-
1
-
-
0019769681
-
CC-1065 (NSC 298223), a Potent New Antitumor Agent: Improved Production and Isolation, Characterization and Antitumor Activity
-
Martin, D. G.; Biles, C.; Gerpheide, S. A.; Hanka, L. J.; Krueger, W. C.; McGovren, J. P.; Mizsak, S. A.; Neil, G. L.; Stewart, J. C.; Visser, J. CC-1065 (NSC 298223), a Potent New Antitumor Agent: Improved Production and Isolation, Characterization and Antitumor Activity J. Antibiot. 1981, 34, 1119-1125
-
(1981)
J. Antibiot.
, vol.34
, pp. 1119-1125
-
-
Martin, D.G.1
Biles, C.2
Gerpheide, S.A.3
Hanka, L.J.4
Krueger, W.C.5
McGovren, J.P.6
Mizsak, S.A.7
Neil, G.L.8
Stewart, J.C.9
Visser, J.10
-
2
-
-
0024996602
-
Duocarmycin SA, a New Antitumor Antibiotic from Streptomyces sp
-
Ichimura, M.; Ogawa, T.; Takahashi, K.; Kobayashi, E.; Kawamoto, I.; Yasuzawa, T.; Takahashi, I.; Nakano, H. Duocarmycin SA, a New Antitumor Antibiotic from Streptomyces sp J. Antibiot. 1990, 43, 1037-1038
-
(1990)
J. Antibiot.
, vol.43
, pp. 1037-1038
-
-
Ichimura, M.1
Ogawa, T.2
Takahashi, K.3
Kobayashi, E.4
Kawamoto, I.5
Yasuzawa, T.6
Takahashi, I.7
Nakano, H.8
-
3
-
-
0024261683
-
Duocarmycin, a New Antitumor Antibiotic from Streptomyces
-
Takahashi, I.; Takahashi, K.; Ichimura, M.; Morimoto, M.; Asano, K.; Kawamoto, I.; Tomita, F.; Nakano, H. Duocarmycin, a New Antitumor Antibiotic from Streptomyces J. Antibiot. 1988, 41, 1915-1917
-
(1988)
J. Antibiot.
, vol.41
, pp. 1915-1917
-
-
Takahashi, I.1
Takahashi, K.2
Ichimura, M.3
Morimoto, M.4
Asano, K.5
Kawamoto, I.6
Tomita, F.7
Nakano, H.8
-
4
-
-
0344837276
-
Yatakemycin, a Novel Antifungal Antibiotic Produced by Streptomyces sp. TP-A0356
-
Igarashi, Y.; Futamata, K.; Fujita, T.; Sekine, A.; Senda, H.; Naoki, H.; Furumai, T. Yatakemycin, a Novel Antifungal Antibiotic Produced by Streptomyces sp. TP-A0356 J. Antibiot. 2003, 56, 107-113
-
(2003)
J. Antibiot.
, vol.56
, pp. 107-113
-
-
Igarashi, Y.1
Futamata, K.2
Fujita, T.3
Sekine, A.4
Senda, H.5
Naoki, H.6
Furumai, T.7
-
5
-
-
0028095610
-
(+)- and ent -(-)-Duocarmycin SA and (+)- and ent -(-)- N -Boc-DSA DNA Alkylation Properties. Alkylation Site Models That Accommodate 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 Accommodate 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
-
6
-
-
0041733260
-
DNA Alkylation Properties of Yatakemycin
-
Parrish, J. P.; Kastrinsky, D. B.; Wolkenberg, S. E.; Igarashi, Y.; Boger, D. L. DNA Alkylation Properties of Yatakemycin J. Am. Chem. Soc. 2003, 125, 10971-10976
-
(2003)
J. Am. Chem. Soc.
, vol.125
, pp. 10971-10976
-
-
Parrish, J.P.1
Kastrinsky, D.B.2
Wolkenberg, S.E.3
Igarashi, Y.4
Boger, D.L.5
-
7
-
-
33644847729
-
Alkylation of Duplex DNA in Nucleosome Core Particles by Duocarmycin SA and Yatakemycin
-
Trzupek, J. D.; Gottesfeld, J. M.; Boger, D. L. Alkylation of Duplex DNA in Nucleosome Core Particles by Duocarmycin SA and Yatakemycin Nat. Chem. Biol. 2006, 2, 79-82
-
(2006)
Nat. Chem. Biol.
, vol.2
, pp. 79-82
-
-
Trzupek, J.D.1
Gottesfeld, J.M.2
Boger, D.L.3
-
8
-
-
34848834561
-
Systematic Exploration of the Structural Features of Yatakemycin Impacting DNA Alkylation and Biological Activity
-
Tichenor, M. S.; MacMillan, K. S.; Trzupek, J. D.; Rayl, T. J.; Hwang, I.; Boger, D. L. Systematic Exploration of the Structural Features of Yatakemycin Impacting DNA Alkylation and Biological Activity J. Am. Chem. Soc. 2007, 129, 10858-10869
-
(2007)
J. Am. Chem. Soc.
, vol.129
, pp. 10858-10869
-
-
Tichenor, M.S.1
MacMillan, K.S.2
Trzupek, J.D.3
Rayl, T.J.4
Hwang, I.5
Boger, D.L.6
-
9
-
-
0024290406
-
Molecular Basis for Sequence-Specific DNA Alkylation by CC-1065
-
Hurley, L. H.; Lee, C.-S.; McGovren, J. P.; Warpehoski, M. A.; Mitchell, M. A.; Kelly, R. C.; Aristoff, P. A. Molecular Basis for Sequence-Specific DNA Alkylation by CC-1065 Biochemistry 1988, 27, 3886-3892
-
(1988)
Biochemistry
, vol.27
, pp. 3886-3892
-
-
Hurley, L.H.1
Lee, C.-S.2
McGovren, J.P.3
Warpehoski, M.A.4
Mitchell, M.A.5
Kelly, R.C.6
Aristoff, P.A.7
-
10
-
-
0025148364
-
Sequence Specificity of DNA Alkylation by the Unnatural Enantiomer of CC-1065 and Its Synthetic Analogues
-
Hurley, L. H.; Warpehoski, M. A.; Lee, C.-S.; McGovren, J. P.; Scahill, T. A.; Kelly, R. C.; Mitchell, M. A.; Wicnienski, N. A.; Gebhard, I.; Johnson, P. D.; Bradford, V. S. Sequence Specificity of DNA Alkylation by the Unnatural Enantiomer of CC-1065 and Its Synthetic Analogues J. Am. Chem. Soc. 1990, 112, 4633-4649
-
(1990)
J. Am. Chem. Soc.
, vol.112
, pp. 4633-4649
-
-
Hurley, L.H.1
Warpehoski, M.A.2
Lee, C.-S.3
McGovren, J.P.4
Scahill, T.A.5
Kelly, R.C.6
Mitchell, M.A.7
Wicnienski, N.A.8
Gebhard, I.9
Johnson, P.D.10
Bradford, V.S.11
-
11
-
-
0028376605
-
Molecular Basis for Sequence Selective DNA Alkylation by (+)- and ent -(-)-CC-1065 and Related Agents: Alkylation Site Models That Accommodate the Offset AT-Rich Adenine N3 Alkylation Selectivity
-
Boger, D. L.; Johnson, D. S.; Yun, W.; Tarby, C. M. Molecular Basis for Sequence Selective DNA Alkylation by (+)- and ent -(-)-CC-1065 and Related Agents: Alkylation Site Models That Accommodate the Offset AT-Rich Adenine N3 Alkylation Selectivity Bioorg. Med. Chem. 1994, 2, 115-135
-
(1994)
Bioorg. Med. Chem.
, vol.2
, pp. 115-135
-
-
Boger, D.L.1
Johnson, D.S.2
Yun, W.3
Tarby, C.M.4
-
12
-
-
0025111222
-
3. Preparation of Key Partial Structures and Definition of an Additional Functional Role of the CC-1065 Central and Right-Hand Subunits
-
3. Preparation of Key Partial Structures and Definition of an Additional Functional Role of the CC-1065 Central and Right-Hand Subunits J. Am. Chem. Soc. 1990, 112, 4623-4632
-
(1990)
J. Am. Chem. Soc.
, vol.112
, pp. 4623-4632
-
-
Boger, D.L.1
Coleman, R.S.2
Invergo, B.J.3
Sakya, S.M.4
Ishizaki, T.5
Munk, S.A.6
Zarrinmayeh, H.7
Kitos, P.A.8
Thompson, S.C.9
-
13
-
-
0025644317
-
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 Pharmacophore
-
Boger, D. L.; Ishizaki, T.; Zarrinmayeh, H.; Munk, S. A.; Kitos, P. A.; Suntornwat, 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 Pharmacophore 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
Suntornwat, O.6
-
14
-
-
0025773799
-
Isolation and Characterization of the Duocarmycin-Adenine DNA Adduct
-
Boger, D. L.; Ishizaki, T.; Zarrinmayeh, H. Isolation and Characterization of the Duocarmycin-Adenine DNA Adduct J. Am. Chem. Soc. 1991, 113, 6645-6649
-
(1991)
J. Am. Chem. Soc.
, vol.113
, pp. 6645-6649
-
-
Boger, D.L.1
Ishizaki, T.2
Zarrinmayeh, H.3
-
15
-
-
0026646153
-
DNA Alkylation Properties of the Duocarmycins: (+)-Duocarmycin A, epi -(+)-Duocarmycin A, ent -(-)-Duocarmycin A and epi, ent -(-)-Duocarmycin A
-
Boger, D. L.; Yun, W.; Terashima, S.; Fukuda, Y.; Nakatani, K.; Kitos, P. A.; Jin, Q. DNA Alkylation Properties of the Duocarmycins: (+)-Duocarmycin A, epi -(+)-Duocarmycin A, ent -(-)-Duocarmycin A and epi, ent -(-)-Duocarmycin A Bioorg. Med. Chem. Lett. 1992, 2, 759-765
-
(1992)
Bioorg. Med. Chem. Lett.
, vol.2
, pp. 759-765
-
-
Boger, D.L.1
Yun, W.2
Terashima, S.3
Fukuda, Y.4
Nakatani, K.5
Kitos, P.A.6
Jin, Q.7
-
16
-
-
0029782488
-
CC-1065 and the Duocarmycins: Understanding Their Biological Function through Mechanistic Studies
-
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
-
17
-
-
0002631330
-
The Duocarmycins: Synthetic and Mechanistic Studies
-
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
-
18
-
-
0029053550
-
CC-1065 and the Duocarmycins: Unraveling the Keys to a New Class of Naturally Derived DNA Alkylating Agents
-
Boger, D. L.; Johnson, D. S. CC-1065 and the Duocarmycins: Unraveling the Keys to a New Class of Naturally 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
-
19
-
-
41749095626
-
Yatakemycin: Total Synthesis, DNA Alkylation, and Biological Properties
-
Tichenor, M. S.; Boger, D. L. Yatakemycin: Total Synthesis, DNA Alkylation, and Biological Properties Nat. Prod. Rep. 2008, 25, 220-226
-
(2008)
Nat. Prod. Rep.
, vol.25
, pp. 220-226
-
-
Tichenor, M.S.1
Boger, D.L.2
-
20
-
-
70349641991
-
Fundamental Relationships between Structure, Reactivity, and Biological Activity for the Duocarmycins and CC-1065
-
MacMillan, K. S.; Boger, D. L. Fundamental Relationships between Structure, Reactivity, and Biological Activity for the Duocarmycins and CC-1065 J. Med. Chem. 2009, 52, 5771-5780
-
(2009)
J. Med. Chem.
, vol.52
, pp. 5771-5780
-
-
MacMillan, K.S.1
Boger, D.L.2
-
21
-
-
0036015565
-
Duocarmycins: Nature's Prodrugs?
-
Searcey, M. Duocarmycins: Nature's Prodrugs? Curr. Pharm. Des. 2002, 8, 1375-1389
-
(2002)
Curr. Pharm. Des.
, vol.8
, pp. 1375-1389
-
-
Searcey, M.1
-
22
-
-
0023858516
-
Total Synthesis of (+)-CC-1065 and ent -(-)-CC-1065
-
Boger, D. L.; Coleman, R. S. Total Synthesis of (+)-CC-1065 and ent -(-)-CC-1065 J. Am. Chem. Soc. 1988, 110, 1321-1323
-
(1988)
J. Am. Chem. Soc.
, vol.110
, pp. 1321-1323
-
-
Boger, D.L.1
Coleman, R.S.2
-
23
-
-
0001607781
-
2 [(±)-(3b R,4a S), (+)-(3b R,4a S), and (-)-(3b S,4a R)-Deoxy-CC-1065]
-
2 [(±)-(3b R*,4a S*), (+)-(3b R,4a S), and (-)-(3b S,4a R)-Deoxy-CC-1065] J. Am. Chem. Soc. 1988, 110, 4796-4807
-
(1988)
J. Am. Chem. Soc.
, vol.110
, pp. 4796-4807
-
-
Boger, D.L.1
Coleman, R.S.2
-
24
-
-
0027067027
-
Total Synthesis of (+)-Duocarmycin SA
-
Boger, D. L.; Machiya, K. Total Synthesis of (+)-Duocarmycin SA J. Am. Chem. Soc. 1992, 114, 10056-10058
-
(1992)
J. Am. Chem. Soc.
, vol.114
, pp. 10056-10058
-
-
Boger, D.L.1
Machiya, K.2
-
25
-
-
0027442101
-
Total Synthesis and Preliminary Evaluation of (+)- and ent -(-)-Duocarmycin SA
-
Boger, D. L.; Machiya, K.; Hertzog, D. L.; Kitos, P. A.; Holmes, D. Total Synthesis and Preliminary Evaluation of (+)- and ent -(-)-Duocarmycin SA J. Am. Chem. Soc. 1993, 115, 9025-9036
-
(1993)
J. Am. Chem. Soc.
, vol.115
, pp. 9025-9036
-
-
Boger, D.L.1
Machiya, K.2
Hertzog, D.L.3
Kitos, P.A.4
Holmes, D.5
-
26
-
-
0028036453
-
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
-
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
-
27
-
-
0029871620
-
Enantioselective Total Synthesis of (+)-Duocarmycin A, epi -(+)-Duocarmycin A, and Their Unnatural Enantiomers
-
Boger, D. L.; McKie, J. A.; Nishi, T.; Ogiku, T. Enantioselective Total Synthesis of (+)-Duocarmycin A, epi -(+)-Duocarmycin A, and Their Unnatural Enantiomers J. Am. Chem. Soc. 1996, 118, 2301-2302
-
(1996)
J. Am. Chem. Soc.
, vol.118
, pp. 2301-2302
-
-
Boger, D.L.1
McKie, J.A.2
Nishi, T.3
Ogiku, T.4
-
28
-
-
0031055494
-
Total Synthesis of (+)-Duocarmycin A, epi -(+)-Duocarmycin A and Their Unnatural Enantiomers: Assessment of Chemical and Biological Properties
-
Boger, D. L.; McKie, J. A.; Nishi, T.; Ogiku, T. Total Synthesis of (+)-Duocarmycin A, epi -(+)-Duocarmycin A and Their Unnatural Enantiomers: Assessment of Chemical and Biological Properties J. Am. Chem. Soc. 1997, 119, 311-325
-
(1997)
J. Am. Chem. Soc.
, vol.119
, pp. 311-325
-
-
Boger, D.L.1
McKie, J.A.2
Nishi, T.3
Ogiku, T.4
-
29
-
-
33845402161
-
Asymmetric Total Synthesis of (+)- and ent -(-)-Yatakemycin and Duocarmycin SA. Evaluation of Yatakemycin Key Partial Structures and Its Unnatural Enantiomer
-
Tichenor, M. S.; Trzupek, J. D.; Kastrinsky, D. B.; Shiga, F.; Hwang, I.; Boger, D. L. Asymmetric Total Synthesis of (+)- and ent -(-)-Yatakemycin and Duocarmycin SA. Evaluation of Yatakemycin Key Partial Structures and Its Unnatural Enantiomer J. Am. Chem. Soc. 2006, 128, 15683-15696
-
(2006)
J. Am. Chem. Soc.
, vol.128
, pp. 15683-15696
-
-
Tichenor, M.S.1
Trzupek, J.D.2
Kastrinsky, D.B.3
Shiga, F.4
Hwang, I.5
Boger, D.L.6
-
30
-
-
61749099637
-
Total Synthesis and Evaluation of iso -Duocarmycin SA and iso -Yatakemycin
-
MacMillan, K. S.; Nguyen, T.; Hwang, I.; Boger, D. L. Total Synthesis and Evaluation of iso -Duocarmycin SA and iso -Yatakemycin J. Am. Chem. Soc. 2009, 131, 1187-1194
-
(2009)
J. Am. Chem. Soc.
, vol.131
, pp. 1187-1194
-
-
MacMillan, K.S.1
Nguyen, T.2
Hwang, I.3
Boger, D.L.4
-
31
-
-
0001699963
-
CC-1065 and the Duocarmycins: Synthetic Studies
-
Boger, D. L.; Boyce, C. E.; Garbaccio, R. M.; Goldberg, J. A. CC-1065 and the Duocarmycins: Synthetic Studies Chem. Rev. 1997, 97, 787-828
-
(1997)
Chem. Rev.
, vol.97
, pp. 787-828
-
-
Boger, D.L.1
Boyce, C.E.2
Garbaccio, R.M.3
Goldberg, J.A.4
-
32
-
-
0030970599
-
Duocarmycin SA Shortened, Simplified, and Extended Agents: A Systematic Examination of the Role of the DNA Binding Subunit
-
Boger, D. L.; Hertzog, D. L.; Bollinger, B.; Johnson, D. S.; Cai, H.; Goldberg, J.; Turnbull, P. Duocarmycin SA Shortened, Simplified, and Extended Agents: A Systematic Examination of the Role of the DNA Binding Subunit J. Am. Chem. Soc. 1997, 119, 4977-4986
-
(1997)
J. Am. Chem. Soc.
, vol.119
, pp. 4977-4986
-
-
Boger, D.L.1
Hertzog, D.L.2
Bollinger, B.3
Johnson, D.S.4
Cai, H.5
Goldberg, J.6
Turnbull, P.7
-
33
-
-
0030904168
-
Reversed and Sandwiched Analogs of Duocarmycin SA: Establishment of the Origin of the Sequence-Selective Alkylation of DNA and New Insights into the Source of Catalysis
-
Boger, D. L.; Bollinger, B.; Hertzog, D. L.; Johnson, D. S.; Cai, H.; Mesini, P.; Garbaccio, R. M.; Jin, Q.; Kitos, P. A. Reversed and Sandwiched Analogs of Duocarmycin SA: Establishment of the Origin of the Sequence-Selective Alkylation of DNA and New Insights into the Source of Catalysis J. Am. Chem. Soc. 1997, 119, 4987-4998
-
(1997)
J. Am. Chem. Soc.
, vol.119
, pp. 4987-4998
-
-
Boger, D.L.1
Bollinger, B.2
Hertzog, D.L.3
Johnson, D.S.4
Cai, H.5
Mesini, P.6
Garbaccio, R.M.7
Jin, Q.8
Kitos, P.A.9
-
34
-
-
0031081549
-
Catalysis of the CC-1065 and Duocarmycin DNA Alkylation Reaction: DNA Binding Induced Conformational Change in the Agent Results in Activation
-
Boger, D. L.; Garbaccio, R. M. Catalysis of the CC-1065 and Duocarmycin DNA Alkylation Reaction: DNA Binding Induced Conformational Change in the Agent Results in Activation Bioorg. Med. Chem. 1997, 5, 263-276
-
(1997)
Bioorg. Med. Chem.
, vol.5
, pp. 263-276
-
-
Boger, D.L.1
Garbaccio, R.M.2
-
35
-
-
0032582736
-
Synthesis and Evaluation of a Carbocyclic Analogue of the CC-1065 and Duocarmycin Alkylation Subunits: Role of the Vinylogous Amide and Implications on DNA Alkylation Catalysis
-
Boger, D. L.; Turnbull, P. Synthesis and Evaluation of a Carbocyclic Analogue of the CC-1065 and Duocarmycin Alkylation Subunits: Role of the Vinylogous Amide and Implications on DNA Alkylation Catalysis J. Org. Chem. 1998, 63, 8004-8011
-
(1998)
J. Org. Chem.
, vol.63
, pp. 8004-8011
-
-
Boger, D.L.1
Turnbull, P.2
-
36
-
-
0033377095
-
Shape-Dependent Catalysis: Insights into the Source of Catalysis for the CC-1065 and Duocarmycin DNA Alkylation Reaction
-
Boger, D. L.; Garbaccio, R. M. Shape-Dependent Catalysis: Insights into the Source of Catalysis for the CC-1065 and Duocarmycin DNA Alkylation Reaction Acc. Chem. Res. 1999, 32, 1043-1052
-
(1999)
Acc. Chem. Res.
, vol.32
, pp. 1043-1052
-
-
Boger, D.L.1
Garbaccio, R.M.2
-
37
-
-
0036628558
-
Mechanisms of in Situ Activation for DNA-Targeting Antitumor Agents
-
Wolkenberg, S. E.; Boger, D. L. Mechanisms of in Situ Activation for DNA-Targeting Antitumor Agents Chem. Rev. 2002, 102, 2477-2495
-
(2002)
Chem. Rev.
, vol.102
, pp. 2477-2495
-
-
Wolkenberg, S.E.1
Boger, D.L.2
-
38
-
-
0030882524
-
Synthesis and Evaluation of CC-1065 and Duocarmycin Analogs Incorporating the 1,2,3,4,11,11a-Hexahydrocyclopropa[ c ]naphtho[2,1- b ]azepin-6-one (CNA) Alkylation Subunit: Structural Features That Govern Reactivity and Reaction Regioselectivity
-
Boger, D. L.; Turnbull, P. Synthesis and Evaluation of CC-1065 and Duocarmycin Analogs Incorporating the 1,2,3,4,11,11a-Hexahydrocyclopropa[ c ]naphtho[2,1- b ]azepin-6-one (CNA) Alkylation Subunit: Structural Features That Govern Reactivity and Reaction Regioselectivity J. Org. Chem. 1997, 62, 5849-5863
-
(1997)
J. Org. Chem.
, vol.62
, pp. 5849-5863
-
-
Boger, D.L.1
Turnbull, P.2
-
39
-
-
0002223415
-
CC-1065 Analogs: Sequence Specific DNA-Alkylating Antitumor Agents
-
Aristoff, P. A. CC-1065 Analogs: Sequence Specific DNA-Alkylating Antitumor Agents Adv. Med. Chem. 1993, 2, 67-110
-
(1993)
Adv. Med. Chem.
, vol.2
, pp. 67-110
-
-
Aristoff, P.A.1
-
40
-
-
0028198475
-
Characteristics of Antitumor Activity of KW-2189, a Novel Water-Soluble Derivative of Duocarmycin, against Murine and Human Tumors
-
Kobayashi, E.; Okamoto, A.; Asada, M.; Okabe, M.; Nagamura, S.; Asai, A.; Saito, H.; Gomi, K.; Hirata, T. Characteristics of Antitumor Activity of KW-2189, a Novel Water-Soluble Derivative of Duocarmycin, against Murine and Human Tumors Cancer Res. 1994, 54, 2404-2410
-
(1994)
Cancer Res.
, vol.54
, pp. 2404-2410
-
-
Kobayashi, E.1
Okamoto, A.2
Asada, M.3
Okabe, M.4
Nagamura, S.5
Asai, A.6
Saito, H.7
Gomi, K.8
Hirata, T.9
-
41
-
-
0033602254
-
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
-
42
-
-
0029827268
-
Synthesis and Antitumor Activity of Duocarmycin Derivatives: Modification of Segment A of Duocarmycin B2
-
Nagamura, S.; Asai, A.; Kanda, Y.; Kobayashi, E.; Gomi, K.; Saito, H. Synthesis and Antitumor Activity of Duocarmycin Derivatives: Modification of Segment A of Duocarmycin B2 Chem. Pharm. Bull. 1996, 44, 1723-1730
-
(1996)
Chem. Pharm. Bull.
, vol.44
, pp. 1723-1730
-
-
Nagamura, S.1
Asai, A.2
Kanda, Y.3
Kobayashi, E.4
Gomi, K.5
Saito, H.6
-
43
-
-
0028840445
-
Synthesis and Antitumor Activity of Duocarmycin Derivatives
-
Nagamura, S.; Kanda, Y.; Kobayashi, E.; Gomi, K.; Saito, H. Synthesis and Antitumor Activity of Duocarmycin Derivatives Chem. Pharm. Bull. 1995, 43, 1530-1535
-
(1995)
Chem. Pharm. Bull.
, vol.43
, pp. 1530-1535
-
-
Nagamura, S.1
Kanda, Y.2
Kobayashi, E.3
Gomi, K.4
Saito, H.5
-
44
-
-
0032813670
-
CBI Prodrug Analogs of CC-1065 and the Duocarmycins
-
Boger, D. L.; Boyce, C. W.; Garbaccio, R. M.; Searcey, M.; Jin, Q. CBI Prodrug Analogs of CC-1065 and the Duocarmycins Synthesis 1999, 1505-1509
-
(1999)
Synthesis
, pp. 1505-1509
-
-
Boger, D.L.1
Boyce, C.W.2
Garbaccio, R.M.3
Searcey, M.4
Jin, Q.5
-
45
-
-
44649194513
-
Duocarmycin-Based Prodrugs for Cancer Prodrug Monotherapy
-
Tietze, L. F.; Schuster, H. J.; Schmuck, K.; Schuberth, I.; Alves, F. Duocarmycin-Based Prodrugs for Cancer Prodrug Monotherapy Bioorg. Med. Chem. 2008, 16, 6312-6318
-
(2008)
Bioorg. Med. Chem.
, vol.16
, pp. 6312-6318
-
-
Tietze, L.F.1
Schuster, H.J.2
Schmuck, K.3
Schuberth, I.4
Alves, F.5
-
46
-
-
0034945043
-
Strategy for Tumor-Selective Chemotherapy by Enzymatic Liberation of seco -Duocarmycin SA Derivatives from Nontoxic Prodrugs
-
Tietze, L. F.; Lieb, M.; Herzig, T.; Haunert, F.; Schuberth, I. Strategy for Tumor-Selective Chemotherapy by Enzymatic Liberation of seco -Duocarmycin SA Derivatives from Nontoxic Prodrugs Bioorg. Med. Chem. 2001, 9, 1929-1939
-
(2001)
Bioorg. Med. Chem.
, vol.9
, pp. 1929-1939
-
-
Tietze, L.F.1
Lieb, M.2
Herzig, T.3
Haunert, F.4
Schuberth, I.5
-
47
-
-
65249102262
-
Studies toward Duocarmycin Prodrugs for the Antibody Prodrug Therapy Approach
-
Li, L. S.; Sinha, S. C. Studies toward Duocarmycin Prodrugs for the Antibody Prodrug Therapy Approach Tetrahedron Lett. 2009, 50, 2932-2935
-
(2009)
Tetrahedron Lett.
, vol.50
, pp. 2932-2935
-
-
Li, L.S.1
Sinha, S.C.2
-
48
-
-
0033581567
-
Synthesis and Antitumor Activity of Water-Soluble Duocarmycin B1 Prodrugs
-
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
-
49
-
-
37049036373
-
A Unique Class of Duocarmycin and CC-1065 Analogues Subject to Reductive Activation
-
Jin, W.; Trzupek, J. D.; Rayl, T. J.; Broward, M. A.; Vielhauer, G. A.; Weir, S. J.; Hwang, I.; Boger, D. L. A Unique Class of Duocarmycin and CC-1065 Analogues Subject to Reductive Activation J. Am. Chem. Soc. 2007, 129, 15391-15397
-
(2007)
J. Am. Chem. Soc.
, vol.129
, pp. 15391-15397
-
-
Jin, W.1
Trzupek, J.D.2
Rayl, T.J.3
Broward, M.A.4
Vielhauer, G.A.5
Weir, S.J.6
Hwang, I.7
Boger, D.L.8
-
50
-
-
78149236204
-
Design, Synthesis, and Evaluation of Duocarmycin O -Amino Phenol Prodrugs Subject to Tunable Reductive Activation
-
Lajiness, J. P.; Robertson, W. M.; Dunwiddie, I.; Broward, M. A.; Vielhauer, G. A.; Weir, S. J.; Boger, D. L. Design, Synthesis, and Evaluation of Duocarmycin O -Amino Phenol Prodrugs Subject to Tunable Reductive Activation J. Med. Chem. 2010, 53, 7731-7738
-
(2010)
J. Med. Chem.
, vol.53
, pp. 7731-7738
-
-
Lajiness, J.P.1
Robertson, W.M.2
Dunwiddie, I.3
Broward, M.A.4
Vielhauer, G.A.5
Weir, S.J.6
Boger, D.L.7
-
51
-
-
84863084739
-
A Novel, Unusually Efficacious Duocarmycin Carbamate Prodrug That Releases No Residual Byproduct
-
Wolfe, A. L.; Duncan, K. K.; Parelkar, N.; Weir, S. J.; Vielhauer, G. A.; Boger, D. L. A Novel, Unusually Efficacious Duocarmycin Carbamate Prodrug That Releases No Residual Byproduct J. Med. Chem. 2012, 55, 5878-5886
-
(2012)
J. Med. Chem.
, vol.55
, pp. 5878-5886
-
-
Wolfe, A.L.1
Duncan, K.K.2
Parelkar, N.3
Weir, S.J.4
Vielhauer, G.A.5
Boger, D.L.6
-
52
-
-
80155209663
-
Modification of the Duocarmycin Pharmacophore Enables CYP1A1 Targeting for Biological Activity
-
Pors, K.; Loadman, P. M.; Shnyder, S. D.; Sutherland, M.; Sheldrake, H. M.; Guino, M.; Kiakos, K.; Hartley, J. A.; Searcey, M.; Patterson, L. H. Modification of the Duocarmycin Pharmacophore Enables CYP1A1 Targeting for Biological Activity Chem. Commun. 2011, 47, 12062-12064
-
(2011)
Chem. Commun.
, vol.47
, pp. 12062-12064
-
-
Pors, K.1
Loadman, P.M.2
Shnyder, S.D.3
Sutherland, M.4
Sheldrake, H.M.5
Guino, M.6
Kiakos, K.7
Hartley, J.A.8
Searcey, M.9
Patterson, L.H.10
-
53
-
-
3343023766
-
A Human Single-Chain Antibody Specific for Integrin α3β1 Capable of Cell Internalization and Delivery of Antitumor Agents
-
Lillo, A. M.; Sun, C.; Gao, C.; Ditzel, H.; Parrish, J. P.; Gauss, C.-M.; Moss, J.; Felding-Habermann, B.; Wirsching, P.; Boger, D. L.; Janda, K. D. A Human Single-Chain Antibody Specific for Integrin α3β1 Capable of Cell Internalization and Delivery of Antitumor Agents Chem. Biol. 2004, 11, 897-906
-
(2004)
Chem. Biol.
, vol.11
, pp. 897-906
-
-
Lillo, A.M.1
Sun, C.2
Gao, C.3
Ditzel, H.4
Parrish, J.P.5
Gauss, C.-M.6
Moss, J.7
Felding-Habermann, B.8
Wirsching, P.9
Boger, D.L.10
Janda, K.D.11
-
54
-
-
79952660539
-
Antibody-Drug Conjugates: Using Monoclonal Antibodies for Delivery of Cytotoxic Payloads to Cancer Cells
-
Goldmacher, V. S.; Kovtun, Y. V. Antibody-Drug Conjugates: Using Monoclonal Antibodies for Delivery of Cytotoxic Payloads to Cancer Cells Ther. Delivery 2011, 2, 397-416
-
(2011)
Ther. Delivery
, vol.2
, pp. 397-416
-
-
Goldmacher, V.S.1
Kovtun, Y.V.2
-
55
-
-
74949107560
-
Antibody-Drug Conjugates: Linking Cytotoxic Payloads to Monoclonal Antibodies
-
Ducry, L.; Stump, B. Antibody-Drug Conjugates: Linking Cytotoxic Payloads to Monoclonal Antibodies Bioconjugate Chem. 2010, 21, 5-13
-
(2010)
Bioconjugate Chem.
, vol.21
, pp. 5-13
-
-
Ducry, L.1
Stump, B.2
-
56
-
-
84856373074
-
Synthesis and Biological Evaluation of Antibody Conjugates of Phosphate Prodrugs of Cytotoxic DNA Alkylators for the Targeted Treatment of Cancer
-
Zhao, R. H.; Erickson, H. K.; Leece, B. A.; Reid, E. E.; Goldmacher, V. S.; Lambert, J. M.; Chari, R. V. J. Synthesis and Biological Evaluation of Antibody Conjugates of Phosphate Prodrugs of Cytotoxic DNA Alkylators for the Targeted Treatment of Cancer J. Med. Chem. 2012, 55, 766-782
-
(2012)
J. Med. Chem.
, vol.55
, pp. 766-782
-
-
Zhao, R.H.1
Erickson, H.K.2
Leece, B.A.3
Reid, E.E.4
Goldmacher, V.S.5
Lambert, J.M.6
Chari, R.V.J.7
-
57
-
-
0030760674
-
High Resolution Solution Structure of a DNA Duplex Alkylated by the Antitumor Agent Duocarmycin SA
-
Eis, P. S.; Smith, J. A.; Rydzewski, J. M.; Case, D. A.; Boger, D. L.; Chazin, W. J. High Resolution Solution Structure of a DNA Duplex Alkylated by the Antitumor Agent Duocarmycin SA J. Mol. Biol. 1997, 272, 237-252
-
(1997)
J. Mol. Biol.
, vol.272
, pp. 237-252
-
-
Eis, P.S.1
Smith, J.A.2
Rydzewski, J.M.3
Case, D.A.4
Boger, D.L.5
Chazin, W.J.6
-
58
-
-
0033597629
-
Binding-Induced Activation of DNA Alkylation by Duocarmycin SA: Insights from the Structure of an Indole Derivative-DNA Adduct
-
Schnell, J. R.; Ketchem, R. R.; Boger, D. L.; Chazin, W. J. Binding-Induced Activation of DNA Alkylation by Duocarmycin SA: Insights from the Structure of an Indole Derivative-DNA Adduct J. Am. Chem. Soc. 1999, 121, 5645-5652
-
(1999)
J. Am. Chem. Soc.
, vol.121
, pp. 5645-5652
-
-
Schnell, J.R.1
Ketchem, R.R.2
Boger, D.L.3
Chazin, W.J.4
-
59
-
-
0034725557
-
The Structural Basis for in Situ Activation of DNA Alkylation by Duocarmycin SA
-
Smith, J. A.; Bifulco, G.; Case, D. A.; Boger, D. L.; Gomez-Paloma, L.; Chazin, W. J. The Structural Basis for in Situ Activation of DNA Alkylation by Duocarmycin SA J. Mol. Biol. 2000, 300, 1195-1204
-
(2000)
J. Mol. Biol.
, vol.300
, pp. 1195-1204
-
-
Smith, J.A.1
Bifulco, G.2
Case, D.A.3
Boger, D.L.4
Gomez-Paloma, L.5
Chazin, W.J.6
-
60
-
-
0344875556
-
NMR Structure of the (+)-CPI-indole/d(GACTAATTGAC)-d(GTCAATTAGTC) Covalent Complex
-
Bassarello, C.; Cimino, P.; Bifulco, G.; Boger, D. L.; Smith, J. A.; Chazin, W. J.; Paloma, L. G. NMR Structure of the (+)-CPI-indole/d(GACTAATTGAC)- d(GTCAATTAGTC) Covalent Complex ChemBioChem 2003, 4, 1188-1193
-
(2003)
ChemBioChem
, vol.4
, pp. 1188-1193
-
-
Bassarello, C.1
Cimino, P.2
Bifulco, G.3
Boger, D.L.4
Smith, J.A.5
Chazin, W.J.6
Paloma, L.G.7
-
61
-
-
77950866467
-
Synthesis and Evaluation of a Series of C5′-Substituted Duocarmycin SA Analogs
-
Robertson, W. M.; Kastrinsky, D. B.; Hwang, I.; Boger, D. L. Synthesis and Evaluation of a Series of C5′-Substituted Duocarmycin SA Analogs Bioorg. Med. Chem. Lett. 2010, 20, 2722-2725
-
(2010)
Bioorg. Med. Chem. Lett.
, vol.20
, pp. 2722-2725
-
-
Robertson, W.M.1
Kastrinsky, D.B.2
Hwang, I.3
Boger, D.L.4
-
62
-
-
10644249279
-
Sequence-Selective DNA Recognition: Natural Products and Nature's Lessons
-
Tse, W. C.; Boger, D. L. Sequence-Selective DNA Recognition: Natural Products and Nature's Lessons Chem. Biol. 2004, 11, 1607-1617
-
(2004)
Chem. Biol.
, vol.11
, pp. 1607-1617
-
-
Tse, W.C.1
Boger, D.L.2
-
63
-
-
0025040890
-
Convenient and Efficient Tosylation of Oligoethylene Glycols and the Related Alcohols in Tetrahydrofuran-Water in the Presence of Sodium Hydroxide
-
Ouchi, M.; Inoue, Y.; Liu, Y.; Nagamune, S.; Nakamura, S.; Wada, K.; Hakaushi, T. Convenient and Efficient Tosylation of Oligoethylene Glycols and the Related Alcohols in Tetrahydrofuran-Water in the Presence of Sodium Hydroxide Bull. Chem. Soc. Jpn. 1990, 63, 1260-1262
-
(1990)
Bull. Chem. Soc. Jpn.
, vol.63
, pp. 1260-1262
-
-
Ouchi, M.1
Inoue, Y.2
Liu, Y.3
Nagamune, S.4
Nakamura, S.5
Wada, K.6
Hakaushi, T.7
-
64
-
-
0025143478
-
Synthesis and Preliminary Evaluation of Agents Incorporating the Pharmacophore of the Duocarmycin/Pyrindamycin Alkylation Subunit: Identification of the CC-1065/Duocarmycin Common Pharmacophore
-
Boger, D. L.; Ishizaki, T.; Zarrinmayeh, H.; Kitos, P. A.; Suntornwat, O. Synthesis and Preliminary Evaluation of Agents Incorporating the Pharmacophore of the Duocarmycin/Pyrindamycin Alkylation Subunit: Identification of the CC-1065/Duocarmycin Common Pharmacophore J. Org. Chem. 1990, 55, 4499-4502
-
(1990)
J. Org. Chem.
, vol.55
, pp. 4499-4502
-
-
Boger, D.L.1
Ishizaki, T.2
Zarrinmayeh, H.3
Kitos, P.A.4
Suntornwat, O.5
-
65
-
-
33845283430
-
Diels-Alder Reactions of Heterocyclic Azadienes: Total Synthesis of PDE I, PDE II, and PDE I Dimer Methyl Ester
-
Boger, D. L.; Coleman, R. S. Diels-Alder Reactions of Heterocyclic Azadienes: Total Synthesis of PDE I, PDE II, and PDE I Dimer Methyl Ester J. Am. Chem. Soc. 1987, 109, 2717-2727
-
(1987)
J. Am. Chem. Soc.
, vol.109
, pp. 2717-2727
-
-
Boger, D.L.1
Coleman, R.S.2
-
66
-
-
0023243692
-
Studies on the Total Synthesis of CC-1065: Preparation of a Synthetic Simplified 3-Carbamoyl-1,2-dihydro-3 H -pyrrolo[3,2- e ]indole Dimer/Trimer/Tetramer (CDPI Dimer/Trimer/Tetramer) and Development of Methodology for PDE-I Dimer Methyl Ester Formation
-
Boger, D. L.; Coleman, R. S.; Invergo, B. J. Studies on the Total Synthesis of CC-1065: Preparation of a Synthetic Simplified 3-Carbamoyl-1,2- dihydro-3 H -pyrrolo[3,2- e ]indole Dimer/Trimer/Tetramer (CDPI Dimer/Trimer/Tetramer) and Development of Methodology for PDE-I Dimer Methyl Ester Formation J. Org. Chem. 1987, 52, 1521-1530
-
(1987)
J. Org. Chem.
, vol.52
, pp. 1521-1530
-
-
Boger, D.L.1
Coleman, R.S.2
Invergo, B.J.3
-
67
-
-
3142723437
-
Total Synthesis, Structure Revision, and Absolute Configuration of (+)-Yatakemycin
-
Tichenor, M. S.; Kastrinsky, D. B.; Boger, D. L. Total Synthesis, Structure Revision, and Absolute Configuration of (+)-Yatakemycin J. Am. Chem. Soc. 2004, 126, 8396-8398
-
(2004)
J. Am. Chem. Soc.
, vol.126
, pp. 8396-8398
-
-
Tichenor, M.S.1
Kastrinsky, D.B.2
Boger, D.L.3
-
68
-
-
0025980193
-
32-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
-
32-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
-
69
-
-
11944251378
-
DNA Alkylation Properties of Enhanced Functional Analogs of CC-1065 Incorporating the 1,2,9,9a-Tetrahydrocyclopropa[1,2- c ]benz[1,2- e ]indol-4-one (CBI) Alkylation Subunit
-
Boger, D. L.; Munk, S. A. DNA Alkylation Properties of Enhanced Functional Analogs of CC-1065 Incorporating the 1,2,9,9a-Tetrahydrocyclopropa[1, 2- c ]benz[1,2- e ]indol-4-one (CBI) Alkylation Subunit J. Am. Chem. Soc. 1992, 114, 5487-5496
-
(1992)
J. Am. Chem. Soc.
, vol.114
, pp. 5487-5496
-
-
Boger, D.L.1
Munk, S.A.2
-
70
-
-
84863205849
-
NIH Image to ImageJ: 25 Years of Image Analysis
-
Schneider, C. A.; Rasband, W. S.; Eliceiri, K. W. NIH Image to ImageJ: 25 Years of Image Analysis Nat. Methods 2012, 9, 671-675
-
(2012)
Nat. Methods
, vol.9
, pp. 671-675
-
-
Schneider, C.A.1
Rasband, W.S.2
Eliceiri, K.W.3
-
71
-
-
0034833710
-
A Simple, High Resolution Method for Establishing DNA Binding Affinity and Sequence Selectivity
-
Boger, D. L.; Fink, B. E.; Brunette, S. R.; Tse, W. C.; Hedrick, M. P. A Simple, High Resolution Method for Establishing DNA Binding Affinity and Sequence Selectivity J. Am. Chem. Soc. 2001, 123, 5878-5891
-
(2001)
J. Am. Chem. Soc.
, vol.123
, pp. 5878-5891
-
-
Boger, D.L.1
Fink, B.E.2
Brunette, S.R.3
Tse, W.C.4
Hedrick, M.P.5
-
72
-
-
1642576322
-
A Fluorescent Intercalator Displacement (FID) Assay for Establishing DNA Binding Selectivity and Affinity
-
Tse, W. C.; Boger, D. L. A Fluorescent Intercalator Displacement (FID) Assay for Establishing DNA Binding Selectivity and Affinity Acc. Chem. Res. 2004, 37, 61-69
-
(2004)
Acc. Chem. Res.
, vol.37
, pp. 61-69
-
-
Tse, W.C.1
Boger, D.L.2
-
73
-
-
0034641332
-
Total Synthesis of Distamycin A and 2640 Analogues: Solution-Phase Combinatorial Approach to the Discovery of New, Bioactive DNA Binding Agents and Development of a Rapid, High-Throughput Screen for Determining Relative DNA Binding Affinity or DNA Binding Sequence Selectivity
-
Boger, D. L.; Fink, B. E.; Hedrick, M. P. Total Synthesis of Distamycin A and 2640 Analogues: Solution-Phase Combinatorial Approach to the Discovery of New, Bioactive DNA Binding Agents and Development of a Rapid, High-Throughput Screen for Determining Relative DNA Binding Affinity or DNA Binding Sequence Selectivity J. Am. Chem. Soc. 2000, 122, 6382-6394
-
(2000)
J. Am. Chem. Soc.
, vol.122
, pp. 6382-6394
-
-
Boger, D.L.1
Fink, B.E.2
Hedrick, M.P.3
-
74
-
-
0034831435
-
Thiazole Orange as the Fluorescent Intercalator in a High Resolution FID Assay for Determining DNA Binding Affinity and Sequence Selectivity of Small Molecules
-
Boger, D. L.; Tse, W. C. Thiazole Orange as the Fluorescent Intercalator in a High Resolution FID Assay for Determining DNA Binding Affinity and Sequence Selectivity of Small Molecules Bioorg. Med. Chem. 2001, 9, 2511-2518
-
(2001)
Bioorg. Med. Chem.
, vol.9
, pp. 2511-2518
-
-
Boger, D.L.1
Tse, W.C.2
-
75
-
-
0141433343
-
Determination of Binding Affinities of Triplex Forming Oligonucleotides Using a Fluorescent Intercalator Displacement (FID) Assay
-
Yeung, B. K. S.; Tse, W. C.; Boger, D. L. Determination of Binding Affinities of Triplex Forming Oligonucleotides Using a Fluorescent Intercalator Displacement (FID) Assay Bioorg. Med. Chem. Lett. 2003, 13, 3801-3804
-
(2003)
Bioorg. Med. Chem. Lett.
, vol.13
, pp. 3801-3804
-
-
Yeung, B.K.S.1
Tse, W.C.2
Boger, D.L.3
-
76
-
-
0141433347
-
High Resolution Assessment of Protein-DNA Binding Affinity and Selectivity Utilizing a Fluorescent Intercalator Displacement (FID) Assay
-
Ham, Y.-W.; Tse, W. C.; Boger, D. L. High Resolution Assessment of Protein-DNA Binding Affinity and Selectivity Utilizing a Fluorescent Intercalator Displacement (FID) Assay Bioorg. Med. Chem. Lett. 2003, 13, 3805-3807
-
(2003)
Bioorg. Med. Chem. Lett.
, vol.13
, pp. 3805-3807
-
-
Ham, Y.-W.1
Tse, W.C.2
Boger, D.L.3
-
77
-
-
0042334776
-
Comprehensive High Resolution Analysis of Hairpin Polyamides Utilizing a Fluorescent Intercalator Displacement (FID) Assay
-
Tse, W. C.; Ishii, T.; Boger, D. L. Comprehensive High Resolution Analysis of Hairpin Polyamides Utilizing a Fluorescent Intercalator Displacement (FID) Assay Bioorg. Med. Chem. 2003, 11, 4479-4486
-
(2003)
Bioorg. Med. Chem.
, vol.11
, pp. 4479-4486
-
-
Tse, W.C.1
Ishii, T.2
Boger, D.L.3
-
78
-
-
0037070591
-
Hairpin versus Extended DNA Binding of a Substituted β-Alanine Linked Polyamide
-
Woods, C. R.; Ishii, T.; Wu, B.; Bair, K. W.; Boger, D. L. Hairpin versus Extended DNA Binding of a Substituted β-Alanine Linked Polyamide J. Am. Chem. Soc. 2002, 124, 2148-2152
-
(2002)
J. Am. Chem. Soc.
, vol.124
, pp. 2148-2152
-
-
Woods, C.R.1
Ishii, T.2
Wu, B.3
Bair, K.W.4
Boger, D.L.5
-
79
-
-
0037063512
-
Synthesis and DNA Binding Properties of Iminodiacetic Acid-Linked Polyamides: Characterization of Cooperative Extended 2:1 Side-by-Side Parallel Binding
-
Woods, C. R.; Ishii, T.; Boger, D. L. Synthesis and DNA Binding Properties of Iminodiacetic Acid-Linked Polyamides: Characterization of Cooperative Extended 2:1 Side-by-Side Parallel Binding J. Am. Chem. Soc. 2002, 124, 10676-10682
-
(2002)
J. Am. Chem. Soc.
, vol.124
, pp. 10676-10682
-
-
Woods, C.R.1
Ishii, T.2
Boger, D.L.3
-
80
-
-
35748934487
-
The Influence of Drug-like Concepts on Decision-Making in Medicinal Chemistry
-
Lessen, P. D.; Springthorpe, B. The Influence of Drug-like Concepts on Decision-Making in Medicinal Chemistry Nat. Rev. Drug Discovery 2007, 6, 881-890
-
(2007)
Nat. Rev. Drug Discovery
, vol.6
, pp. 881-890
-
-
Lessen, P.D.1
Springthorpe, B.2
-
81
-
-
77957804992
-
Role of Physicochemical Properties and Ligand Lipophilicity Efficiency in Addressing Drug Safety Risks
-
Edwards, M. P.; Price, D. A. Role of Physicochemical Properties and Ligand Lipophilicity Efficiency in Addressing Drug Safety Risks Annu. Rep. Med. Chem. 2010, 45, 381-391
-
(2010)
Annu. Rep. Med. Chem.
, vol.45
, pp. 381-391
-
-
Edwards, M.P.1
Price, D.A.2
-
82
-
-
0027982335
-
Hydrogen Bonding. 32. An Analysis of Water-Octanol and Water-Alkane Partitioning and the ΔlogP Parameter of Seiler
-
Mitchell, R. C. Hydrogen Bonding. 32. An Analysis of Water-Octanol and Water-Alkane Partitioning and the ΔLogP Parameter of Seiler J. Pharm. Sci. 1994, 83, 1085-1100
-
(1994)
J. Pharm. Sci.
, vol.83
, pp. 1085-1100
-
-
Mitchell, R.C.1
-
83
-
-
84888206273
-
-
A cLogP value of approximately 2 or lower is often consistent with reasonable in vivo clearance, solubility, and protein binding. High-LiPE compounds should outperform low-LiPE compounds, as these will be compromised by reduced potency or increased lipophilicity. A recent analysis of animal safety studies revealed an increased risk of adverse outcome for compounds with cLogP > 3. While achievable LiPE values are target- and series-specific, compounds with LiPE > 5 are usually considered highly optimized
-
A cLogP value of approximately 2 or lower is often consistent with reasonable in vivo clearance, solubility, and protein binding. High-LiPE compounds should outperform low-LiPE compounds, as these will be compromised by reduced potency or increased lipophilicity. A recent analysis of animal safety studies revealed an increased risk of adverse outcome for compounds with cLogP > 3. While achievable LiPE values are target- and series-specific, compounds with LiPE > 5 are usually considered highly optimized.
-
-
-
-
84
-
-
0032568397
-
Physicochemical High Throughput Screening: Parallel Artificial Membrane Permeability Assay in the Description of Passive Absorption Processes
-
5 range (2 vs 10e). See: Kansy, M.; Senner, F.; Gubernator, K. Physicochemical High Throughput Screening: Parallel Artificial Membrane Permeability Assay in the Description of Passive Absorption Processes J. Med. Chem. 1998, 41, 1007-1010
-
(1998)
J. Med. Chem.
, vol.41
, pp. 1007-1010
-
-
Kansy, M.1
Senner, F.2
Gubernator, K.3
-
85
-
-
0025021874
-
A Demonstration of the Intrinsic Importance of Stabilizing Hydrophobic Binding and Non-Covalent van der Waals Contacts Dominant in the Non-Covalent CC-1065/B-DNA Binding
-
Boger, D. L.; Coleman, R. S.; Invergo, B. J.; Zarrinmayeh, H.; Kitos, P. A.; Thompson, S. C.; Leong, T.; McLaughlin, L. W. A Demonstration of the Intrinsic Importance of Stabilizing Hydrophobic Binding and Non-Covalent van der Waals Contacts Dominant in the Non-Covalent CC-1065/B-DNA Binding Chem.-Biol. Interact. 1990, 73, 29-52
-
(1990)
Chem.-Biol. Interact.
, vol.73
, pp. 29-52
-
-
Boger, D.L.1
Coleman, R.S.2
Invergo, B.J.3
Zarrinmayeh, H.4
Kitos, P.A.5
Thompson, S.C.6
Leong, T.7
McLaughlin, L.W.8
-
86
-
-
0027367893
-
Reversibility of the Duocarmycin A and SA DNA Alkylation Reaction
-
Boger, D. L.; Yun, W. Reversibility of the Duocarmycin A and SA DNA Alkylation Reaction J. Am. Chem. Soc. 1993, 115, 9872-9873
-
(1993)
J. Am. Chem. Soc.
, vol.115
, pp. 9872-9873
-
-
Boger, D.L.1
Yun, W.2
-
87
-
-
0026092765
-
Demonstration of a Pronounced Effect of Noncovalent Binding Selectivity on the (+)-CC-1065 DNA Alkylation and Identification of the Pharmacophore of the Alkylation Subunit
-
Boger, D. L.; Zarrinmayeh, H.; Munk, S. A.; Kitos, P. A.; Suntornwat, O. Demonstration of a Pronounced Effect of Noncovalent Binding Selectivity on the (+)-CC-1065 DNA Alkylation and Identification of the Pharmacophore of the Alkylation Subunit Proc. Natl. Acad. Sci. U.S.A. 1991, 88, 1431-1435
-
(1991)
Proc. Natl. Acad. Sci. U.S.A.
, vol.88
, pp. 1431-1435
-
-
Boger, D.L.1
Zarrinmayeh, H.2
Munk, S.A.3
Kitos, P.A.4
Suntornwat, O.5
-
88
-
-
0025900895
-
(+)-CC-1065 DNA Alkylation: Key Studies Demonstrating a Noncovalent Binding Selectivity Contribution to the Alkylation Selectivity
-
Boger, D. L.; Munk, S. A.; Zarrinmayeh, H. (+)-CC-1065 DNA Alkylation: Key Studies Demonstrating a Noncovalent Binding Selectivity Contribution to the Alkylation Selectivity J. Am. Chem. Soc. 1991, 113, 3980-3983
-
(1991)
J. Am. Chem. Soc.
, vol.113
, pp. 3980-3983
-
-
Boger, D.L.1
Munk, S.A.2
Zarrinmayeh, H.3
-
89
-
-
0028809915
-
Second Definitive Test of Proposed Models for the Origin of the CC-1065 and Duocarmycin DNA Alkylation Selectivity
-
Boger, D. L.; Johnson, D. S. Second Definitive Test of Proposed Models for the Origin of the CC-1065 and Duocarmycin DNA Alkylation Selectivity J. Am. Chem. Soc. 1995, 117, 1443-1444
-
(1995)
J. Am. Chem. Soc.
, vol.117
, pp. 1443-1444
-
-
Boger, D.L.1
Johnson, D.S.2
-
90
-
-
0029894362
-
Demonstration and Definition of the Noncovalent Binding Selectivity of Agents Related to CC-1065 by an Affinity Cleavage Agent: Noncovalent Binding Coincidental with Alkylation
-
Boger, D. L.; Zhou, J.; Cai, H. Demonstration and Definition of the Noncovalent Binding Selectivity of Agents Related to CC-1065 by an Affinity Cleavage Agent: Noncovalent Binding Coincidental with Alkylation Bioorg. Med. Chem. 1996, 4, 859-868
-
(1996)
Bioorg. Med. Chem.
, vol.4
, pp. 859-868
-
-
Boger, D.L.1
Zhou, J.2
Cai, H.3
-
91
-
-
0025045711
-
2: CC-1065 Functional Analogs Incorporating the Parent 1,2,7,7a-Tetrahydrocyclopropa[1,2- c ]indol-4-one (CI) Left-Hand Subunit
-
2: CC-1065 Functional Analogs Incorporating the Parent 1,2,7,7a- Tetrahydrocyclopropa[1,2- c ]indol-4-one (CI) Left-Hand Subunit J. Am. Chem. Soc. 1990, 112, 5230-5240
-
(1990)
J. Am. Chem. Soc.
, vol.112
, pp. 5230-5240
-
-
Boger, D.L.1
Wysocki, R.J.2
Ishizaki, T.3
-
92
-
-
0028592579
-
Design, Synthesis, and Evaluation of CC-1065 and Duocarmycin Analogs Incorporating the 2,3,10,10a-Tetrahydro-1 H -cyclopropa[ d ]benzo[ f ]quinol-5-one (CBQ) Alkylation Subunit: Identification and Structural Origin of Subtle Stereoelectronic Features That Govern Reactivity and Regioselectivity
-
Boger, D. L.; Mesini, P. Design, Synthesis, and Evaluation of CC-1065 and Duocarmycin Analogs Incorporating the 2,3,10,10a-Tetrahydro-1 H -cyclopropa[ d ]benzo[ f ]quinol-5-one (CBQ) Alkylation Subunit: Identification and Structural Origin of Subtle Stereoelectronic Features That Govern Reactivity and Regioselectivity J. Am. Chem. Soc. 1994, 116, 11335-11348
-
(1994)
J. Am. Chem. Soc.
, vol.116
, pp. 11335-11348
-
-
Boger, D.L.1
Mesini, P.2
-
93
-
-
0034733133
-
Synthesis and Evaluation of 1,2,8,8a-Tetrahydrocyclopropa[ c ]pyrrolo[3,2- e ]indol-4(5 H)-one, the Parent Alkylation Subunit of CC-1065 and the Duocarmycins: Impact of the Alkylation Subunit Substituents and Its Implications for DNA Alkylation Catalysis
-
Boger, D. L.; Santillan, A., Jr.; Searcey, M.; Brunette, S. R.; Wolkenberg, S. E.; Hedrick, M. P.; Jin, Q. Synthesis and Evaluation of 1,2,8,8a-Tetrahydrocyclopropa[ c ]pyrrolo[3,2- e ]indol-4(5 H)-one, the Parent Alkylation Subunit of CC-1065 and the Duocarmycins: Impact of the Alkylation Subunit Substituents and Its Implications for DNA Alkylation Catalysis J. Org. Chem. 2000, 65, 4101-4111
-
(2000)
J. Org. Chem.
, vol.65
, pp. 4101-4111
-
-
Boger, D.L.1
Santillan Jr., A.2
Searcey, M.3
Brunette, S.R.4
Wolkenberg, S.E.5
Hedrick, M.P.6
Jin, Q.7
-
94
-
-
0035817354
-
Substituent Effects within the DNA Binding Subunit of CBI Analogues of the Duocarmycins and CC-1065
-
Boger, D. L.; Stauffer, F.; Hedrick, M. P. Substituent Effects within the DNA Binding Subunit of CBI Analogues of the Duocarmycins and CC-1065 Bioorg. Med. Chem. Lett. 2001, 11, 2021-2024
-
(2001)
Bioorg. Med. Chem. Lett.
, vol.11
, pp. 2021-2024
-
-
Boger, D.L.1
Stauffer, F.2
Hedrick, M.P.3
-
95
-
-
0347760081
-
Establishing the Parabolic Relationship between Reactivity and Activity for Derivatives and Analogues of the Duocarmycin and CC-1065 Alkylation Subunits
-
Parrish, J. P.; Hughes, T. V.; Hwang, I.; Boger, D. L. Establishing the Parabolic Relationship between Reactivity and Activity for Derivatives and Analogues of the Duocarmycin and CC-1065 Alkylation Subunits J. Am. Chem. Soc. 2004, 126, 80-81
-
(2004)
J. Am. Chem. Soc.
, vol.126
, pp. 80-81
-
-
Parrish, J.P.1
Hughes, T.V.2
Hwang, I.3
Boger, D.L.4
-
96
-
-
0025099719
-
2: Enhanced Functional Analogs of (+)-CC-1065. A Critical Appraisal of the Proposed Relationship between Electrophile Reactivity, DNA Binding Properties, and Cytotoxic Potency
-
2: Enhanced Functional Analogs of (+)-CC-1065. A Critical Appraisal of the Proposed Relationship between Electrophile Reactivity, DNA Binding Properties, and Cytotoxic Potency Tetrahedron Lett. 1990, 31, 793-796
-
(1990)
Tetrahedron Lett.
, vol.31
, pp. 793-796
-
-
Boger, D.L.1
Ishizaki, T.2
-
97
-
-
0025891696
-
2: An Enhanced Functional Analog of (+)-CC-1065
-
2: An Enhanced Functional Analog of (+)-CC-1065 Bioorg. Med. Chem. Lett. 1991, 1, 115-120
-
(1991)
Bioorg. Med. Chem. Lett.
, vol.1
, pp. 115-120
-
-
Boger, D.L.1
Ishizaki, T.2
Sakya, S.M.3
Munk, S.A.4
Kitos, P.A.5
Jin, Q.6
Besterman, J.M.7
-
98
-
-
0025811775
-
The (+)-CC-1065 DNA Alkylation: Observation of an Unexpected Relationship between Cyclopropane Electrophile Reactivity and the Efficiency of DNA Alkylation
-
Boger, D. L.; Munk, S. A.; Ishizaki, T. The (+)-CC-1065 DNA Alkylation: Observation of an Unexpected Relationship between Cyclopropane Electrophile Reactivity and the Efficiency of DNA Alkylation J. Am. Chem. Soc. 1991, 113, 2779-2780
-
(1991)
J. Am. Chem. Soc.
, vol.113
, pp. 2779-2780
-
-
Boger, D.L.1
Munk, S.A.2
Ishizaki, T.3
-
99
-
-
0028100406
-
Role of the CC-1065 and Duocarmycin N2 Substituent: Validation of a Direct Relationship between Solvolysis Chemical Stability and in Vitro Biological Potency
-
Boger, D. L.; Yun, W. Role of the CC-1065 and Duocarmycin N2 Substituent: Validation of a Direct Relationship between Solvolysis Chemical Stability and in Vitro Biological Potency J. Am. Chem. Soc. 1994, 116, 5523-5524
-
(1994)
J. Am. Chem. Soc.
, vol.116
, pp. 5523-5524
-
-
Boger, D.L.1
Yun, W.2
-
100
-
-
36148931005
-
Rational Design, Synthesis, and Evaluation of Key Analogues of CC-1065 and the Duocarmycins
-
Tichenor, M. S.; MacMillan, K. S.; Stover, J. S.; Wolkenberg, S. E.; Pavani, M. G.; Zanella, L.; Zaid, A. N.; Spalluto, G.; Rayl, T. J.; Hwang, I.; Baraldi, P. G.; Boger, D. L. Rational Design, Synthesis, and Evaluation of Key Analogues of CC-1065 and the Duocarmycins J. Am. Chem. Soc. 2007, 129, 14092-14099
-
(2007)
J. Am. Chem. Soc.
, vol.129
, pp. 14092-14099
-
-
Tichenor, M.S.1
MacMillan, K.S.2
Stover, J.S.3
Wolkenberg, S.E.4
Pavani, M.G.5
Zanella, L.6
Zaid, A.N.7
Spalluto, G.8
Rayl, T.J.9
Hwang, I.10
Baraldi, P.G.11
Boger, D.L.12
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