메뉴 건너뛰기




Volumn , Issue , 2009, Pages 389-419

DNA Damage Due to Diradical-Generating Cyclizations

Author keywords

DNA damage due to diradical generating cyclizations; Enyne cumulene cyclization of NCS chromophore; Myers Saito cyclization of enyne allenes

Indexed keywords


EID: 79960628970     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9780470526279.ch13     Document Type: Chapter
Times cited : (4)

References (119)
  • 1
    • 0024322591 scopus 로고
    • Calicheamicins, a novel family of antitumor antibiotics. 3. Isolation, purification and characterization of calicheamicin-bBr1 , calicheamicin-gBr1 , calicheamicin-aI2, calicheamicin-aI3, calicheamicin-bI1, calicheamicin-gI1 and calicheamicin-dI1
    • Lee, M. D.; Manning, J. K.; Williams, D. R.; Kuck, N. A.; Testa, R. T.; Borders, D. B. Calicheamicins, a novel family of antitumor antibiotics. 3. Isolation, purification and characterization of calicheamicin-bBr1 , calicheamicin-gBr1 , calicheamicin-aI2, calicheamicin-aI3, calicheamicin-bI1, calicheamicin-gI1 and calicheamicin-dI1. J. Antibiotics. 1989, 42, 1070-1087
    • (1989) J. Antibiotics , vol.42 , pp. 1070-1087
    • Lee, M.D.1    Manning, J.K.2    Williams, D.R.3    Kuck, N.A.4    Testa, R.T.5    Borders, D.B.6
  • 2
    • 0023221289 scopus 로고
    • Esperamicins, a novel class of potent antitumor antibiotic. 3. Structures of esperamicins-A1, esperamicin-A2, and esperamicin-Ab 1
    • Golik, J.; Dubay, G.; Groenewold, G.; Kawaguchi, H.; Konishi, M.; Krishnan, B.; Ohkuma, H.; Saitoh, K.; Doyle, T. W. Esperamicins, a novel class of potent antitumor antibiotic. 3. Structures of esperamicins-A1, esperamicin-A2, and esperamicin-Ab 1. J. Am. Chem. Soc.. 1987, 109, 3462-3464
    • (1987) J. Am. Chem. Soc. , vol.109 , pp. 3462-3464
    • Golik, J.1    Dubay, G.2    Groenewold, G.3    Kawaguchi, H.4    Konishi, M.5    Krishnan, B.6    Ohkuma, H.7    Saitoh, K.8    Doyle, T.W.9
  • 6
    • 0037467004 scopus 로고    scopus 로고
    • Shishijimicins A-C, novel enediyne antitumor antibiotics from the ascidian didemnum proliferum
    • Oku, N.; Matsunaga, S.; Fusetani, N. Shishijimicins A-C, novel enediyne antitumor antibiotics from the ascidian didemnum proliferum. J. Am. Chem. Soc.. 2003, 125, 2044-2045
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 2044-2045
    • Oku, N.1    Matsunaga, S.2    Fusetani, N.3
  • 7
    • 0019156607 scopus 로고
    • Isolation of a non-protein component and a protein-component from neocarzinostatin (NCS) and their biological-activities
    • Koide,Y.; Ishii, F.; Hasuda, K.; Koyama, Y.; Edo, K.; Katamine, S.; Kitame, F.; Ishida, N. Isolation of a non-protein component and a protein-component from neocarzinostatin (NCS) and their biological-activities. J. Antibiotics. 1980, 33, 342-346
    • (1980) J. Antibiotics , vol.33 , pp. 342-346
    • Koide, Y.1    Ishii, F.2    Hasuda, K.3    Koyama, Y.4    Edo, K.5    Katamine, S.6    Kitame, F.7    Ishida, N.8
  • 8
    • 0023276787 scopus 로고
    • Proposed structure of the neocarzinostatin chromophore-methyl thioglycolate adduct: A mechanism for the nucleophilic activation of neocarzinostatin
    • Myers, A. G. Proposed structure of the neocarzinostatin chromophore-methyl thioglycolate adduct: A mechanism for the nucleophilic activation of neocarzinostatin. Tetrahedron Lett.. 1987, 28, 4493-4496
    • (1987) Tetrahedron Lett. , vol.28 , pp. 4493-4496
    • Myers, A.G.1
  • 9
    • 0027526565 scopus 로고
    • Structure and cycloaromatization of a novel enediyne, C-1027 chromophore
    • Yoshida, K.; Minami, Y.; Azuma, R.; Saeki, M.; Otani, T. Structure and cycloaromatization of a novel enediyne, C-1027 chromophore. Tetrahedron Lett.. 1993, 34, 2637-2640
    • (1993) Tetrahedron Lett. , vol.34 , pp. 2637-2640
    • Yoshida, K.1    Minami, Y.2    Azuma, R.3    Saeki, M.4    Otani, T.5
  • 10
    • 41649113407 scopus 로고    scopus 로고
    • Enediyne anticancer antibiotic lidamycin: Chemistry, biology and pharmacology
    • Shao, R. G.; Zhen, Y. S. Enediyne anticancer antibiotic lidamycin: Chemistry, biology and pharmacology. Anti-Cancer Agents Med. Chem.. 2008, 8, 123-131
    • (2008) Anti-Cancer Agents Med. Chem. , vol.8 , pp. 123-131
    • Shao, R.G.1    Zhen, Y.S.2
  • 11
    • 0032171502 scopus 로고    scopus 로고
    • A new non-protein enediyne antibiotic N1999A2: Unique enediyne chromophore similar to neocarzinostatin and DNA cleavage feature
    • Ando, T.; Ishii, M.; Kajiura, T.; Kameyama, T.; Miwa, K.; Sugiura, Y. A new non-protein enediyne antibiotic N1999A2: Unique enediyne chromophore similar to neocarzinostatin and DNA cleavage feature. Tetrahedron Lett.. 1998, 39, 6495-6498
    • (1998) Tetrahedron Lett. , vol.39 , pp. 6495-6498
    • Ando, T.1    Ishii, M.2    Kajiura, T.3    Kameyama, T.4    Miwa, K.5    Sugiura, Y.6
  • 13
    • 0029112037 scopus 로고
    • Maduropeptin-An antitumor chromoprotein with selective protease activity and DNA-cleaving properties
    • Zein, N.; Solomon, W.; Colson, K. L.; Schroeder, D. R. Maduropeptin-An antitumor chromoprotein with selective protease activity and DNA-cleaving properties. Biochemistry. 1995, 34, 11591-11597
    • (1995) Biochemistry , vol.34 , pp. 11591-11597
    • Zein, N.1    Solomon, W.2    Colson, K.L.3    Schroeder, D.R.4
  • 14
    • 0026718016 scopus 로고
    • Designed enediynes-A newclass ofDNA-cleaving molecules with potent and selective anticancer activity
    • Nicolaou, K. C.; Dai, W. M.; Tsay, S. C.; Estevez, V. A.; Wrasidlo, W. Designed enediynes-A newclass ofDNA-cleaving molecules with potent and selective anticancer activity. Science. 1992, 256, 1172-1178
    • (1992) Science , vol.256 , pp. 1172-1178
    • Nicolaou, K.C.1    Dai, W.M.2    Tsay, S.C.3    Estevez, V.A.4    Wrasidlo, W.5
  • 15
    • 33947088453 scopus 로고
    • p-Benzyne. Generation as an intermediate in a thermal isomerization reaction and trapping evidence for the 1,4-benzenediyl structure
    • Jones, R. R.; Bergman, R. G. p-Benzyne. Generation as an intermediate in a thermal isomerization reaction and trapping evidence for the 1,4-benzenediyl structure. J. Am. Chem. Soc.. 1972, 94, 660-661
    • (1972) J. Am. Chem. Soc. , vol.94 , pp. 660-661
    • Jones, R.R.1    Bergman, R.G.2
  • 16
    • 0036398483 scopus 로고    scopus 로고
    • Styrene maleic acid neocarzinostatin treatment for hepatocellular carcinoma
    • Abe, S.; Otsuki, M. Styrene maleic acid neocarzinostatin treatment for hepatocellular carcinoma. Curr. Med. Chem. Anticancer Agents. 2002, 2, 715-726
    • (2002) Curr. Med. Chem. Anticancer Agents , vol.2 , pp. 715-726
    • Abe, S.1    Otsuki, M.2
  • 19
    • 44649201476 scopus 로고    scopus 로고
    • Biosynthesis of enediyne antitumor antibiotics
    • Van Lanen, S. G.; Shen, B. Biosynthesis of enediyne antitumor antibiotics. Curr. Top. Med. Chem.. 2008, 8, 448-459
    • (2008) Curr. Top. Med. Chem. , vol.8 , pp. 448-459
    • Van Lanen, S.G.1    Shen, B.2
  • 20
    • 39549092885 scopus 로고    scopus 로고
    • Advances in polyketide synthase structure and function
    • Van Lanen, S. G.; Shen, B. Advances in polyketide synthase structure and function. Curr. Opin. Drug Discov. Dev.. 2008, 11, 186-195
    • (2008) Curr. Opin. Drug Discov. Dev. , vol.11 , pp. 186-195
    • Van Lanen, S.G.1    Shen, B.2
  • 21
    • 0033673757 scopus 로고    scopus 로고
    • Understanding and exploiting nature's chemical arsenal: The past, present and future of calicheamicin research
    • Thorson, J. S.; Sievers, E. L.; Ahlert, J.; Shepard, E.; Whitwam, R. E.; Onwueme, K. C.; Ruppen, M. Understanding and exploiting nature's chemical arsenal: The past, present and future of calicheamicin research. Curr. Pharm. Design. 2000, 6, 1841-1879
    • (2000) Curr. Pharm. Design , vol.6 , pp. 1841-1879
    • Thorson, J.S.1    Sievers, E.L.2    Ahlert, J.3    Shepard, E.4    Whitwam, R.E.5    Onwueme, K.C.6    Ruppen, M.7
  • 22
    • 40849086473 scopus 로고    scopus 로고
    • Target directed enediynes: Chemical and biological significance
    • Rawat, D. S. Target directed enediynes: Chemical and biological significance. J. Ind. Chem. Soc.. 2008, 85, 130-141
    • (2008) J. Ind. Chem. Soc. , vol.85 , pp. 130-141
    • Rawat, D.S.1
  • 23
    • 0036430176 scopus 로고    scopus 로고
    • Designed enediyne antitumor agents
    • Jones, G. B.; Fouad, F. S. Designed enediyne antitumor agents. Curr. Pharm. Des.. 2002, 8, 2415-2440
    • (2002) Curr. Pharm. Des. , vol.8 , pp. 2415-2440
    • Jones, G.B.1    Fouad, F.S.2
  • 24
    • 44649133221 scopus 로고    scopus 로고
    • The critical distance for the cycloaromatization reactions of enediynes
    • Capitani, J. F.; Gaffney, S. M.; Castaldo, L.; Mitra, A. The critical distance for the cycloaromatization reactions of enediynes. Curr. Top. Med. Chem.. 2008, 8, 470-486
    • (2008) Curr. Top. Med. Chem. , vol.8 , pp. 470-486
    • Capitani, J.F.1    Gaffney, S.M.2    Castaldo, L.3    Mitra, A.4
  • 25
    • 35448965670 scopus 로고    scopus 로고
    • Cycloaromatization reactions: The testing ground for theory and experiment
    • Alabugin, I.; Breiner, B.; Manoharan, M. Cycloaromatization reactions: The testing ground for theory and experiment. Adv. Phys. Org. Chem.. 2008, 42, 1-33
    • (2008) Adv. Phys. Org. Chem. , vol.42 , pp. 1-33
    • Alabugin, I.1    Breiner, B.2    Manoharan, M.3
  • 26
    • 33744770998 scopus 로고    scopus 로고
    • Enediynes from aza-enediynes: C,N-dialkynyl imines undergo both aza-Bergman rearrangement and conversion to enediynes and fumaronitriles
    • Feng, L. P.; Zhang, A. B.; Kerwin, S. M. Enediynes from aza-enediynes: C,N-dialkynyl imines undergo both aza-Bergman rearrangement and conversion to enediynes and fumaronitriles. Org. Lett.. 2006, 8, 1983-1986
    • (2006) Org. Lett. , vol.8 , pp. 1983-1986
    • Feng, L.P.1    Zhang, A.B.2    Kerwin, S.M.3
  • 27
    • 3042837537 scopus 로고    scopus 로고
    • a,5-didehydro-3-picoline diradicals from skipped aza-enediynes: Computational and trapping studies of an aza-Myers-Saito cyclization
    • Feng, L.; Kumar, D.; Birney, D.; Kerwin, S. M. a,5-didehydro-3-picoline diradicals from skipped aza-enediynes: Computational and trapping studies of an aza-Myers-Saito cyclization. Org. Lett.. 2004, 6, 2059-2062
    • (2004) Org. Lett. , vol.6 , pp. 2059-2062
    • Feng, L.1    Kumar, D.2    Birney, D.3    Kerwin, S.M.4
  • 28
    • 5344278331 scopus 로고
    • Synthetic and mechanistic studies on esperamicin-A1 and calicheamicin-gamma-1-molecular strain rather than pi-bond proximity determines the cycloaromatization tates of bicyclo[7.3.1] enediynes
    • Magnus, P.; Fortt, S.; Pitterna, T.; Snyder, J. P. Synthetic and mechanistic studies on esperamicin-A1 and calicheamicin-gamma-1-molecular strain rather than pi-bond proximity determines the cycloaromatization tates of bicyclo[7.3.1] enediynes. J. Am. Chem. Soc.. 1990, 112, 4986-4987
    • (1990) J. Am. Chem. Soc. , vol.112 , pp. 4986-4987
    • Magnus, P.1    Fortt, S.2    Pitterna, T.3    Snyder, J.P.4
  • 30
    • 36549030815 scopus 로고    scopus 로고
    • The reactivity of calicheamicin gI 1 in the minor groove of DNA: The decisive role of the environment
    • Kraka, E. Tuttle, T.; Cremer, D. The reactivity of calicheamicin gI 1 in the minor groove of DNA: The decisive role of the environment. Chem. Eur. J.. 2007, 13, 9256-9269
    • (2007) Chem. Eur. J. , vol.13 , pp. 9256-9269
    • Kraka, E.1    Tuttle, T.2    Cremer, D.3
  • 31
    • 84985741751 scopus 로고
    • The energy well of diradicals. 5. 1,3,5-Cyclohexatriene-1,4-diyl and 2,4-cyclohexadiene-1,4-diyl
    • Roth,W. R.; Hopf, H.; Horn, C. The energy well of diradicals. 5. 1,3,5-Cyclohexatriene-1,4-diyl and 2,4-cyclohexadiene-1,4-diyl. Chem. Ber.. 1994, 127, 1765-1779
    • (1994) Chem. Ber. , vol.127 , pp. 1765-1779
    • Roth, W.R.1    Hopf, H.2    Horn, C.3
  • 32
    • 0029927534 scopus 로고    scopus 로고
    • The role of the aminosugar and helix binding in the thiol-induced activation of calicheamicin for DNA cleavage
    • Chatterjee, M.; Smith, P. J.; Townsend, C. A. The role of the aminosugar and helix binding in the thiol-induced activation of calicheamicin for DNA cleavage. J. Am. Chem. Soc.. 1996, 118, 1938-1948
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 1938-1948
    • Chatterjee, M.1    Smith, P.J.2    Townsend, C.A.3
  • 33
    • 0030005931 scopus 로고    scopus 로고
    • Ab initio calculation of hydrogen abstraction reactions of phenyl radical and p-benzyne
    • Logan, C. F.; Chen, P. Ab initio calculation of hydrogen abstraction reactions of phenyl radical and p-benzyne. J. Am. Chem. Soc.. 1996, 118, 2113-2114
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 2113-2114
    • Logan, C.F.1    Chen, P.2
  • 34
    • 34247513435 scopus 로고    scopus 로고
    • Nucleophilic addition to a p-benzyne derived from an enediyne: A new mechanism for halide incorporation into biomolecules
    • Perrin, C. L.; Rodgers, B. L.; O'Connor, J. M. Nucleophilic addition to a p-benzyne derived from an enediyne: A new mechanism for halide incorporation into biomolecules. J. Am. Chem. Soc.. 2007, 129, 4795-4799
    • (2007) J. Am. Chem. Soc. , vol.129 , pp. 4795-4799
    • Perrin, C.L.1    Rodgers, B.L.2    O'Connor, J.M.3
  • 35
    • 29844440702 scopus 로고    scopus 로고
    • Sporolides A and B: Structurally unprecedented halogenated macrolides from the marine actinomycete Salinispora tropica
    • Buchanan, G. O.;Williams, P. G.; Feling, R. H.; Kauffman, C. A.; Jensen, P. E.; Fenical, W. Sporolides A and B: Structurally unprecedented halogenated macrolides from the marine actinomycete Salinispora tropica. Org. Lett.. 2005, 7, 2731-2734
    • (2005) Org. Lett. , vol.7 , pp. 2731-2734
    • Buchanan, G.O.1    Williams, P.G.2    Feling, R.H.3    Kauffman, C.A.4    Jensen, P.E.5    Fenical, W.6
  • 36
    • 33646463757 scopus 로고    scopus 로고
    • Cyanosporasides A and B, chloroand cyano-cyclopenta[a]indene glycosides from the marine Actinomycete "Salinispora pacifica"
    • Oh, D. C.; Williams, P. G.; Jensen, P. R.; Fenical, W. Cyanosporasides A and B, chloroand cyano-cyclopenta[a]indene glycosides from the marine Actinomycete "Salinispora pacifica". Org. Lett.. 2006, 8, 1021-1024
    • (2006) Org. Lett. , vol.8 , pp. 1021-1024
    • Oh, D.C.1    Williams, P.G.2    Jensen, P.R.3    Fenical, W.4
  • 37
    • 0026709243 scopus 로고
    • Free-radical mechanisms involved in the formation of sequence-dependent bistranded DNA lesions by the antitumor antibiotics bleomycin, neocarzinostatin, and calicheamicin
    • Dedon, P.C.; Goldberg, I. H. Free-radical mechanisms involved in the formation of sequence-dependent bistranded DNA lesions by the antitumor antibiotics bleomycin, neocarzinostatin, and calicheamicin. Chem. Res. Toxicol.. 1992, 5, 317-332
    • (1992) Chem. Res. Toxicol. , vol.5 , pp. 317-332
    • Dedon, P.C.1    Goldberg, I.H.2
  • 38
    • 0022607439 scopus 로고
    • Generation of superoxide free-radical by neocarzinostatin and its possible role in DNA damage
    • Chin, D. H.; Goldberg, I. H. Generation of superoxide free-radical by neocarzinostatin and its possible role in DNA damage. Biochemistry. 1986, 25, 1009-1015
    • (1986) Biochemistry , vol.25 , pp. 1009-1015
    • Chin, D.H.1    Goldberg, I.H.2
  • 39
    • 0027717160 scopus 로고
    • Site-specific cleavage at a DNA bulge by neocarzinostatin chromophore via a novel mechanism
    • Kappen, L. S.; Goldberg, I. H. Site-specific cleavage at a DNA bulge by neocarzinostatin chromophore via a novel mechanism. Biochemistry. 1993, 32, 13138-13145
    • (1993) Biochemistry , vol.32 , pp. 13138-13145
    • Kappen, L.S.1    Goldberg, I.H.2
  • 41
    • 0027526565 scopus 로고
    • Structure and cycloaromatization of a novel enediyne, C-1027 chromophore
    • Yoshida, K.; Minami, Y.; Azuma, R.; Saeki, M.; Otani, T. Structure and cycloaromatization of a novel enediyne, C-1027 chromophore. Tetrahedron Lett.. 1993, 34, 2637-2640
    • (1993) Tetrahedron Lett. , vol.34 , pp. 2637-2640
    • Yoshida, K.1    Minami, Y.2    Azuma, R.3    Saeki, M.4    Otani, T.5
  • 42
    • 0036570339 scopus 로고    scopus 로고
    • Evidence for facile atropisomerism and simple (non-nucleophilic) biradical-forming cycloaromatization within kedarcidin chromophore aglycon
    • Myers, A. G.; Hurd, A. R.; Hogan, P. C. Evidence for facile atropisomerism and simple (non-nucleophilic) biradical-forming cycloaromatization within kedarcidin chromophore aglycon. J. Am. Chem. Soc.. 2002, 124, 4583-4585
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 4583-4585
    • Myers, A.G.1    Hurd, A.R.2    Hogan, P.C.3
  • 43
    • 0001163468 scopus 로고
    • Calicheamicins-Discovery, structure, chemistry, and interaction with DNA
    • Lee, M. D.; Ellestad, G. A.; Borders, D. B. Calicheamicins-Discovery, structure, chemistry, and interaction with DNA. Acc. Chem. Res. 1991, 24, 235-243
    • (1991) Acc. Chem. Res , vol.24 , pp. 235-243
    • Lee, M.D.1    Ellestad, G.A.2    Borders, D.B.3
  • 44
    • 12044260107 scopus 로고
    • Mechanism of neocarzinostatin action: Role of DNA microstructure in determination of chemistry of bistranded oxidative damage
    • Goldberg, I. H. Mechanism of neocarzinostatin action: Role of DNA microstructure in determination of chemistry of bistranded oxidative damage. Acc. Chem. Res.. 1991, 24, 191-202
    • (1991) Acc. Chem. Res. , vol.24 , pp. 191-202
    • Goldberg, I.H.1
  • 45
    • 0026709243 scopus 로고
    • Free-radical mechanisms involved in the formation of sequence-dependent bistranded DNA lesions by the antitumor antibiotics bleomycin, neocarzinostatin, and calicheamicin
    • Dedon, P. C.; Goldberg, I. H. Free-radical mechanisms involved in the formation of sequence-dependent bistranded DNA lesions by the antitumor antibiotics bleomycin, neocarzinostatin, and calicheamicin. Chem. Res. Toxicol.. 1992, 5, 311-332
    • (1992) Chem. Res. Toxicol. , vol.5 , pp. 311-332
    • Dedon, P.C.1    Goldberg, I.H.2
  • 46
    • 0027714672 scopus 로고
    • A survey of natural-products which abstract hydrogen-atoms from nucleic-acids
    • Murphy, J. A.; Griffiths, J. A survey of natural-products which abstract hydrogen-atoms from nucleic-acids. Nat. Prod. Rep.. 1993, 10, 551-564
    • (1993) Nat. Prod. Rep. , vol.10 , pp. 551-564
    • Murphy, J.A.1    Griffiths, J.2
  • 47
    • 0029103994 scopus 로고
    • Carbon-hydrogen bonds of DNA sugar units as targets for chemical nucleases and drugs
    • Pratviel, G.; Bernadou, J.; Meunier, B. Carbon-hydrogen bonds of DNA sugar units as targets for chemical nucleases and drugs. Angew Chem. Int. Ed.. 1995, 34, 746-769
    • (1995) Angew Chem. Int. Ed. , vol.34 , pp. 746-769
    • Pratviel, G.1    Bernadou, J.2    Meunier, B.3
  • 48
    • 11544314893 scopus 로고    scopus 로고
    • Oxidative strand scission of nucleic acids: Routes initiated by hydrogen abstraction from the sugar moiety
    • Pogozelski, W. K.; Tullius, T. D. Oxidative strand scission of nucleic acids: Routes initiated by hydrogen abstraction from the sugar moiety. Chem. Rev.. 1998, 98, 1089-1107
    • (1998) Chem. Rev. , vol.98 , pp. 1089-1107
    • Pogozelski, W.K.1    Tullius, T.D.2
  • 49
    • 0030591651 scopus 로고    scopus 로고
    • DNA damage and mutagenesis by radiomimetic DNA-cleaving agents: Bleomycin, neocarzinostatin and other enediynes
    • Povirk, L. F. DNA damage and mutagenesis by radiomimetic DNA-cleaving agents: Bleomycin, neocarzinostatin and other enediynes. Mutat. Res. 1996, 355, 71-89.
    • (1996) Mutat. Res , vol.355 , pp. 71-89
    • Povirk, L.F.1
  • 50
    • 38949209141 scopus 로고    scopus 로고
    • The chemical toxicology of 2-deoxyribose oxidation in DNA
    • Dedon, P. The chemical toxicology of 2-deoxyribose oxidation in DNA. Chem. Res. Toxicol.. 2008, 21, 206-219
    • (2008) Chem. Res. Toxicol. , vol.21 , pp. 206-219
    • Dedon, P.1
  • 51
    • 0028518829 scopus 로고
    • The deoxyfucose-anthranilate of esperamicin A1 confers intercalative DNA binding and causes a switch in the chemistry of bistranded DNA lesions
    • Yu, L.; Golik, J.; Harrison, R.; Dedon, P. The deoxyfucose-anthranilate of esperamicin A1 confers intercalative DNA binding and causes a switch in the chemistry of bistranded DNA lesions. J. Am. Chem. Soc.. 1994, 116, 9733-9738
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 9733-9738
    • Yu, L.1    Golik, J.2    Harrison, R.3    Dedon, P.4
  • 52
    • 0023936872 scopus 로고
    • Atypical abasic sites generated by neocarzinostatin at sequence-specific cytidylate residues in oligodeoxynucleotides
    • Kappen, L. S.; Chen, C.-Q.; Goldberg, I. H. Atypical abasic sites generated by neocarzinostatin at sequence-specific cytidylate residues in oligodeoxynucleotides. Biochemistry. 1988, 27, 4331-4340
    • (1988) Biochemistry , vol.27 , pp. 4331-4340
    • Kappen, L.S.1    Chen, C.-Q.2    Goldberg, I.H.3
  • 53
    • 0025279517 scopus 로고
    • Isotope effects on the sequence-specific cleavage of dC in d(AGC) sequences by neocarzinostatin: Elucidation of chemistry of minor lesions
    • Kappen, L. S.; Goldberg, I. H.;Wu, S. H.; Stubbe, J.;Worth, L., Jr.;Kozarich, J.W. Isotope effects on the sequence-specific cleavage of dC in d(AGC) sequences by neocarzinostatin: Elucidation of chemistry of minor lesions. J. Am. Chem. Soc.. 1990, 112, 2729-2728
    • (1990) J. Am. Chem. Soc. , vol.112 , pp. 2729-2728
    • Kappen, L.S.1    Goldberg, I.H.2    Wu, S.H.3    Stubbe, J.4    Worth Jr, L.5    Kozarich, J.W.6
  • 54
    • 0025295356 scopus 로고
    • Molecular-models of neocarzinostatin damage of DNA-Analysis of sequence dependence in 50-GAGCG-50CGCTC
    • Galat, A.; Goldberg, I. H. Molecular-models of neocarzinostatin damage of DNA-Analysis of sequence dependence in 50-GAGCG-50CGCTC. Nucl. Acids Res.. 1990, 18, 2093-2099
    • (1990) Nucl. Acids Res. , vol.18 , pp. 2093-2099
    • Galat, A.1    Goldberg, I.H.2
  • 55
    • 0028915755 scopus 로고
    • Structural basis for the sequence-specific DNA strand cleavage by the enediyne neocarzinostatin chromophore-structure of the post-activated chromophore DNA complex
    • Gao, X. L.; Stassinopoulos, A.; Rice, J. S.; Goldberg, I. H. Structural basis for the sequence-specific DNA strand cleavage by the enediyne neocarzinostatin chromophore-structure of the post-activated chromophore DNA complex. Biochemistry. 1995, 34, 40-49
    • (1995) Biochemistry , vol.34 , pp. 40-49
    • Gao, X.L.1    Stassinopoulos, A.2    Rice, J.S.3    Goldberg, I.H.4
  • 56
    • 0026497897 scopus 로고
    • C-10 hydrogen abstraction of deoxyribose in DNA strand scission by dynemicin-A
    • Shiraki, T.; Uesugi, M.; Sugiura, Y. C-10 hydrogen abstraction of deoxyribose in DNA strand scission by dynemicin-A. Biochem. Biophys. Res. Comm.. 1992, 188, 584-589
    • (1992) Biochem. Biophys. Res. Comm. , vol.188 , pp. 584-589
    • Shiraki, T.1    Uesugi, M.2    Sugiura, Y.3
  • 57
    • 0024501789 scopus 로고
    • Identification of 2-deoxyribonolactone at the site of neocarzinostatin-induced cytosine release in the sequence d(AGC)
    • Kappen, L.; Goldberg, I. H. Identification of 2-deoxyribonolactone at the site of neocarzinostatin-induced cytosine release in the sequence d(AGC). Biochemistry. 1989, 28, 1027-1032
    • (1989) Biochemistry , vol.28 , pp. 1027-1032
    • Kappen, L.1    Goldberg, I.H.2
  • 58
    • 1342268141 scopus 로고    scopus 로고
    • Half-life and DNA strand scission products of 2-deoxyribonolactone oxidative DNA damage lesions
    • Zheng, Y.; Sheppard, T. L. Half-life and DNA strand scission products of 2-deoxyribonolactone oxidative DNA damage lesions. Chem. Res. Toxicol.. 2004, 17, 197-207
    • (2004) Chem. Res. Toxicol. , vol.17 , pp. 197-207
    • Zheng, Y.1    Sheppard, T.L.2
  • 59
    • 0022600959 scopus 로고
    • Base substitution mutations induced in the Ci gene of lambda-phage by neocarzinostatin chromophore-Correlation with depyrimidination hot-spots at the sequence AGC
    • Povirk, L. F.; Goldberg, I. H. Base substitution mutations induced in the Ci gene of lambda-phage by neocarzinostatin chromophore-Correlation with depyrimidination hot-spots at the sequence AGC. Nucl. Acids Res.. 1986, 14, 1417-1426
    • (1986) Nucl. Acids Res. , vol.14 , pp. 1417-1426
    • Povirk, L.F.1    Goldberg, I.H.2
  • 60
    • 2542545190 scopus 로고    scopus 로고
    • Mutagenic effects of 2-deoxyribonolactone in Escherichia coli. An abasic lesion that disobeys the A-rule
    • Kroeger, K. M.; Jiang, Y. L.; Kow, Y.W.; Goodman, M. F.; Greenberg, M. M. Mutagenic effects of 2-deoxyribonolactone in Escherichia coli. An abasic lesion that disobeys the A-rule. Biochemistry. 2004, 43, 6723-6733
    • (2004) Biochemistry , vol.43 , pp. 6723-6733
    • Kroeger, K.M.1    Jiang, Y.L.2    Kow, Y.W.3    Goodman, M.F.4    Greenberg, M.M.5
  • 61
    • 2442710480 scopus 로고    scopus 로고
    • 20-Deoxyribonolactone lesion produces G!A transitions in Escherichia coli
    • Faure, V.; Constant, J. F.; Dumy, P.; Saparbaev, M. 20-Deoxyribonolactone lesion produces G!A transitions in Escherichia coli. Nucl. Acids Res.. 32, 2004, 2937-2946
    • (2004) Nucl. Acids Res. , vol.32 , pp. 2937-2946
    • Faure, V.1    Constant, J.F.2    Dumy, P.3    Saparbaev, M.4
  • 63
    • 0034830066 scopus 로고    scopus 로고
    • The 2-deoxyribonolactone lesion produced in DNA by neocarzinostatin and other damaging agents forms crosslinks with the base-excision repair enzyme endonuclease III
    • Hashimoto, M.; Greenberg, M. M.; Kow, Y. W.; Hwang, J. T.; Cunningham, R. P. The 2-deoxyribonolactone lesion produced in DNA by neocarzinostatin and other damaging agents forms crosslinks with the base-excision repair enzyme endonuclease III. J. Am. Chem. Soc.. 2001, 123, 3161-3162
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 3161-3162
    • Hashimoto, M.1    Greenberg, M.M.2    Kow, Y.W.3    Hwang, J.T.4    Cunningham, R.P.5
  • 64
    • 0037040891 scopus 로고    scopus 로고
    • Covalent trapping of human DNA polymerase beta by the oxidative DNA lesion 2-deoxyribonolactone
    • DeMott, M. S.; Beyret, E.; Wong, D.; Bales, B. C.; Hwang, J. T.; Greenberg, M. M.; Demple, B. Covalent trapping of human DNA polymerase beta by the oxidative DNA lesion 2-deoxyribonolactone. J. Biol. Chem.. 2002, 277, 7637-7640
    • (2002) J. Biol. Chem. , vol.277 , pp. 7637-7640
    • DeMott, M.S.1    Beyret, E.2    Wong, D.3    Bales, B.C.4    Hwang, J.T.5    Greenberg, M.M.6    Demple, B.7
  • 65
    • 0000705699 scopus 로고
    • Specific abstraction of the 50(S)-deoxyribosyl and 40-deoxyribosyl hydrogen-atoms from DNA by calicheamicin-gamma-1(I)
    • Hangeland, J. J.; Devoss, J. J.; Heath, J. A.; Townsend, C. A.; Ding,W. D.; Ashcroft, J. S.; Ellestad, G. A. Specific abstraction of the 50(S)-deoxyribosyl and 40-deoxyribosyl hydrogen-atoms from DNA by calicheamicin-gamma-1(I). J. Am. Chem. Soc.. 1992, 114, 9200-9202
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 9200-9202
    • Hangeland, J.J.1    Devoss, J.J.2    Heath, J.A.3    Townsend, C.A.4    Ding, W.D.5    Ashcroft, J.S.6    Ellestad, G.A.7
  • 66
    • 0025774650 scopus 로고
    • Isotope effects on the sequence-specific cleavage of DNA by neocarzinostatin-kinetic partitioning between 40-hydrogen and 50-hydrogen abstraction at unique thymidine sites
    • Frank, B. L.; Worth, L.; Christner, D. F.; Kozarich, J. W.; Stubbe, J.; Kappen, L. S.; Goldberg, I. H. Isotope effects on the sequence-specific cleavage of DNA by neocarzinostatin-kinetic partitioning between 40-hydrogen and 50-hydrogen abstraction at unique thymidine sites. J. Am. Chem. Soc.. 1991, 113, 2271-2275
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 2271-2275
    • Frank, B.L.1    Worth, L.2    Christner, D.F.3    Kozarich, J.W.4    Stubbe, J.5    Kappen, L.S.6    Goldberg, I.H.7
  • 67
    • 0024378463 scopus 로고
    • A novel ribose C-40 hydroxylation pathway in neocarzinostatin-mediated degradation of Oligonucleotides
    • Saito, I.; Kawabata, H.; Fujiwara, T.; Sugiyama, H.; Matsuura, T. A novel ribose C-40 hydroxylation pathway in neocarzinostatin-mediated degradation of Oligonucleotides. J. Am. Chem. Soc.. 1989, 111, 8302-8303
    • (1989) J. Am. Chem. Soc. , vol.111 , pp. 8302-8303
    • Saito, I.1    Kawabata, H.2    Fujiwara, T.3    Sugiyama, H.4    Matsuura, T.5
  • 68
    • 0026695943 scopus 로고
    • Neocarzinostatin acts as a sensitive probe of DNA microheterogeneity-Switching of chemistry from C-10 to C-40 by a G.T mismatch 50 to the site of DNA damage
    • Kappen, L. S.; Goldberg, I. H. Neocarzinostatin acts as a sensitive probe of DNA microheterogeneity-Switching of chemistry from C-10 to C-40 by a G.T mismatch 50 to the site of DNA damage. Proc. Natl. Acad. Sci.. 1992, 89, 6706-6710
    • (1992) Proc. Natl. Acad. Sci. , vol.89 , pp. 6706-6710
    • Kappen, L.S.1    Goldberg, I.H.2
  • 69
    • 0001413651 scopus 로고
    • Unmasking the chemistry of DNA cleavage by the esperamicins-Modulation of 40-hydrogen abstraction and bistranded damage by the fucose anthranilate moiety
    • Christner, D. F.; Frank, B. L.; Kozarich, J. W.; Stubbe, J.; Golik, J.; Doyle, T. W.; Rosenberg, I. E.; Krishnan, B. Unmasking the chemistry of DNA cleavage by the esperamicins-Modulation of 40-hydrogen abstraction and bistranded damage by the fucose anthranilate moiety. J. Am. Chem. Soc.. 1992, 114, 8763-8767
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 8763-8767
    • Christner, D.F.1    Frank, B.L.2    Kozarich, J.W.3    Stubbe, J.4    Golik, J.5    Doyle, T.W.6    Rosenberg, I.E.7    Krishnan, B.8
  • 70
    • 0029147278 scopus 로고
    • A single binding mode of activated enediyne C1027 generates 2 Types of double-strand DNA lesions-deuterium isotopeinduced shuttling between adjacent nucleotide target sites
    • Xu, Y. J.; Xi, Z.; Zhen, Y. S.; Goldberg, I. H. A single binding mode of activated enediyne C1027 generates 2 Types of double-strand DNA lesions-deuterium isotopeinduced shuttling between adjacent nucleotide target sites. Biochemistry. 1995, 34, 12451-12460
    • (1995) Biochemistry , vol.34 , pp. 12451-12460
    • Xu, Y.J.1    Xi, Z.2    Zhen, Y.S.3    Goldberg, I.H.4
  • 71
    • 0025035579 scopus 로고
    • Identification of the source of oxygen in the alkaline-labile product accompanying cytosine release during bleomycinmediated oxidative degradation of d(CGCGCG)
    • Rabow, L. E.; McGall, G. H.; Stubbe, J.; Kozarich, J. W. Identification of the source of oxygen in the alkaline-labile product accompanying cytosine release during bleomycinmediated oxidative degradation of d(CGCGCG). J.Am.Chem. Soc.. 1990, 112, 3203-3208
    • (1990) J.Am.Chem. Soc. , vol.112 , pp. 3203-3208
    • Rabow, L.E.1    McGall, G.H.2    Stubbe, J.3    Kozarich, J.W.4
  • 72
    • 0035008498 scopus 로고    scopus 로고
    • Thiols alter the partitioning of calicheamicin-induced deoxyribose 4 0-oxidation reactions in the absence of DNA radical repair
    • Lopez-Larraza, D. M.; Moore, K.; Dedon, P. C. Thiols alter the partitioning of calicheamicin-induced deoxyribose 4 0-oxidation reactions in the absence of DNA radical repair. Chem. Res. Toxicol.. 2001, 14, 528-535
    • (2001) Chem. Res. Toxicol. , vol.14 , pp. 528-535
    • Lopez-Larraza, D.M.1    Moore, K.2    Dedon, P.C.3
  • 73
    • 0029310521 scopus 로고
    • The chemistry of single-stranded 40-DNA radicals-influence of the radical precursor on anaerobic and aerobic strand cleavage
    • Giese, B.; Beyrichgraf, X.; Erdmann, P.; Petretta, M.; Schwitter, U. The chemistry of single-stranded 40-DNA radicals-influence of the radical precursor on anaerobic and aerobic strand cleavage. Chem. Biol.. 1995, 2, 367-375
    • (1995) Chem. Biol. , vol.2 , pp. 367-375
    • Giese, B.1    Beyrichgraf, X.2    Erdmann, P.3    Petretta, M.4    Schwitter, U.5
  • 74
    • 0032486755 scopus 로고    scopus 로고
    • Spontaneous cleavage of 40-DNA radicals under aerobic conditions: Apparent discrepancy between trapping rates and cleavage products
    • Dussy, A.; Meggers, E.; Giese, B. Spontaneous cleavage of 40-DNA radicals under aerobic conditions: Apparent discrepancy between trapping rates and cleavage products. J. Am. Chem. Soc.. 1998, 120, 7399-7403
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 7399-7403
    • Dussy, A.1    Meggers, E.2    Giese, B.3
  • 75
    • 0026360193 scopus 로고
    • Selective abstraction of H-2 from C-50 of thymidylate in an oligodeoxynucleotide by the radical center at C-6 of the diradical species of neocarzinostatin-Chemical evidence for the structure of the activated drug DNA Complex
    • Meschwitz, S. M.; Goldberg, I. H. Selective abstraction of H-2 from C-50 of thymidylate in an oligodeoxynucleotide by the radical center at C-6 of the diradical species of neocarzinostatin-Chemical evidence for the structure of the activated drug DNA Complex. Proc. Natl. Acad. Sci. USA. 1991, 88, 3047-3051
    • (1991) Proc. Natl. Acad. Sci. USA , vol.88 , pp. 3047-3051
    • Meschwitz, S.M.1    Goldberg, I.H.2
  • 76
    • 0021285421 scopus 로고
    • Incorporation of O-18(2) into thymidine 50-aldehyde in neocarzinostatin chromophore-damaged DNA
    • Chin, D. H.; Carr, S. A.; Goldberg, I. H. Incorporation of O-18(2) into thymidine 50-aldehyde in neocarzinostatin chromophore-damaged DNA. J. Biol. Chem.. 1984, 259, 9975-9978
    • (1984) J. Biol. Chem. , vol.259 , pp. 9975-9978
    • Chin, D.H.1    Carr, S.A.2    Goldberg, I.H.3
  • 77
    • 0024450867 scopus 로고
    • Chemistry of neocarzinostatin-mediated degradation of d(GCATGC)-Mechanism of spontaneous thymine release
    • Kawabata, H.; Takeshita, H.; Fujiwara, T.; Sugiyama, H.; Matsuura, T.; Saito, I. chemistry of neocarzinostatin-mediated degradation of d(GCATGC)-Mechanism of spontaneous thymine release. Tetrahedron Lett.. 1989, 30, 4263-4266
    • (1989) Tetrahedron Lett. , vol.30 , pp. 4263-4266
    • Kawabata, H.1    Takeshita, H.2    Fujiwara, T.3    Sugiyama, H.4    Matsuura, T.5    Saito, I.6
  • 78
    • 33748667523 scopus 로고    scopus 로고
    • Formation of 1,4-dioxo-2-butene-derived adducts of 20-deoxyadenosine and 20-deoxycytidine in Oxidized DNA
    • Chen, B.; Vu, C. C.; Byrnes, M. C.; Dedon, P.; Peterson, L. A. Formation of 1,4-dioxo-2-butene-derived adducts of 20-deoxyadenosine and 20-deoxycytidine in Oxidized DNA. Chem. Res. Toxicol.. 2006, 19, 982-985
    • (2006) Chem. Res. Toxicol. , vol.19 , pp. 982-985
    • Chen, B.1    Vu, C.C.2    Byrnes, M.C.3    Dedon, P.4    Peterson, L.A.5
  • 79
    • 0001468013 scopus 로고
    • Covalent adducts of DNA and the non-protein chromophore of neocarzinostatin contain a modified deoxyribose
    • Povirk, L. F.; Goldberg, I. H. Covalent adducts of DNA and the non-protein chromophore of neocarzinostatin contain a modified deoxyribose. Proc. Natl. Acad. Sci. USA. 1982, 79, 369-373
    • (1982) Proc. Natl. Acad. Sci. USA , vol.79 , pp. 369-373
    • Povirk, L.F.1    Goldberg, I.H.2
  • 80
    • 0030734671 scopus 로고    scopus 로고
    • Mechanism of formation of novel covalent drug center dot DNA interstrand cross-links and monoadducts by enediyne antitumor antibiotics
    • Xu, Y. J.; Xi, Z.; Zhen, Y. S.; Goldberg, I. H. Mechanism of formation of novel covalent drug center dot DNA interstrand cross-links and monoadducts by enediyne antitumor antibiotics. Biochemistry. 1997, 36, 14975-14984
    • (1997) Biochemistry , vol.36 , pp. 14975-14984
    • Xu, Y.J.1    Xi, Z.2    Zhen, Y.S.3    Goldberg, I.H.4
  • 81
    • 0027818189 scopus 로고
    • DNA conformation induced activation of an enediyne for site-specific cleavage
    • Kappen, L. S.; Goldberg, I. H. DNA conformation induced activation of an enediyne for site-specific cleavage. Science. 1993, 261, 1319-1321
    • (1993) Science , vol.261 , pp. 1319-1321
    • Kappen, L.S.1    Goldberg, I.H.2
  • 82
    • 0030017851 scopus 로고    scopus 로고
    • Solution structure of a two-base DNA bulge complexed with an enediyne cleaving analog
    • Stassinopoulos, A.; Ji, J.; Gao, X.; Goldberg, I. H. Solution structure of a two-base DNA bulge complexed with an enediyne cleaving analog. Science. 1996, 272, 1943-1964
    • (1996) Science , vol.272 , pp. 1943-1964
    • Stassinopoulos, A.1    Ji, J.2    Gao, X.3    Goldberg, I.H.4
  • 83
    • 0033524496 scopus 로고    scopus 로고
    • Replication block by an enediyne drug-DNA deoxyribose adduct
    • Kappen, L. S.; Goldberg, I. H. Replication block by an enediyne drug-DNA deoxyribose adduct. Biochemistry. 1999, 38, 235-242
    • (1999) Biochemistry , vol.38 , pp. 235-242
    • Kappen, L.S.1    Goldberg, I.H.2
  • 84
    • 0031030330 scopus 로고    scopus 로고
    • Enediyne C1027 induces the formation of novel covalent DNA interstrand cross-links and monoadducts
    • Xu, Y. J.; Zhen, Y. S.; Goldberg, I. H. Enediyne C1027 induces the formation of novel covalent DNA interstrand cross-links and monoadducts. J. Am. Chem. Soc.. 1997, 119, 1133-1134
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 1133-1134
    • Xu, Y.J.1    Zhen, Y.S.2    Goldberg, I.H.3
  • 85
    • 36749074497 scopus 로고    scopus 로고
    • Designer enediynes generate DNA breaks, interstrand cross-links, or both, with concomitant changes in the regulation of DNA damage responses
    • Kennedy, D. R.; Ju, J.; Shen, B.; Beerman, T. A. Designer enediynes generate DNA breaks, interstrand cross-links, or both, with concomitant changes in the regulation of DNA damage responses. Proc. Natl. Acad. Sci. USA. 2007, 104, 17632-17637
    • (2007) Proc. Natl. Acad. Sci. USA , vol.104 , pp. 17632-17637
    • Kennedy, D.R.1    Ju, J.2    Shen, B.3    Beerman, T.A.4
  • 86
    • 0030591651 scopus 로고    scopus 로고
    • DNA damage and mutagenesis by radiomimetic DNA-cleaving agents: Bleomycin, neocarzinostatin and other enediynes
    • Povirk, L. F. DNA damage and mutagenesis by radiomimetic DNA-cleaving agents: Bleomycin, neocarzinostatin and other enediynes. Mutat. Res.. 1996, 355, 71-89
    • (1996) Mutat. Res. , vol.355 , pp. 71-89
    • Povirk, L.F.1
  • 87
    • 0037012388 scopus 로고    scopus 로고
    • Formation and structure of a novel enediyne-RNA base covalent adduct
    • Jiang, Z. H.; Hwang, G. S.; Xi, Z.; Goldberg, I. H. Formation and structure of a novel enediyne-RNA base covalent adduct. J. Am. Chem. Soc.. 2002, 124, 3216-3217
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 3216-3217
    • Jiang, Z.H.1    Hwang, G.S.2    Xi, Z.3    Goldberg, I.H.4
  • 88
    • 0024800209 scopus 로고
    • Design and dynamics of a chemically triggered reaction cascade leading to biradical formation at subambient temperature
    • Myers, A. G.; Dragovich, P. S. Design and dynamics of a chemically triggered reaction cascade leading to biradical formation at subambient temperature. J. Am. Chem. Soc.. 1989, 111, 9130-9132
    • (1989) J. Am. Chem. Soc. , vol.111 , pp. 9130-9132
    • Myers, A.G.1    Dragovich, P.S.2
  • 89
    • 0024343657 scopus 로고
    • Biradical formation from acyclic conjugated enyne-allene system related to neocarzinostatin and esperamicin-calichemicin
    • Nagata, R.; Yamanaka, H.; Okazaki, E.; Saito, I. Biradical formation from acyclic conjugated enyne-allene system related to neocarzinostatin and esperamicin-calichemicin. Tetrahedron Lett.. 1989, 30, 4995-4998
    • (1989) Tetrahedron Lett. , vol.30 , pp. 4995-4998
    • Nagata, R.1    Yamanaka, H.2    Okazaki, E.3    Saito, I.4
  • 90
    • 0001380819 scopus 로고
    • "Thermal generation of a,3-dehydrotoluene from (Z)-1,2,4-heptatrien-6-yne" J
    • Myers, A. G.; Kuo, E. Y.; Finney, N. S. "Thermal generation of a,3-dehydrotoluene from (Z)-1,2,4-heptatrien-6-yne" J. Am. Chem. Soc.. 1989, 111, 8097-8059
    • (1989) Am. Chem. Soc. , vol.111 , pp. 8097-8059
    • Myers, A.G.1    Kuo, E.Y.2    Finney, N.S.3
  • 91
    • 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
    • Cremeens, M. E.; Hughes, T. S.; Carpenter, B. K. Mechanistic studies on the cyclization of (Z)-1,2,4-Heptatrien-6-yne in methanol: A possible nonadiabatic thermal reaction. J. Am. Chem. Soc. 2005, 127(18), 6652-6661.
    • (2005) J. Am. Chem. Soc , vol.127 , Issue.18 , pp. 6652-6661
    • Cremeens, M.E.1    Hughes, T.S.2    Carpenter, B.K.3
  • 92
    • 33746270466 scopus 로고    scopus 로고
    • Electronically nonadiabatic thermal reactions of organic molecules
    • Carpenter, B. K. Electronically nonadiabatic thermal reactions of organic molecules. Chem. Soc. Rev.. 2006, 35, 736-747
    • (2006) Chem. Soc. Rev. , vol.35 , pp. 736-747
    • Carpenter, B.K.1
  • 93
    • 0038306205 scopus 로고    scopus 로고
    • Synthesis, reactions and DNA damaging abilities of 10-membered enediyne-sulfone and related compounds
    • Suzuki, I.; Shigenaga, A.; Manabe, A.; Nemoto, H.; Shibuya, M. Synthesis, reactions and DNA damaging abilities of 10-membered enediyne-sulfone and related compounds. Tetrahedron. 2003, 59, 5691-5704
    • (2003) Tetrahedron , vol.59 , pp. 5691-5704
    • Suzuki, I.1    Shigenaga, A.2    Manabe, A.3    Nemoto, H.4    Shibuya, M.5
  • 94
    • 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.; Shibuya, M. Cycloaromatization of a 10-membered enediyne derivative via an allenic sulfone intermediate and its DNA cleaving activity. Tetrahedron Lett.. 1992, 33, 957-960
    • (1992) Tetrahedron Lett. , vol.33 , pp. 957-960
    • Sakai, Y.1    Bando, Y.2    Shishido, K.3    Shibuya, M.4
  • 95
    • 0026787045 scopus 로고
    • Design and synthesis of 1-thia-3,8-diyn-5-ene systems with DNA-cleaving properties related to the neocarzinostatin chromophore
    • Toshima, K.; Ohta, K.; Ohashi, A.; Nakata, M.; Tatsuta, K. Design and synthesis of 1-thia-3,8-diyn-5-ene systems with DNA-cleaving properties related to the neocarzinostatin chromophore. J. Chem. Soc. Chem. Commun. 1992, 1306-1308.
    • (1992) J. Chem. Soc. Chem. Commun , pp. 1306-1308
    • Toshima, K.1    Ohta, K.2    Ohashi, A.3    Nakata, M.4    Tatsuta, K.5
  • 96
    • 3042983008 scopus 로고    scopus 로고
    • Novel heterocyclic enediynes. Molecular design, chemical synthesis and DNA cleavage
    • Toshima, K.; Ohishi, K.; Tomishima, M.; Matsumura, S. Novel heterocyclic enediynes. Molecular design, chemical synthesis and DNA cleavage. Heterocycles. 1997, 45, 851-855
    • (1997) Heterocycles , vol.45 , pp. 851-855
    • Toshima, K.1    Ohishi, K.2    Tomishima, M.3    Matsumura, S.4
  • 97
    • 37049078487 scopus 로고
    • Design, synthesis and DNA-cleaving profiles of hybrids containing the novel enediyne and naturally-occurring DNA intercalators
    • Toshima, K.; Ohta, K.; Ohashi, A.; Nakamura, T.; Nakata, M.; Matsumura, S. Design, synthesis and DNA-cleaving profiles of hybrids containing the novel enediyne and naturally-occurring DNA intercalators. J. Chem. Soc., Chem. Comm. 1993, 1525-1527.
    • (1993) J. Chem. Soc., Chem. Comm , pp. 1525-1527
    • Toshima, K.1    Ohta, K.2    Ohashi, A.3    Nakamura, T.4    Nakata, M.5    Matsumura, S.6
  • 98
    • 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.; Matsumura, S. Novel designed enediynes: Molecular design, chemical synthesis, mode of cycloaromatization and guanine-specific DNA cleavage. Bioorg. Med. Chem.. 1996, 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
  • 99
    • 0025299412 scopus 로고
    • DNA cleavage by acyclic eneyneallene systems related to neocarzinostatin and esperamicin-calicheamicin
    • Nagata, R.; Yamanaka, H.; Murahashi, E.; Saito, I. DNA cleavage by acyclic eneyneallene systems related to neocarzinostatin and esperamicin-calicheamicin. Tetrahedron Lett.. 1990, 31, 2907-2910
    • (1990) Tetrahedron Lett. , vol.31 , pp. 2907-2910
    • Nagata, R.1    Yamanaka, H.2    Murahashi, E.3    Saito, I.4
  • 100
    • 0030135375 scopus 로고    scopus 로고
    • DNA cleavage by an a,3-dehydrotoluene precursor conjugated to a minor groove binding element
    • Myers, A. G.; Parrish, C. A. DNA cleavage by an a,3-dehydrotoluene precursor conjugated to a minor groove binding element. Bioconj. Chem.. 1996, 7, 322-331
    • (1996) Bioconj. Chem. , vol.7 , pp. 322-331
    • Myers, A.G.1    Parrish, C.A.2
  • 101
    • 0029034833 scopus 로고
    • Switching from the Myers reaction to a new thermal cyclization mode in enyne-allenes
    • Schmittel, M.; Strittmatter, M.; Kiau, S. Switching from the Myers reaction to a new thermal cyclization mode in enyne-allenes. Tetrahedron Lett.. 1995, 36, 4975-4978
    • (1995) Tetrahedron Lett. , vol.36 , pp. 4975-4978
    • Schmittel, M.1    Strittmatter, M.2    Kiau, S.3
  • 102
    • 0030515269 scopus 로고    scopus 로고
    • An unprecedented biradical cyclization as an alternative pathway to the Myers-Saito cycloaromatization in the thermal reactions of enyne allenes
    • Schmittel, M.; Strittmatter, M.; Kiau, S. An unprecedented biradical cyclization as an alternative pathway to the Myers-Saito cycloaromatization in the thermal reactions of enyne allenes. Ang. Chem. Int. Ed.. 1996, 35, 1843-1845
    • (1996) Ang. Chem. Int. Ed. , vol.35 , pp. 1843-1845
    • Schmittel, M.1    Strittmatter, M.2    Kiau, S.3
  • 103
    • 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
    • Schmittel, M.; Vavilala, C. Kinetic isotope effects in the thermal C-2-C-6 cyclization of enyne-allenes: Experimental evidence supports a stepwise mechanism. J. Org. Chem.. 2005, 70, 4865-4868
    • (2005) J. Org. Chem. , vol.70 , pp. 4865-4868
    • Schmittel, M.1    Vavilala, C.2
  • 104
    • 0002974462 scopus 로고    scopus 로고
    • Synthesis of novel enyne-allenes, their thermal C-2-C-6 cyclization, and the importance of a benzofulvene biradical in the DNA strand cleavage
    • Schmittel, M.; Maywald, M.; Strittmatter, M. Synthesis of novel enyne-allenes, their thermal C-2-C-6 cyclization, and the importance of a benzofulvene biradical in the DNA strand cleavage. Synlett 1997, 165-166.
    • (1997) Synlett , pp. 165-166
    • Schmittel, M.1    Maywald, M.2    Strittmatter, M.3
  • 105
    • 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.; Strittmatter, M. Steric effects in enyne-allene thermolyses: Switch from Myers-Saito reaction to the C2-C6-cyclization and DNA strand cleavage. Tetrahedron Lett.. 1996, 37, 7691-7694
    • (1996) Tetrahedron Lett. , vol.37 , pp. 7691-7694
    • Schmittel, M.1    Kiau, S.2    Siebert, T.3    Strittmatter, M.4
  • 107
    • 0002365528 scopus 로고
    • Ring expansions of cyclobutenones-Synthetic utility
    • Moore, H. W.; Yerxa, B. R. Ring expansions of cyclobutenones-Synthetic utility. Chemtracts-Org. Chem.. 1992, 5, 273-313
    • (1992) Chemtracts-Org. Chem. , vol.5 , pp. 273-313
    • Moore, H.W.1    Yerxa, B.R.2
  • 108
    • 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
    • Musch, P. W.; Remenyi, C.; Helten, H.; Engels, B. 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.. 2002, 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
  • 110
    • 0028293297 scopus 로고
    • Photoinduced DNA cleavage by designed molecules with conjugated Ene-yne-ketene functionalities
    • Nakatani, K.; Isoe, S.; Maekawa, S.; Saito, I. Photoinduced DNA cleavage by designed molecules with conjugated Ene-yne-ketene functionalities. Tetrahedron Lett.. 1994, 35, 605-608
    • (1994) Tetrahedron Lett. , vol.35 , pp. 605-608
    • Nakatani, K.1    Isoe, S.2    Maekawa, S.3    Saito, I.4
  • 111
    • 0028972693 scopus 로고
    • Alpha-diazo ketones as photochemical DNA cleavers-A Mimic for the radical generating-system of neocarzinostatin chromophore
    • Nakatani, K.; Maekawa, S.; Tanabe, K.; Saito, I. Alpha-diazo ketones as photochemical DNA cleavers-A Mimic for the radical generating-system of neocarzinostatin chromophore. J. Am. Chem. Soc.. 1995, 117, 10635-10644
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 10635-10644
    • Nakatani, K.1    Maekawa, S.2    Tanabe, K.3    Saito, I.4
  • 112
    • 0034694361 scopus 로고    scopus 로고
    • Synthesis of a heterocyclic aza-enediyne and Its DNA-cleavage properties
    • David,W. M.; Kumar, D.; Kerwin, S. M. Synthesis of a heterocyclic aza-enediyne and Its DNA-cleavage properties. Bioorg. Med. Chem. Lett.. 2000, 10, 2509-2512
    • (2000) Bioorg. Med. Chem. Lett. , vol.10 , pp. 2509-2512
    • David, W.M.1    Kumar, D.2    Kerwin, S.M.3
  • 113
    • 0035914607 scopus 로고    scopus 로고
    • N-Propargyl-2-Alkynylbenzothiazolium azaenediynes: Role of the 2-alkynylbenzothiazolium functionality inDNAcleavage
    • Kumar, D.; David, W. M.; Kerwin, S. M. N-Propargyl-2-Alkynylbenzothiazolium azaenediynes: Role of the 2-alkynylbenzothiazolium functionality inDNAcleavage. Bioorg. Med. Chem. Lett.. 2001, 11, 2971-2974
    • (2001) Bioorg. Med. Chem. Lett. , vol.11 , pp. 2971-2974
    • Kumar, D.1    David, W.M.2    Kerwin, S.M.3
  • 114
    • 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
    • Tuntiwechapikul, W.; David, W. M.; Kumar, D.; Salazar, M.; Kerwin, S. M. DNA modification by 4-aza-3-ene-1,6-diynes: DNA cleavage, pH-dependent cytosine-specific interactions, and cancer cell cytotoxicity. Biochemistry. 2002, 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
  • 115
    • 33748975581 scopus 로고    scopus 로고
    • identification of the adduct between a 4-aza-3-ene-1,6-diyne and DNA using electrospray ionization mass spectrometry
    • Sherman, C. L.; Pierce, S. E.; Brodbelt, J. S.; Tuesuwan, B.; Kerwin, S. M. identification of the adduct between a 4-aza-3-ene-1,6-diyne and DNA using electrospray ionization mass spectrometry. J. Am. Soc. Mass Spectrom.. 2006, 17, 1342-1352
    • (2006) J. Am. Soc. Mass Spectrom. , vol.17 , pp. 1342-1352
    • Sherman, C.L.1    Pierce, S.E.2    Brodbelt, J.S.3    Tuesuwan, B.4    Kerwin, S.M.5
  • 116
    • 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
    • Musch, P. W.; Remenyi, C.; Helten, H.; Engels, B. 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.. 2002, 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
  • 117
    • 42149177341 scopus 로고    scopus 로고
    • Thermal C-2-C-6 cyclization of enyne-carbodiimides: Experimental evidence contradicts a diradical and suggests a carbene intermediate
    • Schmittel, M.; Steffen, J. P.; Rodriguez, D.; Engelen, B.; Neumann, E.; Cinar, M. E. Thermal C-2-C-6 cyclization of enyne-carbodiimides: Experimental evidence contradicts a diradical and suggests a carbene intermediate. J. Org. Chem.. 2008, 73, 3005-3016
    • (2008) J. Org. Chem. , vol.73 , pp. 3005-3016
    • Schmittel, M.1    Steffen, J.P.2    Rodriguez, D.3    Engelen, B.4    Neumann, E.5    Cinar, M.E.6
  • 118
    • 33745049226 scopus 로고    scopus 로고
    • 2-Alkynyl-N-propargyl pyridinium salts: Pyridinium-based heterocyclic skipped aza-enediynes that cleave DNA by deoxyribosyl hydrogen-atom abstraction and guanine oxidation
    • Tuesuwan, B.; Kerwin, S. M. 2-Alkynyl-N-propargyl pyridinium salts: Pyridinium-based heterocyclic skipped aza-enediynes that cleave DNA by deoxyribosyl hydrogen-atom abstraction and guanine oxidation. Biochemistry. 2006, 45, 7265-7276
    • (2006) Biochemistry , vol.45 , pp. 7265-7276
    • Tuesuwan, B.1    Kerwin, S.M.2
  • 119
    • 33747112997 scopus 로고    scopus 로고
    • Electron transfer through DNA and peptides
    • Giese, B. Electron transfer through DNA and peptides. Bioorg. Med. Chem.. 2006, 14, 6139-6143
    • (2006) Bioorg. Med. Chem. , vol.14 , pp. 6139-6143
    • Giese, B.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.