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Volumn 18, Issue 5, 2008, Pages 961-972

A spectroscopic study of the interaction of the fluorescent β-carboline-3-carboxylic acid N-methylamide with DNA constituents: nucleobases, nucleosides and nucleotides

Author keywords

carboline; Absorption; Fluorescence; Nucleobases; Nucleosides; Nucleotides

Indexed keywords

ABSORPTION; FLUORESCENCE; NUCLEOBASES; NUCLEOSIDES;

EID: 51649083707     PISSN: 10530509     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10895-008-0355-9     Document Type: Article
Times cited : (9)

References (54)
  • 1
    • 1242351299 scopus 로고    scopus 로고
    • Exposure to β-carbolines norharman and harman
    • 1
    • Pfau W, Skog K (2004) Exposure to β-carbolines norharman and harman. J Chromatogr B 802(1):115-126
    • (2004) J Chromatogr B , vol.802 , pp. 115-126
    • Pfau, W.1    Skog, K.2
  • 3
    • 4644300544 scopus 로고    scopus 로고
    • Structures of new β-carboline-type alkaloids with antiallergic effects from Stellaria dichotoma
    • 9
    • Sun B, Morikawa T, Matsuda H, Tewtrakul S, Wu LJ, Harima S, Yoshikawa M (2004) Structures of new β-carboline-type alkaloids with antiallergic effects from Stellaria dichotoma. J Nat Prod 67(9):1464-1469
    • (2004) J Nat Prod , vol.67 , pp. 1464-1469
    • Sun, B.1    Morikawa, T.2    Matsuda, H.3    Tewtrakul, S.4    Wu, L.J.5    Harima, S.6    Yoshikawa, M.7
  • 4
    • 0043199852 scopus 로고    scopus 로고
    • Plants and the central nervous system
    • 3
    • Carlini EA (2003) Plants and the central nervous system. Pharmacol Biochem Behav 75(3):501-512
    • (2003) Pharmacol Biochem Behav , vol.75 , pp. 501-512
    • Carlini, E.A.1
  • 6
    • 11944275594 scopus 로고    scopus 로고
    • Relative exposure to beta-carbolines norharman and harman from foods and tobacco smoke
    • 11
    • Herraiz T (2004) Relative exposure to beta-carbolines norharman and harman from foods and tobacco smoke. Food Addit Contam 21(11):1041-1050
    • (2004) Food Addit Contam , vol.21 , pp. 1041-1050
    • Herraiz, T.1
  • 7
    • 2342527245 scopus 로고    scopus 로고
    • Identification and occurrence of output this record tryptamine- and tryptophan-derived tetrahydro-beta-carbolines in commercial sausages
    • 9
    • Herraiz T, Papavergou E (2004) Identification and occurrence of output this record tryptamine- and tryptophan-derived tetrahydro-beta-carbolines in commercial sausages. J Agric Food Chem 52(9):2652-2658
    • (2004) J Agric Food Chem , vol.52 , pp. 2652-2658
    • Herraiz, T.1    Papavergou, E.2
  • 9
    • 0034723254 scopus 로고    scopus 로고
    • β-carbolines that accumulate in human tissues may serve a protective role against oxidative stress
    • 4
    • Pari K, Sundari CS, Chandani S, Balasubramanian D (2000) β-carbolines that accumulate in human tissues may serve a protective role against oxidative stress. J Biol Chem 275(4):2455-2462
    • (2000) J Biol Chem , vol.275 , pp. 2455-2462
    • Pari, K.1    Sundari, C.S.2    Chandani, S.3    Balasubramanian, D.4
  • 10
    • 0025903790 scopus 로고
    • Therapeutic potential of plant photosenistizers
    • 3
    • Hudson JB, Towers GH (1991) Therapeutic potential of plant photosenistizers. Pharmac Ther 49(3):81-122
    • (1991) Pharmac Ther , vol.49 , pp. 81-122
    • Hudson, J.B.1    Towers, G.H.2
  • 12
    • 24344487709 scopus 로고    scopus 로고
    • Simultaneous determination of nineteen hallucinogenic tryptamines/β-carbolines and phenthylamines using gas chromatography-mass spectrometry and liquid chromatography-electrospray ionisation-mass spectrometry
    • 1
    • Kikura-Hanajiri R, Hayashi M, Saisho K, Goda Y (2005) Simultaneous determination of nineteen hallucinogenic tryptamines/β-carbolines and phenthylamines using gas chromatography-mass spectrometry and liquid chromatography-electrospray ionisation-mass spectrometry. J Chromatogr B 825(1):29-37
    • (2005) J Chromatogr B , vol.825 , pp. 29-37
    • Kikura-Hanajiri, R.1    Hayashi, M.2    Saisho, K.3    Goda, Y.4
  • 13
    • 0345599950 scopus 로고    scopus 로고
    • Effects of the β-carbolines, harmane and pinoline, on insulin secretion from isolated human islets of Langerhans
    • 1-3
    • Cooper EJ, Hudson AL, Parker CA, Morgan NG (2003) Effects of the β-carbolines, harmane and pinoline, on insulin secretion from isolated human islets of Langerhans. Eur J Pharmacol 482(1-3):189-196
    • (2003) Eur J Pharmacol , vol.482 , pp. 189-196
    • Cooper, E.J.1    Hudson, A.L.2    Parker, C.A.3    Morgan, N.G.4
  • 14
    • 7044272523 scopus 로고    scopus 로고
    • Synthesis and biological studies of 1-amino- β-carbolines
    • 23
    • Boursereau Y, Coldham I (2004) Synthesis and biological studies of 1-amino- β-carbolines. Bioorg Med Chem Lett 14(23):5841-5844
    • (2004) Bioorg Med Chem Lett , vol.14 , pp. 5841-5844
    • Boursereau, Y.1    Coldham, I.2
  • 18
    • 33644624640 scopus 로고    scopus 로고
    • β-Carboline derivatives: Novel photosensitizers that intercalate into DNA to cause direct DNA damage in photodynamic therapy
    • 3
    • Guan H, Liu X, Peng W, Cao R, Ma Y, Chen H, Xu A (2006) β-Carboline derivatives: Novel photosensitizers that intercalate into DNA to cause direct DNA damage in photodynamic therapy. Biochem Biophys Res Commun 342(3):894-901
    • (2006) Biochem Biophys Res Commun , vol.342 , pp. 894-901
    • Guan, H.1    Liu, X.2    Peng, W.3    Cao, R.4    Ma, Y.5    Chen, H.6    Xu, A.7
  • 19
    • 0242691743 scopus 로고    scopus 로고
    • Tetrahydro-β-carboline alkaloids occur in fruits and fruit juices. Activity as antioxidants and radical scavengers
    • 24
    • Herraiz T, Galisteo J (2003) Tetrahydro-β-carboline alkaloids occur in fruits and fruit juices. Activity as antioxidants and radical scavengers. J Agric Food Chem 51(24):7156-7161
    • (2003) J Agric Food Chem , vol.51 , pp. 7156-7161
    • Herraiz, T.1    Galisteo, J.2
  • 20
    • 1242283910 scopus 로고    scopus 로고
    • Investigation of the genotoxic effects of 2-amino-9H-pyrido[2,3-b]indole in different organs of rodents and in human derived cells
    • 1
    • Majer BJ, Kassie F, Sasaki Y, Pfau W, Glatt H, Meinl W, Darroudi F, Knasmüller S (2004) Investigation of the genotoxic effects of 2-amino-9H-pyrido[2,3-b]indole in different organs of rodents and in human derived cells. J Chromatogr B 802(1):167-173
    • (2004) J Chromatogr B , vol.802 , pp. 167-173
    • Majer, B.J.1    Kassie, F.2    Sasaki, Y.3    Pfau, W.4    Glatt, H.5    Meinl, W.6    Darroudi, F.7    Knasmüller, S.8
  • 21
    • 1642321287 scopus 로고    scopus 로고
    • Possibility of the involvement of 9H-pyrido[3,4-b]indole (norharman) in carcinogenesis via inhibition of cytochrome P450-related activities and intercalation to DNA
    • 1-2
    • Nii H (2003) Possibility of the involvement of 9H-pyrido[3,4-b]indole (norharman) in carcinogenesis via inhibition of cytochrome P450-related activities and intercalation to DNA. Mutat Res 541(1-2):123-136
    • (2003) Mutat Res , vol.541 , pp. 123-136
    • Nii, H.1
  • 22
    • 0037139155 scopus 로고    scopus 로고
    • Genotoxic and recombinogenic activities of the two β-carboline alkaloids harman and harmine in Saccharomyces cerevisiae
    • 1-2
    • Boeira JM, Viana AF, Picada JN, Henriques JAP (2002) Genotoxic and recombinogenic activities of the two β-carboline alkaloids harman and harmine in Saccharomyces cerevisiae. Mutat Res 500(1-2):39-48
    • (2002) Mutat Res , vol.500 , pp. 39-48
    • Boeira, J.M.1    Viana, A.F.2    Picada, J.N.3    Henriques, J.A.P.4
  • 23
    • 0035907135 scopus 로고    scopus 로고
    • Studies on single-strand scissions to cell-free plasmid DNA by the dopaminergic neurotoxin 'TaClo' (1-trichloromethyl-1,2,3,4-tetrahydro-β- carboline)
    • 1
    • Bringmann G, Münchbach M, Feineis D, Faulhaber K, Ihmels H (2001) Studies on single-strand scissions to cell-free plasmid DNA by the dopaminergic neurotoxin 'TaClo' (1-trichloromethyl-1,2,3,4-tetrahydro-β-carboline). Neurosci Lett 304(1):41-44
    • (2001) Neurosci Lett , vol.304 , pp. 41-44
    • Bringmann, G.1    Münchbach, M.2    Feineis, D.3    Faulhaber, K.4    Ihmels, H.5
  • 24
    • 0030922249 scopus 로고    scopus 로고
    • Human exposure to mutagenic/carcinogenic heterocyclic amines and comutagenic β-carbolines
    • 1-2
    • Wakabayashi K, Totsuka Y, Fukutome K, Oguri A, Ushiyama H, Sugimura T (1997) Human exposure to mutagenic/carcinogenic heterocyclic amines and comutagenic β-carbolines. Mutat Res 376(1-2):253-259
    • (1997) Mutat Res , vol.376 , pp. 253-259
    • Wakabayashi, K.1    Totsuka, Y.2    Fukutome, K.3    Oguri, A.4    Ushiyama, H.5    Sugimura, T.6
  • 26
    • 0029416917 scopus 로고
    • Genotoxic potential of β-carbolines: A review
    • Meester C (1995) Genotoxic potential of β-carbolines: a review. Mutat Res 339:139-153
    • (1995) Mutat Res , vol.339 , pp. 139-153
    • Meester, C.1
  • 27
    • 0026731211 scopus 로고
    • Enhancing effects of heterocyclic amines and β-carbolines on the induction of chromosome aberrations in cultured mammalian cells
    • 1
    • Sasaki YF, Yamada H, Shimoi K, Kinae N, Tomita I, Matsumura H, Ohta T, Shirasu Y (1992) Enhancing effects of heterocyclic amines and β-carbolines on the induction of chromosome aberrations in cultured mammalian cells. Mutat Res 269(1):79-95
    • (1992) Mutat Res , vol.269 , pp. 79-95
    • Sasaki, Y.F.1    Yamada, H.2    Shimoi, K.3    Kinae, N.4    Tomita, I.5    Matsumura, H.6    Ohta, T.7    Shirasu, Y.8
  • 28
    • 0026642376 scopus 로고
    • Enhancing effect of heterocyclic amines and β-carbolines on UV or chemically induced mutagenesis in e
    • 2
    • Shimoi K, Kawabata H, Tomita I (1992) Enhancing effect of heterocyclic amines and β-carbolines on UV or chemically induced mutagenesis in E. coli. Mutat Res 268(2):287-295
    • (1992) Coli. Mutat Res , vol.268 , pp. 287-295
    • Shimoi, K.1    Kawabata, H.2    Tomita, I.3
  • 29
    • 0035952254 scopus 로고    scopus 로고
    • Synthesis and biological evaluation of DNA targeting flexible side-chain substituted β-carboline derivatives
    • 4
    • Xiao S, Lin W, Wang C, Yang M (2001) Synthesis and biological evaluation of DNA targeting flexible side-chain substituted β-carboline derivatives. Bioorg Med Chem Lett 11(4):437-441
    • (2001) Bioorg Med Chem Lett , vol.11 , pp. 437-441
    • Xiao, S.1    Lin, W.2    Wang, C.3    Yang, M.4
  • 32
    • 36248955403 scopus 로고    scopus 로고
    • Effects of the interaction between β-carboline-3-carboxylic acid N-methylamide and polynucleotide on singlet oxygen quantum yield and DNA oxidative damage
    • García-Zubiri IX, Burrows HD, Seixas de Melo JS, Pina J, Monteserín M, Tapia MJ (2007) Effects of the interaction between β-carboline-3-carboxylic acid N-methylamide and polynucleotide on singlet oxygen quantum yield and DNA oxidative damage. Photochem Photobiol 83:1455-1464
    • (2007) Photochem Photobiol , vol.83 , pp. 1455-1464
    • García-Zubiri, I.X.1    Burrows, H.D.2    Seixas De Melo, J.S.3    Pina, J.4    Monteserín, M.5    Tapia, M.J.6
  • 33
    • 0033584208 scopus 로고    scopus 로고
    • A fluorescence study of the molecular interactions of harmane with the nucleobases, their nucleosides and mononucleotides
    • 1
    • Balón M, Muñoz MA, Carmona C, Guardado P, Galán M (1999) A fluorescence study of the molecular interactions of harmane with the nucleobases, their nucleosides and mononucleotides. Biophys Chem 80(1):41-52
    • (1999) Biophys Chem , vol.80 , pp. 41-52
    • Balón, M.1    Muñoz, M.A.2    Carmona, C.3    Guardado, P.4    Galán, M.5
  • 34
    • 0037363344 scopus 로고    scopus 로고
    • Acid-base equilibria of methyl β-carboline-3-carboxylate in aqueous solution
    • 3
    • Tapia MJ, Reyman D, Viñas MH, Carcedo C, Poyato JML (2003) Acid-base equilibria of methyl β-carboline-3-carboxylate in aqueous solution. J Lumin 101(3):227-234
    • (2003) J Lumin , vol.101 , pp. 227-234
    • Tapia, M.J.1    Reyman, D.2    Viñas, M.H.3    Carcedo, C.4    Poyato, J.M.L.5
  • 35
    • 0041663867 scopus 로고    scopus 로고
    • Photophysical properties of methyl β-carboline-3-carboxylate mediated by hydrogen-bonded complexes-a comparative study in different solvents
    • 3
    • Reyman D, Tapia MJ, Carcedo C, Viñas MH (2003) Photophysical properties of methyl β-carboline-3-carboxylate mediated by hydrogen-bonded complexes-a comparative study in different solvents. Biophys Chem 104(3):683-696
    • (2003) Biophys Chem , vol.104 , pp. 683-696
    • Reyman, D.1    Tapia, M.J.2    Carcedo, C.3    Viñas, M.H.4
  • 37
    • 0000114248 scopus 로고
    • β-carboline photosensitizers. 1. Photophysics, kinetics and excited-state equilibria in organic solvents, and theoretical calculations
    • 25
    • Dias A, Varela AP, Miguel MG, Maçanita AL, Becker RS (1992) β-carboline photosensitizers. 1. Photophysics, kinetics and excited-state equilibria in organic solvents, and theoretical calculations. J Phys Chem 96(25):10290-10296
    • (1992) J Phys Chem , vol.96 , pp. 10290-10296
    • Dias, A.1    Varela, A.P.2    Miguel, M.G.3    MaçAnita, A.L.4    Becker, R.S.5
  • 39
    • 0026853846 scopus 로고
    • Some β-carboline derivatives as fluorescence standards
    • 5
    • Pardo A, Reyman D, Poyato JML, Medina F (1992) Some β-carboline derivatives as fluorescence standards. J Lumin 51(5):269-274
    • (1992) J Lumin , vol.51 , pp. 269-274
    • Pardo, A.1    Reyman, D.2    Poyato, J.M.L.3    Medina, F.4
  • 40
    • 0037456625 scopus 로고    scopus 로고
    • An experimental and theoretical approach to the acid-base and photophysical properties of 3-substituted β-carbolines in aqueous solutions
    • 1
    • Tapia MJ, Reyman D, Viñas MH, Arroyo A, Poyato JML (2003) An experimental and theoretical approach to the acid-base and photophysical properties of 3-substituted β-carbolines in aqueous solutions. J Photochem Photobiol A: Chem 156(1):1-7
    • (2003) J Photochem Photobiol A: Chem , vol.156 , pp. 1-7
    • Tapia, M.J.1    Reyman, D.2    Viñas, M.H.3    Arroyo, A.4    Poyato, J.M.L.5
  • 42
    • 0028981694 scopus 로고
    • Anxiogenic effects of a beta-carboline on tonic immobility and open field behaviour in chickens (Gallus gallus)
    • 4
    • Moriarty DD (1995) Anxiogenic effects of a beta-carboline on tonic immobility and open field behaviour in chickens (Gallus gallus). Pharmacol Biochem Behav 51(4):795-798
    • (1995) Pharmacol Biochem Behav , vol.51 , pp. 795-798
    • Moriarty, D.D.1
  • 43
    • 0008264289 scopus 로고    scopus 로고
    • Spectroscopy and photophysics of 4- and 7-hydroxycoumarins and their thione analogs
    • Seixas de Melo J, Fernandez PF (2001) Spectroscopy and photophysics of 4- and 7-hydroxycoumarins and their thione analogs. J Mol Struct 565-566:69-78
    • (2001) J Mol Struct , vol.565-566 , pp. 69-78
    • Seixas De Melo, J.1    Fernandez, P.F.2
  • 44
    • 0000839617 scopus 로고    scopus 로고
    • Photochromicity and fluorescence lifetimes of green fluorescent protein
    • 40
    • Striker G, Subramaniam V, Seidel CAM, Volkmer A (1999) Photochromicity and fluorescence lifetimes of green fluorescent protein. J Phys Chem B 103(40):8612-8617
    • (1999) J Phys Chem B , vol.103 , pp. 8612-8617
    • Striker, G.1    Subramaniam, V.2    Seidel, C.A.M.3    Volkmer, A.4
  • 45
    • 33746190548 scopus 로고
    • A Spectrophotometric investigation of the interaction of iodine with aromatic hydrocarbons
    • 8
    • Benesi HA, Hildebrand JH (1949) A Spectrophotometric investigation of the interaction of iodine with aromatic hydrocarbons. J Am Chem Soc 71(8):2703-2707
    • (1949) J Am Chem Soc , vol.71 , pp. 2703-2707
    • Benesi, H.A.1    Hildebrand, J.H.2
  • 47
    • 27444438167 scopus 로고    scopus 로고
    • Isolation and chemical characterization of PwTx-II: A novel alkaloid toxin from the venom of the spider Parawixia bistriata (Araneidae, Araneae)
    • 7
    • Cesar LMM, Mendes MA, Tormena CF, Marques MR, de Souza BM, Saidemberg DM, Bittencourt JC, Palma MS (2005) Isolation and chemical characterization of PwTx-II: a novel alkaloid toxin from the venom of the spider Parawixia bistriata (Araneidae, Araneae). Toxicon 46(7):786-796
    • (2005) Toxicon , vol.46 , pp. 786-796
    • Cesar, L.M.M.1    Mendes, M.A.2    Tormena, C.F.3    Marques, M.R.4    De Souza, B.M.5    Saidemberg, D.M.6    Bittencourt, J.C.7    Palma, M.S.8
  • 48
    • 0042415668 scopus 로고    scopus 로고
    • Combined effects of electrostatic and π-π Stacking interactions: Selective binding of nucleotides and aromatic carboxylates by platinum(II)-aromatic ligand complexes
    • 14
    • Yahima T, Maccarrone G, Takani M, Contino A, Arena G, Takamido R, Hanaki M, Funahashi Y, Odani A, Yamauchi O (2003) Combined effects of electrostatic and π-π stacking interactions: selective binding of nucleotides and aromatic carboxylates by platinum(II)-aromatic ligand complexes. Chem Eur J 9(14):3341-3352
    • (2003) Chem Eur J , vol.9 , pp. 3341-3352
    • Yahima, T.1    MacCarrone, G.2    Takani, M.3    Contino, A.4    Arena, G.5    Takamido, R.6    Hanaki, M.7    Funahashi, Y.8    Odani, A.9    Yamauchi, O.10
  • 50
    • 0001158384 scopus 로고    scopus 로고
    • Nucleotide complexes with azoniacyclophanes containing phenyl-, biphenyl- or bipyridyl-units
    • Ragunathan KG, Schneider H-J (1996) Nucleotide complexes with azoniacyclophanes containing phenyl-, biphenyl- or bipyridyl-units. J Chem Soc Perkin Trans 2:2597-2600
    • (1996) J Chem Soc Perkin Trans , vol.2 , pp. 2597-2600
    • Ragunathan, K.G.1    Schneider, H.-J.2
  • 52
    • 33748595282 scopus 로고    scopus 로고
    • Nucleobase-specific quenching of fluorescent dyes. 1. Nucleobase one-electr on redox potentials and their correlation with static and dynamic quenching efficiencies
    • 13
    • Seidel CAM, Schulz A, Sauer MHM (1996) Nucleobase-specific quenching of fluorescent dyes. 1. Nucleobase one-electr on redox potentials and their correlation with static and dynamic quenching efficiencies. J Phys Chem 100(13):5541-5553
    • (1996) J Phys Chem , vol.100 , pp. 5541-5553
    • Seidel, C.A.M.1    Schulz, A.2    Sauer, M.H.M.3
  • 53
    • 0031027125 scopus 로고    scopus 로고
    • How easily oxidizable is DNA? One-electron reduction potentials of adenosine and guanosine radicals in aqueous solution
    • Steenken S, Jovanovic SV (1997) How easily oxidizable is DNA? One-electron reduction potentials of adenosine and guanosine radicals in aqueous solution. J Am Chem Soc 119:617-618
    • (1997) J Am Chem Soc , vol.119 , pp. 617-618
    • Steenken, S.1    Jovanovic, S.V.2
  • 54
    • 0026766945 scopus 로고
    • One-electron-reduction potentials of pyrimidine bases, nucleosides and nucleotides in aqueous solution. Consequences for DNA redox chemistry
    • Steenken S, Telo JP, Novais HM, Candeias LP (1992) One-electron-reduction potentials of pyrimidine bases, nucleosides and nucleotides in aqueous solution. Consequences for DNA redox chemistry. J Am Chem Soc 114:4701-4709
    • (1992) J Am Chem Soc , vol.114 , pp. 4701-4709
    • Steenken, S.1    Telo, J.P.2    Novais, H.M.3    Candeias, L.P.4


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