메뉴 건너뛰기




Volumn 3, Issue 4, 1997, Pages 307-316

Interaction of doxorubicin and its derivatives with DNA: Elucidation by resonance Raman and surface-enhanced resonance Raman spectroscopy

Author keywords

Doxorubicin; Intercalation; Resonance Raman; SERRS

Indexed keywords


EID: 0000313917     PISSN: 10754261     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1520-6343(1997)3:4<307::AID-BSPY6>3.0.CO;2-0     Document Type: Article
Times cited : (40)

References (44)
  • 4
    • 0023934383 scopus 로고
    • Quantitative study of doxorubicin in living cell nuclei by microspectrofluorometry
    • M. Gigli, S. M. Doglia, J. M. Millot, L. Valentini, and M. Manfait, "Quantitative study of doxorubicin in living cell nuclei by microspectrofluorometry," Biochim. Biophys. Acta, 950, 13-20 (1988).
    • (1988) Biochim. Biophys. Acta , vol.950 , pp. 13-20
    • Gigli, M.1    Doglia, S.M.2    Millot, J.M.3    Valentini, L.4    Manfait, M.5
  • 5
    • 0025037693 scopus 로고
    • Sequence-selective topoisomerase II inhibition by anthracycline derivatives in SV40 DNA: Relationship with DNA binding affinity and cytoxicity
    • G. Capranico, F. Zunino, K. Kohn, and Y. Pommier, "Sequence-selective topoisomerase II inhibition by anthracycline derivatives in SV40 DNA: relationship with DNA binding affinity and cytoxicity," Biochemistry, 29, 562-569 (1990).
    • (1990) Biochemistry , vol.29 , pp. 562-569
    • Capranico, G.1    Zunino, F.2    Kohn, K.3    Pommier, Y.4
  • 6
    • 13044274590 scopus 로고
    • Antitumor active drugs as intercalators of deoxyribonucleic acid
    • U. Pindur, M. Haber, and K. Sattler, "Antitumor active drugs as intercalators of deoxyribonucleic acid," J. Chem. Educ., 70, 263-272 (1993).
    • (1993) J. Chem. Educ. , vol.70 , pp. 263-272
    • Pindur, U.1    Haber, M.2    Sattler, K.3
  • 8
    • 0023182937 scopus 로고
    • 5-Iminodaunomycin: An anthracycline with unique properties
    • C. E. Myers, J. R. F. Muindi, J. Zweier, and B. K. Sinha, "5-Iminodaunomycin: an anthracycline with unique properties," J. Biol. Chem., 262, 11571-11577 (1987).
    • (1987) J. Biol. Chem. , vol.262 , pp. 11571-11577
    • Myers, C.E.1    Muindi, J.R.F.2    Zweier, J.3    Sinha, B.K.4
  • 9
    • 0018201228 scopus 로고
    • Doxorubicin and related anthracycline antibiotics
    • J. R. Brown, "Doxorubicin and related anthracycline antibiotics," Progr. Med. Chem., 15, 125-136 (1978).
    • (1978) Progr. Med. Chem. , vol.15 , pp. 125-136
    • Brown, J.R.1
  • 10
    • 0002246510 scopus 로고
    • The biochemical basis of anthracycline toxicity and antitumor activity
    • ed. by E. Hodgson, J. R. Bend and R. M. Philpot, Elsevier Scientific Publishing Co., New York
    • L. Gianni, B. J. Croden, amd C. E. Myers, "The biochemical basis of anthracycline toxicity and antitumor activity," in Reviews in Biochemical Toxicology, Vol. 5, ed. by E. Hodgson, J. R. Bend and R. M. Philpot, Elsevier Scientific Publishing Co., New York, 1983, pp. 1-82.
    • (1983) Reviews in Biochemical Toxicology , vol.5 , pp. 1-82
    • Gianni, L.1    Croden, B.J.2    Myers, C.E.3
  • 11
    • 0001929802 scopus 로고
    • Daunomycin and doxorubicin and structral analogues: Biological activity and mechanism of action
    • ed. by J. W. Corcoran and F. E. Hahn, Springer-Verlag, Berlin
    • A. DiMarco, F. Arcamone, and F. Zunino, "Daunomycin and doxorubicin and structral analogues: biological activity and mechanism of action," in Antibiotics, ed. by J. W. Corcoran and F. E. Hahn, Springer-Verlag, Berlin, 1974, pp. 101-128.
    • (1974) Antibiotics , pp. 101-128
    • DiMarco, A.1    Arcamone, F.2    Zunino, F.3
  • 12
    • 33748633401 scopus 로고
    • Biological effects of deamination at C-3N. Evaluation of 3N-hydroxy-doxorubicin (Hydroxyrubicin)
    • W. Priebe, N. T. Van, and R. Perez-Soler, "Biological effects of deamination at C-3N. Evaluation of 3N-hydroxy-doxorubicin (Hydroxyrubicin)," J. Cancer Res. Clin. Oncol., 116 (Suppl., Part I), 439 (1990).
    • (1990) J. Cancer Res. Clin. Oncol. , vol.116 , Issue.1 SUPPL. AND PART , pp. 439
    • Priebe, W.1    Van, N.T.2    Perez-Soler, R.3
  • 13
    • 0025336851 scopus 로고
    • 3N-Hydroxyesorubicin. Synthesis and antitumor activity
    • W. Priebe, N. Neamati, and R. Perez-Soler, "3N-Hydroxyesorubicin. Synthesis and antitumor activity," J. Antibiot., 43, 838-846 (1990).
    • (1990) J. Antibiot. , vol.43 , pp. 838-846
    • Priebe, W.1    Neamati, N.2    Perez-Soler, R.3
  • 14
    • 0025829055 scopus 로고
    • A facile method for preparation of 3-thio-sugars and 3-thio-glycols. Synthesis of 3N-mercapto-3N-deamino-doxorubicin
    • W. Priebe, G. Grynkiewicz, N. Neamati, and R. Perez-Soler, "A facile method for preparation of 3-thio-sugars and 3-thio-glycols. Synthesis of 3N-mercapto-3N-deamino-doxorubicin," Tetrahedron Lett., 32, 3313-3316 (1991).
    • (1991) Tetrahedron Lett. , vol.32 , pp. 3313-3316
    • Priebe, W.1    Grynkiewicz, G.2    Neamati, N.3    Perez-Soler, R.4
  • 15
    • 0026581010 scopus 로고
    • 3N-Hydroxy-esorubicin halogenated at C-2N
    • W. Priebe, N. Neamati, and R. Perez-Soler, "3N-Hydroxy-esorubicin halogenated at C-2N," J. Antibiot., 45, 386-393 (1992).
    • (1992) J. Antibiot. , vol.45 , pp. 386-393
    • Priebe, W.1    Neamati, N.2    Perez-Soler, R.3
  • 16
    • 0027397433 scopus 로고
    • Removal of the basic center from doxorubicin partially overcomes multidrug resistance and decreases cardiotoxicity
    • W. Priebe, N. T. Van, T. G. Burke, and R. Perez-Soler, "Removal of the basic center from doxorubicin partially overcomes multidrug resistance and decreases cardiotoxicity," Anti-Cancer Drugs, 4, 37-48 (1993).
    • (1993) Anti-Cancer Drugs , vol.4 , pp. 37-48
    • Priebe, W.1    Van, N.T.2    Burke, T.G.3    Perez-Soler, R.4
  • 17
    • 0027892892 scopus 로고
    • Design and tumor targeting of anthracyclines able to overcome multi-drug resistance: A double-advantage approach
    • W. Priebe, and R. Perez-Soler, "Design and tumor targeting of anthracyclines able to overcome multi-drug resistance: a double-advantage approach," Pharmacol. Ther., 60, 215-324, (1993).
    • (1993) Pharmacol. Ther. , vol.60 , pp. 215-324
    • Priebe, W.1    Perez-Soler, R.2
  • 18
    • 0003434635 scopus 로고
    • Non-cross-resitant anthracyclines with reduced basicity and increased stability of the glycosidic bond
    • ed. by W. Priebe, American Chemical Society, Washington, DC
    • W. Priebe, P. Skibicki, and O. Varela, "Non-cross-resitant anthracyclines with reduced basicity and increased stability of the glycosidic bond," in Antracycline Antibiotics. Novel Analogues, Methods of Delivery, and Mechanisms of Action, ed. by W. Priebe, American Chemical Society, Washington, DC, 1995, pp. 14-46.
    • (1995) Antracycline Antibiotics. Novel Analogues, Methods of Delivery, and Mechanisms of Action , pp. 14-46
    • Priebe, W.1    Skibicki, P.2    Varela, O.3
  • 19
    • 0002548608 scopus 로고
    • Mechanism of action-governed design of anthracycline antibiotics: A 'turn-off/turn-on' approach
    • W. Priebe, "Mechanism of action-governed design of anthracycline antibiotics: a 'turn-off/turn-on' approach," Curr. Pharmac. Design, 1, 51-68 (1995).
    • (1995) Curr. Pharmac. Design , vol.1 , pp. 51-68
    • Priebe, W.1
  • 21
    • 0002427030 scopus 로고
    • The interaction of daunomycin and doxorubicin with nucleic acids
    • ed. by S. Neidle and M. J. Waring, MacMillan Press, London
    • S. Neidle and M. R. Sanderson, "The interaction of daunomycin and doxorubicin with nucleic acids," in Molecular Aspects of Anti-cancer Drug DNA Action, ed. by S. Neidle and M. J. Waring, MacMillan Press, London, 1983, pp. 35-55.
    • (1983) Molecular Aspects of Anti-cancer Drug DNA Action , pp. 35-55
    • Neidle, S.1    Sanderson, M.R.2
  • 22
    • 0019309966 scopus 로고
    • Predicted mode of intercalation of doxorubicin with dinucleotide dimers
    • Y. Nakata and A. J. Hopfinger, "Predicted mode of intercalation of doxorubicin with dinucleotide dimers," Biochem. Biophys. Res. Commun., 95, 583-588 (1980).
    • (1980) Biochem. Biophys. Res. Commun. , vol.95 , pp. 583-588
    • Nakata, Y.1    Hopfinger, A.J.2
  • 23
    • 0022339618 scopus 로고
    • A theoretical investigation on the sequence selective binding of daunomycin to double-stranded polynucleotides
    • K.-X. Chen, N. Gresh, and B. Pullman, "A theoretical investigation on the sequence selective binding of daunomycin to double-stranded polynucleotides," J. Biomol. Struct. Dynam., 3, 445-466 (1985).
    • (1985) J. Biomol. Struct. Dynam. , vol.3 , pp. 445-466
    • Chen, K.-X.1    Gresh, N.2    Pullman, B.3
  • 24
    • 0003889369 scopus 로고
    • Drug-nucleic acid interactions
    • ed. by R. J. H. Clark and R. E. Hester, John Wiley & Sons Ltd., Chichester
    • M. Manfait and T. Theophanides, "Drug-nucleic acid interactions," in Spectroscopy of Biological Systems, ed. by R. J. H. Clark and R. E. Hester, John Wiley & Sons Ltd., Chichester, 1986, pp. 311-346.
    • (1986) Spectroscopy of Biological Systems , pp. 311-346
    • Manfait, M.1    Theophanides, T.2
  • 25
    • 33845373659 scopus 로고
    • Surface-enhanced resonance Raman spectra of doxorubicin, 11-deoxycarminomycin, their model chromophores, and their complexes with DNA
    • G. Smulevich and A. Feis, "Surface-enhanced resonance Raman spectra of doxorubicin, 11-deoxycarminomycin, their model chromophores, and their complexes with DNA," J. Phys. Chem., 90, 6388-6392 (1986).
    • (1986) J. Phys. Chem. , vol.90 , pp. 6388-6392
    • Smulevich, G.1    Feis, A.2
  • 26
    • 0000612904 scopus 로고
    • Surface-enhanced Raman spectroscopy and its biomedical applications
    • ed. by R. J. H. Clark and R. E. Hester, John Wiley & Sons Ltd., Chichester
    • I. R. Nabiev, K. V. Sokolov, and M. Manfait, "Surface-enhanced Raman spectroscopy and its biomedical applications," in Biomolecular Spectroscopy, Part A, ed. by R. J. H. Clark and R. E. Hester, John Wiley & Sons Ltd., Chichester, 1993, pp. 267-338.
    • (1993) Biomolecular Spectroscopy , Issue.PART A , pp. 267-338
    • Nabiev, I.R.1    Sokolov, K.V.2    Manfait, M.3
  • 27
    • 0027517775 scopus 로고
    • Molecular and cellular interactions between intoplicine, DNA, and topoisomerase II studied by surface-enhanced Raman scattering spectroscopy
    • H. Morjani, J.-F. Riou, I. R. Nabiev, F. Lavelle, and M. Manfait, "Molecular and cellular interactions between intoplicine, DNA, and topoisomerase II studied by surface-enhanced Raman scattering spectroscopy," Cancer Res., 53, 4784-4790 (1993).
    • (1993) Cancer Res. , vol.53 , pp. 4784-4790
    • Morjani, H.1    Riou, J.-F.2    Nabiev, I.R.3    Lavelle, F.4    Manfait, M.5
  • 28
    • 0000540549 scopus 로고
    • Comparative studies of antitumor DNA intercalating agents, aclacinomycin and saintopin, by means of surface-enhanced Raman scattering spectroscopy
    • I. R. Nabiev, I. Chourpa, and M. Manfait, "Comparative studies of antitumor DNA intercalating agents, aclacinomycin and saintopin, by means of surface-enhanced Raman scattering spectroscopy," J. Phys. Chem., 98, 1344-1350 (1994).
    • (1994) J. Phys. Chem. , vol.98 , pp. 1344-1350
    • Nabiev, I.R.1    Chourpa, I.2    Manfait, M.3
  • 29
    • 0021220264 scopus 로고
    • Synthesis and antitumor activity of 3N-deamino-3N-hydroxydoxorubicin. A facile procedure for the preparation of doxorubicin analogs
    • D. Horton, W. Priebe, and O. Varela, "Synthesis and antitumor activity of 3N-deamino-3N-hydroxydoxorubicin. A facile procedure for the preparation of doxorubicin analogs," J. Antibiot., 37, 853-858 (1984).
    • (1984) J. Antibiot. , vol.37 , pp. 853-858
    • Horton, D.1    Priebe, W.2    Varela, O.3
  • 30
    • 0020452657 scopus 로고
    • Studies on the interaction of anthracycline antibiotics and DNA: Equilibrium binding studies
    • J. B. Chaires, N. Datagupta, and D. M. Crothers, "Studies on the interaction of anthracycline antibiotics and DNA: equilibrium binding studies," Biochemistry, 21, 3933-3940 (1982).
    • (1982) Biochemistry , vol.21 , pp. 3933-3940
    • Chaires, J.B.1    Datagupta, N.2    Crothers, D.M.3
  • 31
    • 2842588851 scopus 로고
    • Adsorption and surface-enhanced Raman of dyes on silver and gold sols
    • P. C. Lee, and D. J. Meisel, "Adsorption and surface-enhanced Raman of dyes on silver and gold sols," J. Phys. Chem., 86, 3391-3395 (1982).
    • (1982) J. Phys. Chem. , vol.86 , pp. 3391-3395
    • Lee, P.C.1    Meisel, D.J.2
  • 32
    • 0006855494 scopus 로고
    • Spinning cell for low temperature resonance Raman spectra without Dewar losses
    • M. A. Walters, "Spinning cell for low temperature resonance Raman spectra without Dewar losses," Appl. Spectrosc., 37, 299-302 (1983).
    • (1983) Appl. Spectrosc. , vol.37 , pp. 299-302
    • Walters, M.A.1
  • 33
    • 0002720372 scopus 로고
    • Resonance and preresonance Raman spectra of the antitumor drugs doxorubicin and daunorubicin
    • M. Manfait, L. Bernard, and T. Theophanides, "Resonance and preresonance Raman spectra of the antitumor drugs doxorubicin and daunorubicin," J. Raman Spectrosc., 11, 68-74 (1981).
    • (1981) J. Raman Spectrosc. , vol.11 , pp. 68-74
    • Manfait, M.1    Bernard, L.2    Theophanides, T.3
  • 34
    • 4243628165 scopus 로고
    • Absorption, fluorescence and resonance Raman spectra of doxorubicin and its complex with DNA
    • L. Angeloni, G. Smulevich, and M. P. Marzocchi, "Absorption, fluorescence and resonance Raman spectra of doxorubicin and its complex with DNA," Spectrochim. Acta, 38, 213-217, (1982).
    • (1982) Spectrochim. Acta , vol.38 , pp. 213-217
    • Angeloni, L.1    Smulevich, G.2    Marzocchi, M.P.3
  • 35
    • 84988148225 scopus 로고
    • Comparative study of aclacinomycin versus doxorubicin by means of resonance Raman spectroscopy
    • Y. Nonaka, M. Tsuboi, and K. Nakamoto, "Comparative study of aclacinomycin versus doxorubicin by means of resonance Raman spectroscopy," J. Raman Spectrosc., 21, 133-141 (1990).
    • (1990) J. Raman Spectrosc. , vol.21 , pp. 133-141
    • Nonaka, Y.1    Tsuboi, M.2    Nakamoto, K.3
  • 36
    • 0023701603 scopus 로고
    • On the interaction of daunomycin with synthetic alternating DNAs: Sequence specificity and polyelectrolyte effects on the intercalation equilibrium
    • L. E. Xodo, G. Manzini, J. Ruggiero, and F. Quadrifoflio, "On the interaction of daunomycin with synthetic alternating DNAs: sequence specificity and polyelectrolyte effects on the intercalation equilibrium," Biopolymers, 27, 1839-1857 (1988).
    • (1988) Biopolymers , vol.27 , pp. 1839-1857
    • Xodo, L.E.1    Manzini, G.2    Ruggiero, J.3    Quadrifoflio, F.4
  • 37
    • 0007739989 scopus 로고
    • Structure of molecular complexes of copper uroporphyrin with aromatic heterocycles
    • J. A. Shelnutt, "Structure of molecular complexes of copper uroporphyrin with aromatic heterocycles," J. Am. Chem. Soc., 103, 4275-4277 (1981).
    • (1981) J. Am. Chem. Soc. , vol.103 , pp. 4275-4277
    • Shelnutt, J.A.1
  • 38
    • 0001567089 scopus 로고
    • Molecular complexes of copper uroporphyrin with aromatic acceptors
    • J. A.Shelnutt, "Molecular complexes of copper uroporphyrin with aromatic acceptors," J. Phys. Chem., 87, 605-616 (1983).
    • (1983) J. Phys. Chem. , vol.87 , pp. 605-616
    • Shelnutt, J.A.1
  • 41
    • 0001152547 scopus 로고
    • Spectroscopic analysis of the binding of doxorubicin to human α-1 acid glycoprotein
    • N. Husain, R. A. Agbaria, and I. M. Warner, "Spectroscopic analysis of the binding of doxorubicin to human α-1 acid glycoprotein," J. Phys. Chem., 97, 10857-10861 (1993).
    • (1993) J. Phys. Chem. , vol.97 , pp. 10857-10861
    • Husain, N.1    Agbaria, R.A.2    Warner, I.M.3
  • 42
    • 0001797992 scopus 로고
    • Surface enhanced Raman scattering of biomolecules
    • E. Koglin, and J.-M. L. Sequaris, "Surface enhanced Raman scattering of biomolecules," Top. Curr. Chem., 134, 1-57 (1986).
    • (1986) Top. Curr. Chem. , vol.134 , pp. 1-57
    • Koglin, E.1    Sequaris, J.-M.L.2
  • 43
    • 0027295656 scopus 로고
    • Dissection of the free energy of anthracycline antibiotic binding to DNA: Electrostatic contributions
    • J. B. Chaires, W. Priebe, D. E. Graves, and T. G. Burke, "Dissection of the free energy of anthracycline antibiotic binding to DNA: electrostatic contributions," J. Am. Chem. Soc., 115, 5360-5371 (1993).
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 5360-5371
    • Chaires, J.B.1    Priebe, W.2    Graves, D.E.3    Burke, T.G.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.