메뉴 건너뛰기




Volumn 105, Issue , 2014, Pages 145-151

Synthesis and evaluation of spectroscopic properties of newly synthesized push-pull 6-amino-8-styryl purines

Author keywords

Direct C H bond functionalization; Fluorescence; Heterocyclic chemistry; Push pull; Solvatochromy; Styrylpurines

Indexed keywords


EID: 84894680348     PISSN: 01437208     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.dyepig.2014.01.025     Document Type: Article
Times cited : (18)

References (38)
  • 1
    • 77952474889 scopus 로고    scopus 로고
    • New strategies for fluorescent probe design in medical diagnostic imaging
    • H. Kobayashi, M. Ogawa, R. Alford, P.L. Choyke, and Y. Urano New strategies for fluorescent probe design in medical diagnostic imaging Chem Rev 110 2009 2620 2640
    • (2009) Chem Rev , vol.110 , pp. 2620-2640
    • Kobayashi, H.1    Ogawa, M.2    Alford, R.3    Choyke, P.L.4    Urano, Y.5
  • 2
    • 77952531703 scopus 로고    scopus 로고
    • Fluorescent analogs of biomolecular building blocks: Design, properties, and applications
    • R.W. Sinkeldam, N.J. Greco, and Y. Tor Fluorescent analogs of biomolecular building blocks: design, properties, and applications Chem Rev 110 2010 2579 2619
    • (2010) Chem Rev , vol.110 , pp. 2579-2619
    • Sinkeldam, R.W.1    Greco, N.J.2    Tor, Y.3
  • 3
    • 79953806936 scopus 로고    scopus 로고
    • A novel peptide probe for imaging and targeted delivery of liposomal doxorubicin to lung tumor
    • X. He, M.-H. Na, J.-S. Kim, G.-Y. Lee, J.Y. Park, and A.S. Hoffman et al. A novel peptide probe for imaging and targeted delivery of liposomal doxorubicin to lung tumor Mol Pharm 8 2011 430 438
    • (2011) Mol Pharm , vol.8 , pp. 430-438
    • He, X.1    Na, M.-H.2    Kim, J.-S.3    Lee, G.-Y.4    Park, J.Y.5    Hoffman, A.S.6
  • 4
    • 14244253595 scopus 로고    scopus 로고
    • 8-vinyl-deoxyadenosine, an alternative fluorescent nucleoside analog to 2'-deoxyribosyl-2-aminopurine with improved properties
    • N. Ben Gaied, N. Glasser, N. Ramalanjaona, H. Beltz, P. Wolff, and R. Marquet et al. 8-vinyl-deoxyadenosine, an alternative fluorescent nucleoside analog to 2'-deoxyribosyl-2-aminopurine with improved properties Nucleic Acids Res 33 2005 1031 1039
    • (2005) Nucleic Acids Res , vol.33 , pp. 1031-1039
    • Ben Gaied, N.1    Glasser, N.2    Ramalanjaona, N.3    Beltz, H.4    Wolff, P.5    Marquet, R.6
  • 6
    • 67849126398 scopus 로고    scopus 로고
    • Synthesis, photophysical behavior, and electronic structure of push-pull purines
    • R.S. Butler, P. Cohn, P. Tenzel, K.A. Abboud, and R.K. Castellano Synthesis, photophysical behavior, and electronic structure of push-pull purines J Am Chem Soc 131 2009 623 633
    • (2009) J Am Chem Soc , vol.131 , pp. 623-633
    • Butler, R.S.1    Cohn, P.2    Tenzel, P.3    Abboud, K.A.4    Castellano, R.K.5
  • 7
    • 77950369852 scopus 로고    scopus 로고
    • Synthesis of novel push-pull-type solvatochromic 2′-deoxyguanosine derivatives with longer wavelength emission
    • Y. Saito, A. Suzuki, K. Imai, N. Nemoto, and I. Saito Synthesis of novel push-pull-type solvatochromic 2′-deoxyguanosine derivatives with longer wavelength emission Tetrahedron Lett 51 2010 2606 2609
    • (2010) Tetrahedron Lett , vol.51 , pp. 2606-2609
    • Saito, Y.1    Suzuki, A.2    Imai, K.3    Nemoto, N.4    Saito, I.5
  • 9
    • 78650519750 scopus 로고    scopus 로고
    • Synthesis and photophysical properties of 8-arylbutadienyl 2′-deoxyguanosines
    • Y. Saito, M. Koda, Y. Shinohara, and I. Saito Synthesis and photophysical properties of 8-arylbutadienyl 2′-deoxyguanosines Tetrahedron Lett 52 2011 491 494
    • (2011) Tetrahedron Lett , vol.52 , pp. 491-494
    • Saito, Y.1    Koda, M.2    Shinohara, Y.3    Saito, I.4
  • 11
    • 84863170603 scopus 로고    scopus 로고
    • Dehydrogenative heck coupling of biologically relevant N-heteroarenes with alkenes: Discovery of fluorescent core frameworks
    • Y. Huang, F. Song, Z. Wang, P. Xi, N. Wu, and Z. Wang et al. Dehydrogenative heck coupling of biologically relevant N-heteroarenes with alkenes: discovery of fluorescent core frameworks Chem Commun 48 2012 2864 2866
    • (2012) Chem Commun , vol.48 , pp. 2864-2866
    • Huang, Y.1    Song, F.2    Wang, Z.3    Xi, P.4    Wu, N.5    Wang, Z.6
  • 12
    • 84865118530 scopus 로고    scopus 로고
    • Fluorescence sensing of caffeine in aqueous solution with carbazole-based probe and imaging application in live cells
    • A.K. Mahapatra, J. Roy, P. Sahoo, S.K. Mukhopadhyay, A.R. Mukhopadhyay, and D. Mandal Fluorescence sensing of caffeine in aqueous solution with carbazole-based probe and imaging application in live cells Bioorg Med Chem Lett 22 2012 5379 5383
    • (2012) Bioorg Med Chem Lett , vol.22 , pp. 5379-5383
    • Mahapatra, A.K.1    Roy, J.2    Sahoo, P.3    Mukhopadhyay, S.K.4    Mukhopadhyay, A.R.5    Mandal, D.6
  • 13
    • 84872305386 scopus 로고    scopus 로고
    • Naphthalene-based environmentally sensitive fluorescent 8-substituted 2'-deoxyadenosines: Application to DNA detection
    • A. Suzuki, N. Takahashi, Y. Okada, I. Saito, N. Nemoto, and Y. Saito Naphthalene-based environmentally sensitive fluorescent 8-substituted 2'-deoxyadenosines: application to DNA detection Bioorg Med Chem Lett 23 2013 886 892
    • (2013) Bioorg Med Chem Lett , vol.23 , pp. 886-892
    • Suzuki, A.1    Takahashi, N.2    Okada, Y.3    Saito, I.4    Nemoto, N.5    Saito, Y.6
  • 14
    • 84872859119 scopus 로고    scopus 로고
    • An acetylene-bridged 6,8-purine dimer as a fluorescent switch-on probe for parallel G-quadruplexes
    • M. Nikan, M. Di Antonio, K. Abecassis, K. McLuckie, and S. Balasubramanian An acetylene-bridged 6,8-purine dimer as a fluorescent switch-on probe for parallel G-quadruplexes Angew Chem Int Ed 52 2013 1428 1431
    • (2013) Angew Chem Int Ed , vol.52 , pp. 1428-1431
    • Nikan, M.1    Di Antonio, M.2    Abecassis, K.3    McLuckie, K.4    Balasubramanian, S.5
  • 15
    • 79851516690 scopus 로고    scopus 로고
    • Design and synthesis of highly solvatochromic fluorescent 2′-deoxyguanosine and 2′-deoxyadenosine analogs
    • K. Matsumoto, N. Takahashi, A. Suzuki, T. Morii, Y. Saito, and I. Saito Design and synthesis of highly solvatochromic fluorescent 2′- deoxyguanosine and 2′-deoxyadenosine analogs Bioorg Med Chem Lett 21 2011 1275 1278
    • (2011) Bioorg Med Chem Lett , vol.21 , pp. 1275-1278
    • Matsumoto, K.1    Takahashi, N.2    Suzuki, A.3    Morii, T.4    Saito, Y.5    Saito, I.6
  • 16
    • 80055000563 scopus 로고    scopus 로고
    • 3-cinnamyl)-modified purine nucleosides as promising fluorescent probes
    • 3- cinnamyl)-modified purine nucleosides as promising fluorescent probes Org Biomol Chem 9 2011 7763 7773
    • (2011) Org Biomol Chem , vol.9 , pp. 7763-7773
    • Zilbershtein, L.1    Silberman, A.2    Fischer, B.3
  • 17
    • 84890101302 scopus 로고    scopus 로고
    • Rules for the design of highly fluorescent nucleoside probes: 8-(substituted cinnamyl)-adenosine analogues
    • L. Zilbershtein-Shklanovsky, M. Weitman, D.T. Major, and B. Fischer Rules for the design of highly fluorescent nucleoside probes: 8-(substituted cinnamyl)-adenosine analogues J Org Chem 78 2013 11999 12008
    • (2013) J Org Chem , vol.78 , pp. 11999-12008
    • Zilbershtein-Shklanovsky, L.1    Weitman, M.2    Major, D.T.3    Fischer, B.4
  • 18
    • 55949100781 scopus 로고    scopus 로고
    • Stereoselective direct copper-catalyzed alkenylation of oxazoles with bromoalkenes
    • F. Besselièvre, S. Piguel, F. Mahuteau-Betzer, and D. Grierson Stereoselective direct copper-catalyzed alkenylation of oxazoles with bromoalkenes Org Lett 10 2008 4029 4032
    • (2008) Org Lett , vol.10 , pp. 4029-4032
    • Besselièvre, F.1    Piguel, S.2    Mahuteau-Betzer, F.3    Grierson, D.4
  • 19
    • 72049120421 scopus 로고    scopus 로고
    • C-H bond activation: A versatile protocol for the direct arylation and alkenylation of oxazoles
    • F. Besselièvre, S. Lebrequier, F. Mahuteau-Betzer, and S. Piguel C-H bond activation: a versatile protocol for the direct arylation and alkenylation of oxazoles Synthesis 20 2009 3511 3518
    • (2009) Synthesis , vol.20 , pp. 3511-3518
    • Besselièvre, F.1    Lebrequier, S.2    Mahuteau-Betzer, F.3    Piguel, S.4
  • 20
    • 81055123640 scopus 로고    scopus 로고
    • Microwave-assisted Pd/Cu-catalyzed C-8 direct alkenylation of purines and related azoles: An alternative access to 6,8,9-trisubstituted purines
    • R. Vabre, F. Chevot, M. Legraverend, and S. Piguel Microwave-assisted Pd/Cu-catalyzed C-8 direct alkenylation of purines and related azoles: an alternative access to 6,8,9-trisubstituted purines J Org Chem 76 2011 9542 9547
    • (2011) J Org Chem , vol.76 , pp. 9542-9547
    • Vabre, R.1    Chevot, F.2    Legraverend, M.3    Piguel, S.4
  • 21
    • 0008971832 scopus 로고
    • Relative fluorescence quantum yields using a computer-controlled luminescence spectrometer
    • A.T. Rhys Williams, S.A. Winfield, and J.N. Miller Relative fluorescence quantum yields using a computer-controlled luminescence spectrometer Analyst 108 1983 1067 1071
    • (1983) Analyst , vol.108 , pp. 1067-1071
    • Rhys Williams, A.T.1    Winfield, S.A.2    Miller, J.N.3
  • 22
    • 34250870683 scopus 로고    scopus 로고
    • Mitsunobu coupling of nucleobases and alcohols: An efficient, practical synthesis for novel nonsugar carbon nucleosides
    • W. Lu, S. Sengupta, J.L. Petersen, N.G. Akhmedov, and X. Shi Mitsunobu coupling of nucleobases and alcohols: an efficient, practical synthesis for novel nonsugar carbon nucleosides J Org Chem 72 2007 5012 5015
    • (2007) J Org Chem , vol.72 , pp. 5012-5015
    • Lu, W.1    Sengupta, S.2    Petersen, J.L.3    Akhmedov, N.G.4    Shi, X.5
  • 23
    • 33947474658 scopus 로고
    • Purine nucleosides. I. The synthesis of certain 6-substituted-9- (tetrahydro-2-pyrany1)-purines as models of purine deoxynucleosides
    • R.K. Robins, E.F. Godefroi, E.C. Taylor, L.R. Lewis, and A. Jackson Purine nucleosides. I. The synthesis of certain 6-substituted-9-(tetrahydro-2- pyrany1)-purines as models of purine deoxynucleosides J Am Chem Soc 83 1961 2574 2579
    • (1961) J Am Chem Soc , vol.83 , pp. 2574-2579
    • Robins, R.K.1    Godefroi, E.F.2    Taylor, E.C.3    Lewis, L.R.4    Jackson, A.5
  • 24
    • 84861168872 scopus 로고    scopus 로고
    • Palladium-catalyzed amidation and amination of 8-iodopurine
    • F. Chevot, R. Vabre, S. Piguel, and M. Legraverend Palladium-catalyzed amidation and amination of 8-iodopurine Eur J Org Chem 15 2012 2889 2893
    • (2012) Eur J Org Chem , vol.15 , pp. 2889-2893
    • Chevot, F.1    Vabre, R.2    Piguel, S.3    Legraverend, M.4
  • 25
    • 25444450832 scopus 로고    scopus 로고
    • Synthesis of enantiomerically pure (purin-6-yl)phenylalanines and their nucleosides, a novel type of purine-amino acid conjugates
    • P. Čapek, R. Pohl, and M. Hocek Synthesis of enantiomerically pure (purin-6-yl)phenylalanines and their nucleosides, a novel type of purine-amino acid conjugates J Org Chem 70 2005 8001 8008
    • (2005) J Org Chem , vol.70 , pp. 8001-8008
    • Čapek, P.1    Pohl, R.2    Hocek, M.3
  • 26
    • 34548750305 scopus 로고    scopus 로고
    • Selective amidation of 2,6-dihalogenopurines: Application to the synthesis of new 2,6,9-trisubstituted purines
    • S. Piguel, and M. Legraverend Selective amidation of 2,6- dihalogenopurines: application to the synthesis of new 2,6,9-trisubstituted purines J Org Chem 72 2007 7026 7029
    • (2007) J Org Chem , vol.72 , pp. 7026-7029
    • Piguel, S.1    Legraverend, M.2
  • 27
    • 33947473632 scopus 로고
    • A new synthesis of 1,1-dibromoölefins via phosphine- dibromomethylenes. The reaction of triphenylphosphine with carbon tetrabromide
    • F. Ramirez, N.B. Desai, and N. McKelvie A new synthesis of 1,1-dibromoölefins via phosphine-dibromomethylenes. The reaction of triphenylphosphine with carbon tetrabromide J Am Chem Soc 84 1962 1745 1747
    • (1962) J Am Chem Soc , vol.84 , pp. 1745-1747
    • Ramirez, F.1    Desai, N.B.2    McKelvie, N.3
  • 28
    • 0034701604 scopus 로고    scopus 로고
    • The Hirao reduction revisited: A procedure for the synthesis of terminal vinyl bromides by the reduction of 1,1-dibromoalkenes
    • S. Abbas, C.J. Hayes, and S. Worden The Hirao reduction revisited: a procedure for the synthesis of terminal vinyl bromides by the reduction of 1,1-dibromoalkenes Tetrahedron Lett 41 2000 3215 3219
    • (2000) Tetrahedron Lett , vol.41 , pp. 3215-3219
    • Abbas, S.1    Hayes, C.J.2    Worden, S.3
  • 29
    • 50449096448 scopus 로고    scopus 로고
    • Solvent effects on fluorescence properties of protochlorophyll and its derivatives with various porphyrin side chains
    • B. Myśliwa-Kurdziel, K. Solymosi, J. Kruk, B. Böddi, and K. Strzałka Solvent effects on fluorescence properties of protochlorophyll and its derivatives with various porphyrin side chains Eur Biophys J 37 2008 1185 1193
    • (2008) Eur Biophys J , vol.37 , pp. 1185-1193
    • Myśliwa-Kurdziel, B.1    Solymosi, K.2    Kruk, J.3    Böddi, B.4    Strzałka, K.5
  • 30
    • 17044389011 scopus 로고    scopus 로고
    • Effects of (multi)branching of dipolar chromophores on photophysical properties and two-photon absorption
    • C. Katan, F. Terenziani, O. Mongin, M.H.V. Werts, L. Porres, and T. Pons et al. Effects of (multi)branching of dipolar chromophores on photophysical properties and two-photon absorption J Phys Chem A 109 2005 3024 3037
    • (2005) J Phys Chem A , vol.109 , pp. 3024-3037
    • Katan, C.1    Terenziani, F.2    Mongin, O.3    Werts, M.H.V.4    Porres, L.5    Pons, T.6
  • 32
    • 77950475768 scopus 로고    scopus 로고
    • Aromatic fumaronitrile core-based donor-linker-acceptor-linker-donor (D-π-A-π-D) compounds: Synthesis and photophysical properties
    • K. Panthi, R.M. Adhikari, and T.H. Kinstle Aromatic fumaronitrile core-based donor-linker-acceptor-linker-donor (D-π-A-π-D) compounds: synthesis and photophysical properties J Phys Chem A 114 2010 4542 4549
    • (2010) J Phys Chem A , vol.114 , pp. 4542-4549
    • Panthi, K.1    Adhikari, R.M.2    Kinstle, T.H.3
  • 33
    • 34247860997 scopus 로고    scopus 로고
    • Vinyl-pyridinium triphenylamines: Novel far-red emitters with high photostability and two-photon absorption for staining DNA
    • C. Allain, F. Schmidt, R. Lartia, G. Bordeau, C. Fiorini-Debuisschert, and F. Charra et al. Vinyl-pyridinium triphenylamines: novel far-red emitters with high photostability and two-photon absorption for staining DNA ChemBioChem 8 2007 424 433
    • (2007) ChemBioChem , vol.8 , pp. 424-433
    • Allain, C.1    Schmidt, F.2    Lartia, R.3    Bordeau, G.4    Fiorini-Debuisschert, C.5    Charra, F.6
  • 34
    • 77955416275 scopus 로고    scopus 로고
    • Meta-substituted triphenylmaines as new dyes displaying exceptionally large stokes shifts
    • G. Bordeau, R. Lartia, and M.-P. Teulade-Ficou meta-substituted triphenylmaines as new dyes displaying exceptionally large stokes shifts Tetrahedron Lett 51 2010 4429 4432
    • (2010) Tetrahedron Lett , vol.51 , pp. 4429-4432
    • Bordeau, G.1    Lartia, R.2    Teulade-Ficou, M.-P.3
  • 35
    • 0035384605 scopus 로고    scopus 로고
    • Photophysical properties of fluorescent DNA-dyes bound to single- and double-stranded DNA in aqueous buffered solution
    • G. Cosa, K.-S. Focsaneanu, J.R.N. McLean, J.P. McNamee, and J.C. Scaiano Photophysical properties of fluorescent DNA-dyes bound to single- and double-stranded DNA in aqueous buffered solution Photochem Photobiol 73 2001 585 599
    • (2001) Photochem Photobiol , vol.73 , pp. 585-599
    • Cosa, G.1    Focsaneanu, K.-S.2    McLean, J.R.N.3    McNamee, J.P.4    Scaiano, J.C.5
  • 36
    • 0034812469 scopus 로고    scopus 로고
    • A highly fluorescent DNA base analogue that forms Watson-Crick base pairs with guanine
    • M.L. Wilhelmsson, A. Holmén, P. Lincoln, P.E. Nielsen, and B. Nordén A highly fluorescent DNA base analogue that forms Watson-Crick base pairs with guanine J Am Chem Soc 123 2001 2434 2435
    • (2001) J Am Chem Soc , vol.123 , pp. 2434-2435
    • Wilhelmsson, M.L.1    Holmén, A.2    Lincoln, P.3    Nielsen, P.E.4    Nordén, B.5
  • 37
    • 34247253265 scopus 로고    scopus 로고
    • Selective fluorometric detection of guanosine-containing sequences by 6-phenylpyrrolocytidine in DNA
    • R.H.E. Hudson, and A. Ghorbani-Choghamarani Selective fluorometric detection of guanosine-containing sequences by 6-phenylpyrrolocytidine in DNA Synlett 6 2007 870 873
    • (2007) Synlett , vol.6 , pp. 870-873
    • Hudson, R.H.E.1    Ghorbani-Choghamarani, A.2
  • 38
    • 70350130625 scopus 로고    scopus 로고
    • Intrinsically fluorescent base-discriminating nucleosides and analogs
    • D.W. Dodd, and R.H.E. Hudson Intrinsically fluorescent base-discriminating nucleosides and analogs Mini Rev Org Chem 6 2009 378 391
    • (2009) Mini Rev Org Chem , vol.6 , pp. 378-391
    • Dodd, D.W.1    Hudson, R.H.E.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.