A study of the relationship between the chemical structures and the fluorescence quantum yields of coumarins, quinoxalinones and benzoxazinones for the development of sensitive fluorescent derivatization reagents

Photochemical and Photobiological Sciences

Volumn 2, Issue 4, 2003, Pages 443-449

  Azuma, Kentaro ^a   Suzuki, Sachiko ^a   Uchiyama, Seiichi ^a   Kajiro, Toshi ^a   Santa, Tomofumi ^a   Imai, Kazuhiro ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

3 PHENYL 7 N PIPERAZINOQUINOXALIN 2(1H) ONE; 7(3 AMINOPYRROLIDIN 1 YL) 3 PHENYLQUINOXALIN 2(1H) ONE; ACETIC ACID ETHYL ESTER; BENZOXAZINONE DERIVATIVE; CARBOXYLIC ACID; COUMARIN; HEXANE; METHANOL; QUINOXALINE DERIVATIVE; QUINOXALINONE; UNCLASSIFIED DRUG; WATER; BENZOXAZOLE DERIVATIVE; COUMARIN DERIVATIVE; FLUORESCENT DYE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; ENERGY TRANSFER; FLUORESCENCE SPECTROSCOPY; MICROANALYSIS; PRIORITY JOURNAL; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; SYNTHESIS; CHEMISTRY; SPECTROSCOPY;

BENZOXAZOLES; COUMARINS; FLUORESCENT DYES; QUINOXALINES; SPECTRUM ANALYSIS;

EID: 0038605291     PISSN: 1474905X     EISSN: 14749092     Source Type: Journal    
DOI: 10.1039/b300196b     Document Type: Article

References (60)

1. T. Toyo'oka, Modern derivatization methods for separation sciences, Wiley, Chichester, 1999.
2. (a) C. E. Wheelock, The fluorescence of some coumarins, J. Am. Chem. Soc., 1959, 81, 1348-1352;
3. (b) W. R. Sherman and E. Robins, Fluorescence of substituted 7-hydroxycoumarins, Anal. Chem., 1968, 40, 803-805;
4. (c) A. Takadate, T. Masuda, C. Murata, M. Shibuya and A. Isobe, Structural features for fluorescing present in methoxycoumarin derivatives, Chem. Pharm. Bull., 2000, 48, 256-260;
5. (d) H. Takechi, Y. Oda, N. Nishizono, K. Oda and M. Machida, Screening search for organic fluorophores: syntheses and fluorescence properties of 3-azolyl-7-diethylaminocoumarin derivatives, Chem. Pharm. Bull., 2000, 48, 1702-1710;
6. 2 complexes as laser dyes:1, Heteroatom Chem., 1990, 1, 389-399;
7. 2 complexes as laser-dyes. 2., Heteroatom Chem., 1993, 4, 39-49.
8. (a) S. Uchiyama, T. Santa, T. Fukushima, H. Homma and K. Imai, Effects of the substituent groups at the 4- and 7-positions on the fluorescence characteristics of benzofurazan compounds, J. Chem. Soc., Perkin Trans. 2, 1998, 2165-2173;
9. (b) S. Uchiyama, T. Santa and K. Imai, Semi-empirical PM3 calculation reveals the relationship between the fluorescence characteristics of 4,7-disubstituted benzofurazan compounds, the LUMO energy and the dipole moment directed from the 4-to the 7-position, J. Chem. Soc., Perkin Trans. 2, 1999, 569-576;
10. (c) S. Uchiyama, T. Santa and K. Imai, Fluorescence characteristics of six 4,7-disubstituted benzofurazan compounds: an experimental and semi-empirical MO study, J. Chem. Soc., Perkin Trans. 2, 1999, 2525-2532;
11. (d) S. Uchiyama, K. Takehira, S. Kohtani, T. Santa, R. Nakagaki, S. Tobita and K. Imai, Photophysical study of 5-substituted benzofurazan compounds as fluorogenic probes, Phys. Chem. Chem. Phys., 2002, 4, 4514-4522;
12. (e) S. Uchiyama, T. Santa, N. Okiyama, K. Azuma and K. Imai, Semi-empirical PM3 calculations predict the fluorescence quantum yields (Φ) of 4-monosubstituted benzofurazan compounds, J. Chem. Soc., Perkin Trans 2, 2000, 1199-1207.
13. C. Hansch, A. Leo and R. W. Taft, A survey of Hammett substituent constants and resonance and field parameters, Chem. Rev., 1991, 91, 165-195.
14. (a) S. Uchiyama, T. Santa and K. Imai, A fluorogenic reagent, 4-mercapto-7-methylthio-2,1,3-benzoxadiazole for carboxylic acids, desiened by prediction of the fluorescence intensity, Anal. Chem., 2001, 73, 2165-2170;
15. (b) A. Toriba, K. Adzuma, T. Santa and K. Imai, Development of an amino acid sequence and D/L-configuration determination method of peptide with a new fluorescence Edman reagent, 7-methylthio-4-(2,1,3-benzoxadiazolyl) isothiocyanate, Anal. Chem., 2000, 72, 732-739;
16. (c) T. Santa, T. Okamoto, S. Uchiyama, K. Mitsuhashi and K. Imai, A new fluorogenic reagent for carboxylic acids, 7-acetylamino-4-mercapto-2,1,3- benzoxadiazole (AABD-SH), derived from an empirical method for predicting fluorescence characteristics, Analyst, 1999, 124, 1689-1693;
17. (d) S. Uchiyama, T. Santa, S. Suzuki, H. Yokosu and K. Imai, A fluorogenic reagent, 7-phenylsulfonyl-4-(2,1,3-benzoxadiazolyl)isocyanate for alcohols, with development based on the empirical method for prediction, Anal. Chem., 1999, 71, 5367-5371.
18. S. Lin and W. S. Struve, Time-resolved fluorescence of nitrobenzoxadiazole-aminohexanoic acid: effect of intermolecular hydrocen-bondina on non-radiative decay, Photochem. Photobiol., 1991, 54, 361-365.
19. I(n,π *) state, J. Phys. Chem., 1994, 98, 6054-6058.
20. S. Hara, K. Inoue, M. Fukuzawa, N. Ono, T. Kurodo and M. Yamaguchi, 6,7-Methylenedioxy-1-methyl-2-oxo-1,2-dihydroquinoxalin-3-ylpropionohydrazide as a highly sensitive fluorescence derivatization reagent for carboxylic acids in high-performance liquid chromatography, Anal. Sci., 1998, 14, 1173-1176.
21. A. Nakanishi, H. Naganuma, J. Kondo, K. Watanabe, K. Hirano, T. Kawasaki and Y. Kawahara, 3-Bromomethyl-7-methoxy-1,4-benzoxazin-2-one as a highly sensitive fluorescence derivatization reagent for carboxylic acids in high-performance liquid chromatography, J. Chromatogr., 1992, 591, 159-164.
22. A. N. Fletcher, Quinine sulfate as a fluorescence quantum yield standard, Photochem. Photobiol., 1969, 9, 439-444.
23. (a) E. Knoevenagel, Condensationen zwischen Malonester und Aldehyden unter dem Einfluss von Ammoniak und organischen Aminen, Chem. Ber., 1898, 31, 2585-2595;
24. (b) E. Knoevenagel, Condensation von Malonsäure mit aromatischen Aldehyden durch Ammoniak und Amine, Chem. Ber., 1898, 31, 2596-2619;
25. (c) E. Knoevenagel and R. Arnot, Condensationen von Salicylaldehyd mit Cyanessigester, Benzoylessigester und Acetylaceton, Chem. Ber., 1904, 37, 4496-4510;
26. (d) S. M. Sethna and N. M. Shah, The chemistry of coumarins, Chem. Rev., 1945, 36, 1-62.
27. H. Hlasiwetz, Ueber das Umbelliferon, Chem. Ber., 1871, 4, 550-553.
28. (a) H. Otomasu and K. Yoshida, On the nitration of quinoxalines (addendum), Chem. Pharm. Bull., 1960, 8, 475-478;
29. (b) T. Nishio, (2 + 2) Photocycloaddition of the carbon-nitrogen double-bond of quinoxalin-2(1H)-ones to electron-deficient olefins, J. Org. Chem., 1984, 49, 827-832;
30. (c) M. I. Abasolo, C. H. Gaozza and B. M. Fernández, Kinetic-study on the annelation of heterocycles. 1. Quinoxalinone derivatives synthesized by Hinsberg reaction, J. Heterocyclic Chem., 1987, 24, 1771-1775;
31. (d) P. Sanna, A. Carta, M. Loriga, S. Zanetti and L. Sechi, Synthesis of substituted 2-ethoxycarbonyl- and 2-carboxyquinoxalin-3-ones for evaluation of antimicrobial and anticancer activity, Farmaco, 1998, 53, 455-461;
32. (e) P. Sanna, A. Carta, M. Loriga, S. Zanetti and L. Sechi, Synthesis of 3,6,7-substituted-quinoxalin-2-ones for evaluation of antimicrobial and anticancer activity. Part 2, Farmaco, 1999, 54, 161-168;
33. (f) P. Sanna, A. Carta, M. Loriga, S. Zanetti and L. Sechi, Preparation and biological evaluation of 6/7-trifluoromethyl(nitro)-, 6,7-difluoro-3-alkyl (aryl)-substitutcd-quinoxalin-2-ones. Part 3, Farmaco, 1999, 54, 169-177.
34. (a) W. Wislicenus and W. Beckh, Ueber die Einwirkung von Ammoniak und Aminen auf Oxalessigester, Justus Liebigs Ann. Chem., 1897, 295, 339-366;
35. (b) E. Biekert, D. Hoffmann and F. J. Meyer, Darstellung kondensierter 1.4-Oxazinone-(2) durch Umsetzuna von o-Aminophenolen mit α-Ketoestern, Chem. Ber., 1961, 94, 1664-1675;
36. (c) R. B. Moffett, 2H-1,4-Benzoxazin-2-ones, J. Med. Chem., 1966, 9, 475-478;
37. (d) D. R. Shridhar, B. Lal, N. K. Vaidya, K. K. Bhopale and H. N. Tripathi, Synthesis & biological activity of some 3-[2-(heteroaryl)-vinyl]- 2H-1, 4-benzoxazin-2-ones, Indian J. Chem., Sect B, 1979, 18B, 251-253.
38. (a) M. J. S. Dewar and W. Thiel, Ground states of molecules. 38. The MNDO method. Approximations and parameters, J. Am. Chem. Soc., 1977, 99,4899-1907;
39. (b) M. J. S. Dewar and W. Thiel, Ground states of molecules. 39. MNDO results for molecules containing hydrogen, carbon, nitrogen, and oxygen, J. Am. Chem. Soc., 1977, 99, 4907-4917.
40. M. J. S. Dewer, E. G. Zoebisch, E. F. Healy and J. J. P. Stewart, Development and use of quantum mechanical molecular models. 76. AM1: a new general purpose quantum mechanical molecular model, J. Am. Chem. Soc., 1985, 107, 3902-3909.
41. (a) J. J. P. Stewart, Optimization of parameters for semiempirical methods. 1. method, J. Comput. Chem., 1989, 10, 209-220;
42. (b) J. J. P. Stewart, Optimization of parameters for semiempirical methods. 2. applications, J. Comput. Chem., 1989, 10, 221-264.
43. (a) J. A. Pople, D. L. Beveridge and P. A. Dobosh, Approximate self-consistent molecular-orbital theory. V. Intermediate neglect of differential Overlap, J. Chem. Phys., 1967, 47, 2026-2033;
44. (b) J. Ridley and M. Zerner, An intermediate neglect of differential overlap technique for spectroscopy: pyrrole and the azines, Theor. Chim. Acta, 1973, 32, 111-134.
45. D. R. Armstrong, R. Fortune, P. G. Perkins and J. J. P. Stewart, Molecular orbital theory for the excited states of transition metal complexes, J. Chem. Soc., Faraday Trans. 2, 1972, 68, 1839-1846.
46. P. K. McCarthy and G. J. Blanchard, AMI study of the electronic-structure of coumarins, J. Phys. Chem., 1993, 97, 12205-12209.
47. A. Takadate, T. Masuda, C. Murata, T. Tanaka, M. Irikura and S. Goya, Fluorescence characteristics of methoxycoumarins as novel fluorophores, Anal. Sci., 1995, 11, 97-101.
48. (a) P. Avouris, W. M. Gelbart and M. A. El-Sayed, Nonradiative electronic relaxation under collision-free conditions, Chew. Rev., 1977, 77, 793-833;
49. (b) M. A. El-Sayed, The radiationless processes involvine change of multiplicity in the diazenes, J. Chem. Phys., 1962, 36, 573-574;
50. (c) M. A. El-Sayed, Spin-orbit coupling and the radiationless processes in nitrogen heterocyclics, J. Chem. Phys., 1963, 38, 2834-2838;
51. (d) M. A. El-Sayed, Vanishing first- and second-order intramolecular heavy-atom effects on the (π*→n) phosphorescence in carbonyls, J. Chem. Phys., 1964, 41, 2462-2467.
52. (a) W. W. Mantulin and P.-S. Song, Excited states of skin-sensitizing coumarins and psoralens. Spectroscopic studies, J. Am. Chem. Soc., 1973, 95, 5122-5129;
53. (b) J. S. deMelo, R. S. Becker, F. Elisei and A. L. Maçanita, The photophysical behavior of 3-chloro-7-methoxy-4-methylcoumarin related to the energy separation of the two lowest-lying singlet excited states, J. Chem. Phys., 1997, 107, 6062-6069;
54. (c) F. Elisei, G. G. Aloisi, F. Dall'Acqua, L. Latterini, F. Masetti and P. Rodighiero, Photophysical behavior of angelicins and thioangelicins: Semiempirical calculations and experimental study, Photochem. Photobiol., 1998, 68, 164-172;
55. (d) A. Kellmann, Intersystem crossing and internal conversion quantum yields of acridine in polar and nonpolar solvents, J. Phys. Chem., 1977, 81, 1195-1198;
56. (e) K. Kasama, K. Kikuchi, S. Yamamoto, K. Uji-ie, Y. Nishida and H. Kokubun, Relaxation mechanism of excited acridine in non-reactive solvents, J. Phys. Chem., 1981, 85, 1291-1296;
57. (f) K. Kasama, K. Kikuchi, Y. Nishida and H. Kokubun, Deactivation mechanism of excited acridine and 9-substituted acridines in water, J. Phys. Chem., 1981, 85, 4148-4153.
58. B. Schade, V. Hagen, R. Schmidt, R. Herbrich, E. Krause, T. Eckardt and J. Bending, Deactivation behavior and excited-state properties of (coumarin-4-yl)methyl derivatives. 1. Photocleavage of (7-methoxycoumarin-4-yl) methyl-caged acids with fluorescence enhancement, J. Org. Chem., 1999, 64, 9109-9117.
59. T. Toyo'oka, M. Ishibashi, Y. Takeda, K. Nakashima, S. Akiyama, S. Uzu and K. Imai, Precolumn fluorescence tagging reagent for carboxylic-acids in high-perfomance liquid-chromatography: 4-substituted-7-aminoalkylamino-2,1,3- benzoxadiazoles, J. Chromatogr., 1991, 588, 61-71.
60. M. Yamaguchi, S. Hara, R. Matsunaga, M. Nakamura and Y. Ohkura, Highly sensitive fluorogenic reagent for carboxylic acid, 3-bromomethyl-6,7-dimethoxyl- 1-methyl-2(1H)-quinoxaIinone, in high performance liquid chromatography, Anal. Sci., 1985, 1, 295-296.