Photochemical and Photophysical Studies of 3-Amino-6-lodoacridine and the Inactivation of λ Phage

Photochemistry and Photobiology

Volumn 64, Issue 4, 1996, Pages 622-631

  Chen, Tongqian ^a   Voelk, Eric ^a   Platz, Matthew S ^a   Goodrich, Raymond P ^b,c  

^a OHIO STATE UNIVERSITY   (United States)

^b Cryopharm Corporation   (United States)

^c Gambro BCT   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

3 AMINO 6 IODOACRIDINE; 3-AMINO-6-IODOACRIDINE; AMINOACRIDINE DERIVATIVE; DNA;

ANIMAL; ARTICLE; BACTERIOPHAGE LAMBDA; CATTLE; CHEMISTRY; DRUG EFFECT; GROWTH, DEVELOPMENT AND AGING; METABOLISM; PHOTOCHEMISTRY; PHOTOLYSIS; PHYSICAL CHEMISTRY; RADIATION EXPOSURE; VIRUS ACTIVATION;

AMINOACRIDINES; ANIMALS; BACTERIOPHAGE LAMBDA; CATTLE; CHEMISTRY, PHYSICAL; DNA; PHOTOCHEMISTRY; PHOTOLYSIS; VIRUS ACTIVATION;

ANIMALIA; BACTERIOPHAGE LAMBDA; BOS TAURUS;

EID: 0030265590     PISSN: 00318655     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1751-1097.1996.tb03115.x     Document Type: Article

References (77)

1. Wallace, E. L., D. M. Surgenor, H. S. Hao, J. An, R. H. Chapman and W. H. Churchill (1993) Collection and transfusion of blood and blood components in the United States, 1989. Transfusion 33, 139-144.
2. Curran, J. W., L. N. Dale, H. Jaffe, J. E. Kaplan, L. D. Zyla, M. Chamberaland, R. Weinstein, K. J. Li, L. B. Schonberger, T. J. Spira, W. J. Alexander, G. Swinger, A. Amman, S. Solomon, D. Auerbach, D. Mildvan, R. Stoneburner, J. M. Jason, H. W. Haverkos and B. L. Evatt (1984) Acquired immune deficiency syndrome (AIDS) associated with transfusions. N. Engl. J. Med. 310, 69-75.
3. Selik, R. M., J. W. Ward and J. W. Buehler (1993) Trends in transfusion-associated acquired immune deficiency syndrome in the United States. Transfusion 33, 890-893.
4. Cohen, N. D., A. Munoz, B. A. Reitz, P. K. Ness, O. H. Frazier, D. H. Yawn, H. Lee, W. Blattner, J. G. Donahue, K. E. Nelson and B. F. Polk (1989) Transmission of retroviruses by transfusion of screened blood in patients undergoing cardiac surgery. N. Engl. J. Med. 320, 1172-1176.
5. Cummings, P. D., E. L. Wallace, J. B. Schort and R. Y. Dodd (1989) Exposure of patients to human immunodeficiency virus through the transfusion of blood components that test antibodynegative. N. Engl. J. Med. 321, 941-946.
6. Ward, J. W., S. D. Holmberg, J. R. Allen, D. L. Cohn, S. E. Critchey, S. H. Kleinman, B. A. Lenes, O. Ravenholt, J. R. Davis, M. G. Quinn and H. W. Jaffe (1988) Transmission of human immunodeficiency virus (HIV) by blood transfusions screened as negative for HIV antibody. N. Engl. J. Med. 318, 473-478.
7. Moroff, A., V. M. George, A. M. Siegl and N. L. C. Lubon (1986) The influence of irradiation on stored platelets. Transfusion 26, 453-456.
8. Horowitz, M. S., C. Rooks, B. Horowitz and M. W. Hilgartner (1988) Virus safety of solvent/detergent treated antihaemophilic factor concentrate. Lancet ii, 186-188.
9. Horowitz, B., M. E. Wiebe, A. Lippin and M. H. Stryker (1985) Inactivation of viruses in labile blood derivatives 1: disruption of lipid-enveloped viruses by tri (n-butyl) phosphate/detergent combinations. Transfusion 25, 516-522.
10. Dodd, R. Y., G. Moroff, S. Wagner, M. H. Dabay, E. Dorfman, V. George, A. Ribeiro, J. Shumaker and L. E. Benade (1991) Inactivation of viruses in platelet suspensions that retain their in vitro characteristics: comparison of psoralen-ultraviolet A and mercocyanine 540-visible light methods. Transfusion 31, 483-490.
11. Lambrecht, B., H. Mohr, J. Knuver-Hopf and H. Schmitt (1991) Photoinactivation of viruses in human fresh plasma by phenothiazine dyes in combination with visible light. Vox Sang. 60, 207-213.
12. Matthews, J. L., J. T. Newman, F. Sogandares-Bernal, M. M. Judy, H. Skiles, J. E. Leveson, A. J. Marengo-Rowe and T. C. Chanh (1988) Photodynamic therapy of viral contaminants with potential for blood-banking applications. Transfusion 28, 81-83.
13. O'Brien, J. M., R. R. Montgomery, W. H. Burns, D. K. Gaffney and F. Sieber (1990) Evaluation of merocyanine-540-sensitized photoirradiation as a means to inactivate enveloped viruses in blood products. J. Lab. Clin. Med. 116, 439-447.
14. Rywkin, S., L. Lenny, J. Goldstein, N. E. Geacintov, H. Margolis-Nunno and B. Horowitz (1992) Importance of type I and type II mechanisms in the photodynamic inactivation of viruses in blood with aluminum phthalocyanine derivatives. Photochem. Photobiol. 56, 463-469.
15. Leonard, J., A. Rabson and R. Vanderoef (1993) Photodynamic inactivation of infectivity of human immunodeficiency virus and other enveloped viruses using hypercin and rose bengal; inhibition of fusion and syncytia formation. Proc. Natl. Acad. Sci. USA 90, 158-162.
16. Leonard, J. and R. Vanderoef (1993) Photoinactivation of influenza virus fusion and infectivity by rose bengal. Photochem. Photobiol. 58, 527-531.
17. Lin, L., H. Lunde, C. V. Hanson, G. Wiesehahn, S. Isaacs, G. Cimino and L. Corash (1993) Photochemical inactivation of cell-associated human immunodeficiency virus in platelet concentrates. Blood 87, 292-297.
18. Lin, L., G. P. Wiesehahn, P. A. Mord and L. Corash (1989) Use of 8-methoxypsoralen and long wavelength ultraviolet radiation for decontamination of platelet concentrates. Blood 74, 517-525.
19. Hanson, C. V., J. C. Riggs and E. H. Lennette (1978) Photochemical inactivation of DNA and RNA viruses by psoralen derivatives. J. Gen. Virol. 40, 345-358.
20. Isaacs, S. T., C. Shen, J. E. Hearst and H. Rapaport (1977) Synthesis and characterization of new psoralen derivatives with superior photoreactivity with DNA and RNA. Biochemistry 16, 1058-1064.
21. Gasparro, F. P. (1988) Psoralen DNA Pholobiology, Vols. 1 and 2. CRC Press, Boca Raton, FL.
22. Cimino, G. D., H. B. Gamper, S. T. Isaacs and J. E. Hearst (1985) Psoralens as photoreactive probes of nucleic acid structure and function: organic chemistry, photochemistry and biochemistry. Annu. Rev. Biochem. 54, 1151-1193.
23. Veronese, P. E., O. Schiavon, R. Bevilacqua, F. Bordin and G. Rodighiero (1982) Photoinactivation of enzymes by linear and angular furocoumarins. Photochem. Photobiol. 36, 25-30.
24. Nielsen, P. E. and V. Bohr (1983) Phototoxic effects of four psoralens on L1210 cells: the correlation with DNA interstrand cross-linking. Photochem. Photobiol. 38, 653-657.
25. Rodighiero, A., L. Musajo and F. Dall'Acqua (1970) Mechanism of skin photosensitization by furocoumarins: photoreactivity of various furocoumarins with native DNA and ribosomal RNA. Biochim. Biophys. Acta 217, 40-49.
26. Dall'Acqua, F., S. Marciani and G. Rodighiero (1969) Photoreactivity (3655 Angstrom) of various skin-photosensitizing furocoumarins with nucleic acids. Z. Naturforsch. B 24, 307-314.
27. Auerbeck, D. (1989) Recent advances in psoralen phototoxicity mechanism. Photochem. Photobiol. 50, 859-882.
28. Altamirano-Dimas, M., J. B. Hudson and G. H. N. Towers (1986) Induction of cross-links in viral DNA by naturally occurring photosensitizers. Photochem. Photobiol. 44, 187-192.
29. Suzuki, K., H. Fujita, F. Yanagisawa and M. Kitakami (1977) Action spectrum for the photoinactivation of lambda and T4 bacteriophages sensitized with 8-methoxypsoralen. Photochem. Photobiol. 26, 49-51.
30. Midden, W. R. (1988) Chemical mechanisms of the bioeffects of furocoumarins: the role of reactions with proteins, lipids, and other cellular components. In Psoraen DNA Photobiology, Vol. 2. (Edited by F. P. Gasparro), pp. 1-50. CRC Press, Boca Raton, FL.
31. Margolis-Nunno, H., B. Williams, S. Rywkin, N. Geacintov and B. Horowitz (1992) Virus sterilization in platelet concentrates with psoralen and ultraviolet A light in the presence of quenchers. Transfusion 32, 541-547.
32. Saroj, R., C. Kasturi, J. Grayzar, M. S. Platz, R. P. Goodrich, N. R. Yerram, V. Wong and B. H. Tay-Goodrich (1993) Dramatic improvements in viral inactivation with brominated psoralens, naphthalenes and anthracenes. Photochem. Photobiol. 58, 59-65.
33. Goodrich, R. P., N. R. Yerram, B. H. Tay-Goodrich, P. Forster, M. S. Platz, C. Kasturi, S. C. Park, J. N. Aebischer and S. Rai (1994) Selective inactivation of viruses in the presence of human platelets: UV sensitization with a new class of psoralen sensitizers. Proc. Natl. Acad. Sci. USA 91, 5552-5556.
34. Mindich, L. (1988) Bacteriophage Φ6: a unique virus having a lipid-containing membrane and a genome composed of three ds RNA segments. Adv. Virus Res. 35, 137-176.
35. Platz, M. S., S. C. Park, C. Kasturi, S. Rai, J. N. Aebischer, T. Chen, L. Kulaga, R. P. Goodrich, N. Yerram, P. Forster, T. Goodrich, S. Coker and S. Crandall (In press) In Design and Development of Selective Viral Inactivation Senstizers for Sterilization of Blood Products (Edited by F. Sieber). CRC Press, Boca Raton, FL.
36. Armitage, W. J., N. Parmar and C. J, Hunt (1985) The effects of osmotic stress on human platelets. J, Cell. Physiol. 123, 241-248.
37. Martin, R. F. and D. P. Kelly (1979) Synthesis and NMR spectra of substituted amino iodo acridines. Aust. J. Chem. 32, 2637-2646.
38. Muller, W. and D. M. Crothers (1975) Direct evidence for intercalation and nucleic acid sequence preferences. Eur. J. Biochem. 54, 267-277.
39. Reinhardt, C. G. and T. R. Krugh (1978) A comparative study of ethidium bromide complexes with dinucleotides and DNA. Biochemistry 17, 4845-4854.
40. Schmechel, D. E. V. and D. M. Crothers (1971) Interactions of heteroaromatic compounds with nucleic acids. Biopolymers 10, 465-480.
41. Hansen, J, B., T. Koch, O. Buchardt, P. E. Nielsen, M. Wirth and B. Norden (1983) Acridine-psoralenamines and their interaction with deoxyribonucleic acid. Biochemistry 22, 4878-4886.
42. Sambrook, J., E. F. Fritsch and T. Maniatis (1989) Molecular Cloning, A Laboratory Manual, 2nd ed. Vol. 1, Ch. 2. Cold Spring Harbor Laboratory Press, Plainview, NY.
43. Oster, G. (1951) Fluorescence quenching by nucleic acids. Trans. Faraday Soc. 47, 660-666.
44. Saenger, W. (1984) Principles of Nucleic Acid Structure. Springer-Verlag, New York.
45. Adams, R. L. P., J. T. Knowler and D. P. Leader (1992) The Biochemistry of the Nucleic Acids, 11th ed. Chapman & Hall, London.
46. Sobell, H. M. (1980) Structural and dynamic aspects of drug intercalation into DNA and RNA. In Nucleic Acid Geometry and Dynamics (Edited by R. H. Sarma), pp. 289-323. Pergamon Press, Elmsford.
47. Lerman, L. S. (1961) Structural considerations in the interaction of DNA and acridines. J. Mol. Biol. 3, 18-30.
48. Brenner, L., L. Barnett, F. H. C. Crick and A. Orgel (1961) The theory of mutagenesis. J. Mol Biol. 3, 121-124.
49. Reuben, J., B. M. Baker and N. R. Kallenbach (1978) Structure of mutagenic nucleic acid complexes in solution. Proton chemical shifts in 9-aminoacridine complexes with dG-dC, dC-dG, and dA-dT-dC-dA-dT. Biochemistry 17, 2915-2919.
50. Seeman, N. C., R. O. Day and A. Rich (1975) Nucleic acidmutagen interactions: crystal structure of adenylyl-3′,5′-uridine plus 9-amino acridine. Nature (Land.) 253, 324-326.
51. Arnolt, S., D. W. L. Hukins, S. D. Dover, W. Fuller and A. R. Hodgson (1973) Structure of synthetic polynucleotides in the A-RNA and AShlashed c sign-RNA conformations; x-ray diffraction analyses of the molecular conformations of polyadenylic acid-polyuridylic acid and polyinosinic acid-polycytidylic acid. J. Mol. Biol. 81, 107-122.
52. Neidle, S., A. Achari, G. L. Taylor, H. M. Berman, H. L. Carrell, J. P. Glusker and W. C. Stallings (1977) Structure of a dinucleoside phosphate-drug complex as model for nucleic acid-drug interaction. Nature 269, 304-307.
53. T) and the melting transition of the complex. Biopolymers 16, 2739-2754.
54. Brandt, K. G., A. Himoe and G. P. Hess (1966) Determination of the binding constant of a specific ester and a specific amide substrate to α-chymotrypsin. Biochem. Biophys. Res. Commun. 22, 447-453.
55. Glazer, A. N. (1965) Spectral studies of the interaction of α-chymotrypsin and trypsin with proflavine. Proc. Nail. Acad. Sci. USA 54, 171-176.
56. Himoe, A., K. G. Brandt and G. P. Hess (1967) Investigations of the chymotrypsin-catalyzed hydrolysis of specific substrates. J. Biol. Chem. 242, 3963-3972.
57. Brandt, K. G., A. Himoe and G. P. Hess (1967) Investigations of the chymotrypsin-catalyzed hydrolysis of specific substrates. J. Biol. Chem. 242, 3973-3982.
58. - and OH adducts. Chem. Rev. 89, 503-520.
59. Jovanovic, S. V. and M. T. Simic (1986) One-electron redox potentials of purines and pyridine. J. Phys. Chem. 90, 974-978.
60. Kittler, L., G. Lober, F. A. Gollmick and H. Berg (1980) Redox processes during photodynamic damage of DNA III, redox mechanism of photosensitization and radical reaction. Bioelectrochem. Bioenerg. 7, 503-511.
61. Dunn, D. A., V. H. Lin and I. E. Kochevar (1992) Base-selective oxidation and cleavage of DNA by photochemical co-sensitized electron transfer. Biochemistry 31, 11620-11625.
62. Steenken, S., J. P. Telo, H. M. Novais and L. P. Candeias (1992) One-electron-reduction potentials of pyrimidine bases, nucleosides and nucleotides in aqueous solution. Consequences for DNA redox chemistry. J. Am. Chem. Soc. 114, 4701-4709.
63. Scholes, G. (1976) In Photochemistry and Photobiology of Nucleic Acids, Vol. 1 (Edited by S. Y. Wang), pp. 521-578. Academic Press, New York.
64. Stern and Volmer (1919) Uber die Abklingungszeit der Fluoreszenz. Physik Z. 20, 183-188.
65. Rehm, D. and A. Weller (1970) Bindungszustand und Fluoreszenspektren von Hetero-Excimeren. Z. Phys. Chem. (NF) 69, 183-200.
66. Freeman, P. K., J.-S. Jang and N. Ramnath (1991) The photochemistry of polyhaloarenes. J. Org. Chem. 56, 6072-6079 (and previous papers in the series).
67. Haselbach, E., Y. Rohmer and P. Suppan (1990) Photodissociation of halonaphthalenes in solution: comparative photochemistry of 1-iodo, 1-bromo and 1-chloronaphthalenes. Helv. Chem. Acta 73, 1-9.
68. Nagamura, T., T. Nakayama and K. Hamanoue (1991) Participation of the lowest excited singlet states of 9-bromoanthracene and 9,10-dibromoanthracene form their photochemical debrominations by amine (triethylamine or N,N-dimethylaniline) in acetonitrile. Chem. Lett., 2051-2054.
69. Symons, M. C. R. (1987) Application of electron spin resonance spectroscopy to study the effects of ionising radiation on DNA and DNA complexes. J. Chem. Soc. Faraday Trans. 1 83, 1-11.
70. Von Sonntag, C. (1987) The Chemical Basis of Radiation Biology, chapters 5-7. Taylor and Francis, London.
71. Von Sonntag, C., U. Hagen, A. Bopp-Schon and D. SchulteFrohlinde (1981) Radiation-induced strand breaks in DNA: chemical and enzymatic analysis of end groups and mechanistic aspects. Adv. Radiat. Biol. 9, 109-142.
72. Rabow, L. E., J. Stubbe and J. W. Kozarich (1990) Identification and quantitation of the lesion accompanying base release in bleomycin-mediated DNA degradation. J. Am. Chem, Soc. 112, 3196-3203.
73. Kozarich, J. W., L. Worth, Jr., B. L. Frank, D. F. Christner, D. E. Vanderwall and J. Stubbe (1989) Sequence-specific isotope effects on the cleavage of DNA by bleomycin. Science 245, 1396-1399.
74. Proskar, A. A., F. P. Gasparro and M. J. Peak (1993) Relaxation of supercoiled DNA by aminomethyltrimethylpsoralen and UV photons: action spectrum. Photochem. Photobiol. 57, 648-654.
75. Kagan, J., X. Chen, T. P. Wang and P. Forlot (1992) Psoralens cleave pBR322 DNA under ultraviolet radiation. Photochem. Photobiol. 56, 185-193.
76. Gasparro, F. P., W. A. Saffran, C. R. Cantor and R. L. Edelson (1984) Wavelength dependence for AMT crosslinking of pBR322 DNA. Photochem. Photobiol. 40, 215-219.
77. Freifelder, D. (1987) Microbial Genetics, 2nd ed., pp. 595-612. Jones and Bartlett Publishers, Boston.