메뉴 건너뛰기




Volumn 33, Issue 8, 2015, Pages 1653-1668

Molecular modeling and spectroscopic studies of semustine binding with DNA and its comparison with lomustine-DNA adduct formation

Author keywords

CD spectroscopy; Drug DNA interaction; FTIR spectroscopy; lomustine; molecular modeling; semustine

Indexed keywords

LOMUSTINE; SEMUSTINE; ALKYLATING AGENT; DNA; DNA ADDUCT;

EID: 84930571766     PISSN: 07391102     EISSN: 15380254     Source Type: Journal    
DOI: 10.1080/07391102.2014.968874     Document Type: Article
Times cited : (27)

References (73)
  • 1
    • 84884212050 scopus 로고    scopus 로고
    • Spectroscopic studies of the effects of anticancer drug mitoxantrone interaction with calf-thymus DNA
    • Agarwal, S., Jangir, D. K., & Mehrotra, R. (2013). Spectroscopic studies of the effects of anticancer drug mitoxantrone interaction with calf-thymus DNA. Journal of Photochemistry and Photobiology B: Biology, 120, 177-182.
    • (2013) Journal of Photochemistry and Photobiology B: Biology , vol.120 , pp. 177-182
    • Agarwal, S.1    Jangir, D.K.2    Mehrotra, R.3
  • 2
    • 84905493971 scopus 로고    scopus 로고
    • A structural insight into major groove directed binding of nitrosourea derivative nimustine with DNA: A spectroscopic study
    • Agarwal, S., Jangir, D. K., Mehrotra, R., Lohani, N., & Rajeswari, M. (2014). A structural insight into major groove directed binding of nitrosourea derivative nimustine with DNA: A spectroscopic study. PLoS ONE, 9, e104115.
    • (2014) PLoS ONE , vol.9 , pp. e104115
    • Agarwal, S.1    Jangir, D.K.2    Mehrotra, R.3    Lohani, N.4    Rajeswari, M.5
  • 4
    • 0037381880 scopus 로고    scopus 로고
    • A comparative study of DNA complexation with Mg(II) and Ca (II) in aqueous solution: Major and minor grooves bindings
    • Ahmad, R., Arakawa, H., & Tajmir-Riahi, H. (2003). A comparative study of DNA complexation with Mg(II) and Ca (II) in aqueous solution: Major and minor grooves bindings. Biophysical Journal, 84, 2460-2466.
    • (2003) Biophysical Journal , vol.84 , pp. 2460-2466
    • Ahmad, R.1    Arakawa, H.2    Tajmir-Riahi, H.3
  • 5
    • 79952478259 scopus 로고    scopus 로고
    • The contribution of entropy, enthalpy, and hydrophobic desolvation to cooperativity in repeat-protein folding
    • Aksel, T., Majumdar, A., & Barrick, D. (2011). The contribution of entropy, enthalpy, and hydrophobic desolvation to cooperativity in repeat-protein folding. Structure, 19, 349-360.
    • (2011) Structure , vol.19 , pp. 349-360
    • Aksel, T.1    Majumdar, A.2    Barrick, D.3
  • 6
    • 45349110886 scopus 로고
    • FT-IR and Raman investigation of cadmium binding by DNA
    • Alex, S., & Dupuis, P. (1989). FT-IR and Raman investigation of cadmium binding by DNA. Inorganica Chimica Acta, 157, 271-281.
    • (1989) Inorganica Chimica Acta , vol.157 , pp. 271-281
    • Alex, S.1    Dupuis, P.2
  • 7
    • 79959629729 scopus 로고    scopus 로고
    • Analysis of deoxyribonucleic acid interstrand cross-links induced by nitrosourea with high performance liquid chromatographyelectrospray ionization tandem mass spectrometry
    • Bai, B.-Q., Zhao, L.-J., & Zhong, R.-G. (2010). Analysis of deoxyribonucleic acid interstrand cross-links induced by nitrosourea with high performance liquid chromatographyelectrospray ionization tandem mass spectrometry. Chinese Journal of Analytical Chemistry, 4, 532-536.
    • (2010) Chinese Journal of Analytical Chemistry , vol.4 , pp. 532-536
    • Bai, B.-Q.1    Zhao, L.-J.2    Zhong, R.-G.3
  • 8
    • 79959652623 scopus 로고    scopus 로고
    • Quantification of meCCNU-induced dG-dC crosslinks in oligonucleotide duplexes by liquid chromatography/electrospray ionization tandem mass spectrometry
    • Bai, B., Zhao, L., & Zhong, R. (2011). Quantification of meCCNU-induced dG-dC crosslinks in oligonucleotide duplexes by liquid chromatography/electrospray ionization tandem mass spectrometry. Rapid Communications in Mass Spectrometry, 25, 2027-2034.
    • (2011) Rapid Communications in Mass Spectrometry , vol.25 , pp. 2027-2034
    • Bai, B.1    Zhao, L.2    Zhong, R.3
  • 10
    • 0038487374 scopus 로고    scopus 로고
    • A library of IR bands of nucleic acids in solution
    • Banyay, M., Sarkar, M., & Gräslund, A. (2003). A library of IR bands of nucleic acids in solution. Biophysical Chemistry, 104, 477-488.
    • (2003) Biophysical Chemistry , vol.104 , pp. 477-488
    • Banyay, M.1    Sarkar, M.2    Gräslund, A.3
  • 13
    • 0023356067 scopus 로고
    • CD of the li-salt of DNA in ethanol/water mixtures: Evidence for the B-to C-form transition in solution
    • Bokma, J. T., Curtis, W. J., & Blok, J. (1987). CD of the li-salt of DNA in ethanol/water mixtures: Evidence for the B-to C-form transition in solution. Biopolymers, 26, 893-909.
    • (1987) Biopolymers , vol.26 , pp. 893-909
    • Bokma, J.T.1    Curtis, W.J.2    Blok, J.3
  • 18
    • 0018785331 scopus 로고
    • Correlations between the duplex winding angle and the circular dichroism spectrum of calf thymus DNA
    • Chan, A., Kilkuskie, R., & Hanlon, S. (1979). Correlations between the duplex winding angle and the circular dichroism spectrum of calf thymus DNA. Biochemistry, 18, 84-91.
    • (1979) Biochemistry , vol.18 , pp. 84-91
    • Chan, A.1    Kilkuskie, R.2    Hanlon, S.3
  • 20
  • 21
    • 0028817155 scopus 로고
    • Validity of nucleic acid purities monitored by 260 nm/280 nm absorbance ratios
    • Glasel, J. (1995). Validity of nucleic acid purities monitored by 260 nm/280 nm absorbance ratios. BioTechniques, 18, 62-63.
    • (1995) BioTechniques , vol.18 , pp. 62-63
    • Glasel, J.1
  • 25
    • 0343167423 scopus 로고    scopus 로고
    • Drug-DNA recognition: Energetics and implications for design
    • Haq, I., & Ladbury, J. (2000). Drug-DNA recognition: energetics and implications for design. Journal of Molecular Recognition, 13, 188-197.
    • (2000) Journal of Molecular Recognition , vol.13 , pp. 188-197
    • Haq, I.1    Ladbury, J.2
  • 26
    • 0030868927 scopus 로고    scopus 로고
    • Mechanism of Action of Fotemustine, a New Chloroethylnitrosourea Anticancer Agent: Evidence for the Formation of Two DNA-Reactive Intermediates Contributing to Cytotoxicity
    • Hayes, M. T., Bartley, J., Parsons, P. G., Eaglesham, G. K., & Prakash, A. S. (1997). Mechanism of Action of Fotemustine, a New Chloroethylnitrosourea Anticancer Agent: Evidence for the Formation of Two DNA-Reactive Intermediates Contributing to Cytotoxicity. Biochemistry, 36, 10646-10654.
    • (1997) Biochemistry , vol.36 , pp. 10646-10654
    • Hayes, M.T.1    Bartley, J.2    Parsons, P.G.3    Eaglesham, G.K.4    Prakash, A.S.5
  • 28
    • 77649221514 scopus 로고    scopus 로고
    • Inclusion of solvation and entropy in the knowledge-based scoring function for protein-ligand interactions
    • Huang, S.-Y., & Zou, X. (2010). Inclusion of solvation and entropy in the knowledge-based scoring function for protein-ligand interactions. Journal of Chemical Information and Modeling, 50, 262-273.
    • (2010) Journal of Chemical Information and Modeling , vol.50 , pp. 262-273
    • Huang, S.-Y.1    Zou, X.2
  • 32
    • 84880852086 scopus 로고    scopus 로고
    • Role of minor groove width and hydration pattern on amsacrine interaction with DNA
    • Jangir, D. K., Kundu, S., & Mehrotra, R. (2013). Role of minor groove width and hydration pattern on amsacrine interaction with DNA. PLoS ONE, 8, e69933.
    • (2013) PLoS ONE , vol.8 , pp. e69933
    • Jangir, D.K.1    Kundu, S.2    Mehrotra, R.3
  • 34
    • 23344443944 scopus 로고    scopus 로고
    • Unfolding of DNA quadruplexes induced by HIV-1 nucleocapsid protein
    • Kankia, B. I., Barany, G., & Musier-Forsyth, K. (2005). Unfolding of DNA quadruplexes induced by HIV-1 nucleocapsid protein. Nucleic Acids Research, 33, 4395-4403.
    • (2005) Nucleic Acids Research , vol.33 , pp. 4395-4403
    • Kankia, B.I.1    Barany, G.2    Musier-Forsyth, K.3
  • 35
  • 37
    • 84861047804 scopus 로고    scopus 로고
    • DNA-destabilizing agents as an alternative approach for targeting DNA: Mechanisms of action and cellular consequences
    • Lenglet, G., & David-Cordonnier, M.-H. (2010). DNA-destabilizing agents as an alternative approach for targeting DNA: Mechanisms of action and cellular consequences. Journal of Nucleic Acids, 2010, 1-17.
    • (2010) Journal of Nucleic Acids , vol.2010 , pp. 1-17
    • Lenglet, G.1    David-Cordonnier, M.-H.2
  • 39
    • 0027155363 scopus 로고
    • Conditions for the stability of the B, C, and Z structural forms of poly(dG-dC) in the presence of lithium, potassium, magnesium, calcium, and zinc cations
    • Loprete, D., & Hartman, K. (1993). Conditions for the stability of the B, C, and Z structural forms of poly(dG-dC) in the presence of lithium, potassium, magnesium, calcium, and zinc cations. Biochemistry, 32, 4077-4082.
    • (1993) Biochemistry , vol.32 , pp. 4077-4082
    • Loprete, D.1    Hartman, K.2
  • 40
    • 23544470464 scopus 로고
    • Interpretation of isosbestic points
    • Mayer, R. G., & Drago, R. S. (1976). Interpretation of isosbestic points. Inorganic Chemistry, 15, 2010-2011.
    • (1976) Inorganic Chemistry , vol.15 , pp. 2010-2011
    • Mayer, R.G.1    Drago, R.S.2
  • 41
    • 0015155662 scopus 로고
    • Cross-linking of DNA by alkylating agents and effects on DNA function in the chick embryo
    • McCann, J. J., Lo, T. M., & Webster, D. (1971). Cross-linking of DNA by alkylating agents and effects on DNA function in the chick embryo. Cancer Research, 31, 1573-1579.
    • (1971) Cancer Research , vol.31 , pp. 1573-1579
    • McCann, J.J.1    Lo, T.M.2    Webster, D.3
  • 43
    • 84891747568 scopus 로고    scopus 로고
    • Interaction studies of anticancer drug lomustine with calf thymus DNA using surface enhanced Raman spectroscopy
    • Mehrotra, R., Jangir, D., Agarwal, S., Ray, B., Singh, P., & Srivastava, A. K. (2013). Interaction studies of anticancer drug lomustine with calf thymus DNA using surface enhanced Raman spectroscopy. MAPAN, 28, 273-277.
    • (2013) MAPAN , vol.28 , pp. 273-277
    • Mehrotra, R.1    Jangir, D.2    Agarwal, S.3    Ray, B.4    Singh, P.5    Srivastava, A.K.6
  • 44
    • 0025241507 scopus 로고
    • Intra-arterial ACNU chemotherapy employing 20% mannitol osmotic blood-brain barrier disruption for malignant brain tumors
    • Miyagami, M., Tsubokawa, T., Tazoe, M., & Kagawa, Y. (1990). Intra-arterial ACNU chemotherapy employing 20% mannitol osmotic blood-brain barrier disruption for malignant brain tumors. Neurologia Medico-Chirurgica, 30, 582-590.
    • (1990) Neurologia Medico-Chirurgica , vol.30 , pp. 582-590
    • Miyagami, M.1    Tsubokawa, T.2    Tazoe, M.3    Kagawa, Y.4
  • 45
    • 84872337340 scopus 로고    scopus 로고
    • Helical structure and circular dichroism spectra of DNA: A theoretical study
    • Miyahara, T., Nakatsuji, H., & Sugiyama, H. (2012). Helical structure and circular dichroism spectra of DNA: A theoretical study. The Journal of Physical Chemistry A, 117, 42-55.
    • (2012) The Journal of Physical Chemistry A , vol.117 , pp. 42-55
    • Miyahara, T.1    Nakatsuji, H.2    Sugiyama, H.3
  • 49
    • 0025045171 scopus 로고
    • Mechanism of action of (2-haloethyl)nitrosoureas on DNA: Discrimination between alternative pathways of DNA base modification by 1,3-bis(2-fluoroethyl)-1-nitrosourea by using specific deuterium labeling and identification of reaction products by HPLC/tandem mass spectrometry
    • Naghipur, A., Ikonomou, M. G., Kebarle, P., & Lown, J. W. (1990). Mechanism of action of (2-haloethyl)nitrosoureas on DNA: discrimination between alternative pathways of DNA base modification by 1,3-bis(2-fluoroethyl)-1-nitrosourea by using specific deuterium labeling and identification of reaction products by HPLC/tandem mass spectrometry. Journal of the American Chemical Society, 112, 3178-3187.
    • (1990) Journal of the American Chemical Society , vol.112 , pp. 3178-3187
    • Naghipur, A.1    Ikonomou, M.G.2    Kebarle, P.3    Lown, J.W.4
  • 50
    • 79952202492 scopus 로고    scopus 로고
    • New approaches to drug-DNA interactions based on graphical representation and numerical characterization of DNA sequences
    • Nandy, A., & Basak, S. C. (2010). New approaches to drug-DNA interactions based on graphical representation and numerical characterization of DNA sequences. Current Computer-Aided Drug Design, 6, 283-289.
    • (2010) Current Computer-Aided Drug Design , vol.6 , pp. 283-289
    • Nandy, A.1    Basak, S.C.2
  • 53
    • 0034326348 scopus 로고    scopus 로고
    • Conformation of oligodeoxynucleotides associated with anionic liposomes
    • Patil, S. D., & Rhodes, D. G. (2000). Conformation of oligodeoxynucleotides associated with anionic liposomes. Nucleic Acids Research, 28, 4125-4129.
    • (2000) Nucleic Acids Research , vol.28 , pp. 4125-4129
    • Patil, S.D.1    Rhodes, D.G.2
  • 55
    • 0022127735 scopus 로고
    • Counterions which favour the C form of DNA
    • Portugal, J., & Subirana, J. (1985). Counterions which favour the C form of DNA. The EMBO journal, 4, 2403-2408.
    • (1985) The EMBO Journal , vol.4 , pp. 2403-2408
    • Portugal, J.1    Subirana, J.2
  • 58
    • 0033397980 scopus 로고    scopus 로고
    • Python: A programming language for software integration and development
    • Sanner, M. F. (1999). Python: A programming language for software integration and development. Journal of Molecular Graphics and Modelling, 17, 57-61.
    • (1999) Journal of Molecular Graphics and Modelling , vol.17 , pp. 57-61
    • Sanner, M.F.1
  • 59
    • 0017143803 scopus 로고
    • Nitrosoureas: A review of experimental antitumor activity
    • Schabel, F., Jr (1976). Nitrosoureas: A review of experimental antitumor activity. Cancer Treatment Reports, 60, 665-698.
    • (1976) Cancer Treatment Reports , vol.60 , pp. 665-698
    • Schabel, F.1
  • 60
    • 0025062053 scopus 로고
    • The mechanism of action of the nitrosourea anti-tumor drugs on thioredoxin reductase, glutathione reductase and ribonucleotide reductase
    • Schallreuter, K. U., Gleason, F. K., & Wood, J. M. (1990). The mechanism of action of the nitrosourea anti-tumor drugs on thioredoxin reductase, glutathione reductase and ribonucleotide reductase. Biochimica et Biophysica Acta (BBA)- Molecular Cell Research, 1054, 14-20.
    • (1990) Biochimica et Biophysica Acta (BBA)- Molecular Cell Research , vol.1054 , pp. 14-20
    • Schallreuter, K.U.1    Gleason, F.K.2    Wood, J.M.3
  • 61
    • 84885855544 scopus 로고    scopus 로고
    • Prediction of noncovalent Drug/DNA interaction using computational docking models: Studies with over 1350 launched drugs
    • Snyder, R. D., Holt, P. A., Maguire, J. M., & Trent, J. O. (2013). Prediction of noncovalent Drug/DNA interaction using computational docking models: Studies with over 1350 launched drugs. Environmental and Molecular Mutagenesis, 54, 668-681.
    • (2013) Environmental and Molecular Mutagenesis , vol.54 , pp. 668-681
    • Snyder, R.D.1    Holt, P.A.2    Maguire, J.M.3    Trent, J.O.4
  • 62
    • 0030176923 scopus 로고    scopus 로고
    • The energetics of ligand binding at catecholamine receptors
    • Strange, P. G. (1996). The energetics of ligand binding at catecholamine receptors. Trends in Pharmacological Sciences, 17, 238-244.
    • (1996) Trends in Pharmacological Sciences , vol.17 , pp. 238-244
    • Strange, P.G.1
  • 64
    • 0020570090 scopus 로고
    • Mechanism of action of the nitrosoureas - V: Formation of O6-(2-fluoroethyl) guanine and its probable role in the crosslinking of deoxyribonucleic acid
    • Tong, W. P., Kirk, M. C., & Ludlum, D. B. (1983). Mechanism of action of the nitrosoureas - V: Formation of O6-(2-fluoroethyl) guanine and its probable role in the crosslinking of deoxyribonucleic acid. Biochemical Pharmacology, 32, 2011-2015.
    • (1983) Biochemical Pharmacology , vol.32 , pp. 2011-2015
    • Tong, W.P.1    Kirk, M.C.2    Ludlum, D.B.3
  • 65
    • 84858295925 scopus 로고    scopus 로고
    • Binding of an indole alkaloid, vinblastine to double stranded DNA: A spectroscopic insight in to nature and strength of interaction
    • Tyagi, G., Charak, S., & Mehrotra, R. (2012). Binding of an indole alkaloid, vinblastine to double stranded DNA: A spectroscopic insight in to nature and strength of interaction. Journal of Photochemistry and Photobiology B: Biology, 108, 48-52.
    • (2012) Journal of Photochemistry and Photobiology B: Biology , vol.108 , pp. 48-52
    • Tyagi, G.1    Charak, S.2    Mehrotra, R.3
  • 66
    • 77958554032 scopus 로고    scopus 로고
    • DNA Interaction Studies of an anticancer plant alkaloid, vincristine, using Fourier transform infrared spectroscopy
    • Tyagi, G., Jangir, D. K., Singh, P., & Mehrotra, R. (2010). DNA Interaction Studies of an anticancer plant alkaloid, vincristine, using Fourier transform infrared spectroscopy. DNA and Cell Biology, 29, 693-699.
    • (2010) DNA and Cell Biology , vol.29 , pp. 693-699
    • Tyagi, G.1    Jangir, D.K.2    Singh, P.3    Mehrotra, R.4
  • 69
    • 0037161985 scopus 로고    scopus 로고
    • Conformational transition of DNA induced by cationic lipid vesicle in acidic solution: Spectroscopy investigation
    • Zhang, Z., Huang, W., Tang, J., Wang, E., & Dong, S. (2002). Conformational transition of DNA induced by cationic lipid vesicle in acidic solution: spectroscopy investigation. Biophysical Chemistry, 97, 7-16.
    • (2002) Biophysical Chemistry , vol.97 , pp. 7-16
    • Zhang, Z.1    Huang, W.2    Tang, J.3    Wang, E.4    Dong, S.5
  • 70
    • 84901944745 scopus 로고    scopus 로고
    • Comparative investigation of the DNA inter-strand crosslinks induced by ACNU, BCNU, CCNU and FTMS using high-performance liquid chromatography-electrospray ionization tandem mass spectrometry
    • Zhao, L., Li, L., Xu, J., & Zhong, R. (2014). Comparative investigation of the DNA inter-strand crosslinks induced by ACNU, BCNU, CCNU and FTMS using high-performance liquid chromatography-electrospray ionization tandem mass spectrometry. International Journal of Mass Spectrometry, 368, 30-36.
    • (2014) International Journal of Mass Spectrometry , vol.368 , pp. 30-36
    • Zhao, L.1    Li, L.2    Xu, J.3    Zhong, R.4
  • 71
    • 84901917609 scopus 로고    scopus 로고
    • Comparative investigations of deoxyribonucleic acid interstrand crosslinks induced by semustine using fluorescence and high performance liquid chromatography-mass spectrometry
    • Zhao, L.-J., Ren, T., Bai, B.-Q., Zhang, R., & Zhong, R.-G. (2011). Comparative investigations of deoxyribonucleic acid interstrand crosslinks induced by semustine using fluorescence and high performance liquid chromatography-mass spectrometry. Chinese Journal of Analytical Chemistry, 4, 476-480.
    • (2011) Chinese Journal of Analytical Chemistry , vol.4 , pp. 476-480
    • Zhao, L.-J.1    Ren, T.2    Bai, B.-Q.3    Zhang, R.4    Zhong, R.-G.5
  • 72
    • 34548453233 scopus 로고    scopus 로고
    • An ONIOM study on the crosslinked base pairs in DNA reacted with chloroethylnitrosoureas
    • Zhao, L., Zhong, R., & Zhen, Y. (2007). An ONIOM study on the crosslinked base pairs in DNA reacted with chloroethylnitrosoureas. Journal of Theoretical & Computational Chemistry, 6, 631-639.
    • (2007) Journal of Theoretical & Computational Chemistry , vol.6 , pp. 631-639
    • Zhao, L.1    Zhong, R.2    Zhen, Y.3
  • 73
    • 84902675104 scopus 로고    scopus 로고
    • Synthesis, structure and molecular docking studies of dicopper (ii) complexes bridged by N-phenolato-N′-[2-(dimethylamino) ethyl] oxamide: The influence of terminal ligands on cytotoxicity and reactivity towards DNA and protein BSA
    • Zheng, K., Liu, F., Xu, X.-M., Li, Y.-T., Wu, Z.-Y., & Yan, C.-W. (2014). Synthesis, structure and molecular docking studies of dicopper (ii) complexes bridged by N-phenolato-N′-[2-(dimethylamino) ethyl] oxamide: The influence of terminal ligands on cytotoxicity and reactivity towards DNA and protein BSA. New Journal of Chemistry, 38, 2964-2978.
    • (2014) New Journal of Chemistry , vol.38 , pp. 2964-2978
    • Zheng, K.1    Liu, F.2    Xu, X.-M.3    Li, Y.-T.4    Wu, Z.-Y.5    Yan, C.-W.6


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.