Organic Letters
Letter
Igarashi, J.; Kimura, M.; Takayama, T.; Fukuda, N.; Sugiyama, H.
Cancer Sci. 2010, 101, 759.
(16) Li, B. C.; Montgomery, D. C.; Puckett, J. W.; Dervan, P. B. J.
apply this methodology to prepare PA libraries incorporating
structural variations at key sites of the PA scaffold in order to
enhance the biological activity of these compounds in cells.
Org. Chem. 2013, 78, 124.
(17) Wurtz, N. R.; Turner, J. M.; Baird, E. E.; Dervan, P. B. Org. Lett.
2001, 3, 1201.
(18) Krutzik, P. O.; Chamberlin, A. R. Bioorg. Med. Chem. Lett. 2002,
12, 2129.
(19) Choi, J. S.; Lee, Y. J.; Kim, E.; Jeong, N.; Yu, H.; Han, H.
Tetrahedron Lett. 2003, 44, 1607.
(20) Bando, T.; Fujimoto, J.; Minoshima, M.; Shinohara, K. I.; Sasaki,
S.; Kashiwazaki, G.; Mizumura, M.; Sugiyama, H. Bioorg. Med. Chem.
2007, 15, 6937.
(21) Puckett, J. W.; Green, J. T.; Dervan, P. B. Org. Lett. 2012, 14,
2774.
(22) Wetzler, M.; Wemmer, D. E. Org. Lett. 2010, 12, 3488.
(23) Su, W.; Gray, S. J.; Dondi, R.; Burley, G. A. Org. Lett. 2009, 11,
3910.
ASSOCIATED CONTENT
* Supporting Information
Synthesis and analytical characterization of PAs can be found in
the Supporting Information. This material is available free of
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S
AUTHOR INFORMATION
Corresponding Authors
■
Present Addresses
§School of Pharmacy, University of Lincoln, Brayford Pool,
Lincoln, LN6 7TS, UK.
(24) Chenoweth, D. M.; Harki, D. A.; Dervan, P. B. J. Am. Chem. Soc.
2009, 131, 7175.
(25) Chenoweth, D. M.; Harki, D. A.; Phillips, J. W.; Dose, C.;
Dervan, P. B. J. Am. Chem. Soc. 2009, 131, 7182.
(26) Baird, E. E.; Dervan, P. B. J. Am. Chem. Soc. 1996, 118, 6141.
∥Department of Pharmacy and Pharmacology, University of
Bath, Claverton Down, Bath, BA2 7AY, UK.
Notes
(27) Matmour, R.; De Cat, I.; George, S. J.; Adriaens, W.; Lecler
̀
e, P.;
Bomans, P. H. H.; Sommerdijk, N. A. J. M.; Gielen, J. C.; Christianen,
The authors declare no competing financial interest.
P. C. M.; Heldens, J. T.; van Hest, J. C. M.; Lowik, D. W. P. M.; De
̈
Feyter, S.; Meijer, E. W.; Schenning, A. P. H. J. J. Am. Chem. Soc. 2008,
130, 14576.
ACKNOWLEDGMENTS
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G.A.B. thanks the EPSRC for funding (ARF, EP/E055095/1
and EP/H02915X/1). A.J.F. thanks the EPSRC and the
University of Leicester for a postgraduate studentship.
(28) Diegelmann, S. R.; Gorham, J. M.; Tovar, J. D. J. Am. Chem. Soc.
2008, 130, 13840.
(29) Vadehra, G. S.; Wall, B. D.; Diegelmann, S. R.; Tovar, J. D.
Chem. Commun. 2010, 46, 3947.
(30) Grehn, L.; Ragnarsson, U. J. Org. Chem. 1981, 46, 3492.
(31) Heckel, A.; Dervan, P. B. Chem.Eur. J. 2003, 9, 3353.
(32) Jacobs, C. S.; Dervan, P. B. J. Med. Chem. 2009, 52, 7380.
(33) Liu, B.; Kodadek, T. J. Med. Chem. 2009, 52, 4604.
(34) Nishijima, S.; Shinohara, K.-i.; Bando, T.; Minoshima, M.;
Kashiwazaki, G.; Sugiyama, H. Bioorg. Med. Chem. 2010, 18, 978.
(35) Edelson, B. S.; Best, T. P.; Olenyuk, B.; Nickols, N. G.; Doss, R.
M.; Foister, S.; Heckel, A.; Dervan, P. B. Nucleic Acids Res. 2004, 32,
2802.
(36) Best, T. P.; Edelson, B. S.; Nickols, N. G.; Dervan, P. B. Proc.
Natl. Acad. Sci. U.S.A. 2003, 100, 12063.
́
(37) Gongora-Benítez, M.; Tulla-Puche, J.; Albericio, F. ACS Combin.
Sci. 2013, 15, 217.
REFERENCES
■
(1) Dervan, P. B.; Edelson, B. S. Curr. Opin. Struct. Biol. 2003, 13,
284.
(2) Raskatov, J. A.; Meier, J. L.; Puckett, J. W.; Yang, F.;
Ramakrishnan, P.; Dervan, P. B. Proc. Natl. Acad. Sci. U.S.A. 2012,
109, 1023.
(3) Muzikar, K. A.; Nickols, N. G.; Dervan, P. B. Proc. Natl. Acad. Sci.
U.S.A. 2009, 106, 16598.
(4) Warren, C. L.; Kratochvil, N. C. S.; Hauschild, K. E.; Foister, S.;
Brezinski, M. L.; Dervan, P. B.; Phillips, G. N.; Ansari, A. Z. Proc. Natl.
Acad. Sci. U.S.A. 2006, 103, 867.
(5) Kashiwazaki, G.; Bando, T.; Yoshidome, T.; Masui, S.; Takagaki,
T.; Hashiya, K.; Pandian, G. N.; Yasuoka, J.; Akiyoshi, K.; Sugiyama,
H. J. Med. Chem. 2012, 55, 2057.
(6) Pandian, G. N.; Shinohara, K.-i.; Ohtsuki, A.; Nakano, Y.;
Masafumi, M.; Bando, T.; Nagase, H.; Yamada, Y.; Watanabe, A.;
Terada, N.; Sato, S.; Morinaga, H.; Sugiyama, H. ChemBioChem 2011,
12, 2822.
(38) Dalcol, I.; Rabanal, F.; Ludevid, M.-D.; Albericio, F.; Giralt, E. J.
Org. Chem. 1995, 60, 7575.
(39) Chen, C.; Li, X.; Neumann, C. S.; Lo, M. M. C.; Schreiber, S. L.
Angew. Chem., Int. Ed. 2005, 44, 2249.
(7) Trauger, J. W.; Baird, E. E.; Dervan, P. B. J. Am. Chem. Soc. 1998,
120, 3534.
(8) Yamamoto, M.; Bando, T.; Kawamoto, Y.; Taylor, R. D.; Hashiya,
K.; Sugiyama, H. Bioconjugate Chem. 2014, 25, 552.
(9) Kawamoto, Y.; Bando, T.; Kamada, F.; Li, Y.; Hashiya, K.;
Maeshima, K.; Sugiyama, H. J. Am. Chem. Soc. 2013, 135, 16468.
(10) Bando, T.; Sugiyama, H. Acc. Chem. Res. 2006, 39, 935.
(11) Yang, F.; Nickols, N. G.; Li, B. C.; Marinov, G. K.; Said, J. W.;
Dervan, P. B. Proc. Natl. Acad. Sci. U.S.A. 2013, 110, 1863.
(12) Raskatov, J. A.; Nickols, N. G.; Hargrove, A. E.; Marinov, G. K.;
Wold, B.; Dervan, P. B. Proc. Natl. Acad. Sci. U.S.A. 2012, 109, 16041.
(13) Yao, E.-H.; Fukuda, N.; Ueno, T.; Matsuda, H.; Nagase, H.;
Matsumoto, Y.; Sugiyama, H.; Matsumoto, K. Cardiovasc. Res. 2009,
81, 797.
(14) Ueno, T.; Fukuda, N.; Tsunemi, A.; Yao, E.-H.; Matsuda, H.;
Tahira, K.; Matsumoto, T.; Matsumoto, K.; Matsumoto, Y.; Nagase,
H.; Sugiyama, H.; Sawamura, T. J. Hypertension 2009, 27, 508.
(15) Wang, X.; Nagase, H.; Watanabe, T.; Nobusue, H.; Suzuki, T.;
Asami, Y.; Shinojima, Y.; Kawashima, H.; Takagi, K.; Mishra, R.;
4657
dx.doi.org/10.1021/ol502203y | Org. Lett. 2014, 16, 4654−4657