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Volumn 45, Issue 23, 2006, Pages 7265-7276

2-Alkynyl-N-propargyl pyridinium salts: Pyridinium-based heterocyclic skipped aza-enediynes that cleave DNA by deoxyribosyl hydrogen-atom abstraction and guanine oxidation

Author keywords

[No Author keywords available]

Indexed keywords

BIOCHEMISTRY; DNA; ISOMERIZATION; OXIDATION; REACTION KINETICS;

EID: 33745049226     PISSN: 00062960     EISSN: None     Source Type: Journal    
DOI: 10.1021/bi052519j     Document Type: Article
Times cited : (20)

References (60)
  • 2
    • 0003815528 scopus 로고
    • Borders, D. B., and Doyle, T. W., Eds. Marcel Dekker, Inc., New York
    • Borders, D. B., and Doyle, T. W., Eds. (1995) Enediyne Antibiotics as Antitumor Agents, Marcel Dekker, Inc., New York.
    • (1995) Enediyne Antibiotics as Antitumor Agents
  • 3
    • 0036430176 scopus 로고    scopus 로고
    • Designed enediyne antitumor agents
    • Jones, G. B., and Fouad, F. S. (2002) Designed Enediyne Antitumor Agents, Curr. Pharm. Des. 8, 2415-2440.
    • (2002) Curr. Pharm. Des. , vol.8 , pp. 2415-2440
    • Jones, G.B.1    Fouad, F.S.2
  • 5
    • 0001380819 scopus 로고
    • Thermal generation of α,3-didehydrotoluene from (Z)-12,4-heptatrien-6-yne
    • (a) Myers, A. G., Kuo, E. Y., and Finney, N. S. (1989) Thermal Generation of α,3-Didehydrotoluene from (Z)-12,4-heptatrien-6-yne, J. Am. Chem. Soc. 111, 8057-8059.
    • (1989) J. Am. Chem. Soc. , vol.111 , pp. 8057-8059
    • Myers, A.G.1    Kuo, E.Y.2    Finney, N.S.3
  • 6
    • 0024343657 scopus 로고
    • Biradical formation from acyclic conjugated enyne-allene system related to neocarzinostatin and esperamicin-calicheamicin
    • (b) Nagata, R., Yamanaka, H., Okazaki, E., and Saito, I. (1989) Biradical Formation from Acyclic Conjugated Enyne-Allene System Related to Neocarzinostatin and Esperamicin-Calicheamicin, Tetrahedron Lett. 30, 4995-4998.
    • (1989) Tetrahedron Lett. , vol.30 , pp. 4995-4998
    • Nagata, R.1    Yamanaka, H.2    Okazaki, E.3    Saito, I.4
  • 7
    • 0345614235 scopus 로고
    • Studies on the thermal generation and reactivity of a class of (σ,π)-1,4-biradicals
    • (c) Myers, A. G., Dragovich, P. S., and Kuo, E. Y. (1992) Studies on the Thermal Generation and Reactivity of a Class of (σ,π)-1,4-Biradicals, J. Am. Chem. Soc. 114, 9369-9386.
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 9369-9386
    • Myers, A.G.1    Dragovich, P.S.2    Kuo, E.Y.3
  • 8
    • 0001818029 scopus 로고    scopus 로고
    • Parallel mechanisms for the cycloaromatization of enyne allenes
    • (a) Hughes, T. S., and Carpenter, B. K. (1999) Parallel Mechanisms for the Cycloaromatization of Enyne Allenes, J. Chem. Soc., Perkin Trans. 2 2291-2298.
    • (1999) J. Chem. Soc., Perkin Trans. , vol.2 , pp. 2291-2298
    • Hughes, T.S.1    Carpenter, B.K.2
  • 9
    • 18644366411 scopus 로고    scopus 로고
    • Mechanistic studies on the cyclization of (Z)-1,2,4-heptatrien-6-yne in methanol: A possible nonadiabatic thermal reaction
    • (b) Cremeens, M. E., Hughes, T. S., and Carpenter, B. K. (2005) Mechanistic Studies on the Cyclization of (Z)-1,2,4-Heptatrien-6-Yne in Methanol: A Possible Nonadiabatic Thermal Reaction, J. Am. Chem. Soc. 127, 6652-6661.
    • (2005) J. Am. Chem. Soc. , vol.127 , pp. 6652-6661
    • Cremeens, M.E.1    Hughes, T.S.2    Carpenter, B.K.3
  • 10
    • 0029034833 scopus 로고
    • Switching from the myers reaction to a new thermal cyclization mode in enyne-allenes
    • (a) Schmittel, M., Strittmatter, M., and Kiau, S. (1995) Switching from the Myers Reaction to a New Thermal Cyclization Mode in Enyne-Allenes, Tetrahedron Lett. 36, 4975-4978.
    • (1995) Tetrahedron Lett. , vol.36 , pp. 4975-4978
    • Schmittel, M.1    Strittmatter, M.2    Kiau, S.3
  • 11
    • 20344378706 scopus 로고    scopus 로고
    • Kinetic isotope effects in the thermal C-2-C-6 cyclization of enyne-allenes: Experimental evidence supports a stepwise mechanism
    • (b) For more recent studies of this cyclization, see Schmittel, M., and Vavilala, C. (2005) Kinetic Isotope Effects in the Thermal C-2-C-6 Cyclization of Enyne-Allenes: Experimental Evidence Supports a Stepwise Mechanism, J. Org. Chem. 70, 4865-4868.
    • (2005) J. Org. Chem. , vol.70 , pp. 4865-4868
    • Schmittel, M.1    Vavilala, C.2
  • 12
    • 0030597031 scopus 로고    scopus 로고
    • Steric effects in enyne-allene thermolyses: Switch from myers-saito reaction to the C2-C6 cyclization and DNA strand cleavage
    • Schmittel, M., Kiau, S., Siebert, T., and Strittmatter, M. (1996) Steric Effects in Enyne-Allene Thermolyses: Switch from Myers-Saito Reaction to the C2-C6 Cyclization and DNA Strand Cleavage, Tetrahedron Lett. 37, 7691-7694.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 7691-7694
    • Schmittel, M.1    Kiau, S.2    Siebert, T.3    Strittmatter, M.4
  • 13
    • 0002974462 scopus 로고    scopus 로고
    • Synthesis of novel enyne-allenes, Their thermal C2-C6 cyclization, and the importance of a benzofulvene biradical in the DNA strand cleavage
    • Schmittel, M., Maywald, M., and Strittmatter, M. (1997) Synthesis of Novel Enyne-Allenes, Their Thermal C2-C6 Cyclization, and the Importance of a Benzofulvene Biradical in the DNA Strand Cleavage, Synlett 165-166.
    • (1997) Synlett , pp. 165-166
    • Schmittel, M.1    Maywald, M.2    Strittmatter, M.3
  • 14
    • 1242338910 scopus 로고    scopus 로고
    • Synthesis and DNA damaging ability of enediyne-polyamine conjugates
    • Suzuki, I., Shigenaga, A., Nemoto, H., and Shibuya, M. (2004) Synthesis and DNA Damaging Ability of Enediyne-Polyamine Conjugates, Tetrahedron Lett. 45, 1955-1959.
    • (2004) Tetrahedron Lett. , vol.45 , pp. 1955-1959
    • Suzuki, I.1    Shigenaga, A.2    Nemoto, H.3    Shibuya, M.4
  • 15
    • 0026502073 scopus 로고
    • Cycloaromatization of a 10-membered enediyne derivative via an allenic sulfone intermediate and its DNA cleaving activity
    • Sakai, Y., Bando, Y., Shishido, K., and Shibuya, M. (1992) Cycloaromatization of a 10-Membered Enediyne Derivative via an Allenic Sulfone Intermediate and Its DNA Cleaving Activity, Tetrahedron Lett. 33, 957-960.
    • (1992) Tetrahedron Lett. , vol.33 , pp. 957-960
    • Sakai, Y.1    Bando, Y.2    Shishido, K.3    Shibuya, M.4
  • 16
    • 0029964457 scopus 로고    scopus 로고
    • Novel designed enediynes: Molecular design, chemical synthesis, mode of cycloaromatization and guanine-specific DNA cleavage
    • Toshima, K., Ohta, K., Kano, T., Nakamura, T., Nakata, M., Kinoshita, M., and Matsumura, S. (1996) Novel Designed Enediynes: Molecular Design, Chemical Synthesis, Mode of Cycloaromatization and Guanine-Specific DNA Cleavage, Bioorg. Med. Chem. 4, 105-113.
    • (1996) Bioorg. Med. Chem. , vol.4 , pp. 105-113
    • Toshima, K.1    Ohta, K.2    Kano, T.3    Nakamura, T.4    Nakata, M.5    Kinoshita, M.6    Matsumura, S.7
  • 17
    • 0030135375 scopus 로고    scopus 로고
    • DNA cleavage by an α,3-dehydrotoluene precursor conjugated to a minor groove binding element
    • Myers, A. G., and Parrish, C. A. (1996) DNA Cleavage by an α,3-Dehydrotoluene Precursor Conjugated to a Minor Groove Binding Element, Bioconjugate Chem. 7, 322-331.
    • (1996) Bioconjugate Chem. , vol.7 , pp. 322-331
    • Myers, A.G.1    Parrish, C.A.2
  • 18
    • 0030945208 scopus 로고    scopus 로고
    • Synthesis and thermal rearrangement of C,N-dialkynyl imines: A potential aza-bergman route to 2,5-didehydropyridine
    • (a) David, W. M., and Kerwin, S. M. (1997) Synthesis and Thermal Rearrangement of C,N-Dialkynyl Imines: A Potential Aza-Bergman Route to 2,5-Didehydropyridine, J. Am. Chem. Soc. 119, 1464-1465.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 1464-1465
    • David, W.M.1    Kerwin, S.M.2
  • 19
    • 0037459725 scopus 로고    scopus 로고
    • An extremely facile aza-bergman rearrangement of sterically unencumbered acyclic 3-aza-3-ene-1,5-diynes
    • (b) Feng, L., Kumar, D., and Kerwin, S. M. (2003) An Extremely Facile Aza-Bergman Rearrangement of Sterically Unencumbered Acyclic 3-Aza-3-ene-1,5-diynes, J. Org. Chem. 68, 2234-2242.
    • (2003) J. Org. Chem. , vol.68 , pp. 2234-2242
    • Feng, L.1    Kumar, D.2    Kerwin, S.M.3
  • 20
    • 0032554066 scopus 로고    scopus 로고
    • Chemistry of the 2,5-didehydropyridine biradical: Computational, kinetic, and trapping studies toward drug design
    • Hoffner, J., Schottelius, M. J., Feichtinger, D., and Chen, P. (1998) Chemistry of the 2,5-Didehydropyridine Biradical: Computational, Kinetic, and Trapping Studies Toward Drug Design, J. Am. Chem. Soc. 120, 376-385.
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 376-385
    • Hoffner, J.1    Schottelius, M.J.2    Feichtinger, D.3    Chen, P.4
  • 21
    • 0032125865 scopus 로고    scopus 로고
    • Bergman, aza-bergman, and protonated aza-bergman cyclizations and intermediate 2,5-arynes: Chemistry and challenge to computation
    • Cramer, C. J. (1998) Bergman, Aza-Bergman, and Protonated Aza-Bergman Cyclizations and Intermediate 2,5-Arynes: Chemistry and Challenge to Computation, J. Am. Chem. Soc. 120, 6261-6269.
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 6261-6269
    • Cramer, C.J.1
  • 22
    • 0034647645 scopus 로고    scopus 로고
    • Structure and stability of enediynes containing heteroatoms a quantum chemical investigation
    • (a) Kraka, E., and Cremer, D. (2000) Structure and Stability of Enediynes Containing Heteroatoms a Quantum Chemical Investigation, J. Mol. Struct. 506, 191-211.
    • (2000) J. Mol. Struct. , vol.506 , pp. 191-211
    • Kraka, E.1    Cremer, D.2
  • 23
    • 0034734315 scopus 로고    scopus 로고
    • Computer design of anticancer drugs. A new enediyne warhead
    • (b) Kraka, E., and Cremer, D. (2000) Computer Design of Anticancer Drugs. A New Enediyne Warhead, J. Am. Chem. Soc. 122, 8245-8264.
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 8245-8264
    • Kraka, E.1    Cremer, D.2
  • 24
    • 3042837537 scopus 로고    scopus 로고
    • α,5-didehydro-3-picoline diradicals from skipped azaenediynes: Computational and trapping studies of an aza-myers-saito cyclization
    • Feng, L., Kumar, D., Birney, D. M., and Kerwin, S. M. (2004) α,5-Didehydro-3-picoline Diradicals from Skipped Azaenediynes: Computational and Trapping Studies of an Aza-Myers-Saito Cyclization, Org. Lett. 6, 2059-2062.
    • (2004) Org. Lett. , vol.6 , pp. 2059-2062
    • Feng, L.1    Kumar, D.2    Birney, D.M.3    Kerwin, S.M.4
  • 26
    • 0037181077 scopus 로고    scopus 로고
    • On the regioselectivity of the cyclization of enyne-ketenes: A computational investigation and comparison with the myers-saito and schmittel reaction
    • (b) Musch, P. W., Remenyi, C., Helten, H., and Engels, B. (2002) On the Regioselectivity of the Cyclization of Enyne-Ketenes: A Computational Investigation and Comparison with the Myers-Saito and Schmittel Reaction, J. Am. Chem. Soc. 124, 1823-1828.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 1823-1828
    • Musch, P.W.1    Remenyi, C.2    Helten, H.3    Engels, B.4
  • 27
    • 0034694361 scopus 로고    scopus 로고
    • Synthesis of a heterocyclic aza-enediyne and its DNA cleavage properties
    • (a) David, W. M., Kumar, D., and Kerwin, S. M. (2000) Synthesis of a Heterocyclic Aza-Enediyne and Its DNA Cleavage Properties, Bioorg. Med. Chem. Lett. 10, 2509-2512.
    • (2000) Bioorg. Med. Chem. Lett. , vol.10 , pp. 2509-2512
    • David, W.M.1    Kumar, D.2    Kerwin, S.M.3
  • 28
    • 0037161278 scopus 로고    scopus 로고
    • DNA modification by 4-aza-3-ene-1,6-diynes: DNA cleavage, pH-dependent cytosine-specific interactions, and cancer cell cytotoxicity
    • (b) Tuntiwechapikul, W., David, W. M., Kumar, D., Salazar, M., and Kerwin, S. M. (2002) DNA Modification by 4-Aza-3-ene-1,6-diynes: DNA Cleavage, pH-Dependent Cytosine-Specific Interactions, and Cancer Cell Cytotoxicity, Biochemistry 41, 5283-5290.
    • (2002) Biochemistry , vol.41 , pp. 5283-5290
    • Tuntiwechapikul, W.1    David, W.M.2    Kumar, D.3    Salazar, M.4    Kerwin, S.M.5
  • 29
    • 0035914607 scopus 로고    scopus 로고
    • N-propargyl-2-alkynylbenzothiazolium aza-enediynes: Role of the 2-alkynylbenzothiazolium functionality in DNA cleavage
    • Kumar, D., David, W. M., and Kerwin, S. M. (2001) N-Propargyl-2- alkynylbenzothiazolium Aza-Enediynes: Role of the 2-Alkynylbenzothiazolium Functionality in DNA Cleavage, Bioorg. Med. Chem. Lett. 11, 2971-2974.
    • (2001) Bioorg. Med. Chem. Lett. , vol.11 , pp. 2971-2974
    • Kumar, D.1    David, W.M.2    Kerwin, S.M.3
  • 30
    • 0037467078 scopus 로고    scopus 로고
    • Reactivity of substituted charged phenyl radicals toward components of nucleic acids
    • Ramírez-Arizmendi, L. E., Heidbrink, J. L., Guler, L. P., and Kenttamaa, H. I. (2003) Reactivity of Substituted Charged Phenyl Radicals toward Components of Nucleic Acids, J. Am. Chem. Soc. 125, 2272-2281.
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 2272-2281
    • Ramírez-Arizmendi, L.E.1    Heidbrink, J.L.2    Guler, L.P.3    Kenttamaa, H.I.4
  • 31
    • 3042781836 scopus 로고    scopus 로고
    • Biradicals/zwitterions from thermolysis of enyne-isocyanates. Application to the synthesis of 2(1H)-pyridones, benxofuro[3,2-dpyridin-1] (2H)-ones, 2,5-didehydro-1H-pyrido[4,3-b]indol-1-ones, and related compounds
    • Li, H., Yang, H., Petersen, J. L., and Wang, K. K. (2004) Biradicals/Zwitterions from Thermolysis of Enyne-Isocyanates. Application to the Synthesis of 2(1H)-Pyridones, Benxofuro[3,2-dpyridin-1] (2H)-ones, 2,5-Didehydro-1H-pyrido[4,3-b]indol-1-ones, and Related Compounds, J. Org. Chem. 69, 4500-4508.
    • (2004) J. Org. Chem. , vol.69 , pp. 4500-4508
    • Li, H.1    Yang, H.2    Petersen, J.L.3    Wang, K.K.4
  • 32
    • 0032544307 scopus 로고    scopus 로고
    • Two novel thermal biradical cyclizations in theory and experiment: New synthetic routes to 6H-Indolo[2,3-b]quinolines and 2-amino-quinolines from enyne-carbodiimides
    • (a) Schmittel, M., Steffen, J. P., Engels, B., Lennartz, C., and Hanrath, M. (1998) Two Novel Thermal Biradical Cyclizations in Theory and Experiment: New Synthetic Routes to 6H-Indolo[2,3-b]quinolines and 2-Amino-Quinolines from Enyne-Carbodiimides, Angew. Chem., Int. Ed. 37, 2371-2373.
    • (1998) Angew. Chem., Int. Ed. , vol.37 , pp. 2371-2373
    • Schmittel, M.1    Steffen, J.P.2    Engels, B.3    Lennartz, C.4    Hanrath, M.5
  • 33
    • 0037178355 scopus 로고    scopus 로고
    • Synthesis of novel heteroaromatics structurally related to ellipticine alkaloids via thermolysis of pyridannulated enyne-carbodiimides
    • (b) Lu, X. L., Petersen, J. L., and Wang, K. K. (2002) Synthesis of Novel Heteroaromatics Structurally Related to Ellipticine Alkaloids via Thermolysis of Pyridannulated Enyne-Carbodiimides, J. Org. Chem. 67, 5412-5415.
    • (2002) J. Org. Chem. , vol.67 , pp. 5412-5415
    • Lu, X.L.1    Petersen, J.L.2    Wang, K.K.3
  • 34
    • 0033525049 scopus 로고    scopus 로고
    • Biradicals from thermolysis of N-[2-(1-alkynyl)phenyl]-N′- phenylcarbodiimides and their subsequent transformations to 6H-indolo[2,3-b] quinolines
    • Shi, C. S., Zhang, Q., and Wang, K. K. (1999) Biradicals from Thermolysis of N-[2-(1-Alkynyl)phenyl]-N′-phenylcarbodiimides and their Subsequent Transformations to 6H-Indolo[2,3-b]quinolines, J. Org. Chem. 64, 925-932.
    • (1999) J. Org. Chem. , vol.64 , pp. 925-932
    • Shi, C.S.1    Zhang, Q.2    Wang, K.K.3
  • 35
    • 0032546774 scopus 로고    scopus 로고
    • Two novel thermal biradical cyclizations of enyne-ketenimines: Theory, experiment, and synthetic potential
    • Schmittel, M., Steffen, J. P., Angel, M. A. W., Engels, B., Lennartz, C., and Hanrath, M. (1998) Two Novel Thermal Biradical Cyclizations of Enyne-Ketenimines: Theory, Experiment, and Synthetic Potential, Angew. Chem., Int. Ed. 37, 1562-1564.
    • (1998) Angew. Chem., Int. Ed. , vol.37 , pp. 1562-1564
    • Schmittel, M.1    Steffen, J.P.2    Angel, M.A.W.3    Engels, B.4    Lennartz, C.5    Hanrath, M.6
  • 36
    • 0141744682 scopus 로고    scopus 로고
    • Biradicals/zwitterions from enallene-isonitriles. Formal [4 + 1] cycloadditions leading to 11H-indeno[1,2-b]quinoline and related compounds
    • Lu, X. L., Petersen, J. L., and Wang, K. K. (2002) Biradicals/Zwitterions From Enallene-Isonitriles. Formal [4 + 1] Cycloadditions Leading to 11H-Indeno[1,2-b]quinoline and Related Compounds, Org. Lett. 5, 3277-3280.
    • (2002) Org. Lett. , vol.5 , pp. 3277-3280
    • Lu, X.L.1    Petersen, J.L.2    Wang, K.K.3
  • 37
    • 0001647738 scopus 로고    scopus 로고
    • Thermolysis of 2-(3-phenylsulfonylprop-1-ynyl)benzonitrile: An aza-myers type cyclization to isoquinolines
    • Wu, M. J., Lin, C. F., Chen, S. H., and Lee, F. C. (1999) Thermolysis of 2-(3-Phenylsulfonylprop-1-ynyl)benzonitrile: An Aza-Myers Type Cyclization to Isoquinolines, J. Chem. Soc., Perkin Trans, 1 2875-2876.
    • (1999) J. Chem. Soc., Perkin Trans , vol.1 , pp. 2875-2876
    • Wu, M.J.1    Lin, C.F.2    Chen, S.H.3    Lee, F.C.4
  • 38
    • 84987551565 scopus 로고
    • Facile synthesis of ethynyl-substituted six-membered W-heteroaromatic compounds
    • Sakamoto, T., Shiraiwa, M., Kondo, Y., and Yamanaka, H. (1983) Facile Synthesis of Ethynyl-Substituted Six-Membered W-Heteroaromatic Compounds, Synthesis 312-314.
    • (1983) Synthesis , pp. 312-314
    • Sakamoto, T.1    Shiraiwa, M.2    Kondo, Y.3    Yamanaka, H.4
  • 39
    • 9644285669 scopus 로고
    • Convenient synthesis of actylenes. Catalytic substitutions of acetylenic hydrogen with bromo alkenes, iodo arenes, and bromopyridines
    • Sonogashira, K., Tohda, Y., and Nobue, H. (1975) Convenient Synthesis of Actylenes. Catalytic Substitutions of Acetylenic Hydrogen with Bromo Alkenes, Iodo Arenes, and Bromopyridines, Tetrahedron Lett. 4467-4470.
    • (1975) Tetrahedron Lett. , pp. 4467-4470
    • Sonogashira, K.1    Tohda, Y.2    Nobue, H.3
  • 40
    • 1842755867 scopus 로고
    • α- and β-rearrangement products, benzoylpyridyltriphenylphosphonium methylides and phenylethynylpyridines, from pyridine N-oxides and phenylethynyltriphenylphosphonium bromide
    • Morita, N., and Miller, S. I. (1977) α- and β-Rearrangement Products, Benzoylpyridyltriphenylphosphonium Methylides and Phenylethynylpyridines, from Pyridine N-oxides and Phenylethynyltriphenylphosphonium Bromide, J. Org. Chem. 42, 4245-4248.
    • (1977) J. Org. Chem. , vol.42 , pp. 4245-4248
    • Morita, N.1    Miller, S.I.2
  • 41
    • 0032567499 scopus 로고    scopus 로고
    • Efficient synthesis of 4-, 5-, and 6-methyl-2,2′-bipyridine by a negishi cross-coupling strategy followed by high-yield conversion to bromo- and chloromethyl-2,2′-bipyridines
    • Savage, S. M., Smith, A. P., and Fraser, C. L. (1998) Efficient Synthesis of 4-, 5-, and 6-Methyl-2,2′-bipyridine by a Negishi Cross-Coupling Strategy Followed by High-Yield Conversion to Bromo- and Chloromethyl-2, 2′-bipyridines, J. Org. Chem. 63, 10048-10051.
    • (1998) J. Org. Chem. , vol.63 , pp. 10048-10051
    • Savage, S.M.1    Smith, A.P.2    Fraser, C.L.3
  • 42
    • 0000758818 scopus 로고
    • Reactive triflate alkylating agents
    • Vedejs, E., Engler, D. A., and Mullins, M. J. (1977) Reactive Triflate Alkylating Agents, J. Org. Chem. 42, 3109-3113.
    • (1977) J. Org. Chem. , vol.42 , pp. 3109-3113
    • Vedejs, E.1    Engler, D.A.2    Mullins, M.J.3
  • 43
    • 0018194944 scopus 로고
    • Bleomycin-specific fragmentation of double-stranded DNA
    • Lloyd, R. S., Haidle, C. W., and Robberson, D. L. (1978) Bleomycin-Specific Fragmentation of Double-Stranded DNA, Biochemistry 17, 1890-1896.
    • (1978) Biochemistry , vol.17 , pp. 1890-1896
    • Lloyd, R.S.1    Haidle, C.W.2    Robberson, D.L.3
  • 44
    • 0027378315 scopus 로고
    • An efficient palladium-catalyzed reaction of vinyl and aryl halides or triflates with terminal alkynes
    • Alami, M., Ferri, F., Linstrumelle, G. (1993) An Efficient Palladium-Catalyzed Reaction of Vinyl and Aryl Halides or Triflates with Terminal Alkynes, Tetrahedron Lett. 34, 6403-6406.
    • (1993) Tetrahedron Lett. , vol.34 , pp. 6403-6406
    • Alami, M.1    Ferri, F.2    Linstrumelle, G.3
  • 45
    • 0032932267 scopus 로고    scopus 로고
    • Propyne iminium salts by N-alkylation of alkynyl imines
    • Schlegel, J., and Maas, G. (1999) Propyne Iminium Salts by N-Alkylation of Alkynyl Imines, Synthesis 1, 100-106.
    • (1999) Synthesis , vol.1 , pp. 100-106
    • Schlegel, J.1    Maas, G.2
  • 46
    • 0023661760 scopus 로고
    • Breakage of double-stranded DNA due to single-stranded nicking
    • The presence of all three forms of DNA (supercoiled form I, nicked relaxed form II, and linear form III) was observed at one or more concentrations of the skipped aza-enediynes 15d-g; however, statistical analysis [Cowan, R., Collis, C. M., and Grigg, G. W. (1987) Breakage of Double-Stranded DNA Due to Single-Stranded Nicking, J. Theor. Biol. 127, 229-245] showed that the double-stranded DNA cleavage activity of these compounds was less than 5% of their single-stranded DNA nicking activity.
    • (1987) J. Theor. Biol. , vol.127 , pp. 229-245
    • Cowan, R.1    Collis, C.M.2    Grigg, G.W.3
  • 47
    • 0344019768 scopus 로고
    • Addition reactions of salts of phenylethynylpyridine
    • Kiprianov, A. I., and Dyadyusha, G. G. (1960) Addition Reactions of Salts of Phenylethynylpyridine, Zh. Obs. Khim. 30, 3647-3654.
    • (1960) Zh. Obs. Khim. , vol.30 , pp. 3647-3654
    • Kiprianov, A.I.1    Dyadyusha, G.G.2
  • 48
    • 29344445057 scopus 로고
    • Nucleophilic additions of N-propargylpyridinium and N-allenylpyridinium salts and to 1,3-propenediylbis(pyridinium) salts
    • Katritzky, A. R., Ramer, W. H., and Ossana, A. (1985) Nucleophilic Additions of N-Propargylpyridinium and N-Allenylpyridinium Salts and to 1,3-Propenediylbis(pyridinium) Salts, J. Org. Chem. 50, 847-852.
    • (1985) J. Org. Chem. , vol.50 , pp. 847-852
    • Katritzky, A.R.1    Ramer, W.H.2    Ossana, A.3
  • 49
    • 4243545125 scopus 로고    scopus 로고
    • Oxidative nucleobase modifications leading to strand scission
    • Burrows, C. J., and Muller, J. G. (1998) Oxidative Nucleobase Modifications Leading to Strand Scission, Chem. Rev. 98, 1109-1151.
    • (1998) Chem. Rev. , vol.98 , pp. 1109-1151
    • Burrows, C.J.1    Muller, J.G.2
  • 50
    • 0028788870 scopus 로고
    • Reactivity toward singlet oxygen of a 7,8-dihydro-8-oxoguanosine ("8-hydroxyguanosine") formed by photooxidation of a guanosine Derivative
    • Sheu, C., and Foote, C. S. (1995) Reactivity toward Singlet Oxygen of a 7,8-Dihydro-8-oxoguanosine ("8-Hydroxyguanosine") Formed by Photooxidation of a Guanosine Derivative, J. Am. Chem. Soc. 117, 6439-6442.
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 6439-6442
    • Sheu, C.1    Foote, C.S.2
  • 51
    • 0037451849 scopus 로고    scopus 로고
    • Photo-oxidation of duplex DNA with the stable trioxatriangulenium ion
    • Pothukuchy, A., Ellapan, S., Gopidas, K. R., and Salazar, M. (2003) Photo-Oxidation of Duplex DNA with the Stable Trioxatriangulenium Ion, Bioorg. Med. Chem. Lett. 13, 1491-1494.
    • (2003) Bioorg. Med. Chem. Lett. , vol.13 , pp. 1491-1494
    • Pothukuchy, A.1    Ellapan, S.2    Gopidas, K.R.3    Salazar, M.4
  • 53
    • 0024411573 scopus 로고
    • Use of the hydroxyl radical and gel electrophoresis to study DNA structure
    • Shafer, G. E., Price, M. A., and Tullius, T. D. (1989) Use of the Hydroxyl Radical and Gel Electrophoresis to Study DNA Structure, Electrophoresis 10, 397-404.
    • (1989) Electrophoresis , vol.10 , pp. 397-404
    • Shafer, G.E.1    Price, M.A.2    Tullius, T.D.3
  • 54
    • 37049092052 scopus 로고
    • Primary processes in the reaction of hydroxyl radicals with sulfoxides
    • Veltwisch, D., Janata, E., and Asmus, K. D. (1980) Primary Processes in the Reaction of Hydroxyl Radicals with Sulfoxides, J. Chem. Soc., Perkin Trans. 2, 146-153.
    • (1980) J. Chem. Soc., Perkin Trans. , vol.2 , pp. 146-153
    • Veltwisch, D.1    Janata, E.2    Asmus, K.D.3
  • 55
    • 0000989226 scopus 로고
    • Rate constants for the reaction of oxygen(1-) radicals with organic substrates in aqueous solution
    • Neta, P., and Schuler, R. H. (1975) Rate Constants for the Reaction of Oxygen(1-) Radicals with Organic Substrates in Aqueous Solution, J. Phys. Chem. 79, 1-6.
    • (1975) J. Phys. Chem. , vol.79 , pp. 1-6
    • Neta, P.1    Schuler, R.H.2
  • 56
    • 0021112472 scopus 로고
    • Methidiumpropyl-EDTA·Fe(II) and DNase-I footprinting report different small molecule-binding site sizes on DNA
    • VanDyke, M. W., and Dervan, P. B. (1983) Methidiumpropyl- EDTA·Fe(II) and DNase-I Footprinting Report Different Small Molecule-Binding Site Sizes on DNA, Nucleic Acids Res. 11, 5555-5567.
    • (1983) Nucleic Acids Res. , vol.11 , pp. 5555-5567
    • Vandyke, M.W.1    Dervan, P.B.2
  • 57
    • 11544314893 scopus 로고    scopus 로고
    • Oxidative strand scission of nucleic acids: Routes initiated by hydrogen abstraction from the sugar moiety
    • Pogozelski, W. K., and Tullius, T. D. (1998) Oxidative Strand Scission of Nucleic Acids: Routes Initiated by Hydrogen Abstraction from the Sugar Moiety, Chem. Rev. 98, 1089-1107.
    • (1998) Chem. Rev. , vol.98 , pp. 1089-1107
    • Pogozelski, W.K.1    Tullius, T.D.2
  • 58
    • 12044260107 scopus 로고
    • Mechanism of neocarzinostatin action: Role of DNA microstructure in determination of chemistry of bistranded oxidative damage
    • Goldberg, I. H. (1991) Mechanism of Neocarzinostatin Action: Role of DNA Microstructure in Determination of Chemistry of Bistranded Oxidative Damage, Acc. Chem. Res. 24, 191-198.
    • (1991) Acc. Chem. Res. , vol.24 , pp. 191-198
    • Goldberg, I.H.1
  • 60
    • 33745036898 scopus 로고    scopus 로고
    • note
    • 6 cyclization of 1-hepta-1,2-dienyl-2-(2-phenyl) ethynyl-benzene has been noted (see ref 9).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.