메뉴 건너뛰기




Volumn 45, Issue 30, 2006, Pages 9145-9155

Influence of base stacking and hydrogen bonding on the fluorescence of 2-aminopurine and pyrrolocytosine in nucleic acids

Author keywords

[No Author keywords available]

Indexed keywords

AMINES; FLUORESCENCE; HYDROGEN BONDS; MOLECULAR STRUCTURE; QUENCHING;

EID: 33746601044     PISSN: 00062960     EISSN: None     Source Type: Journal    
DOI: 10.1021/bi060479t     Document Type: Article
Times cited : (75)

References (42)
  • 1
    • 0036308302 scopus 로고    scopus 로고
    • Fluorescent nucleotide base analogs as probes of nucleic acid structure, dynamics and interactions
    • Rist, M. J., and Marino, J. P. (2002) Fluorescent nucleotide base analogs as probes of nucleic acid structure, dynamics and interactions, Curr. Org. Chem. 6, 775-793.
    • (2002) Curr. Org. Chem. , vol.6 , pp. 775-793
    • Rist, M.J.1    Marino, J.P.2
  • 2
    • 0346905479 scopus 로고    scopus 로고
    • Evaluation of fluorescence spectroscopy methods for mapping melted regions of DNA along the transcription pathway
    • Martin, C. T., Újvári, A., and Liu, C. (2003) Evaluation of fluorescence spectroscopy methods for mapping melted regions of DNA along the transcription pathway, Methods Enzymol. 371, 13-33.
    • (2003) Methods Enzymol. , vol.371 , pp. 13-33
    • Martin, C.T.1    Újvári, A.2    Liu, C.3
  • 3
    • 14644433046 scopus 로고    scopus 로고
    • One-electron reduction of 2-aminopurine in the aqueous phase. A DFT and pulse radiolysis study
    • Reynisson, J., and Steenken, S. (2005) One-electron reduction of 2-aminopurine in the aqueous phase. A DFT and pulse radiolysis study, Phys. Chem. Chem. Phys. 7, 659-665.
    • (2005) Phys. Chem. Chem. Phys. , vol.7 , pp. 659-665
    • Reynisson, J.1    Steenken, S.2
  • 4
    • 23244461855 scopus 로고    scopus 로고
    • Ultrafast unequilibrated charge transfer: A new channel in the quenching of fluorescent biological probes
    • Wan, C., Xia, T., Becker, H.-C., and Zewail, A. H. (2005) Ultrafast unequilibrated charge transfer: A new channel in the quenching of fluorescent biological probes, Chem. Phys. Lett. 412, 158-163.
    • (2005) Chem. Phys. Lett. , vol.412 , pp. 158-163
    • Wan, C.1    Xia, T.2    Becker, H.-C.3    Zewail, A.H.4
  • 5
    • 11444261395 scopus 로고    scopus 로고
    • Fluorescence quenching of 2-aminopurine in dinucleotides
    • Somsen, O. J. G., van Hoek, A., and van Amerongen, H. (2005) Fluorescence quenching of 2-aminopurine in dinucleotides, Chem. Phys. Lett. 402, 61-65.
    • (2005) Chem. Phys. Lett. , vol.402 , pp. 61-65
    • Somsen, O.J.G.1    Van Hoek, A.2    Van Amerongen, H.3
  • 6
    • 3543088541 scopus 로고    scopus 로고
    • Stacking-unstacking dynamics of oligodeoxynucleotide trimers
    • Jean, J. M., and Hall, K. B. (2004) Stacking-unstacking dynamics of oligodeoxynucleotide trimers, Biochemistry 43, 10277-10284.
    • (2004) Biochemistry , vol.43 , pp. 10277-10284
    • Jean, J.M.1    Hall, K.B.2
  • 7
    • 0346158946 scopus 로고    scopus 로고
    • Ultrafast dynamics in DNA-mediated electron transfer: Base gating and the role of temperature
    • O'Neill, M. A. T., Becker, H.-C., Wan, C., Barton, J. K., and Zewail, A. H. (2003) Ultrafast dynamics in DNA-mediated electron transfer: Base gating and the role of temperature, Angew. Chem., Int. Ed. 42, 5896-5900.
    • (2003) Angew. Chem., Int. Ed. , vol.42 , pp. 5896-5900
    • O'Neill, M.A.T.1    Becker, H.-C.2    Wan, C.3    Barton, J.K.4    Zewail, A.H.5
  • 8
    • 0037120095 scopus 로고    scopus 로고
    • Femtosecond charge-transfer dynamics of a modified DNA base: 2-Aminopurine in complexes with nucleotides
    • Fiebig, T., Wan, C., and Zewail, A. H. (2002) Femtosecond charge-transfer dynamics of a modified DNA base: 2-Aminopurine in complexes with nucleotides, ChemPhysChem 3, 781-788.
    • (2002) ChemPhysChem , vol.3 , pp. 781-788
    • Fiebig, T.1    Wan, C.2    Zewail, A.H.3
  • 9
    • 0034896734 scopus 로고    scopus 로고
    • Probing the structure and dynamics of a DNA hairpin by ultrafast quenching and fluorescence depolarization
    • Larsen, O. F. A., van Stokkum, I. H. M., Gobets, B., van Grondelle, R., and van Amerongen, H. (2001) Probing the structure and dynamics of a DNA hairpin by ultrafast quenching and fluorescence depolarization, Biophys. J. 81, 1115-1126.
    • (2001) Biophys. J. , vol.81 , pp. 1115-1126
    • Larsen, O.F.A.1    Van Stokkum, I.H.M.2    Gobets, B.3    Van Grondelle, R.4    Van Amerongen, H.5
  • 11
    • 0033555454 scopus 로고    scopus 로고
    • Electron transfer between bases in double helical DNA
    • Kelley, S. O., and Barton, J. K. (1999) Electron transfer between bases in double helical DNA, Science 283, 375.
    • (1999) Science , vol.283 , pp. 375
    • Kelley, S.O.1    Barton, J.K.2
  • 13
    • 0035969981 scopus 로고    scopus 로고
    • Conformation and dynamics of abasic sites in DNA investigated by time-resolved fluorescence of 2-aminopurine
    • Rachofsky, E. L., Seibert, E., Stivers, J. T., Osman, R., and Ross, J. B. (2001) Conformation and dynamics of abasic sites in DNA investigated by time-resolved fluorescence of 2-aminopurine, Biochemistry 40, 957-967.
    • (2001) Biochemistry , vol.40 , pp. 957-967
    • Rachofsky, E.L.1    Seibert, E.2    Stivers, J.T.3    Osman, R.4    Ross, J.B.5
  • 15
    • 0024456523 scopus 로고
    • Structure and dynamics of a fluorescent DNA oligomer containing the EcoRI recognition sequence: Fluorescence, molecular-dynamics, and NMR-studies
    • Nordlund, T. M., Andersson, T. M., Nilsson, L., Rigler, R., Gräslund, A., and McLaughlin, L. W. (1989) Structure and dynamics of a fluorescent DNA oligomer containing the EcoRI recognition sequence: Fluorescence, molecular-dynamics, and NMR-studies, Biochemistry 28, 9095-9103.
    • (1989) Biochemistry , vol.28 , pp. 9095-9103
    • Nordlund, T.M.1    Andersson, T.M.2    Nilsson, L.3    Rigler, R.4    Gräslund, A.5    McLaughlin, L.W.6
  • 16
    • 0037027319 scopus 로고    scopus 로고
    • 2-Aminopurine electronic structure and fluorescence properties in DNA
    • Jean, J. M., and Hall, K. B. (2002) 2-Aminopurine electronic structure and fluorescence properties in DNA, Biochemistry 41, 13152-13161.
    • (2002) Biochemistry , vol.41 , pp. 13152-13161
    • Jean, J.M.1    Hall, K.B.2
  • 17
    • 0035793105 scopus 로고    scopus 로고
    • 2-Aminopurine fluorescence quenching and lifetimes: Role of base stacking
    • Jean, J. M., and Hall, K. B. (2001) 2-Aminopurine fluorescence quenching and lifetimes: Role of base stacking, Proc. Natl. Acad. Sci. U.S.A. 98, 37-41.
    • (2001) Proc. Natl. Acad. Sci. U.S.A. , vol.98 , pp. 37-41
    • Jean, J.M.1    Hall, K.B.2
  • 18
    • 0000189651 scopus 로고
    • Density-functional thermochemistry. 3. The role of exact exchange
    • Becke, A. D. (1993) Density-functional thermochemistry. 3. The role of exact exchange, J. Chem. Phys. 98, 5648-5652.
    • (1993) J. Chem. Phys. , vol.98 , pp. 5648-5652
    • Becke, A.D.1
  • 19
    • 0345491105 scopus 로고
    • Development of the Colle-Salvetti correlation-energy formula into a functional of the electron-density
    • Lee, C. T., Yang, W. T., and Parr, R. G. (1988) Development of the Colle-Salvetti correlation-energy formula into a functional of the electron-density, Phys. Rev. B 37, 785-789.
    • (1988) Phys. Rev. B , vol.37 , pp. 785-789
    • Lee, C.T.1    Yang, W.T.2    Parr, R.G.3
  • 20
    • 0000703066 scopus 로고
    • Toward a systematic molecular-orbital theory for excited-states
    • Foresman, J. B., Head-Gordon, M., Pople, J. A., and Frisch, M. J. (1992) Toward a systematic molecular-orbital theory for excited-states, J. Phys. Chem. 96, 135-149.
    • (1992) J. Phys. Chem. , vol.96 , pp. 135-149
    • Foresman, J.B.1    Head-Gordon, M.2    Pople, J.A.3    Frisch, M.J.4
  • 21
    • 1242338125 scopus 로고    scopus 로고
    • Pyrrolo-dC and pyrrolo-C: Fluorescent analogs of cytidine and 2′-deoxycytidine for the study of oligonucleotides
    • Berry, D. A., Jung, K. Y., Wise, D. S., Sercel, A. D., Pearson, W. H., Mackie, H., Randolph, J. B., and Somers, R. L. (2004) Pyrrolo-dC and pyrrolo-C: Fluorescent analogs of cytidine and 2′-deoxycytidine for the study of oligonucleotides, Tetrahedron Lett. 45, 2457-2461.
    • (2004) Tetrahedron Lett. , vol.45 , pp. 2457-2461
    • Berry, D.A.1    Jung, K.Y.2    Wise, D.S.3    Sercel, A.D.4    Pearson, W.H.5    Mackie, H.6    Randolph, J.B.7    Somers, R.L.8
  • 22
    • 33344477201 scopus 로고    scopus 로고
    • Pyrrolo-C as a fluorescent probe for monitoring RNA secondary structure formation
    • 10.1261/rna.2165806
    • Tinsley, R. A., and Walter, N. G. (2006) Pyrrolo-C as a fluorescent probe for monitoring RNA secondary structure formation, RNA (10.1261/rna.2165806).
    • (2006) RNA
    • Tinsley, R.A.1    Walter, N.G.2
  • 23
    • 33746609515 scopus 로고    scopus 로고
    • Wavefunction Inc., Irvine, CA
    • Spartan02 (2002) Wavefunction Inc., Irvine, CA.
    • (2002) Spartan02
  • 24
    • 17144414126 scopus 로고    scopus 로고
    • Properties of a new fluorescent cytosine analogue, pyrrolocytosine
    • Thompson, K. C., and Miyake, N. (2005) Properties of a new fluorescent cytosine analogue, pyrrolocytosine, J. Phys. Chem. B 109, 6012-6019.
    • (2005) J. Phys. Chem. B , vol.109 , pp. 6012-6019
    • Thompson, K.C.1    Miyake, N.2
  • 29
    • 0000045103 scopus 로고    scopus 로고
    • Calculations and characterization of the electronic spectra of DNA bases based on ab initio MP2 geometries of different tautomeric forms
    • Broo, A., and Holmén, A. (1997) Calculations and characterization of the electronic spectra of DNA bases based on ab initio MP2 geometries of different tautomeric forms, J. Phys. Chem. A 101, 3589-3600.
    • (1997) J. Phys. Chem. A , vol.101 , pp. 3589-3600
    • Broo, A.1    Holmén, A.2
  • 30
    • 0035121180 scopus 로고    scopus 로고
    • CASSCF investigation of electronic excited states of 2-aminopurine
    • Rachofsky, E. L., Ross, J. B. A., Krauss, M., and Osman, R. (2001) CASSCF investigation of electronic excited states of 2-aminopurine, J. Phys. Chem. A 105, 190-197.
    • (2001) J. Phys. Chem. A , vol.105 , pp. 190-197
    • Rachofsky, E.L.1    Ross, J.B.A.2    Krauss, M.3    Osman, R.4
  • 31
    • 28544448728 scopus 로고    scopus 로고
    • Single-reference ab initio methods for the calculation of excited states of large molecules
    • Dreuw, A., and Head-Gordon, M. (2005) Single-reference ab initio methods for the calculation of excited states of large molecules, Chem. Rev. 105, 4009-4037.
    • (2005) Chem. Rev. , vol.105 , pp. 4009-4037
    • Dreuw, A.1    Head-Gordon, M.2
  • 32
    • 33344455128 scopus 로고    scopus 로고
    • The application of CAMB3LYP to the charge-transfer band problem of the zincbacteriochlorin-bacteriochlorin complex
    • Kobayashi, R., and Amos, R. D. (2006) The application of CAMB3LYP to the charge-transfer band problem of the zincbacteriochlorin-bacteriochlorin complex, Chem. Phys. Lett. 420, 106-109.
    • (2006) Chem. Phys. Lett. , vol.420 , pp. 106-109
    • Kobayashi, R.1    Amos, R.D.2
  • 33
    • 0035799966 scopus 로고    scopus 로고
    • Excited-state energy transfer processes in phenylene- and biphenylene-linked and directly-linked zinc-(II) and free-base hybrid diporphyrins
    • Cho, H. S., Jeong, D. H., Yoon, M.-C., Kim, Y. H., Kim, Y.-R., Kim, D., Jeoung, S. C., Kim, S. K., Aratani, N., Shinmori, H., and Osuka, A. (2001) Excited-State Energy Transfer Processes in Phenylene- and Biphenylene-Linked and Directly-Linked Zinc-(II) and Free-Base Hybrid Diporphyrins, J. Phys. Chem. A 105, 4200-4210.
    • (2001) J. Phys. Chem. A , vol.105 , pp. 4200-4210
    • Cho, H.S.1    Jeong, D.H.2    Yoon, M.-C.3    Kim, Y.H.4    Kim, Y.-R.5    Kim, D.6    Jeoung, S.C.7    Kim, S.K.8    Aratani, N.9    Shinmori, H.10    Osuka, A.11
  • 34
    • 0000162043 scopus 로고    scopus 로고
    • Theoretical determination of electron affinity and ionization potential of DNA and RNA bases
    • Russo, N., Toscano, M., and Grand, A. (2000) Theoretical determination of electron affinity and ionization potential of DNA and RNA bases, J. Comput. Chem. 21, 1243-1250.
    • (2000) J. Comput. Chem. , vol.21 , pp. 1243-1250
    • Russo, N.1    Toscano, M.2    Grand, A.3
  • 35
    • 0029773892 scopus 로고    scopus 로고
    • Theoretical studies of GG-specific photocleavage of DNA via electron transfer: Significant lowering of ionization potential and 5′-localization of HOMO of stacked GG bases in B-from DNA
    • Sugiyama, H., and Saito, I. (1996) Theoretical studies of GG-specific photocleavage of DNA via electron transfer: significant lowering of ionization potential and 5′-localization of HOMO of stacked GG bases in B-from DNA, J. Am. Chem. Soc. 118, 7063-7068.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 7063-7068
    • Sugiyama, H.1    Saito, I.2
  • 36
    • 0035969959 scopus 로고    scopus 로고
    • Probing structure and dynamics of DNA with 2-aminopurine: Effects of local environment on fluorescence
    • Rachofsky, E. L., Osman, R., and Ross, J. B. A. (2001) Probing structure and dynamics of DNA with 2-aminopurine: Effects of local environment on fluorescence. Biochemistry 40, 946-956.
    • (2001) Biochemistry , vol.40 , pp. 946-956
    • Rachofsky, E.L.1    Osman, R.2    Ross, J.B.A.3
  • 37
    • 36849126497 scopus 로고
    • Relationship between absorption intensity and fluorescence lifetime of molecules
    • Strickler, S. J., and Berg, R. A., (1962) Relationship between absorption intensity and fluorescence lifetime of molecules, J. Chem. Phys. 37, 814-822.
    • (1962) J. Chem. Phys. , vol.37 , pp. 814-822
    • Strickler, S.J.1    Berg, R.A.2
  • 39
    • 0014669561 scopus 로고
    • Fluorescence studies of nucleotides and polynucleotides
    • Ward, D. C., Reich, E., and Stryer, L. (1969) Fluorescence studies of nucleotides and polynucleotides, J. Biol. Chem. 244, 1228-1237.
    • (1969) J. Biol. Chem. , vol.244 , pp. 1228-1237
    • Ward, D.C.1    Reich, E.2    Stryer, L.3
  • 40
    • 0031011001 scopus 로고    scopus 로고
    • Electronic transition moments of 2-aminopurine
    • Holmén, A., Nordén, B., and Albinsson, B. (1997) Electronic transition moments of 2-aminopurine, J. Am. Chem. Soc. 119, 3114-3121.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 3114-3121
    • Holmén, A.1    Nordén, B.2    Albinsson, B.3
  • 41
    • 9144265600 scopus 로고    scopus 로고
    • Evidence of tautomerism in 2-aminopurine from fluorescence lifetime measurements
    • Neely, R. K., Magennis, S. W., Dryden, D. T. F., and Jones, A. C. (2004) Evidence of tautomerism in 2-aminopurine from fluorescence lifetime measurements, J. Phys. Chem. B 108, 17606-17610.
    • (2004) J. Phys. Chem. B , vol.108 , pp. 17606-17610
    • Neely, R.K.1    Magennis, S.W.2    Dryden, D.T.F.3    Jones, A.C.4
  • 42
    • 14644388252 scopus 로고
    • Electronic spectra of 2-aminopurine and 2,6-diaminopurine: Phototautomerism and fluorescence reabsorption
    • Santhosh, C., and Mishra, P. C. (1991) Electronic spectra of 2-aminopurine and 2,6-diaminopurine: Phototautomerism and fluorescence reabsorption, Spectrochim. Acta 47A, 1685-1693.
    • (1991) Spectrochim. Acta , vol.47 A , pp. 1685-1693
    • Santhosh, C.1    Mishra, P.C.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.