메뉴 건너뛰기




Volumn 22, Issue 1, 2003, Pages 85-98

Fluorescent 7- and 8-methyl etheno derivatives of adenosine and 6-amino-9-ethylpurine: Syntheses and fluorescence properties

Author keywords

Fluorescence; Nucleosides

Indexed keywords

3 ETHYL 3H 7 METHYLIMIDAZO[2,1 I]PURINE; 3 ETHYL 3H 8 METHYLIMIDAZO[2,1 I]PURINE; 7 METHYL 3 (BETA DEXTRO RIBOFURANOSYL)IMIDAZO[2,1 I]PURINE; 8 METHYL 3 (BETA DEXTRO RIBOFURANOSYL)IMIDAZO[2,1 I]PURINE; ALDEHYDE DERIVATIVE; FLUORESCENT DYE; UNCLASSIFIED DRUG;

EID: 0037244691     PISSN: 15257770     EISSN: None     Source Type: Journal    
DOI: 10.1081/NCN-120018625     Document Type: Article
Times cited : (8)

References (37)
  • 1
    • 0035928695 scopus 로고    scopus 로고
    • Linear fluorescent oligonucleotide probes with an acridine quencher generate a signal upon hydridization
    • (a) Ranasinghe, R.T.; Brown, L.J.; Brown, T. Linear fluorescent oligonucleotide probes with an acridine quencher generate a signal upon hydridization. Chem. Comm. 2001, 16, 1480-1481.
    • (2001) Chem. Comm. , vol.16 , pp. 1480-1481
    • Ranasinghe, R.T.1    Brown, L.J.2    Brown, T.3
  • 2
    • 0035969613 scopus 로고    scopus 로고
    • Facile synthesis of a fluorescent deoxycytidine analogue suitable for probing the RecA nucleoprotein filament
    • (b) Singleton, S.F.; Shan, F.; Kanan, M.W.; McIntosh, C.M.; Stearman, C.J.; Helm, J.S.; Webb, K.J. Facile synthesis of a fluorescent deoxycytidine analogue suitable for probing the RecA nucleoprotein filament. Org. Lett. 2001, 3 (24), 3919-3922.
    • (2001) Org. Lett. , vol.3 , Issue.24 , pp. 3919-3922
    • Singleton, S.F.1    Shan, F.2    Kanan, M.W.3    McIntosh, C.M.4    Stearman, C.J.5    Helm, J.S.6    Webb, K.J.7
  • 3
    • 0034238088 scopus 로고    scopus 로고
    • 4-Amino-1H-benzo[g]quinazoline-2-one: A fluorescent analog of cytosine to probe protonation sites in triplex forming oligonucleotides
    • (c) Godde, F.; Toulmé, J.J.; Moreau, S. 4-amino-1H-benzo[g]quinazoline-2-one: a fluorescent analog of cytosine to probe protonation sites in triplex forming oligonucleotides. Nucleic Acids Res. 2000, 28 (15), 2977-2985.
    • (2000) Nucleic Acids Res. , vol.28 , Issue.15 , pp. 2977-2985
    • Godde, F.1    Toulmé, J.J.2    Moreau, S.3
  • 4
    • 0031758714 scopus 로고    scopus 로고
    • Synthesis and hybridization studies of oligonucleotide sequences with modified fluorescent nucleoside analogs
    • (d)Pandey, R.K.; Tripatni, S.; Misra, K. Synthesis and hybridization studies of oligonucleotide sequences with modified fluorescent nucleoside analogs. Nucleos. Nucleot. 1998, 17 (9-11), 1937-1948.
    • (1998) Nucleos. Nucleot. , vol.17 , Issue.9-11 , pp. 1937-1948
    • Pandey, R.K.1    Tripatni, S.2    Misra, K.3
  • 5
    • 0030865018 scopus 로고    scopus 로고
    • Study of the substrate-binding properties of bovine liver adenosine kinase and inhibition by fluorescent nucleoside analogs
    • (e) Pelicano, H.; Maury, G.; Elalaoui, A.; Shafiee, M.; Imbach, J.L., Goody, R.S.; Divita, G. Study of the substrate-binding properties of bovine liver adenosine kinase and inhibition by fluorescent nucleoside analogs. Eur. J. Biochem. 1997, 248, 930-937.
    • (1997) Eur. J. Biochem. , vol.248 , pp. 930-937
    • Pelicano, H.1    Maury, G.2    Elalaoui, A.3    Shafiee, M.4    Imbach, J.L.5    Goody, R.S.6    Divita, G.7
  • 6
    • 0030448581 scopus 로고    scopus 로고
    • Targeted base stacking disruption by the EcoRI DNA methyltransferase
    • (f) Allan, B.W.; Reich, N.O. Targeted base stacking disruption by the EcoRI DNA methyltransferase. Biochemistry 1996, 35, 14,757-14,762.
    • (1996) Biochemistry , vol.35 , pp. 14757-14762
    • Allan, B.W.1    Reich, N.O.2
  • 7
    • 0029790461 scopus 로고    scopus 로고
    • Synthesis of a fluorescent 7-methylguanosine analog and a fluorescence spectroscopic study of its reaction with wheatgerm cap binding proteins
    • (g) Ren, J.; Goss, D.J. Synthesis of a fluorescent 7-methylguanosine analog and a fluorescence spectroscopic study of its reaction with wheatgerm cap binding proteins. Nucleic Acids Res. 1996, 24 (18), 3629-3634.
    • (1996) Nucleic Acids Res. , vol.24 , Issue.18 , pp. 3629-3634
    • Ren, J.1    Goss, D.J.2
  • 8
    • 0029085240 scopus 로고
    • The nucleotide analog 2-aminopurine as a spectroscopic probe of nucleotide incorporation by the Klenow fragment of Escherichia coli polymerase I and bacteriophage T4 DNA polymerase
    • (h) Frey, M.W.; Sowers, L.C.; Millar, D.P.; Benkovic, S.J. The nucleotide analog 2-aminopurine as a spectroscopic probe of nucleotide incorporation by the Klenow fragment of Escherichia coli polymerase I and bacteriophage T4 DNA polymerase. Biochemistry 1995, 34, 9185-9192.
    • (1995) Biochemistry , vol.34 , pp. 9185-9192
    • Frey, M.W.1    Sowers, L.C.2    Millar, D.P.3    Benkovic, S.J.4
  • 9
    • 0029118594 scopus 로고
    • Incorporation of a fluorescent guanosine analog into oligonucleotides and its application to a real time assay for the HIV-1 integrase 3′-processing reaction
    • (i) Hawkins, M.E.; Pfleiderer, W.; Mazumder, A.; Pommier, Y.G.; Balls, F.M. Incorporation of a fluorescent guanosine analog into oligonucleotides and its application to a real time assay for the HIV-1 integrase 3′-processing reaction. Nucleic Acids Res. 1995, 23 (15), 2872-2880.
    • (1995) Nucleic Acids Res. , vol.23 , Issue.15 , pp. 2872-2880
    • Hawkins, M.E.1    Pfleiderer, W.2    Mazumder, A.3    Pommier, Y.G.4    Balls, F.M.5
  • 10
    • 0024456523 scopus 로고
    • Structure and dynamics of a fluorescent DNA oligomer containing the EcoRI recognition sequence: Fluorescence, molecular dynamics, and NMR studies
    • (j) Nordlund, T.M.; Andersson, S.; Nilsson, L.; Rigler, R. Structure and dynamics of a fluorescent DNA oligomer containing the EcoRI recognition sequence: fluorescence, molecular dynamics, and NMR studies. Biochemistry 1989, 28, 9095-9103.
    • (1989) Biochemistry , vol.28 , pp. 9095-9103
    • Nordlund, T.M.1    Andersson, S.2    Nilsson, L.3    Rigler, R.4
  • 11
    • 0034409924 scopus 로고    scopus 로고
    • Synthesis of fluorescently labelled oligonucleotides and nucleic acids
    • (a) Davies, M.J.; Shah, A.; Bruce, I.J. Synthesis of fluorescently labelled oligonucleotides and nucleic acids. Chem. Soc. Rev. 2000, 29, 97-107.
    • (2000) Chem. Soc. Rev. , vol.29 , pp. 97-107
    • Davies, M.J.1    Shah, A.2    Bruce, I.J.3
  • 12
    • 0029859430 scopus 로고    scopus 로고
    • Chemical methods of DNA and RNA fluorescent labeling
    • (b) Proudnikov, D.; Mirzabekov, A. Chemical methods of DNA and RNA fluorescent labeling. Nucleic Acids Res. 1996, 24 (22), 4535-4542.
    • (1996) Nucleic Acids Res. , vol.24 , Issue.22 , pp. 4535-4542
    • Proudnikov, D.1    Mirzabekov, A.2
  • 13
    • 0032825423 scopus 로고    scopus 로고
    • Fluorescent oligonucleotides versatile tools as probes and primers for DNA and RNA analysis
    • (c) Wojczewski, C.; Stolze, K.; Engels, J.W. Fluorescent oligonucleotides versatile tools as probes and primers for DNA and RNA analysis. Synlett 1999, 10, 1667-1678.
    • (1999) Synlett , vol.10 , pp. 1667-1678
    • Wojczewski, C.1    Stolze, K.2    Engels, J.W.3
  • 14
    • 0038268731 scopus 로고    scopus 로고
    • Novel nucleoside analogues with fluorophores replacing the DNA base
    • (d) Strāssler, C.; Davis, N.E.; Kool, E.T. Novel nucleoside analogues with fluorophores replacing the DNA base. Helv. Chim. Acta 1999, 82, 2160-2171.
    • (1999) Helv. Chim. Acta , vol.82 , pp. 2160-2171
    • Strassler, C.1    Davis, N.E.2    Kool, E.T.3
  • 15
  • 16
    • 0021295867 scopus 로고
    • Etheno-substituted nucleotides and coenzymes fluorescence and biological activity
    • (a) Leonard, N.J. Etheno-substituted nucleotides and coenzymes fluorescence and biological activity. CRC Crit. Rev. Biochem. 1984, 15 (2), 125-199.
    • (1984) CRC Crit. Rev. Biochem. , vol.15 , Issue.2 , pp. 125-199
    • Leonard, N.J.1
  • 17
    • 0029762376 scopus 로고    scopus 로고
    • 2-Aminopurine labeled RNA bulge loops Synthesis and thermodynamics
    • (b) Zagorowska, I.; Adamiak, R.W. 2-Aminopurine labeled RNA bulge loops Synthesis and thermodynamics. Biochemie 1996, 78 (2), 123-130.
    • (1996) Biochemie , vol.78 , Issue.2 , pp. 123-130
    • Zagorowska, I.1    Adamiak, R.W.2
  • 18
    • 0000032454 scopus 로고
    • Fluorescent nucleoside analogs. Synthesis of fluorescent pyrido[2,1-i]purines, and their corresponding ribosides
    • (c) Odijk, W.M.; Koomen, G.J. Fluorescent nucleoside analogs. Synthesis of fluorescent pyrido[2,1-i]purines, and their corresponding ribosides. Tetrahedron 1985, 41 (10), 1893-1904.
    • (1985) Tetrahedron , vol.41 , Issue.10 , pp. 1893-1904
    • Odijk, W.M.1    Koomen, G.J.2
  • 19
    • 0030823054 scopus 로고    scopus 로고
    • Fluorescence properties of a new guanosine analog incorporated into small oligonucleotides
    • (d) Driscoll, S.L.; Hawkins, M.E.; Balis, F.M.; Pfleiderer, W.; Laws, W.R., Fluorescence properties of a new guanosine analog incorporated into small oligonucleotides. Biophys. J. 1997, 73, 3277-3286.
    • (1997) Biophys. J. , vol.73 , pp. 3277-3286
    • Driscoll, S.L.1    Hawkins, M.E.2    Balis, F.M.3    Pfleiderer, W.4    Laws, W.R.5
  • 20
    • 0017805515 scopus 로고
    • New observations concerning the chloroacetaldehyde reaction with some RNA constituents. Stable intermediates, kinetics and selectivity of the reaction
    • (a) Biernat, J.; Ciesiolka, J.; Gornicki, P.; Adamiak, R.W.; Krzyzosiak, W.J.; Wiewiorowski, M. New observations concerning the chloroacetaldehyde reaction with some RNA constituents. Stable intermediates, kinetics and selectivity of the reaction. Nucleic Acids Res. 1978, 5 (3), 789-804.
    • (1978) Nucleic Acids Res. , vol.5 , Issue.3 , pp. 789-804
    • Biernat, J.1    Ciesiolka, J.2    Gornicki, P.3    Adamiak, R.W.4    Krzyzosiak, W.J.5    Wiewiorowski, M.6
  • 22
    • 0012750670 scopus 로고
    • Comparative studies on reactions of adenosine and cytidine with chloroacetaldehyde, α-bromopropionaldehyde and chloroacetone. Synthesis of 1, N6-ethenoadenosine and 3, N4-ethenocytidine derivatives methylated at the etheno bridge
    • (c) Krzyzosiak, W.J.; Biernat, J.; Ciesiolka, J.; Gornicki, P.; Wiewiorowski, M. Comparative studies on reactions of adenosine and cytidine with chloroacetaldehyde, α-bromopropionaldehyde and chloroacetone. Synthesis of 1, N6-ethenoadenosine and 3, N4-ethenocytidine derivatives methylated at the etheno bridge. Pol. J. Chem. 1983, 57, 779-787.
    • (1983) Pol. J. Chem. , vol.57 , pp. 779-787
    • Krzyzosiak, W.J.1    Biernat, J.2    Ciesiolka, J.3    Gornicki, P.4    Wiewiorowski, M.5
  • 23
    • 85047671069 scopus 로고
    • Etheno derivatives of adenine and cytosine
    • (d) Kost, A.A.; Ivanov, M.V. Etheno derivatives of adenine and cytosine. (Review). Chem. Heterocycl. Comp. 1980, 16 (3), 209-221.
    • (1980) Chem. Heterocycl. Comp. , vol.16 , Issue.3 , pp. 209-221
    • Kost, A.A.1    Ivanov, M.V.2
  • 25
    • 0025681762 scopus 로고
    • 1, N2-Ethenoguanosine: Three methods of synthesis
    • (f) Boryski, J. 1, N2-Ethenoguanosine: three methods of synthesis. Nucleos. Nucleot. 1990, 9 (6), 803-813.
    • (1990) Nucleos. Nucleot. , vol.9 , Issue.6 , pp. 803-813
    • Boryski, J.1
  • 26
    • 0028176309 scopus 로고
    • 1, N6-etheno deoxy and ribo adenosine and 3, N4-etheno deoxy and ribo cytidine phosphoramidites. Strongly fluorescent structures for selective introduction in defined sequence DNA and RNA molecules
    • Srisvastava, S.; Raza, S.K.; Misra, R. 1, N6-etheno deoxy and ribo adenosine and 3, N4-etheno deoxy and ribo cytidine phosphoramidites. Strongly fluorescent structures for selective introduction in defined sequence DNA and RNA molecules. Nucleic Acids Res. 1994, 22 (7), 1296-1304.
    • (1994) Nucleic Acids Res. , vol.22 , Issue.7 , pp. 1296-1304
    • Srisvastava, S.1    Raza, S.K.2    Misra, R.3
  • 27
    • 0012753726 scopus 로고
    • Modification of nucleic acid components with α-halo aldehydes
    • Kochetkov, N.K.; Shibaev, V.N.; Kost, A.A. Modification of nucleic acid components with α-halo aldehydes. Dokl. Akad. Nauk. SSSR 1972, 205 (1), 100-103.
    • (1972) Dokl. Akad. Nauk. SSSR , vol.205 , Issue.1 , pp. 100-103
    • Kochetkov, N.K.1    Shibaev, V.N.2    Kost, A.A.3
  • 28
    • 0015504246 scopus 로고
    • Fluorescent modification of adenosine containing coenzymes. Biological activities and spectroscopic properties
    • (a) Secrist, J.A.; Barrio, J.R.; Leonard, N.J.; Weber, G. Fluorescent modification of adenosine containing coenzymes. Biological activities and spectroscopic properties. Biochemistry 1972, 11 (19), 3499-3506,
    • (1972) Biochemistry , vol.11 , Issue.19 , pp. 3499-3506
    • Secrist, J.A.1    Barrio, J.R.2    Leonard, N.J.3    Weber, G.4
  • 29
    • 0033920188 scopus 로고    scopus 로고
    • Reactions of adenosine with bromoand chloromalonaldehydes in aqueous solution kinetics and mechanism
    • (b) Mikkola, S.; Koissi, N.; Ketomäki, K.; Rauvala, S.; Neuvonen, K. Reactions of adenosine with bromoand chloromalonaldehydes in aqueous solution kinetics and mechanism. Eur. J. Org. Chem. 2000, 12, 2315-2323.
    • (2000) Eur. J. Org. Chem. , vol.12 , pp. 2315-2323
    • Mikkola, S.1    Koissi, N.2    Ketomäki, K.3    Rauvala, S.4    Neuvonen, K.5
  • 30
    • 0000167674 scopus 로고
    • Structural alteration of nucleic acid bases by bromomalonaldehyde
    • (c) Nair, V.; Offerman, R.J.; Turner, G.A. Structural alteration of nucleic acid bases by bromomalonaldehyde. J. Org. Chem. 1984, 49 (21), 4021-4025.
    • (1984) J. Org. Chem. , vol.49 , Issue.21 , pp. 4021-4025
    • Nair, V.1    Offerman, R.J.2    Turner, G.A.3
  • 32
    • 37049138857 scopus 로고
    • Purines pyrimidines, and imidazoles XXXIV. Synthesis and some reactions of N(6)-(formlmethyl)adenine
    • (a) Shaw, G.; Smallwood, B.M. Purines pyrimidines, and imidazoles XXXIV. Synthesis and some reactions of N(6)-(formlmethyl)adenine. J. Chem. Soc. C 1970, 16, 2206-2208,
    • (1970) J. Chem. Soc. C , vol.16 , pp. 2206-2208
    • Shaw, G.1    Smallwood, B.M.2
  • 33
    • 33847085423 scopus 로고
    • 1, N6-Etheno-bridged adenines and adenosines. Alkyl substitution, fluorescence properties, and synthetic applications
    • (b) Sattsangi, P.D.; Barrio, J.R.; Leonard, N.J. 1, N6-Etheno-bridged adenines and adenosines. Alkyl substitution, fluorescence properties, and synthetic applications. J. Am. Chem. Soc. 1980, 102 (2), 770-774.
    • (1980) J. Am. Chem. Soc. , vol.102 , Issue.2 , pp. 770-774
    • Sattsangi, P.D.1    Barrio, J.R.2    Leonard, N.J.3
  • 34
    • 0000829896 scopus 로고
    • Synthesis of fluorescent adenosine derivatives
    • (c) Yip, K.F.; Tsou, K.C. Synthesis of fluorescent adenosine derivatives. Tetrahedron Lett. 1973, 33, 3087-3090.
    • (1973) Tetrahedron Lett. , vol.33 , pp. 3087-3090
    • Yip, K.F.1    Tsou, K.C.2
  • 35
    • 0019196854 scopus 로고
    • Utility of purinyl radicals in the synthesis of basemodified nucleosides and alkylpurines: 6-Amino group replacement by hydrogen, chlorine, bromine, and iodine
    • Nair, V.; Richardson, S.G. Utility of purinyl radicals in the synthesis of basemodified nucleosides and alkylpurines: 6-amino group replacement by hydrogen, chlorine, bromine, and iodine. J. Org. Chem. 1980, 45, 3969-3974.
    • (1980) J. Org. Chem. , vol.45 , pp. 3969-3974
    • Nair, V.1    Richardson, S.G.2
  • 37
    • 33847088401 scopus 로고
    • Determination of absolute fluorescence quantum efficiency of quinine bisulfate in aqueous medium by optoacoustic spectrometry
    • Adams, M.J.; Highfield, J.G.; Kirkbright, G.F. Determination of absolute fluorescence quantum efficiency of quinine bisulfate in aqueous medium by optoacoustic spectrometry. Anal. Chem. 1977, 49, 1850-1852.
    • (1977) Anal. Chem. , vol.49 , pp. 1850-1852
    • Adams, M.J.1    Highfield, J.G.2    Kirkbright, G.F.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.