Spectroscopic study of interactions between polymethine dyes and liposomes in aqueous solutions
Abstract
Interaction between cationic polymethine dyes 3,3'-dioctadecyloxacarbocyanine perchlorate (DiO), 1,1’-
dioctadecyl-3,3,3’,3’-tetramethylindocarbocyanine perchlorate (DiI), 1,1’-dioctadecyl-3,3,3’,3’-
tetramethylindodicarbocyanine perchlorate (DiD) and zwitterionic liposomes of L-α -Phosphatidylcholine
from egg yolk (PC) has been studied by spectroscopic method. Analyzing changes in the dye absorption
spectra under the variation of PC concentration and using Scott equation, binding constants (Kc) and
thermodynamic parameters ( ΔG 0 , ΔH 0 и ΔS 0 ) of ―dye-to-liposome‖ complex formation have been
calculated. It has been shown that the complex formation is spontaneous and energetically favorable
process associated with the change in dye aggregate state from associates to monomer form. The main
contribution in complex formation process belongs to hydrophobic and Van der Waals forces, while the
contribution of electrostatic interactions is negligible.
Downloads
References
2. Добрецов Г.Е. Флуоресцентные зонды в исследовании клеток, мембран и липопротеинов / Г.Е. Добрецов. – М: Наука. – 1989 – 273 с. /Dobrecov G.E. Fluorescentnye zondy v issledovanii kletok, membran i lipoproteinov / G.E. Dobrecov. – M: Nauka. – 1989 – 273 s./
3. Применение карбоцианиновых флуоресцентных зондов для оценки функционального состояния культивированных клеток после криоконсервации / Е.И.Гончарук, Е.В. Онищенко, В.В. Тимон, [и др.] // Биополимеры и клетка. – 2008. – T. 24, № 3. – С. 225-231. /Primenenie karbocianinovyh fluorescentnyh zondov dlja ocenki funkcional'nogo sostojanija kul'tivirovannyh kletok posle kriokonservacii / E.I.Goncharuk, E.V. Onishhenko, V.V. Timon, [i dr.] // Biopolimery i kletka. – 2008. – t. 24, № 3. – S. 225-231./
4. Накопление оксакарбоцианинов с различной длиной алкильных цепей в клетках костного мозга и гепатоцитах / Ю.В. Малюкин, И.А. Боровой, Н.С. Кавок, [и др.] // Биофизика. – 2007. – Т. 52, № 4. – С. 667-673. /Nakoplenie oksakarbocianinov s razlichnoj dlinoj alkil'nyh cepej v kletkah kostnogo mozga i gepatocitah / Ju.V. Maljukin, I.A. Borovoj, N.S. Kavok, [i dr.] // Biofizika. – 2007. – T. 52, № 4. – S. 667-673./
5. Newly synthesized fluorescent probes, their characteristics and behavior in proliferating cultures / E.I. Goncharuk, I.A. Borovoy, E.V. Pavlovich, [et al.] // Biopolymers and Cell. – 2009. – V.25, № 6. – P. 484-490.
6. Waggoner A.S. Dye indicators of membrane potential / A.S. Waggoner // Ann. Rev. Biophys. Bioeng. – 1979. – V. 8. – 47-68.
7. Generation of a proton motive force by the excretion of metal-phosphate in the polyphosphate-accumulating acinetobacter johnsonii strain 210A / H.W van Veen , T. Abee , G.J Kortstee, [et al.] // J. Biol. Chem. – 1994. – V.269, №47. – P. 29509-29514.
8. Accumulate flow cytometric membrane potential measurement in bacteria using diethyloxacarbocyanine and a ratiometric technique / D. Novo, N.G. Perlmutter, R.H. Hunt, H.M. Shapiro // Cytometry. – 1999. – V. 35. – P. 55-63.
9. Multiparameter flow cytometric analysis of antibiotic effects on membrane potential, membrane permeability, and bacterial counts of staphylococcus aureus and micrococcus luteus / D. Novo, N.G. Perlmutter, R.H. Hunt, H.M. Shapiro // Antimicrobial Agents and Chemotherapy. – 2000. – V. 44, №4. – P. 827-834.
10. The antibacterial mechanism of carvacrol and thymol against Escherichia coli / J. Xu, F. Zhou, B.-P. Ji, [et al.] // Letters in Applied Microbiology. – 2008. – V.47, №3. – P. 174-179.
11. Wiegand D.H. Spectroscopic and Fluorometric Characterization of Oxacyanine Dyes in Water and Nitrobenzene / D. H. Wiegand, P. Vanýsek // Appl. Spectrosc. – 1988. – V. 42. – P. 958-961.
12. Koti A.S.R. Cyanine induced aggregation in meso-tetrakis(4-sulfonatophenyl)porphyrin anions / A.S.R. Koti, N. Periasamy // Journal of Material Chemistry. – 2002. – V. 12, №8. – P. 2312-2317.
13. Studies on the mechanism by which cyanine dyes measure membrane potential in red blood cells and phosphatidylcholine vesicles / P.J. Sims, A.S. Waggoner, C.H. Wang, J.F. Hoffman // Biochemistry. – 1974. – V. 13. – P.3315-3330.
14. Block copolymer nanostructures / T. Smart, H. Lomas, M. Massignani, [et al.] //NanoToday. – 2008. – V. 3, №3-4. – P. 38-46.
15. Liposomal drug delivery, a novel approach: PLARosomes / A. Kozubek, J. Gubernator, E. Przeworska, M. Stasiuk //Acta Biochimica Polonica. – 2000. – V. 47, №3. –P. 639-649.
16. Liposomal drug delivery systems – clininal applications / P. Goyal, K. Goyal, S.G.V. Kumar, [et al.] // Acta Pharm. – 2005. – V. 55. – P. 1-25.
17. Petros R.A. Strategies in the design of nanoparticles for therapeutic application / R.A. Petros, J.M. DeSimone //Nature Reviews Drug Discovery. – 2010. – V. 9. – P. 615-627.
18. Nishiyama N. Current state, achievements, and future prospects of polymeric micelles as nanocarriers for drug and gene delivery / N.Nishiyama, K.Kataoka // Pharmacology and Therapeutics. – 2006. – V. 112. – P. 630-648.
19. Liposomes: a practical approach. – 2nd ed. – [ed. by V. Torchilin and V. Weissig]. – Oxford: Oxford Univ. Press. – 2003. – 396 p.
20. Ефимова С.Л. Спектрально-люминесцентные свойства 1,1-диоктадецил-3,3’,3’-тетраметилиндодикарбоцианинперхлората в бинарных растворах / С.Л. Ефимова, Ю.В. Малюкин, К. Кемнитц // Журн. прикл. спектр. – 2001. – T. 68. – С. 569-572. /Efimova S.L. Spektral'no-ljuminescentnye svojstva 1,1-dioktadecil-3,3’,3’-tetrametilindodikarbocianinperhlorata v binarnyh rastvorah / S.L. Efimova, Ju.V. Maljukin, K. Kemnitc // Zhurn. prikl. spektr. – 2001. – T. 68. – S. 569-572./
21. Malyukin Yu.V. Spectroscopy of intermolecular interaction in the system: dye-sodium dodecylsulphate micelle / Yu.V. Malyukin, S.L. Efimova, K. Kemnitz // J. Lumin. – 2001. - 94-95. – P. 239-242.
22. Безызлучательный перенос энергии в композициях карбоцианиновых красителей в нанообъеме мицеллы ПАВ / С.Л. Ефимова, А.В. Сорокин, А.Н. Лебеденко, [и др.] // Журн. прикл. спектр. – 2006. – Т. 73. – С. 152-157. /Bezyzluchatel'nyj perenos jenergii v kompozicijah karbocianinovyh krasitelej v nanoob#eme micelly PAV / S.L. Efimova, A.V. Sorokin, A.N. Lebedenko, [i dr.] // Zhurn. prikl. spektr. – 2006. – T. 73. – S. 152-157./
23. Influence of dye hydrophobicity on the efficiency of fluorescence resonance energy transfer between dyes in surfactant micelles / S.L. Yefimova, A.S. Lebed, G.Ya. Guralchuk, [et al.] // Mol. Cryst. Liq. Cryst. – 2001. – V. 535. – P. 204-211.
24. Влияние гидрофобности катионных карбоцианиновых красителей DiOCn на эффективность связывания с мицеллами поверхностно-активного вещества / А.С. Лебедь, С.Л. Ефимова, Г.Я. Гуральчук, [и др.] // Журн. прикл. спектр. – 2010. – Т. 77, №2. – С. 198-203. /Vlijanie gidrofobnosti kationnyh karbocianinovyh krasitelej DiOCn na jeffektivnost' svjazyvanija s micellami poverhnostno-aktivnogo veshhestva / A.S. Lebed', S.L. Efimova, G.Ja. Gural'chuk, [i dr.] // Zhurn. prikl. spektr. – 2010. – T. 77, №2. – S. 198-203./
25. Райхард Х. Растворители в органической химии / Х. Райхард; [пер. с нем. Э.Р. Захса]. – Л.: Химия, 1973. – 152 с. /Rajhard H. Rastvoriteli v organicheskoj himii / H. Rajhard; [per. s nem. Je.R. Zahsa]. – L.: Himija, 1973. – 152 s./
26. Nano-scale liposomal container with a “signal system” for substances delivering in living cells / S.L. Yefimova, A.S. Lebed', G.Ya. Guralchuk, [et al.] // Biopolymer and Cell. - 2011. - V. 27(1). – P.47-52.
27. Comparative study of dye-loaded liposome accumulation in sensitive and resistant human breast cancer cells / S.L. Yefimova, I.Yu. Kurilchenko, T.N. Tkacheva, [et al.] // Experimental Oncology. - 2012. - V. 34(2). – P. 101-106.
28. Колычев В.Б. Спектроскопические методы в химии комплексных соединений / В.Б. Колычев, В.И. Парамонов; [под редакцией В.М. Вдовенко]. – Л.: Химия, 1964. – с. 30–73. /Kolychev V.B. Spektroskopicheskie metody v himii kompleksnyh soedinenij / V.B. Kolychev, V.I. Paramonov; [pod redakciej V.M. Vdovenko]. – L.: Himija, 1964. – s. 30–73./
29. О.В. Свердлова. Электронные спектры в органической химии. Л.: Химия, 1985. – 248 с. /O.V. Sverdlova. Jelektronnye spektry v organicheskoj himii. L.: Himija, 1985. – 248 s./
30. Bhowmik B.B. Photophysical studies of 3,3’ dioctadecyloxacarbocyanine dye in model biological membranes and different solvents / B.B. Bhowmik, S. Basu, D. Ray // Chemistry and Physics of Lipids. – 2001. – V. 109. – P. 175-183.
31. Göktürk S. Spectral studies of safranin-O in different surfactant solutions / S. Göktürk, M. Tuncay // Spectrochimica Acta Part A. – 2003. – V. 59. – P. 1857-1866.
32. Семиохин И.А. Физическая химия: Учебник / И.А. Семиохин. — Изд-во МГУ, 2001. —. 272 с. /Semiohin I.A. Fizicheskaja himija: Uchebnik / I.A. Semiohin. — Izd-vo MGU, 2001. —. 272 s./
33. Ross P.D. Thermodynamics of protein association reactions: forces contributing to stability / P.D. Ross, S.Subramanian // Biochemistry. – 1981. – V. 20. – P. 3096-3102.
34. Study of interaction of carprofen and its enantiomers with human serium albumin-I.Mechanism of binding studied by dialysis an spectroscopic methods / M.H. Rahman, T.Maruyama, T. Okada, [et al.] // Biochemical Pharmacology. – 1993. – V. 46(10). – P. 1721-1731.
Authors who publish with this journal agree to the following terms:
- Authors retain copyright and grant the journal right of first publication with the work simultaneously licensed under a Creative Commons Attribution License that allows others to share the work with an acknowledgement of the work's authorship and initial publication in this journal.
- Authors are able to enter into separate, additional contractual arrangements for the non-exclusive distribution of the journal's published version of the work (e.g., post it to an institutional repository or publish it in a book), with an acknowledgement of its initial publication in this journal.
- Authors are permitted and encouraged to post their work online (e.g., in institutional repositories or on their website) prior to and during the submission process, as it can lead to productive exchanges, as well as earlier and greater citation of published work (See The Effect of Open Access).