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Volumn 48, Issue 14, 2005, Pages 4504-4506

Highly stable phenanthridinium frameworks as a new class of tunable DNA binding agents with cytotoxic properties

Author keywords

[No Author keywords available]

Indexed keywords

7 HYDROXY 8 METHOXY 5 METHYL 2,3 METHYLENEDIOXYBENZO[C]PHENANTHRIDINIUM HYDROGEN SULFATE; BENZO[C]PHENANTHRIDINIUM; CARBOPLATIN; CHELERYTHRINE; DIHYDROPYRROLOPHENANTHRIDINIUM; DIOXOLOPHENANTHRIDINIUM; FAGARIDINE; FAGARONINE; INTERCALATING AGENT; NITIDINE; PHENANTHRIDINE DERIVATIVE; PYRROLOPHENANTHRIDINIUM; SANGUINARINE; UNCLASSIFIED DRUG;

EID: 22244493849     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm050320z     Document Type: Article
Times cited : (72)

References (22)
  • 2
    • 0021098336 scopus 로고
    • Exploratory and mechanistic aspects of the electron-transfer photochemistry of Olefin-N-heteroaromatic cation systems
    • Yoon, U. C.; Quillen, S. L.; Mariano, P. S.; Swanson, R.; Stavinoha, J. L.; Bay, E. Exploratory and Mechanistic Aspects of the Electron-Transfer Photochemistry of Olefin-N-Heteroaromatic Cation Systems. J. Am. Chem. Soc. 1983, 105, 1204-1218.
    • (1983) J. Am. Chem. Soc. , vol.105 , pp. 1204-1218
    • Yoon, U.C.1    Quillen, S.L.2    Mariano, P.S.3    Swanson, R.4    Stavinoha, J.L.5    Bay, E.6
  • 3
    • 0035829166 scopus 로고    scopus 로고
    • Synthesis, biological activity and comparative analysis of DNA binding affinities and human DNA topoisomerase I inhibitory activities of novel 12-alkoxy-benzo-[c]phenanthridinium salts
    • Lynch, M. A.; Duval, O.; Sukhanova, A.; Devy, J.; Mackay, S. P.; Waigh, R. D.; Nabiev, I. Synthesis, biological activity and comparative analysis of DNA binding affinities and human DNA topoisomerase I inhibitory activities of novel 12-alkoxy-benzo-[c]phenanthridinium salts. Bioorg. Med. Chem. Lett. 2001, 11, 2643-2646.
    • (2001) Bioorg. Med. Chem. Lett. , vol.11 , pp. 2643-2646
    • Lynch, M.A.1    Duval, O.2    Sukhanova, A.3    Devy, J.4    Mackay, S.P.5    Waigh, R.D.6    Nabiev, I.7
  • 6
    • 0035727277 scopus 로고    scopus 로고
    • The interaction of DNA-targeted platinum phenanthridinium complexes with DNA in human cells
    • Whittaker, J.; McFadyen, W. D.; Baguley, B. C.; Murray, V. The interaction of DNA-targeted platinum phenanthridinium complexes with DNA in human cells. Anti-Cancer Drug Des. 2001, 16, 81-89.
    • (2001) Anti-Cancer Drug Des. , vol.16 , pp. 81-89
    • Whittaker, J.1    McFadyen, W.D.2    Baguley, B.C.3    Murray, V.4
  • 8
    • 19644367830 scopus 로고    scopus 로고
    • Synthesis of some derivatives of pyrrolo[a]-, pyrrolo[c]phenanthridines as well as of indolinyl- and indolyl- substituted 6-phenanthridines
    • Baberkina, E. P.; Buyanov, V. N.; Zhukova, M. E.; Shchekotikhin, A. E.; Zhigachev, V. E.; Suvorov, N. N. Synthesis of some derivatives of pyrrolo[a]-, pyrrolo[c]phenanthridines as well as of indolinyl- and indolyl- substituted 6-phenanthridines. Khim. Geterotsikl. Soedin. 2001, 1350-1353.
    • (2001) Khim. Geterotsikl. Soedin. , pp. 1350-1353
    • Baberkina, E.P.1    Buyanov, V.N.2    Zhukova, M.E.3    Shchekotikhin, A.E.4    Zhigachev, V.E.5    Suvorov, N.N.6
  • 9
    • 0027143718 scopus 로고
    • Synthesis and evaluation of new 6-Amino-substituted Benzo[c] phenanthridine derivatives
    • Janin, Y. L.; Croisy, A.; Riou, J. F.; Bisagni, E. Synthesis and Evaluation of New 6-Amino-Substituted Benzo[c]phenanthridine Derivatives. J. Med. Chem. 1993, 36, 3686-3692.
    • (1993) J. Med. Chem. , vol.36 , pp. 3686-3692
    • Janin, Y.L.1    Croisy, A.2    Riou, J.F.3    Bisagni, E.4
  • 10
    • 0034685857 scopus 로고    scopus 로고
    • Total synthesis of Amaryllidaceae pyrrolophenanthridinium alkaloids via the Ziegler-Ullmann reaction: Tortuosine, criasbetaine, and ungeremine
    • Stark, L. M.; Lin, X. F.; Flippin, L. A. Total synthesis of Amaryllidaceae pyrrolophenanthridinium alkaloids via the Ziegler-Ullmann reaction: Tortuosine, criasbetaine, and ungeremine. J. Org. Chem. 2000, 65, 3227-3230.
    • (2000) J. Org. Chem. , vol.65 , pp. 3227-3230
    • Stark, L.M.1    Lin, X.F.2    Flippin, L.A.3
  • 11
    • 0034792744 scopus 로고    scopus 로고
    • Cytotoxic quaternary alkaloids from the flowers of Narcissus tazetta
    • Youssef, D. T. A.; Khalifa, A. A. Cytotoxic quaternary alkaloids from the flowers of Narcissus tazetta. Pharmazie 2001, 56, 818-822.
    • (2001) Pharmazie , vol.56 , pp. 818-822
    • Youssef, D.T.A.1    Khalifa, A.A.2
  • 12
    • 0033059590 scopus 로고    scopus 로고
    • Structural considerations of NK109, an antitumor benzo[c]phenanthridine alkaloid
    • Nakanishi, T.; Suzuki, M.; Saimoto, A.; Kabasawa, T. Structural considerations of NK109, an antitumor benzo[c]phenanthridine alkaloid. J. Nat. Prod. 1999, 62, 864-867.
    • (1999) J. Nat. Prod. , vol.62 , pp. 864-867
    • Nakanishi, T.1    Suzuki, M.2    Saimoto, A.3    Kabasawa, T.4
  • 13
    • 0000605895 scopus 로고
    • Lifetimes of Iminium Ions in Aqueous-Solution
    • Eldin, S.; Jencks, W. P. Lifetimes of Iminium Ions in Aqueous-Solution. J. Am. Chem. Soc. 1995, 117, 4851-4857.
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 4851-4857
    • Eldin, S.1    Jencks, W.P.2
  • 14
    • 4344593931 scopus 로고    scopus 로고
    • General one-pot, three-step methodology leading to an extended class of N-heterocyclic cations: Spontaneous nucleophilic addition, cyclization, and hydride loss
    • Parenty, A. D. C.; Smith, L. V.; Pickering, A. L.; Long, D. L.; Cronin, L. General one-pot, three-step methodology leading to an extended class of N-heterocyclic cations: Spontaneous nucleophilic addition, cyclization, and hydride loss. J. Org. Chem. 2004, 69, 5934-5946.
    • (2004) J. Org. Chem. , vol.69 , pp. 5934-5946
    • Parenty, A.D.C.1    Smith, L.V.2    Pickering, A.L.3    Long, D.L.4    Cronin, L.5
  • 15
    • 14944382879 scopus 로고    scopus 로고
    • A new synthetic method for alpha-alkoxycarbonyl iminium salt and its reaction with nudeophiles
    • Shimizu, M.; Itou, H.; Miura, M. A new synthetic method for alpha-alkoxycarbonyl iminium salt and its reaction with nudeophiles. J. Am. Chem. Soc. 2005, 127, 3296-3297.
    • (2005) J. Am. Chem. Soc. , vol.127 , pp. 3296-3297
    • Shimizu, M.1    Itou, H.2    Miura, M.3
  • 16
    • 0032705881 scopus 로고    scopus 로고
    • Direct oxidative carbon-carbon bond formation-using the "cation pool" method. 1. Generation of iminium cation pools and their reaction with carbon nucleophiles
    • Yoshida, J.; Suga, S.; Suzuki, S.; Kinomura, N.; Yamamoto, A.; Fujiwara, K. Direct oxidative carbon-carbon bond formation-using the "cation pool" method. 1. Generation of iminium cation pools and their reaction with carbon nucleophiles. J. Am. Chem. Soc. 1999, 121, 9546-9549.
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 9546-9549
    • Yoshida, J.1    Suga, S.2    Suzuki, S.3    Kinomura, N.4    Yamamoto, A.5    Fujiwara, K.6
  • 17
    • 0034675704 scopus 로고    scopus 로고
    • Synthesis of derivatives of NK109, 7-OH benzo[c]phenanthridine alkaloid, and evaluation of their cytotoxicities and reduction- Resistant properties
    • Nakanishi, T.; Masuda, A.; Suwa, M.; Akiyama, Y.; Hoshino-Abe, N.; Suzuki, M. Synthesis of derivatives of NK109, 7-OH benzo[c]phenanthridine alkaloid, and evaluation of their cytotoxicities and reduction- resistant properties. Bioorg., Med. Chem. Lett. 2000, 10, 2321-2323.
    • (2000) Bioorg., Med. Chem. Lett. , vol.10 , pp. 2321-2323
    • Nakanishi, T.1    Masuda, A.2    Suwa, M.3    Akiyama, Y.4    Hoshino-Abe, N.5    Suzuki, M.6
  • 18
    • 0017863106 scopus 로고
    • Antileukemic activity of ungeremine and related compounds. Preparation of analogues of ungeremine by a practical photochemical reaction
    • Zee-Cheng, R. K. Y.; Yan, S. J.; Cheng, C. C. Antileukemic Activity of Ungeremine and Related Compounds. Preparation of Analogues of Ungeremine by a Practical Photochemical Reaction. J. Med. Chem. 1978, 21, 199-203.
    • (1978) J. Med. Chem. , vol.21 , pp. 199-203
    • Zee-Cheng, R.K.Y.1    Yan, S.J.2    Cheng, C.C.3
  • 19
    • 0019425250 scopus 로고
    • A Review of the chemistry of the antitumor benzo[C]phenanthridine alkaloids nitidine and fagaronine and of the related anti-tumor alkaloid coralyne
    • Phillips, S. D.; Castle, R. N. A Review of the Chemistry of the Antitumor Benzo[C]Phenanthridine Alkaloids Nitidine and Fagaronine and of the Related Anti-tumor Alkaloid Coralyne. J. Heterocycl. Chem. 1981, 18, 223-232.
    • (1981) J. Heterocycl. Chem. , vol.18 , pp. 223-232
    • Phillips, S.D.1    Castle, R.N.2
  • 22
    • 0034713855 scopus 로고    scopus 로고
    • Energetics of DNA intercalation reactions
    • Ren, J. S.; Jenkins, T. C.; Chaires, J. B. Energetics of DNA intercalation reactions. Biochemistry 2000, 39, 8439-8447.
    • (2000) Biochemistry , vol.39 , pp. 8439-8447
    • Ren, J.S.1    Jenkins, T.C.2    Chaires, J.B.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.