Fluorescence and surface-enhanced Raman study of 9-aminoacridine in relation to its aggregation and excimer emission in aqueous solution and on silver surface

Biospectroscopy

Volumn 4, Issue 5, 1998, Pages 327-339

  Murza, A ^a   Sanchez Cortes S ^b   Garcia Ramos J V ^b  

^a HOSPITAL CLÍNICO SAN CARLOS   (Spain)

^b INSTITUTO DE ESTRUCTURA DE LA MATERIA   (Spain)

Author keywords

9 aminoacridine; Dimerization; Excimer; Fluorescence; SERS

Indexed keywords

AMINOACRIDINE; SILVER; WATER;

ARTICLE; CHEMISTRY; COLLOID; METHODOLOGY; RAMAN SPECTROMETRY; SOLUTION AND SOLUBILITY; SPECTROFLUOROMETRY;

AMINACRINE; COLLOIDS; SILVER; SOLUTIONS; SPECTROMETRY, FLUORESCENCE; SPECTRUM ANALYSIS, RAMAN; WATER;

EID: 0031603244     PISSN: 10754261     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1520-6343(1998)4:5<327::aid-bspy4>3.0.co;2-h     Document Type: Article

References (42)

1. H. Zhu, S. M. Clark, S. C. Benson, H. S. Rye, A. N. and R. A Mathies, "High- sensitivity capillary electrophoresis of double-stranded DNA fragments using monomeric and dimeric fluorescent intercalating dyes," Anal. Chem., 66, 1941-1948 (1994).
2. C. Rehn and U. Pindur, "Molecular modeling of intercalation complexes of antitumor active 9-aminoacridine and a (d,e)-anellated isoquinoline derivative with base paired deoxytetranucleotides," Monatshefte fur Chemie, 127, 645-658 (1996).
3. E. L. Loechler and J. King, "Identification of the 9-aminoacridine/DNA complex responsible for photodynamic inactivation of P22," Biochem., 25, 5858-5864 (1986).
4. D. Fornasiero and T. Kurucsev, "The binding of 9-aminoacridine to calf thymus DNA in aqueous solution. Electronic spectral studies," Biophys. Chem., 23, 31-37 (1985).
5. P. Gangola, N. B. Joshi, and D. D. Pant, "Excimer emission in 9-aminoacridine hydrochloride," Chem. Phys. Lett., 80, 418-421 (1981).
6. S. Grzesiek, H. Otto, and N. A. Dencher, "pH induced fluorescence quenching of 9-aminoacridine in lipid vesicles is due to excimer formation at the membrane," Biophys. J., 55, 1101-1109 (1989).
7. S. Grzesiek and N. A. Dencher, "The pH probe 9-aminoacridine: response-time, binding behaviour and dimerization at the membrane," Biochim. Biophys. Acta., 938, 411-424 (1988).
8. J. B. Birks and L. G. Christophorou, "Excimer fluorescence IV. Solution spectra of polycyclic hydrocarbons," Proc. Roy. Soc. A, 274, 571-582 (1963).
9. K. Y. Horiuchi, Z. Wang, and S. Chacko, "Inhibition of smooth muscle actomyosin ATPase by Caldesmon is associated with Caldesmon-induced conformational changes in tropomyosin bound to actin," Biochem., 34, 16815-16820 (1995).
10. A. Marty, M. Bordeaux, M. D. Amico, and P. Viallet, "The α-chymotrypsin effect on various 9-aminoacridine fluorescent probe emission," Photochem. Photobiol., 40, 175-183 (1984).
11. F. S. Steven, M. M. Griffin, and R. K. A. Ahmad, "Design of fluorescent probes for an enzyme on the surface of tumour cells," J. Chromatogr., 376, 211-219 (1986).
12. F. Steven, U. Suresh, T. L. H. Wong, and M. M. Griffin, "The role of inhibitors in the fluorescent staining of benign naevus and malignant melanoma cells with 9-aminoacridine and acridine orange," J Enzyme Inhibition, 1, 275-287 (1987).
13. S. Grinstein and W. Furuya, "Intracellular distribution of acridine derivatives in platellets and their suitability for cytoplasmic pH measurements," Biochim. Biophys. Acta, 803, 221-228 (1984).
14. S. Schuldiner, H. Rottenberg, and M. Avron, "Determination of ΔpHl in chloroplasts," Eur. J. Biochem., 25, 64-70 (1972).
15. R. Casadio and B. A. Melandri, "Calibration of the response of 9-amino acridine fluorescence to transmembrane pH differences in bacterial chromatophores," Arch. Biochem. Biophys., 238, 219-228 (1985).
16. C. A. Smith, H. C. Chang, and Walter S. Struve, "Excited-state proton transfers in 9-aminoacridine carboxamides," J. Phys. Chem., 99, 8927-8935 (1995).
17. F. Steven and M. M. Griffin, "Inhibitors of guanidinobenzoatase and their possible role in cell migration," Biol. Chem. Hoppe-Seyler, 369, 137-143 (1988).
18. M. Moskovits, "Surface-enhanced spectroscopy," Rev. Mod. Phys., 55, 783-826 (1985).
19. R. E. Holt, D. L. Farrens, P. S. Song, and T. M. Cotton, "Surface-enhanced Raman scattering spectroscopy applied to phytochrome and its model compounds. I. Biliverdin photoisomers," J. Am. Soc., 111, 9156-9162 (1989).
20. P. Hilldebrandt and M. Stockburger, "Surface-enhanced Raman spectroscopy of rhodamine 6G adsorbed on colloidal silver," J. Phys. Chem., 88, 5935-5944 (1984).
21. D. Jancura, S. Sánchez-Cortés, E. Kocisova, A. Tinti, P. Miskovsky, and A.Bertoluzza, "Surface-enhanced resonance Raman spectroscopy of hypericin and emodin on silver colloids: SERRS and NIR FTSERS study," Biospectroscopy, 1, 265-273 (1995).
22. L. M. Caballin and J. J. Laserna, "Fast spatially resolved surface-enhanced Raman spectroscopy on a silver coated filter paper using charge-coupled device detection," Anal. Chim Acta, 310, 337-345 (1995).
23. A. Ruperez and J. J. Laserna, "Surface-enhanced Raman spectroscopy on a silver substrate prepared by the nitre acid etching method," Anal. Chim. Acta, 291, 147-153 (1994).
24. Y. Chourpa and M. Manfait, "Specific molecular interactions of acridine drugs in complexes with topoisomerase II and DNA.SERS and resonance Raman study of m-AMSA in comparison with o-AMSA," J. Raman Spectrosc., 26, 813-819 (1995).
25. P. C. Lee and D. Meisel, "Adsorption and surface-enhanced Raman of dyes on silver and gold colloids," J. Phys. Chem., 86, 3391-3395 (1983).
26. H. Shizuka, M. Nakamura, and T. Morita, "Anion-induced fluorescence of aromatic molecules," J. Phys. Chem., 84, 989-994 (1980).
27. A. Treinin and E. Hayon, "Quenching of triplet states by inorganic ions. Energy transfer and charge transfer mechanism," J. Am. Chem. Soc., 98, 3884-3891 (1975).
28. S. Chaudhuri, "Symmetry and hydrogen bonding in the crystal structure of 9-aminoacridine hemihydrate," J. Chem. Soc, Chem. Commun., 1242-1243 (1983).
29. J. Rak, P. Skurski, M. Gutowski, L. Jozwiak, and J. Blazejowski, "Hartree-Fock and density functional methods and IR and NMR spectroscopies in the examination of tautomerism and features of neutral 9-acridinamine in gaseous and condensed media," J. Phys Chem. A, 101, 283-292 (1997).
30. P. Carmona and M. Molina, "Studies on aminopyridines in aqueous solution by laser Raman Spectroscopy," Spectrochim. Acta A, 49, 1-9 (1993).
31. L. E. Orgel in The Chemistry of Heterocyclic Compounds: Acridines, ed. by R. M. Acheson, Wiley Interscience, New York, 1956.
32. C. C. Chiang, C. Y. Mou, and T. C. Chang, "Photoreaction of neutral 9-aminoacridine in glycerol: Water glass characterized by satellite holes and antiholes," Chem. Phys. Lett., 273, 153-158 (1997).
33. L. Jozwiak, P. Skurski, J. Rak, and J. Blazejowski, "Stationary and time-resolved fluorescence investigations combined with PM3/CI studies of tautomeric phenomena in neutral and protonated 9-acridinamine," Spectrochim. Acta. Part. A, 53, 1723-1733 (1997).
34. N. Mataga, Molecular Interactions and Electronic Spectra, Marcel Dekker, Inc., New York, 1970.
35. R. D. Lowde, D. C. Phillips, and R. G. Wood, "The crystallography of acridine.I," Acta Cryst., 6, 553-556 (1953).
36. G. Levi, J. Pantigny, J. P. Marsault, and J. Aubard, "SER spectra of acridine and acridinium ions in colloidal silver sols. Electrolytes and pH effects," J. Raman Spectrosc., 24, 745-752 (1993).
37. T. Iliescu, M. Vlassa, M. Caragiu, I. Marian, and S. Astilean, "Raman study of 9-methylacridine adsorbed on silver sol," Vibr. Spectr., 8, 451-456 (1995).
38. S. T. Oh, K. Kim, and M. S. Kim, "Adsorption and surface reaction of acridine in silver sol: Surface enhanced Raman spectroscopy study," J. Phys. Chem., 95, 8844-8849 (1991).
39. M.Brigodiot and J.M.Lebas, "Étude vibrationelle de l'acridine et de l'ion acridinium par spectroscopie infrarouge et Raman.Comparaison avec l'anthracene," J. Chim. Phys. Phys. Chim. Biol., 69, 964-971 (1972).
40. S. C. Laperriere, J. W. Mullens, D. L'Espérance, and E. L. Chronister, "Optical energy transfer and trapping in 9-aminoacridine doped sol-gel glasses," Chem. Phys. Lett., 243, 114-124 (1995).
41. I. Martini, J. H. Hodak, and G. V. Hartland, "Effect of water on the electron transfer dynamics of 9-aminoacridine acid bound to TiO2 nanoparticles: Demonstartion of the Marcus inverted region," J. Phys. Chem., 102, 607-614 (1998).
42. D. Roy and T. E. Furtak, "Evidence for Ag clusters vibrations in enhanced scattering from the Ag/electrolite interfase," Chem. Phys. Lett., 124, 299-303 (1986).