Application of DNA-Alkylating Pyrrole-Imidazole Polyamides for Cancer Treatment.
DNA alkylation
DNA recognition
cancer
drug discovery
sequence-specificity
Journal
Chembiochem : a European journal of chemical biology
ISSN: 1439-7633
Titre abrégé: Chembiochem
Pays: Germany
ID NLM: 100937360
Informations de publication
Date de publication:
04 05 2021
04 05 2021
Historique:
revised:
28
12
2020
received:
01
11
2020
pubmed:
17
1
2021
medline:
15
12
2021
entrez:
16
1
2021
Statut:
ppublish
Résumé
Pyrrole-imidazole (PI) polyamides, which target specific DNA sequences, have been studied as a class of DNA minor-groove-binding molecules. To investigate the potential of compounds for cancer treatment, PI polyamides were conjugated with DNA-alkylating agents, such as seco-CBI and chlorambucil. DNA-alkylating PI polyamides have attracted attention because of their sequence-specific alkylating activities, which contribute to reducing the severe side effects of current DNA-damaging drugs. Many of these types of conjugates have been developed as new candidates for anticancer drugs. Herein, we review recent progress into research on DNA-alkylating PI polyamides and their sequence-specific action on targets associated with cancer development.
Identifiants
pubmed: 33453075
doi: 10.1002/cbic.202000752
doi:
Substances chimiques
Antineoplastic Agents, Alkylating
0
Imidazoles
0
KRAS protein, human
0
Nylons
0
Pyrroles
0
DNA
9007-49-2
Proto-Oncogene Proteins p21(ras)
EC 3.6.5.2
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Review
Langues
eng
Sous-ensembles de citation
IM
Pagination
1538-1545Subventions
Organisme : AMED
ID : JP18am0301005
Organisme : Basic Science and Platform Technology Program for Innovative Biological Medicine
ID : JP18am0101101
Organisme : Platform Project for Supporting Drug Discovery
Organisme : Life Science Research
ID : JP16H06356
Organisme : JSPS
Informations de copyright
© 2021 Wiley-VCH GmbH.
Références
L. H. Hurley, Nat. Rev. Cancer 2002, 2, 188-200.
C. Sawyers, Nature 2004, 432, 294-297.
J. W. Trauger, E. E. Baird, P. B. Dervan, Nature 1996, 382, 559-561.
S. White, J. W. Szewczyk, J. M. Turner, E. E. Baird, P. B. Dervan, Nature 1998, 391, 468-471.
A. C. Finlay, F. A. Hochstein, B. A. Sobin, F. X. Murphy, J. Am. Chem. Soc. 1951, 73, 341-343.
F. Arcamone, S. Penco, P. Orezzi, V. Nicolella, A. Pirelli, Nature 1964, 203, 1064-1065.
M. L. Kopka, C. Yoon, D. Goodsell, P. Pjura, R. E. Dickerson, J. Mol. Biol. 1985, 183, 553-563.
M. Coll, C. A. Frederick, A. H. J. Wang, A. Rich, Proc. Natl. Acad. Sci. USA 1987, 84, 8385-8389.
J. G. Pelton, D. E. Wemmer, Proc. Natl. Acad. Sci. USA 1989, 86, 5723-5727.
S. E. Swalley, E. E. Baird, P. B. Dervan, Chem. Eur. J. 1997, 3, 1600-1607.
J. M. Turner, S. E. Swalley, E. E. Baird, P. B. Dervan, J. Am. Chem. Soc. 1998, 120, 6219-6226.
M. Mrksich, M. E. Parks, P. B. Dervan, J. Am. Chem. Soc. 1994, 116, 7983-7988.
S. E. Swalley, E. E. Baird, P. B. Dervan, J. Am. Chem. Soc. 1999, 121, 1113-1120.
S. White, E. E. Baird, P. B. Dervan, J. Am. Chem. Soc. 1997, 119, 8756-8765.
N. R. Wurtz, J. M. Turner, E. E. Baird, P. B. Dervan, Org. Lett. 2001, 3, 1201-1203.
D. M. Chenoweth, P. B. Dervan, J. Am. Chem. Soc. 2010, 132, 14521-14529.
L. A. Dickinson, R. J. Gulizia, J. W. Trauger, E. E. Baird, D. E. Mosier, J. M. Gottesfeld, P. B. Dervan, Proc. Natl. Acad. Sci. USA 1998, 95, 12890-12895.
V. L. Reynolds, I. J. Molineux, D. J. Kaplan, D. H. Swenson, L. H. Hurley, Biochemistry 1985, 24, 6228-6237.
L. H. Hurley, D. R. Needham-VanDevanter, Acc. Chem. Res. 1986, 19, 230-237.
D. L. Boger, T. Ishizaki, P. A. Kitos, O. Suntornwat, J. Org. Chem. 1990, 55, 5823-5832.
D. L. Boger, W. Yun, B. R. Teegarden, J. Org. Chem. 1992, 57, 2873-2876.
D. L. Boger, S. A. Munk, J. Am. Chem. Soc. 1992, 114, 5487-5496.
D. L. Boger, D. S. Johnson, Proc. Natl. Acad. Sci. USA 1995, 92, 3642-3649.
D. L. Boger, T. Ishizaki, H. Zarrinmayeh, P. A. Kitos, O. Suntornwat, Bioorg. Med. Chem. Lett. 1991, 1, 55-58.
A. Y. Chang, P. B. Dervan, J. Am. Chem. Soc. 2000, 122, 4856-4864.
Y.-D. Wang, J. Dziegielewski, A. Y. Chang, P. B. Dervan, T. A. Beerman, J. Biol. Chem. 2002, 277, 42431-42437.
T. Bando, A. Narita, K. Asada, H. Ayame, H. Sugiyama, J. Am. Chem. Soc. 2004, 126, 8948-8955.
T. Takagaki, T. Bando, H. Sugiyama, J. Am. Chem. Soc. 2012, 134, 13074-13081.
T. Bando, S. Sasaki, M. Minoshima, C. Dohno, K. Shinohara, A. Narita, H. Sugiyama, Bioconjugate Chem. 2006, 17, 715-720.
K. Shinohara, T. Bando, S. Sasaki, Y. Sakakibara, M. Minoshima, H. Sugiyama, Cancer Sci. 2006, 97, 219-225.
G. Kashiwazaki, T. Bando, T. Yoshidome, S. Masui, T. Takagaki, K. Hashiya, G. N. Pandian, J. Yasuoka, K. Akiyoshi, H. Sugiyama, J. Med. Chem. 2012, 55, 2057-2066.
A. Chandran, J. Syed, R. D. Taylor, G. Kashiwazaki, S. Sato, K. Hashiya, T. Bando, H. Sugiyama, Nucleic Acids Res. 2016, 44, 4014-4024.
C. Guo, S. Asamitsu, G. Kashiwazaki, S. Sato, T. Bando, H. Sugiyama, ChemBioChem 2017, 18, 166-170.
W. B. Mattes, J. A. Hartley, Nucleic Acids Res. 1986, 14, 2971-2987.
K. W. Kohn, J. A. Hartley, W. B. Mattes, Nucleic Acids Res. 1987, 15, 10531-10549.
P. Wang, G. B. Bauer, R. A. O. Bennett, L. F. Povirk, Biochemistry 1991, 30, 11515-11521.
J. H. Yoon, C. S. Lee, Arch. Pharmacal Res. 1997, 20, 550.
N. R. Wurtz, P. B. Dervan, Chem. Biol. 2000, 7, 153-161.
Y. D. Wang, J. Dziegielewski, N. R. Wurtz, B. Dziegielewska, P. B. Dervan, T. A. Beerman, Nucleic Acids Res. 2003, 31, 1208-1215.
M. Minoshima, T. Bando, K. Shinohara, G. Kashiwazaki, S. Nishijima, H. Sugiyama, Bioorg. Med. Chem. 2010, 18, 1236-1243.
E. H. Blackburn, Cell 2001, 106, 661-673.
C. B. Harley, A. B. Futcher, C. W. Greider, Nature 1990, 345, 458-460.
C. K. Dong, K. Masutomi, W. C. Hahn, Crit. Rev. Oncol. Hematol. 2005, 54, 85-93.
A. Smogorzewska, T. D. Lange, Annu. Rev. Biochem. 2004, 73, 177-208.
K. A. Olaussen, K. Dubrana, J. Domont, J.-P. Spano, L. Sabatier, J.-C. Soria, Crit. Rev. Oncol. Hematol. 2006, 57, 191-214.
S. Sasaki, T. Bando, M. Minoshima, T. Shimizu, K. Shinohara, T. Takaoka, H. Sugiyama, J. Am. Chem. Soc. 2006, 128, 12162-12168.
G. Kashiwazaki, T. Bando, K. Shinohara, M. Minoshima, S. Nishijima, H. Sugiyama, Bioorg. Med. Chem. 2009, 17, 1393-1397.
G. Kashiwazaki, T. Bando, K. Shinohara, M. Minoshima, H. Kumamoto, S. Nishijima, H. Sugiyama, Bioorg. Med. Chem. 2010, 18, 2887-2893.
M. Yamamoto, T. Bando, Y. Kawamoto, R. D. Taylor, K. Hashiya, H. Sugiyama, Bioconjugate Chem. 2014, 25, 552-559.
C. J. Der, T. G. Krontiris, G. M. Cooper, Proc. Natl. Acad. Sci. USA 1982, 79, 3637-3640.
J. L. Bos, Mutat. Res. 1988, 195, 255-271.
A. A. Adjei, J. Natl. Cancer Inst. 2001, 93,1062-1074.
B. B. Friday, A. A. Adjei, Biochim. Biophys. Acta Rev. Cancer 2005, 1756, 127-144.
R. D. Taylor, S. Asamitsu, T. Takenaka, M. Yamamoto, K. Hashiya, Y. Kawamoto, T. Bando, H. Nagase, H. Sugiyama, Chem. Eur. J. 2014, 20, 1310-1317.
R. D. Taylor, A. Chandran, G. Kashiwazaki, K. Hashiya, T. Bando, H. Nagase, H. Sugiyama, Chem. Eur. J. 2015, 21,14996-15003.
K. Hiraoka, T. Inoue, R. D. Taylor, T. Watanabe, N. Koshikawa, H. Yoda, K. Shinohara, A. Takatori, H. Sugimoto, Y. Maru, T. Denda, K. Fujiwara, A. Balmain, T. Ozaki, T. Bando, H. Sugiyama, H. Nagase, Nat. Commun. 2015, 6, 6706.
Y. Ito, S. C. Bae, L. S. H. Chuang, Nat. Rev. Cancer 2015, 15, 81-95.
S. Meyers, J. R. Downing, S. W. Hiebert, Mol. Cell. Biol. 1993, 13, 6336-6345.
D. Bartfeld, L. Shimon, G. C. Couture, D. Rabinovich, F. Frolow, D. Levanon, Y. Groner, Z. Shakked, Structure 2002, 10, 1395-1407.
P. Liu, S. A. Tarle, A. Hajra, D. F. Claxton, P. Marlton, M. Freedman, M. J. Siciliano, F. S. Collins, Science 1993, 261, 1041-1044.
S. Goyama, J. Schibler, L. Cunningham, Y. Zhang, Y. Rao, N. Nishimoto, M. Nakagawa, A. Olsson, M. Wunderlich, K. A. Link, B. Mizukawa, H. L. Grimes, M. Kurokawa, P. P. Liu, G. Huang, J. C. Mulloy, J. Clin. Invest. 2013, 123, 3876-3888.
K. Blyth, E. R. Cameron, J. C. Neil, Nat. Rev. Cancer 2005, 5, 376-387.
K. T. Bieging, S. S. Mello, L. D. Attardi, Nat. Rev. Cancer 2014, 14, 359-370.
T. Ozaki, A. Nakagawara, H. Nagase, Int. J. Genome Res. 2013, DOI: 10.1155/2013/271347.
K. Morita, K. Suzuki, S. Maeda, A. Matsuo, Y. Mitsuda, C. Tokushige, G. Kashiwazaki, J. Taniguchi, R. Maeda, M. Noura, M. Hirata, T. Kataoka, A. Yano, Y. Yamada, H. Kiyose, M. Tokumasu, H. Matsuo, S. Tanaka, Y. Okuno, M. Muto, K. Naka, K. Ito, T. Kitamura, Y. Kaneda, P. P. Liu, T. Bando, S. Adachi, H. Sugiyama, Y. Kamikubo, J. Clin. Invest. 2017, 127, 2815-2828.
Y. Mitsuda, K. Morita, G. Kashiwazaki, J. Taniguchi, T. Bando, M. Obara, M. Hirata, T. R. Kataoka, M. Muto, Y. Kaneda, T. Nakahata, P. P. Liu, S. Adachi, H. Sugiyama, Y. Kamikubo, Sci. Rep. 2018, 8 : 6423.
R. Maeda, S. Sato, S. Obata, T. Ohno, K. Hashiya, T. Bando, H. Sugiyama, J. Am. Chem. Soc. 2019, 141, 4257-4263.
T. Bando, M. Minoshima, G. Kashiwazaki, K. Shinohara, S. Sasaki, J. Fujimoto, A. Ohtsuki, M. Murakami, S. Nakazono, H. Sugiyama, Bioorg. Med. Chem. 2008, 16, 2286-2291.
Y.-W. Han, G. Kashiwazaki, H. Morinaga, T. Matsumoto, K. Hashiya, T. Bando, Y. Harada, H. Sugiyama, Bioorg. Med. Chem. 2013, 21, 5436-5441.
G. Kashiwaszaki, R. Maeda, T. Kawase, K. Hashiya, T. Bando, H. Sugiyama, Bioorg. Med. Chem. 2018, 26, 1-7.
R. Maeda, S. Ito, K. Hashiya, T. Bando, H. Sugiyama, Chem. Eur. J. 2020, 26, 14639-14644.