DNA Alkylation of the RUNX-Binding Sequence by CBI-PI Polyamide Conjugates*.

Tytuł:: DNA Alkylation of the RUNX-Binding Sequence by CBI-PI Polyamide Conjugates*.
Autorzy:: Maeda R; Graduate School of Advanced Integrated Studies in Human Survivability, Kyoto University, Sakyo-ku, Kyoto, 6068306, Japan.
Ito S; Medical Research Support Center, Graduate School of Medicine, Kyoto University, Sakyo-ku, Kyoto, 6068501, Japan.
Hashiya K; Department of Chemistry, Graduate School of Science, Kyoto University, Kitashirakawa-Oiwakecho, Sakyo-ku, Kyoto, 6068502, Japan.
Bando T; Department of Chemistry, Graduate School of Science, Kyoto University, Kitashirakawa-Oiwakecho, Sakyo-ku, Kyoto, 6068502, Japan.
Sugiyama H; Department of Chemistry, Graduate School of Science, Kyoto University, Kitashirakawa-Oiwakecho, Sakyo-ku, Kyoto, 6068502, Japan.; Institute for Integrated Cell-Material Science (iCeMS), Kyoto University, Yoshida-ushinomiyacho Sakyo-ku, Kyoto, 6068501, Japan.
Źródło:: Chemistry (Weinheim an der Bergstrasse, Germany) [Chemistry] 2020 Nov 17; Vol. 26 (64), pp. 14639-14644. Date of Electronic Publication: 2020 Oct 06.
Typ publikacji:: Journal Article
Język:: English
Imprint Name(s):: Original Publication: Weinheim, Germany : Wiley-VCH
MeSH Terms:: Nylons*
Pyrroles*
Alkylation ; DNA/metabolism ; Imidazoles
References:: C. Sawyers, Nature 2004, 432, 294-297.
Y. Ito, S. C. Bae, L. S. H. Chuang, Nat. Rev. Cancer 2015, 15, 81-95.
D. Bartfeld, L. Shimon, G. C. Conture, D. Rabinovich, F. Frolow, D. Levanon, Y. Groner, Z. Shakked, Structure 2002, 10, 1395-1407.
S. Meyers, J. R. Downing, S. W. Hiebert, Mol. Cell. Biol. 1993, 13, 6336-6345.
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.
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.
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.
D. L. Boger, T. Ishizaki, P. A. Litos, 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, J. A. McKie, J. Org. Chem. 1995, 60, 1271-1275.
M. Minoshima, T. Bando, K. Shinohara, G. Kashiwazaki, S. Nishijima, H. Sugiyama, Bioorg. Med. Chem. 2010, 18, 1236-1243.
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.
G. Kashiwazaki, R. Maeda, T. Kawase, K. Hashiya, T. Bando, H. Sugiyama, Bioorg. Med. Chem. 2018, 26, 1-7.
R. Maeda, S. Sato, T. Ohno, S. Obata, K. Hashiya, T. Bando, H. Sugiyama, J. Am. Chem. Soc. 2019, 141, 4257-4263.
T. Bando, S. Sasaki, M. Minoshima, C. Dohno, K. Shinohara, A. Narita, H. Sugiyama, Bioconjugate Chem. 2006, 17, 715-720.
S. Asamitsu, Y. Kawamoto, F. Hashiya, K. Hashiya, M. Yamamoto, S. Kizaki, T. Bando, H. Sugiyama, Bioorg. Med. Chem. 2014, 22, 4646-4657.
Y. Kawamoto, A. Sasaki, K. Hashiya, S. Ide, T. Bando, K. Maeshima, H. Sugiyama, Chem. Sci. 2015, 6, 2307-2312.
B. C. Li, D. C. Montgomery, J. W. Puckett, P. B. Dervan, J. Org. Chem. 2013, 78, 124-133.
J. P. Lajiness, D. L. Boger, J. Org. Chem. 2011, 76, 583-587.
Grant Information:: JP18am0301005 Japan Agency for Medical Research and Development; JP20am0101101j004 Japan Agency for Medical Research and Development; JP16H06356 Japan Society for the Promotion of Science
Contributed Indexing:: Keywords: DNA recognition; cancer; drug delivery; drug discovery; sequence-specificity
Substance Nomenclature:: 0 (Imidazoles)
0 (Nylons)
0 (Pyrroles)
9007-49-2 (DNA)
Entry Date(s):: Date Created: 20200717 Date Completed: 20210210 Latest Revision: 20210210
Update Code:: 20240105
DOI:: 10.1002/chem.202002166
PMID:: 32672369
: Czasopismo naukowe

Pełny tekst

Many types of molecular targeted drugs that inhibit cancer growth by acting on specific molecules have been developed. The runt-related transcription factor (RUNX) family, which induces cancer development by binding to a specific DNA sequence, has attracted attention as a new target for cancer treatment. We have developed Chb-M', which targets the RUNX-binding sequence. Chb-M' was developed by conjugating pyrrole-imidazole (PI) polyamides and chlorambucil as an anticancer agent. It was recently reported that Chb-M' had a remarkable anticancer effect in vivo. In this study, to explore the possibility of an alternative structure, we designed a new series of CBI-PI polyamides, in which seco-CBI was applied as a DNA-alkylating agent. We examined the characteristics of the CBI-PI polyamides targeting the RUNX-binding sequence and found that these conjugates have great potential for cancer treatment.
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