Characterization of 2-phenylbenzo[g]quinoxaline derivatives as viscosity-sensitive fluorescent probes.

To develop viscosity-sensitive fluorescent probes, five different substituted 2-phenylbenzo[g]quinoxaline derivatives (3a-e) were designed and synthesized by using benzo[g]quinoxaline as a fluorophore and phenyl ring bearing a rotatable single bond as a viscosity-sensitive unit. The fluorescence properties of these compounds were investigated in the media of the ethylene glycol-glycerol mixture with varied viscosity. It is found that 2-(4-hydroxyphenyl)benzo[g]quinoxaline (3d) and 2-(4-dimethylaminophenyl)-benzo[g]quinoxaline (3e) carrying stronger electron-donating groups in the phenyl ring show more sensitive fluorescence response to viscosity, revealing their potential use in viscosity detection and the key role of the substituted groups. The effects of solvent polarity and pH on the fluorescent properties of 3d and 3e were also discussed. The present study might be useful in developing viscosity-sensitive fluorescent probes.

[1]  Guilford Jones,et al.  Solvent effects on emission yield and lifetime for coumarin laser dyes. Requirements for a rotatory decay mechanism , 1983 .

[2]  Hong Wang,et al.  Spectrofluorimetric determination of trace nitrite in food products with a new fluorescent probe 1,3,5,7-tetramethyl-2,6-dicarbethoxy-8-(3',4'-diaminophenyl)-difluoroboradiaza-s-indacene. , 2006, Talanta.

[3]  H. Ihmels,et al.  9-donor-substituted acridizinium salts: versatile environment-sensitive fluorophores for the detection of biomacromolecules. , 2007, Journal of the American Chemical Society.

[4]  J. Lakowicz.  Principles of fluorescence spectroscopy , 1983 .

[5]  B. Tang,et al.  Rapid and sensitive spectrofluorimetric determination of trace amount of Cr(III) with o-vanillin-8-aminoquinoline. , 2004, Talanta.

[6]  B. Valeur,et al.  Molecular Fluorescence: Principles and Applications , 2001 .

[7]  G. Fodor,et al.  A synthesis of adrenaline-like compounds. , 1949, Journal of the American Chemical Society.

[8]  F. Ulberth,et al.  Nutritional Antioxidants, Red Cell Membrane Fluidity and Blood Viscosity in Type 1 (insulin dependent) Diabetes Mellitus , 1996 .

[9]  Hong Wang,et al.  Sensitive determination of S-nitrosothiols in human blood by spectrofluorimetry using a fluorescent probe: 1,3,5,7-tetramethyl-8-(3',4'-diaminophenyl)-difluoroboradiaza-s-indacene. , 2007, Talanta.

[10]  G. Mcmahon,et al.  Tyrphostins. 5. Potent inhibitors of platelet-derived growth factor receptor tyrosine kinase: structure-activity relationships in quinoxalines, quinolines, and indole tyrphostins. , 1996, Journal of medicinal chemistry.

[11]  C E Kung,et al.  Fluorescent molecular rotors: a new class of probes for tubulin structure and assembly. , 1989, Biochemistry.

[12]  Mark A Haidekker,et al.  A ratiometric fluorescent viscosity sensor. , 2006, Journal of the American Chemical Society.

[13]  C. Roberts,et al.  Elevated protein tyrosine phosphatase activity and increased membrane viscosity are associated with impaired activation of the insulin receptor kinase in old rats. , 1994, The Biochemical journal.

[14]  John Aurie Dean,et al.  Lange's Handbook of Chemistry , 1978 .

[15]  Shun-Li Wang,et al.  Substituent effects on intramolecular charge-transfer behaviour of styrylheterocycles , 2000 .

[16]  Th. Förster,et al.  Die Viskositätsabhängigkeit der Fluoreszenzquantenausbeuten einiger Farbstoffsysteme , 1971 .

[17]  Huimin Ma,et al.  Progress in Spectroscopic Probes with Cleavable Active Bonds , 2006 .

[18]  S Chien,et al.  Direct relationship between blood pressure and blood viscosity in normal and hypertensive subjects. Role of fibrinogen and concentration. , 1981, The American journal of medicine.

[19]  M. Haidekker,et al.  Effects of solvent polarity and solvent viscosity on the fluorescent properties of molecular rotors and related probes. , 2005, Bioorganic chemistry.

[20]  T. Fayed.  Intramolecular charge transfer and photoisomerization of 2-(p-dimethylaminostyryl)benzoxazole:: A new fluorescent probe , 1999 .

[21]  H. Pal,et al.  Dual Solvatochromism of Neutral Red , 1998 .

[22]  Meir Shinitzky,et al.  Physiology of membrane fluidity , 1984 .

[23]  R. Loutfy,et al.  Non-radiative deactivation channels of molecular rotors , 1989 .

[24]  D E McMillan,et al.  Further observations on serum viscosity changes in diabetes mellitus. , 1982, Metabolism: clinical and experimental.

[25]  V. Villiotou,et al.  Modulation of particulate nitric oxide synthase activity and peroxynitrite synthesis in cholesterol enriched endothelial cell membranes. , 1995, Biochemical pharmacology.

[26]  G. Durocher,et al.  Excited-state dynamics and viscosity-dependent internal conversion in 3,3-dimethyl-2-phenyl-3H-indole , 1993 .