Abstract
The spectral-luminescent characteristics of newly synthesized styrylcyanine dyes on the base of dyes Sbo ((E)-2-(4-(dimethylamino)styryl)-3-methylbenzo[d]oxazol-3-ium iodide) and Sil ((E)-2-(4-(dimethylamino)styryl)-1,3,3-trimethyl-3H-indolium perchlorate) in aqueous solutions without and in the presence of bovine serum albumin (BSA) were studied. It was established that the absorption spectra of dyes Tol-6, Dbo-10 and Dil-10 with increasing amount of BSA appear new bands with λmax = 505 nm, λmax = 512 nm and λmax = 566 nm, respectively, whose intensity increases in proportion to the amount of albumin. The intensity of the glow of the main band of fluorescence in the presence of BSA sharply increases. The binding constant (K) and the number of binding sites (N) of studied dyes with BSA were determined. The dependence of binding constants with BSA on the dipole moment of dye molecules was determined, which indicates that besides electrostatic forces of attraction between molecules styrylcyanine dyes with BSA, hydrophobic interactions are essential.
Similar content being viewed by others
References
Zakerhamidi MS, Ghanadzadeh A, Tajalli H, Moghadam M, Jassas M, Hosseininia R (2010) Substituent and solvent effects on the photo-physical properties of some coumarin dyes. Spectrochim Acta Part A: Mol Biomol Spectrosc 77(2):337–341
Kurtaliev EN, Nizomov N, Rahimov ShI (2011) The spectral-luminescent and photochemical characteristics of several styrylcyanine dyes in solution. J Mol Liq 158:43–49
Al-Shamiri HAS, Abou Kana MTH, Azzouz IM, Badr YA (2009) Photo-physical properties and quantum yield of some laser dyes in new polymer host. Optics & Laser Tech 41(4):415–418
Song B, Zhang Q, Maa WH, Penga XJ, Fua XM, Wanga BSh (2009) The synthesis and photostability of novel squarylium indocyanine dyes. Dyes Pigm 82(3):396–400
Mazieres MR, Duprat C, Wolf JG, Roshal AD (2009) pH dependent spectral properties and electronic structure of benzothiazol containing cyanine dyes. Dyes Pigm 80(3):355–360
Zhang W, Tang B, Liu X, Liu Y, Xu K, Ma J, Tong L, Yang G (2009) A highly sensitive acidic pH fluorescent probe and its application to HepG2 cells. Analyst 134(2):367–371
Lee H, Berezin MY, Henary M, Strekowski L, Achilefu S (2008) Fluorescence lifetime properties of near-infrared cyanine dyes in relation to their structures. J Photochem Photobiol A: Chem 200(2–3):438–444
Yukruk F, Dogan AL, Canpinar H, Guc D, Akkaya EU (2005) Water-soluble green perylenediimide (PDI) dyes as potential sensitizers for photodynamic therapy. Org Lett 7(14):2885–2887
Smith HJ, Gray B, Muirhead K, Ohlsson-Wilhelm B, Fritzsch B (2007) Long-distance three-color neuronal tracing in fixed tissue using neurovue dyes. Immunol Invest 36(5–6):763–789
Schneckenburger H, Stock K, Lyttek M, Strauss WS, Sailer R (2004) Fluorescence lifetime imaging (FLIM) of rhodamine 123 in living cells. J Photochem Photobiol Sci 3:127–131
Hilal H, Taylor JA (2008) Cyanine dyes for the detection of double stranded DNA. J Biochem Biophys Methods 70(6):1104–1108
Nizomov N, Ismailov ZF, Kurtaliev EN, Nizamov ShN, Khodzhaev G, Patsenker LD (2006) Luminescent spectral properties of rhodamine derivatives while binding to serum albumin. J Appl Spectrosc 73(3):432–436
Nizomov N, Ismailov ZF, Nizamov ShN, Salakhitdinova MK, Tatarets AL, Patsenker LD, Khodjayev G (2006) Spectral-luminescent study of interaction between squaraine dyes and biological matters. J Mol Struct 788(1–3):36–42
Oswald B, Patsenker L, Duschl J, Szmancinski H, Wolfbeis OS, Terpetschnig E (1999) Synthesis, spectral properties and detection limits of reactive squarylium dyes, a new class of diode laser compatible Fluorescent Protein labels. Bioconjug Chem 10(6):925–931
Kurtaliev EN, Nizamov N, Nizamov ShN, Khodjayev G (2009) Spectral-luminescent study of the interaction of some styrylcyanine dyes with bovine serum albumin and DNA in aqueous solution. J Mol Struct 936:199–205
Yarmoluk SM, Kovalska VB, Kryvorotenko DV, Balanda AO, Ogul’chansky YuT (2001) Interaction of cyanine dyes with nucleic acids XXV. Influence of affinity-modifying groups in the structure of benzothiazol-4-[2,6-dimethylpyridinium] dyes on the spectral properties of the dyes in the presence of nucleic acids. Spectrochim Acta Part A 57(7):1533–1540
Kovalska VB, Losytskyy MYu, Kryvorotenko DV, Balanda AO, Tokar VP, Yarmoluk SM (2006) Synthesis of novel fluorescent styryl dyes based on the imidazo[1, 2-a]pyridinium chromophore and their spectral-fluorescent properties in the presence of nucleic acids and proteins. Dyes Pigm 68(1):39–45
Baulie EK, Raynaud JP (1970) A «proportional graph» method for measuring binding system. Eur J Biochem 13(2):293–304
Gerhard Ph (1981) Manual of methods for general bacteriology. American Society of Microbiology, Washington
McGhee JD, von Hippel PH (1974) Theoretical aspects of DNA protein interactions: cooperative and non cooperative binding of large ligands to a one dimensional homogeneous lattice. J Mol Biol 86:469–489
Stewart JJP (1990) MOPAC: a semiempirical molecular orbital program. J Comput Aided Mol Desing 4:1–103
Ishchenko AA (1994) Construction and spectral-luminescent properties polymethyne dyes, Naukova dumka, Kyiv. (in Russian)
Luik AI, Lukyanchik VD (1984) Serum albumin, and transportation of poisons, Medicine, Moskow. (in Russian)
Pham W, Medarova Z, Moore A (2005) Synthesis and application of a water-soluble near-infrared dye for cancer detection using optical imaging. Bioconjug Chem 16:735–740
Welder F, Paul B, Nakazumi H, Yagi S, Colyer CL (2003) Symmetric and assymetric squarylium dyes as noncovalent protein labels: a study by fluorimetry and capillary electrophoresis. J Chromatogr B 793:93–105
Sophianopoulos AJ, Lipowsky J, Narayanan N, Patonay G (1997) Association of near-infrared dyes with bovine serum albumin. Appl Spectrosc 51(10):1511–1515
Acknowledgments
The author is grateful to Dr. S.M. Yarmoluk from the Institute of Molecular Biology and Genetics NAS of Ukraine for allotment of dyes and Professor N. Nizomov from Samarkand State University for his fruitful participation in the discussion of the results. This work was supported by grant 3104 (STCU, Ukraine).
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Kurtaliev, E.N. Spectroscopic Study of the Interaction of Styrylcyanine Dyes Sbo, Sil and Their Derivatives with Bovine Serum Albumin. J Fluoresc 21, 1713–1719 (2011). https://doi.org/10.1007/s10895-011-0866-7
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10895-011-0866-7