메뉴 건너뛰기




Volumn 48, Issue 11, 2005, Pages 3903-3918

A novel class of in vivo active anticancer agents: Achiral seco-amino- and seco-hydroxycyclopropylbenz[e]indolone (seco-CBI) analogues of the duocarmycins and CC-1065

Author keywords

[No Author keywords available]

Indexed keywords

1,2,9,9A TETRAHYDROPROPA[C]BENZO[E]INDOL 4 ONE; 2 [4 AMINO 2 (5,6,7 TRIMETHOXYINDOLE 2 CARBOXAMIDO)NAPHTHALEN 1 YL]ETHANOL; 2 [4 AMINO 2 (5,6,7 TRIMETHOXYINDOLE 2 CARBOXAMIDO)NAPHTHALEN 1 YL]ETHYL ACETATE; 4 (2 CHLOROETHYL) 3 (3 AZA 2,4 DIMETHOXYCINNAMOYLAMIDO) 1 NAPHTHYLAMINE; 4 (2 CHLOROETHYL) 3 (3 AZA 4 METHOXYCINNAMOYLAMIDO) 1 NAPHTHYLAMINE; 4 (2 CHLOROETHYL) 3 (5 METHOXYINDOLE 2 CARBOXAMIDO) 1 NAPHTHYLAMINE; 4 (2 CHLOROETHYL) 3 (5,6,7 TRIMETHOXYINDOLE 2 CARBOXAMIDO) 1 NAPHTHOL; 4 (2 CHLOROETHYL) 3 (5,6,7 TRIMETHOXYINDOLYL 2 CARBOXAMIDO) 1 NAPHTHYLAMINE; 4 (2 CHLOROETHYL) 3 [5 (5 BENZOFURAN 2 CARBOXAMIDO)INDOLE 2 CARBOXAMIDO] 1 NAPHTHYLAMINE; ADOZELESIN; ANTINEOPLASTIC AGENT; CYCLOPROPANE DERIVATIVE; DUOCARMYCIN DERIVATIVE; INDOLE DERIVATIVE; RACHELMYCIN; UNCLASSIFIED DRUG;

EID: 20144380099     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm050179u     Document Type: Article
Times cited : (50)

References (66)
  • 1
    • 77957096511 scopus 로고    scopus 로고
    • Jones, G. B., Palumbo, M., Eds.; JAI Press Inc.; Greenwich, CT
    • (a) Advances in DNA Sequence Specific Agents; Jones, G. B., Palumbo, M., Eds.; JAI Press Inc.; Greenwich, CT, 1998; Vol. 3.
    • (1998) Advances in DNA Sequence Specific Agents , pp. 3
  • 3
    • 0025753312 scopus 로고
    • Adozelesin, a selected lead among cyclopropylpyrroloindole analogs of the DNA-binding antibiotic, CC-1065
    • (c) Li, L. H.; Kelly, R. C.; Warpehoski, M. A.; McGovern, J. P.; Gebhard, I.; DeKoning, T. F. Adozelesin, a Selected Lead among Cyclopropylpyrroloindole Analogs of the DNA-Binding Antibiotic, CC-1065. Invest. New Drugs 1991, 9,137-148.
    • (1991) Invest. New Drugs , vol.9 , pp. 137-148
    • Li, L.H.1    Kelly, R.C.2    Warpehoski, M.A.3    McGovern, J.P.4    Gebhard, I.5    DeKoning, T.F.6
  • 4
    • 0001124924 scopus 로고
    • The DNA sequence selectivity of CC-1065
    • Hurley, L. H., Ed.; JAI Press: Greenwich, CT
    • (d) Warpehoski, M. The DNA Sequence Selectivity of CC-1065. In Advances in DNA Sequence Specific Agents; Hurley, L. H., Ed.; JAI Press: Greenwich, CT, 1992; Vol. 1, pp 217-245.
    • (1992) Advances in DNA Sequence Specific Agents , vol.1 , pp. 217-245
    • Warpehoski, M.1
  • 5
    • 0029782488 scopus 로고    scopus 로고
    • CC-1065 and the duocarmycins; understanding their biological function through mechanistic studies
    • (a) Boger, D. L.; Johnson, D. S. CC-1065 and the Duocarmycins; Understanding their Biological Function through Mechanistic Studies. Angew. Chem., Int. Ed. Engl. 1996, 35, 1438-1474.
    • (1996) Angew. Chem., Int. Ed. Engl. , vol.35 , pp. 1438-1474
    • Boger, D.L.1    Johnson, D.S.2
  • 6
    • 0029053550 scopus 로고
    • CC-1065 and the Duocarmycins: Unraveling the Keys to a New Class of Natural Derived DNA Alkylating Agents
    • (b) Boger, D. L.; Johnson, D. S. CC-1065 and the Duocarmycins: Unraveling the Keys to a New Class of Natural Derived DNA Alkylating Agents. Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 3642-3649.
    • (1995) Proc. Natl. Acad. Sci. U.S.A. , vol.92 , pp. 3642-3649
    • Boger, D.L.1    Johnson, D.S.2
  • 7
    • 0002631330 scopus 로고
    • The duocarmycins: Synthetic and mechanistic studies
    • (a) Boger, D. L. The Duocarmycins: Synthetic and Mechanistic Studies. Acc. Chem. Res. 1995, 28, 20-29.
    • (1995) Acc. Chem. Res. , vol.28 , pp. 20-29
    • Boger, D.L.1
  • 8
    • 0000923199 scopus 로고
    • Duocarmycins: A new class of sequence selective DNA minor groove alkylating agents
    • (b) Boger, D. L. Duocarmycins: A New Class of Sequence Selective DNA Minor Groove Alkylating Agents. Chemtracts: Org. Chem. 1991, 4, 329-349.
    • (1991) Chemtracts: Org. Chem. , vol.4 , pp. 329-349
    • Boger, D.L.1
  • 9
    • 0018239716 scopus 로고
    • CC-1065 (NSC-298223), a new antitumor antibiotic, production in-vivo biological activity, microbiological assays, and taxonomy of the producing microorganism
    • (a) Hanka, L. J.; Dietz, A.; Gerpheide, S. A.; Kuentzel, S. L.; Martin, D. G. CC-1065 (NSC-298223), a New Antitumor Antibiotic. Production in-vivo Biological Activity, Microbiological Assays, and Taxonomy of the Producing Microorganism. J. Antibiot. 1978, 31, 1211-1217.
    • (1978) J. Antibiot. , vol.31 , pp. 1211-1217
    • Hanka, L.J.1    Dietz, A.2    Gerpheide, S.A.3    Kuentzel, S.L.4    Martin, D.G.5
  • 10
    • 0021319952 scopus 로고
    • Preliminary toxicity studies with the DNA-binding antibiotic, CC-1065
    • (b) McGovern, J. P.; Clarke, G. L.; Pratte, E. A.; DeKoning, T. F. Preliminary Toxicity Studies with the DNA-Binding Antibiotic, CC-1065 J. Antibiot. 1983, 37, 63-70.
    • (1983) J. Antibiot. , vol.37 , pp. 63-70
    • McGovern, J.P.1    Clarke, G.L.2    Pratte, E.A.3    DeKoning, T.F.4
  • 11
    • 0023906926 scopus 로고
    • Stereoelectronic factors influencing the biological activity and DNA interaction of synthetic antitumor agents modeled on CC-1065
    • (c) Warpehoski, M. A.; Gebhard, J.; Kelly, R. C.; Krueger, W. C.; Li, L. H.; McGovern, J. P. Stereoelectronic Factors Influencing the Biological Activity and DNA Interaction of Synthetic Antitumor Agents Modeled on CC-1065. J. Med. Chem. 1988, 31, 590-603.
    • (1988) J. Med. Chem. , vol.31 , pp. 590-603
    • Warpehoski, M.A.1    Gebhard, J.2    Kelly, R.C.3    Krueger, W.C.4    Li, L.H.5    McGovern, J.P.6
  • 15
    • 0027382382 scopus 로고
    • Interconversion and stability of duocarmycins, a new family of antitumor antibiotics: Correlation to their cytotoxic and antimicrobial activities in-vitro
    • (d) Ichimura, M.; Ogawa, T.; Takahashi, K.; Mihara, A.; Takahashi, I.; Nakano, H. Interconversion and Stability of Duocarmycins, a New Family of Antitumor Antibiotics: Correlation to Their Cytotoxic and Antimicrobial Activities In-vitro. Oncol. Res. 1993, 5, 165-171.
    • (1993) Oncol. Res. , vol.5 , pp. 165-171
    • Ichimura, M.1    Ogawa, T.2    Takahashi, K.3    Mihara, A.4    Takahashi, I.5    Nakano, H.6
  • 17
    • 0021715394 scopus 로고
    • Reaction of the antitumor antibiotic CC-1065 with DNA: Structure of a DNA adduct with DNA sequence specificity
    • Hurley, L. H.; Reynolds, V. S.; Swenson, D. H.; Petzold, G. L.; Scahill, T. A. Reaction of the Antitumor Antibiotic CC-1065 with DNA: Structure of a DNA Adduct with DNA Sequence Specificity. Science 1984, 226, 843-844.
    • (1984) Science , vol.226 , pp. 843-844
    • Hurley, L.H.1    Reynolds, V.S.2    Swenson, D.H.3    Petzold, G.L.4    Scahill, T.A.5
  • 18
    • 0028095610 scopus 로고
    • (+)- and ent-(-)-duocarmycin SA and (+)- and ent-(-)-N-BOC-DSA DNA alkylation properties. Alkylation site models that accomodate the offset AT-rich adenine N3 alkylation selectivity of the enantiomeric agents
    • Boger, D. L.; Johnson, D. S.; Yun, W. (+)- and ent-(-)-Duocarmycin SA and (+)- and ent-(-)-N-BOC-DSA DNA Alkylation Properties. Alkylation Site Models that Accomodate the Offset AT-Rich Adenine N3 Alkylation Selectivity of the Enantiomeric Agents. J. Am. Chem. Soc. 1994, 116, 1635-1656.
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 1635-1656
    • Boger, D.L.1    Johnson, D.S.2    Yun, W.3
  • 19
    • 0022358966 scopus 로고
    • Reaction of the antitumor antibiotic CC-1065 with DNA location of the site of thermally induced strand breakage and analysis of DNA sequence specificity
    • Reynolds, V. L.; Molineux, I. J.; Kaplan, D. J.; Swenson, D. H.; Hurley, L. H. Reaction of the Antitumor Antibiotic CC-1065 with DNA Location of the Site of Thermally Induced Strand Breakage and Analysis of DNA Sequence Specificity. Biochemistry 1985, 24, 6228-6237.
    • (1985) Biochemistry , vol.24 , pp. 6228-6237
    • Reynolds, V.L.1    Molineux, I.J.2    Kaplan, D.J.3    Swenson, D.H.4    Hurley, L.H.5
  • 20
    • 20144379744 scopus 로고
    • In-vitro evaluation of the novel chemotherapeutic agents U-73975, U-77779, and U-80244
    • (a) Hightower, R. D.; Sevin, B. U.; Pevras, J. P.; Untch, M.; Angioli, R.; Averette, H. In-Vitro Evaluation of the Novel Chemotherapeutic Agents U-73975, U-77779, and U-80244. Gynecol. Oncol. 1992, 42, 186-190.
    • (1992) Gynecol. Oncol. , vol.42 , pp. 186-190
    • Hightower, R.D.1    Sevin, B.U.2    Pevras, J.P.3    Untch, M.4    Angioli, R.5    Averette, H.6
  • 21
    • 0027180722 scopus 로고
    • Evaluation of the antineoplastic activity of adozelesin alone and in combination with 5-Aza-2′-deoxycytidine and cytosine arabinoside on DLD-1 human colon carcinoma cells
    • (b) Cote, S.; Momparler, R. L. Evaluation of the Antineoplastic Activity of Adozelesin Alone and in Combination with 5-Aza-2′-deoxycytidine and Cytosine Arabinoside on DLD-1 Human Colon Carcinoma Cells. Anti-Cancer Drugs 1993, 4, 327-333.
    • (1993) Anti-Cancer Drugs , vol.4 , pp. 327-333
    • Cote, S.1    Momparler, R.L.2
  • 29
    • 0028361852 scopus 로고
    • Preclinical pharmacology of bizelesin, a potent bifunctional analog of the DNA-binding antibiotic CC-1065
    • (a) Walker, D. L.; Reid, F. M.; Ames, M. M. Preclinical Pharmacology of Bizelesin, a Potent Bifunctional Analog of the DNA-Binding Antibiotic CC-1065. Cancer Chemother. Pharmacol. 1994, 34, 317-322.
    • (1994) Cancer Chemother. Pharmacol. , vol.34 , pp. 317-322
    • Walker, D.L.1    Reid, F.M.2    Ames, M.M.3
  • 32
    • 0030567868 scopus 로고    scopus 로고
    • Studies on the active metabolite (DU-86) of KW-2189, a novel derivative of duocarmycin
    • and references therein
    • (a) Nagamura, S.; Kobayashi, E.; Gomi, K.; Saito, H. Studies on the Active Metabolite (DU-86) of KW-2189, A Novel Derivative of Duocarmycin. Bioorg. Med. Chem. Lett. 1996, 6, 2147-2150, and references therein,
    • (1996) Bioorg. Med. Chem. Lett. , vol.6 , pp. 2147-2150
    • Nagamura, S.1    Kobayashi, E.2    Gomi, K.3    Saito, H.4
  • 37
    • 0033581567 scopus 로고    scopus 로고
    • Synthesis and antitumor activity of water-soluble duocarmycin B1 prodrugs
    • (f) Asai, A.; Nagamura, S.; Kobayashi, E.; Gomi, K.; Saito, H. Synthesis and Antitumor Activity of Water-Soluble Duocarmycin B1 Prodrugs. Bioorg. Med. Chem. Lett. 1999, 9, 2995-2998.
    • (1999) Bioorg. Med. Chem. Lett. , vol.9 , pp. 2995-2998
    • Asai, A.1    Nagamura, S.2    Kobayashi, E.3    Gomi, K.4    Saito, H.5
  • 38
    • 0029872086 scopus 로고    scopus 로고
    • The Hammett correlation for CC-1065 and duocarmycin analogs: Magnitude of substituent electronic effects on functional reactivity
    • and references therein
    • Boger, D. L.; McKie, J. A.; Han, N.; Tarbie, C. M.; Riggs, H. W.; Kitos, P. A. The Hammett Correlation for CC-1065 and Duocarmycin Analogs: Magnitude of Substituent Electronic Effects on Functional Reactivity. Bioorg. Med. Chem. Lett. 1996, 6, 659, and references therein.
    • (1996) Bioorg. Med. Chem. Lett. , vol.6 , pp. 659
    • Boger, D.L.1    McKie, J.A.2    Han, N.3    Tarbie, C.M.4    Riggs, H.W.5    Kitos, P.A.6
  • 39
    • 0028920020 scopus 로고
    • An efficient synthesis of 1, 2, 9, 9a-tetrahydropropa[c]benzo[e]indol-4- one (CBI): An enhanced and simplified analog of the CC-1065 and duocarmycin alkylation subunits
    • (a) Boger, D. L.; McKie, J. A. An Efficient Synthesis of 1, 2, 9, 9a-Tetrahydropropa[c]benzo[e]indol-4-one (CBI): An Enhanced and Simplified Analog of the CC-1065 and Duocarmycin Alkylation Subunits. J. Org. Chem. 1995, 60, 1271-1275.
    • (1995) J. Org. Chem. , vol.60 , pp. 1271-1275
    • Boger, D.L.1    McKie, J.A.2
  • 40
    • 0028790373 scopus 로고
    • 1,2,9,9a-tetrahydrocyclopropa[c]benz-[e]indol-4-one (CBI) analogs of CC-1065 and the duocarmycins: Synthesis and evaluation
    • (b) Boger, D. L.; Yun, W.; Han, N. 1,2,9,9a-Tetrahydrocyclopropa[c]benz- [e]indol-4-one (CBI) Analogs of CC-1065 and the Duocarmycins: Synthesis and Evaluation. Bioorg. Med. Chem. 1995, 3, 1429-1453.
    • (1995) Bioorg. Med. Chem. , vol.3 , pp. 1429-1453
    • Boger, D.L.1    Yun, W.2    Han, N.3
  • 41
    • 0026677093 scopus 로고
    • Synthesis of CBI-PDE-I dimer, the benzannelated analogue of CC-1065
    • (c) Aristoff, P. A.; Johnson, P. D. Synthesis of CBI-PDE-I Dimer, the Benzannelated Analogue of CC-1065. J. Org. Chem. 1992, 57, 6234-6239.
    • (1992) J. Org. Chem. , vol.57 , pp. 6234-6239
    • Aristoff, P.A.1    Johnson, P.D.2
  • 42
    • 0031028037 scopus 로고    scopus 로고
    • Synthesis, chemical solvolytic stability and preliminary biological evaluation of (±)-N-BOC-CPzI: A pyrazole analog of the left-hand segment of the antitumor agent CC-1065
    • Baraldi, P. G.; Cacciari, B.; Pinedo de las Infantas, M. J.; Romagnoli, R.; Spatullo, G.; Cozzi, P.; Mongelli, N. Synthesis, Chemical Solvolytic Stability and Preliminary Biological Evaluation of (±)-N-BOC-CPzI: A Pyrazole Analog of the Left-Hand Segment of the Antitumor Agent CC-1065. Anti-Cancer Drug Design 1997, 12, 67-74.
    • (1997) Anti-Cancer Drug Design , vol.12 , pp. 67-74
    • Baraldi, P.G.1    Cacciari, B.2    Pinedo De Las Infantas, M.J.3    Romagnoli, R.4    Spatullo, G.5    Cozzi, P.6    Mongelli, N.7
  • 43
    • 0028009270 scopus 로고
    • Total synthesis and biological properties of novel antineoplastic (chloromethyl)furanoindolines: An asymmetric hydroboraton method synthesis of the alkylation subunits
    • Mohamadi, F.; Spees, M. M.; Staten, G. S.; Marder, P.; Kipka, J. K.; Johnson, D. A. Total Synthesis and Biological Properties of Novel Antineoplastic (Chloromethyl)furanoindolines: An Asymmetric Hydroboraton Method Synthesis of the Alkylation Subunits. J. Med. Chem. 1994, 37, 232-239.
    • (1994) J. Med. Chem. , vol.37 , pp. 232-239
    • Mohamadi, F.1    Spees, M.M.2    Staten, G.S.3    Marder, P.4    Kipka, J.K.5    Johnson, D.A.6
  • 44
    • 0025980193 scopus 로고
    • 32P-end labeled double-stranded DNA for binding studies: Development of a protocol for examination of functional features of (+)-CC-1065 and the duocarmycins that contribute to their sequence-selective DNA alkylation properties
    • 32P-End Labeled Double-Stranded DNA for Binding Studies: Development of a Protocol for Examination of Functional Features of (+)-CC-1065 and the Duocarmycins that Contribute to Their Sequence-Selective DNA Alkylation Properties. Tetrahedron 1991, 47, 2661-2682.
    • (1991) Tetrahedron , vol.47 , pp. 2661-2682
    • Boger, D.L.1    Munk, S.A.2    Zarrinmayeh, H.3    Ishizaki, T.4    Haught, J.5    Bina, M.6
  • 45
    • 0025644317 scopus 로고
    • Duocarmycin-pyrindamycin DNA alkylation properties and identification, synthesis, and evaluation of agents incorporating the pharmacophore of the duocarmycin-pyrindamycin alkylation subunit. Identification of the CC-1065-duocarmycin common chromophore
    • (b) Boger, D. L.; Ishizaki, T.; Zarrinmayeh, H.; Munk, S. A.; Kitos, P. A.; Suntorwart, O. Duocarmycin-Pyrindamycin DNA Alkylation Properties and Identification, Synthesis, and Evaluation of Agents Incorporating the Pharmacophore of the Duocarmycin-Pyrindamycin Alkylation Subunit. Identification of the CC-1065-Duocarmycin Common Chromophore. J. Am. Chem. Soc. 1990, 112, 8961-8971.
    • (1990) J. Am. Chem. Soc. , vol.112 , pp. 8961-8971
    • Boger, D.L.1    Ishizaki, T.2    Zarrinmayeh, H.3    Munk, S.A.4    Kitos, P.A.5    Suntorwart, O.6
  • 46
    • 0032509496 scopus 로고    scopus 로고
    • Synthesis and cytotoxicity of 5-amino-1-(chloromethyl)-3-[(5,6,7- trimethoxyindol-2-yl)carbonyl]-1,2-dihydro-3if'-benz[e]indole (amino-seco-CBI-TMI) and related 5-alkylamino analogues: New DNA minor groove alkylating agents
    • (a) Atwell, G. J.; Tercel, M.; Boyd, M.; Wilson, W. R.; Denny, W. A. Synthesis and Cytotoxicity of 5-Amino-1-(chloromethyl)-3-[(5,6,7- trimethoxyindol-2-yl)carbonyl]-1,2-dihydro-3if'-benz[e]indole (Amino-seco-CBI-TMI) and Related 5-Alkylamino Analogues: New DNA Minor Groove Alkylating Agents. J. Org. Chem. 1998, 63, 9414-9420.
    • (1998) J. Org. Chem. , vol.63 , pp. 9414-9420
    • Atwell, G.J.1    Tercel, M.2    Boyd, M.3    Wilson, W.R.4    Denny, W.A.5
  • 47
    • 0033606952 scopus 로고    scopus 로고
    • 5-Amino-1-(chloromethyl)-1,2-dihydro-3H-benz[e]indoles: Relationships between structure and cytotoxicity for analogues bearing different DNA minor groove binding subunits
    • (b) Atwell, G. J.; Milbank, J. J. B.; Wilson, W. R.; Hogg, A.; Denny, W. A. 5-Amino-1-(chloromethyl)-1,2-dihydro-3H-benz[e]indoles: Relationships between Structure and Cytotoxicity for Analogues Bearing Different DNA Minor Groove Binding Subunits. J. Med. Chem. 1999, 42, 3400-3411.
    • (1999) J. Med. Chem. , vol.42 , pp. 3400-3411
    • Atwell, G.J.1    Milbank, J.J.B.2    Wilson, W.R.3    Hogg, A.4    Denny, W.A.5
  • 48
    • 0033529886 scopus 로고    scopus 로고
    • Synthesis and cytotoxicity of amino-Seco-DSA: An amino analogue of the DNA alkylating agent duocarmycin SA
    • (c) Tercel, M.; Gieseg, M. A.; Denny, W. A.; Wilson, W. R. Synthesis and Cytotoxicity of Amino-Seco-DSA: An Amino Analogue of the DNA Alkylating Agent Duocarmycin SA. J. Org. Chem. 1999, 64, 5946-5953.
    • (1999) J. Org. Chem. , vol.64 , pp. 5946-5953
    • Tercel, M.1    Gieseg, M.A.2    Denny, W.A.3    Wilson, W.R.4
  • 49
    • 0036310887 scopus 로고    scopus 로고
    • Novel furano analogs of duocarmycin C1 and C2: Design, synthesis and biological evaluation of seco-iso-cyclopropyl-furano[e]indoline (seco-iso-CFI) and the unexpected seco-cyclopropyltetrahydrofurano[f]quinoline (seco-CFQ) analogs
    • Howard, T. T.; Lingerfelt, B. M.; Purnell, B. L.; Scott, A. E.; Price, C. A.; Townes, H. M.; McNulty, L.; Handl, H. L.; Summerville, K; Hudson, S. J.; Bowen, P. J.; Kiakos, K; Hartley, J. A.; Lee, M. Novel Furano Analogs of Duocarmycin C1 and C2: Design, Synthesis and Biological Evaluation of seco-iso-Cyclopropyl-furano[e]indoline (seco-iso-CFI) and the Unexpected seco-Cyclopropyltetrahydrofurano[f]quinoline (seco-CFQ) Analogs. Bioorg. Med. Chem. 2002, 10, 2941-2952.
    • (2002) Bioorg. Med. Chem. , vol.10 , pp. 2941-2952
    • Howard, T.T.1    Lingerfelt, B.M.2    Purnell, B.L.3    Scott, A.E.4    Price, C.A.5    Townes, H.M.6    McNulty, L.7    Handl, H.L.8    Summerville, K.9    Hudson, S.J.10    Bowen, P.J.11    Kiakos, K.12    Hartley, J.A.13    Lee, M.14
  • 51
    • 20144383449 scopus 로고    scopus 로고
    • A novel aohiral seco-amino-cyclopropylindoline (CI) analog of CC-1065 and the duocarmycins: Design, synthesis and biological studies
    • Toth, J. L.; Trzupek, J. D.; Flores, L. V.; Kiakos, K.; Hartley, J. A.; Pennington, W. T.; Lee, M. A Novel Aohiral seco-Amino-Cyclopropylindoline (CI) Analog of CC-1065 and the Duocarmycins: Design, Synthesis and Biological Studies. Med. Chem. 2005, 1, 13-19.
    • (2005) Med. Chem. , vol.1 , pp. 13-19
    • Toth, J.L.1    Trzupek, J.D.2    Flores, L.V.3    Kiakos, K.4    Hartley, J.A.5    Pennington, W.T.6    Lee, M.7
  • 54
    • 84982075251 scopus 로고
    • Rec. The replaceability of the halogen atom in 1-chloro-2,4-dinitro- and -2,4,5-trinitronaphthalenes
    • (a) Talen, H. W. Rec. The Replaceability of the Halogen Atom in 1-Chloro-2,4-dinitro- and -2,4,5-Trinitronaphthalenes. Trav. Chim. 1928, 47, 329-345.
    • (1928) Trav. Chim. , vol.47 , pp. 329-345
    • Talen, H.W.1
  • 55
    • 84917920574 scopus 로고
    • 1,2-Dinitro-α-naphthol
    • (b) Ullmann, F.; Brück, W. 1,2-Dinitro-α-naphthol. Ber. 1908, 41, 3932-3939.
    • (1908) Ber. , vol.41 , pp. 3932-3939
    • Ullmann, F.1    Brück, W.2
  • 56
    • 0033602254 scopus 로고    scopus 로고
    • New water-soluble duocarmycin derivatives: Synthesis and antitumor activity of A-ring pyrrole compounds bearing β-heteroarylacryloyl groups
    • Amishiro, N.; Nagamura, S.; Kobayashi, E.; Gomi, K.; Saito, H. New Water-Soluble Duocarmycin Derivatives: Synthesis and Antitumor Activity of A-ring Pyrrole Compounds Bearing β-Heteroarylacryloyl Groups. J. Med. Chem. 1999, 42, 669-676.
    • (1999) J. Med. Chem. , vol.42 , pp. 669-676
    • Amishiro, N.1    Nagamura, S.2    Kobayashi, E.3    Gomi, K.4    Saito, H.5
  • 57
    • 0025877161 scopus 로고
    • Measurement of the sequence specificity of covalent DNA modification by antineoplastic agents using taq DNA polymerase
    • Ponti, M.; Forrow, S. M.; Souhami, R. L.; D'Incalci, M.; Hartley, J. A. Measurement of the Sequence Specificity of Covalent DNA Modification by Antineoplastic Agents Using Taq DNA Polymerase. Nucl. Acids Res. 1991, 19, 2929-2933.
    • (1991) Nucl. Acids Res. , vol.19 , pp. 2929-2933
    • Ponti, M.1    Forrow, S.M.2    Souhami, R.L.3    D'Incalci, M.4    Hartley, J.A.5
  • 58
    • 0023130372 scopus 로고
    • Evaluation of a tetrazolium-based semi-automated colorimetric assay: Assessment of chemosensitivity testing
    • Carmichael, J.; DeGraff, W. G.; Gadzar, A. F.; Minna, J. D.; Mitchell, J. B.; Evaluation of a Tetrazolium-based Semi-automated Colorimetric Assay: Assessment of Chemosensitivity Testing. Cancer Res. 1987, 47, 936-946.
    • (1987) Cancer Res. , vol.47 , pp. 936-946
    • Carmichael, J.1    DeGraff, W.G.2    Gadzar, A.F.3    Minna, J.D.4    Mitchell, J.B.5
  • 59
    • 0028036453 scopus 로고
    • CBI-TMI synthesis and evaluation of a key analog of the duocarmycins. Validation of a direct relationship between chemical solvolytic stability and cytotoxic potency and confirmation of the structural features responsible for the distinguishing behavior of enantiomeric pairs of agents
    • (a) Boger, D. L.; Yun, W. CBI-TMI: Synthesis And Evaluation of a Key Analog of the Duocarmycins. Validation of a Direct Relationship Between Chemical Solvolytic Stability and Cytotoxic Potency and Confirmation of the Structural Features Responsible for the Distinguishing Behavior of Enantiomeric Pairs of Agents. J. Am. Chem. Soc. 1994, 116, 7996-8006.
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 7996-8006
    • Boger, D.L.1    Yun, W.2
  • 60
    • 0030916634 scopus 로고    scopus 로고
    • Synthesis and cytotoxicity of amino analogues of the potent DNA alkylating agent seco-CBI-TMI
    • (b) Atwell, G. J.; Wilson, W. R.; Denny, W. A. Synthesis and Cytotoxicity of Amino Analogues of the Potent DNA Alkylating Agent Seco-CBI-TMI. Bioorg. Med. Chem. Lett. 1997, 7, 1493-1496.
    • (1997) Bioorg. Med. Chem. Lett. , vol.7 , pp. 1493-1496
    • Atwell, G.J.1    Wilson, W.R.2    Denny, W.A.3
  • 61
    • 0000719887 scopus 로고
    • Status of the NCI preclinical antitumor drug discovery screen
    • Boyd, R. B. Status of the NCI Preclinical Antitumor Drug Discovery Screen. Principles Practices Oncol. 1989, 3, 1-12.
    • (1989) Principles Practices Oncol. , vol.3 , pp. 1-12
    • Boyd, R.B.1
  • 62
    • 0028219281 scopus 로고
    • Induction of endonucleolytic DNA fragmentation and apoptosis by the duocarmycins
    • (a) Wrasidlo, W.; Johnson, D. S.; Boger, D. L. Induction of Endonucleolytic DNA Fragmentation and Apoptosis by the Duocarmycins. Bioorg. Med. Chem. Lett. 1994, 4, 631-636.
    • (1994) Bioorg. Med. Chem. Lett. , vol.4 , pp. 631-636
    • Wrasidlo, W.1    Johnson, D.S.2    Boger, D.L.3
  • 63
    • 0034692179 scopus 로고    scopus 로고
    • Synthesis and preliminary biological evaluations of CC-1065 analogues: Effects of different linkers and terminal amides on biological activity
    • (b) Wang, Y.; Yuan, H.; Ye, W.; Wright, S. C.; Wang, H.; Larrick, J. W. Synthesis and Preliminary Biological Evaluations of CC-1065 Analogues: Effects of Different Linkers and Terminal Amides on Biological Activity. J. Med. Chem. 2000, 43, 1541-1549.
    • (2000) J. Med. Chem. , vol.43 , pp. 1541-1549
    • Wang, Y.1    Yuan, H.2    Ye, W.3    Wright, S.C.4    Wang, H.5    Larrick, J.W.6


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.