Journal of Medicinal Chemistry
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mL of 80% cold ethanol in test tubes and incubated at 4 °C for 15
conserved mechanism for binding of p53 DNA-binding domain and
anti-apoptotic Bcl-2 family proteins. Mol. Cells 2014, 37, 264−269.
(11) Yao, H.; Mi, S.; Gong, W.; Lin, J.; Xu, N.; Perrett, S.; Xia, B.;
Wang, J.; Feng, Y. Anti-apoptosis proteins Mcl-1 and Bcl-xL have
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(12) Xu, H.; Ye, H.; Osman, N. E.; Sadler, K.; Won, E. Y.; Chi, S. W.;
Yoon, H. S. The MDM2-binding region in the transactivation domain
min. After incubation, cells were centrifuged at 1500 rpm for 5 min
and cell pellets were resuspended in 500 μL of propidium iodine (10
μg/mL) containing 300 μg/mL RNase (Sigma, MO, USA). Then cells
were incubated on ice for 30 min and filtered with nylon mesh. Cell
cycle distribution was calculated from 10000 cells with ModFit LT
software (Becton Dickinson, CA, USA) using a FACSCalibur
instrument (Becton Dickinson, CA, USA).
of p53 also acts as a Bcl-X -binding motif. Biochemistry 2009, 48,
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2159−12168.
ASSOCIATED CONTENT
13) Shin, J. S.; Ha, J. H.; Chi, S. W. Targeting of p53 peptide
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Supporting Information
analogues to anti-apoptotic Bcl-2 family proteins as revealed by NMR
spectroscopy. Biochem. Biophys. Res. Commun. 2014, 443, 882−887.
(14) Ha, J. H.; Won, E. Y.; Shin, J. S.; Jang, M.; Ryu, K. S.; Bae, K. H.;
Park, S. G.; Park, B. C.; Yoon, H. S.; Chi, S. W. Molecular mimicry-
based repositioning of nutlin-3 to anti-apoptotic Bcl-2 family proteins.
J. Am. Chem. Soc. 2011, 133, 1244−1247.
(15) Yin, H.; Lee, G. I.; Park, H. S.; Payne, G. A.; Rodriguez, J. M.;
Sebti, S. M.; Hamilton, A. D. Terphenyl-based helical mimetics that
disrupt the p53/HDM2 interaction. Angew. Chem., Int. Ed. 2005, 44,
Additional text, table, and three figures with experimental
procedures and full NMR, spectroscopic data for all new
Molecular formula strings (CSV)
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704−2707.
16) Yin, H.; Lee, G. I.; Sedey, K. A.; Kutzki, O.; Park, H. S.; Orner,
AUTHOR INFORMATION
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B. P.; Ernst, J. T.; Wang, H. G.; Sebti, S. M.; Hamilton, A. D.
Terphenyl-based bak BH3 alpha-helical proteomimetics as low-
Corresponding Author
molecular-weight antagonists of Bcl-X . J. Am. Chem. Soc. 2005, 127,
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0191−10196.
17) Li, X.; Wang, Z.; Feng, Y.; Song, T.; Su, P.; Chen, C.; Chai, G.;
Author Contributions
Z.W. and T.S. contributed equally to this work.
Notes
Yang, Y.; Zhang, Z. Two-face, two-turn alpha-helix mimetics based on
a cross-acridine scaffold: analogues of the Bim BH3 domain.
ChemBioChem 2014, 15, 1280−1285.
The authors declare no competing financial interest.
(18) Guichard, G.; Huc, I. Synthetic foldamers. Chem. Commun.
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011, 47, 5933−5941.
ACKNOWLEDGMENTS
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(19) Mathew, S. M.; Engle, J. T.; Ziegler, C. J.; Hartley, C. S. The role
of arene-arene interactions in the folding of ortho-phenylenes. J. Am.
Chem. Soc. 2013, 135, 6714−6722.
We thank Prof. Baomin Wang (Dalian University of
Technology) for insightful discussion of synthesis. The work
was supported by the National Natural Science Foundation of
China (21372036, 81570129, 81430083, 21502015, and
(
20) He, J.; Crase, J. L.; Wadumethrige, S. H.; Thakur, K.; Dai, L.;
Zou, S.; Rathore, R.; Hartley, C. S. ortho-Phenylenes: unusual
conjugated oligomers with a surprisingly long effective conjugation
length. J. Am. Chem. Soc. 2010, 132, 13848−13857.
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1402022).
(
21) Vassilev, L. T.; Vu, B. T.; Graves, B.; Carvajal, D.; Podlaski, F.;
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