyes J. Phys. Chem. A 109 5571 5578 10.1021/jp051338o 10.1021/jp051338o 1:CAS:528: DC%2BD2MXkslOmur8%3D 16833888 (Pubitemid 41027877)
18. H Itabe T Kobayashi K Inoue 1988 Generation of toxic phospholipids during oxyhemoglobin-induced peroxidation of phosphatidylcholines Biochim. Biophys. Acta 961 13 21 1:CAS:528:DyaL1cXltVKlsLo%3D 3382689
19. J Szebeni CC Winterbourn RW Carrel 1984 Oxidative interactions between haemoglobin and membrane lipids Biochem. J. 220 685 692 1:CAS:528: DyaL2cXktlKltrg%3D 6466294
20. T Heimburg D Marsh 1993 Investigation of secondary and tertiary structural changes of cytochrome c in complexes with anionic lipids using amide hydrogen exchange measurements: an FTIR study Biophys. J. 65 2408 2417 10.1016/S0006-3495(93)81299-2 10.1016/S0006-3495(93)81299-2 1:CAS:528: DyaK2cXhsFOisLw%3D 8312479
21. MS Rogers RP Patel BJ Reeder P Sarti MT Wilson A Alayash 1995 Pro-oxidant effects of cross-linked haemoglobins explored using liposome and cytochrome c oxidase vesicle model membranes Biochem. J. 310 827 833 1:CAS:528: DyaK2MXot1aktLw%3D 7575415
22. SM Sadrzadeh E Graf SS Panter PE Hallaway JW Eaton 1984 Hemoglobin. A biologic Fenton reagent J. Biol. Chem. 259 14354 14356 1:CAS:528: DyaL2cXmtVKgt7s%3D 6094553
23. L Tarazi N Narayanan J Sowell G Patonay L Strekowski 2002 Investigation of the spectral properties of a squarylium near-infrared dye and its complexation with Fe(III) and Co(II) ions Spectrochim. Acta [A] 58 257 264 10.1016/S1386-1425(01)00542-X 10.1016/S1386-1425(01)00542-X
24. J Wong-ekkabut Z Xu W Triampo IM Tang DP Tieleman L Monticelli 2007 Effect of lipid peroxidation on the properties of lipid bilayers: a molecular dynamics study Biophys. J. 93 4225 4236 10.1529/biophysj.107.112565 10.1529/biophysj.107.112565 1:CAS:528:DC%2BD1cXhvVM%3D 17766354 (Pubitemid 350294470)
25. ML Wratten G Vanginkel AA Vantveld A Bekker EE Vanfaassen A Sevanian 1992 Structural and dynamic effects of oxidatively modified phospholipids in unsaturated lipid membranes Biochemistry 31 10901 10907 10.1021/bi00159a034 10.1021/bi00159a034 1:CAS:528:DyaK38XmtVOmsrk%3D 1329957
26. RP Mason MF Walter PE Mason 1997 Effect of oxidative stress on membrane structure: small-angle X-ray diffraction analysis Free Radic. Biol. Med. 23 419 425 10.1016/S0891-5849(97)00101-9 10.1016/S0891-5849(97)00101-9 1:CAS:528:DyaK2sXksVahtb8%3D 9214578 (Pubitemid 27276778)
27. C Richter 1987 Biophysical consequences of lipid peroxidation in membranes Chem. Phys. Lipids 44 175 189 10.1016/0009-3084(87)90049-1 10.1016/0009-3084(87)90049-1 1:CAS:528:DyaL1cXltFehsA%3D%3D 3311416 (Pubitemid 17157977)
28. AC Nicolescu Q Li L Brown GRJ Thatcher 2006 Nitroxidation, nitration, and oxidation of a BODIPY fluorophore by RNOS and ROS Nitric Oxide 15 163 176 10.1016/j.niox.2006.01.010 10.1016/j.niox.2006.01.010 1:CAS:528: DC%2BD28XotV2ksrc%3D 16549377 (Pubitemid 44175886)
29. E Guivarch S Trevin C Lahitte MA Oturan 2003 Degradation of azo dyes in water by Electro-Fenton process Environ. Chem. Lett. 1 38 44 10.1007/s10311-002-0017-0 10.1007/s10311-002-0017-0 1:CAS:528: DC%2BD2MXmtFKmt74%3D