SAR optimization studies on modified salicylamides as a potential treatment for acute myeloid leukemia through inhibition of the CREB pathway
Abstract
Disruption of cyclic adenosine monophosphate response element binding protein (CREB) provides a potential new strategy to address acute leukemia, a disease associated with poor prognosis, and for which conventional treatment options often carry a significant risk of morbidity and mortality. In this paper, we describe the structure-activity relationships (SAR) for a series of XX-650-23 derived from naphthol AS-E phosphate that disrupts binding and activation of CREB by the CREB-binding protein (CBP). Through the development of this series, we identified several salicylamides that are potent inhibitors of acute leukemia cell viability through inhibition of CREB-CBP interaction. Among them, a biphenyl salicylamide, compound 71, was identified as a potent inhibitor of CREB-CBP interaction with improved physicochemical properties relative to previously described derivatives of naphthol AS-E phosphate.
- Authors:
-
[2];
[2];
- Stanford Univ. School of Medicine, Stanford, CA (United States)
- Medicinal Chemistry Knowledge Center, Stanford, CA (United States)
- Stanford Univ. School of Medicine, Stanford, CA (United States); Univ. of Tsukuba (Japan)
- Stanford Univ., CA (United States)
- Macromolecular Structure Knowledge Center, Stanford, CA (United States)
- Stanford Univ. School of Medicine, Stanford, CA (United States); SLAC National Accelerator Lab., Menlo Park, CA (United States)
- Publication Date:
- Research Org.:
- SLAC National Accelerator Laboratory (SLAC), Menlo Park, CA (United States)
- Sponsoring Org.:
- USDOE
- OSTI Identifier:
- 1560676
- Grant/Contract Number:
- AC02-76SF00515
- Resource Type:
- Accepted Manuscript
- Journal Name:
- Bioorganic and Medicinal Chemistry Letters
- Additional Journal Information:
- Journal Volume: 29; Journal Issue: 16; Journal ID: ISSN 0960-894X
- Publisher:
- Elsevier
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 59 BASIC BIOLOGICAL SCIENCES; 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; 60 APPLIED LIFE SCIENCES; Salicylamide; Acute myeloid leukemia; Small molecule; CREB; CBP
Citation Formats
Chae, Hee-Don, Cox, Nick, Capolicchio, Samanta, Lee, Jae Wook, Horikoshi, Naoki, Kam, Sharon, Ng, Andrew A., Edwards, Jeffrey, Butler, Tae-León, Chan, Justin, Lee, Yvonne, Potter, Garrett, Capece, Mark C., Liu, Corey W., Wakatsuki, Soichi, Smith, Mark, and Sakamoto, Kathleen M. SAR optimization studies on modified salicylamides as a potential treatment for acute myeloid leukemia through inhibition of the CREB pathway. United States: N. p., 2019.
Web. doi:10.1016/j.bmcl.2019.06.023.
Chae, Hee-Don, Cox, Nick, Capolicchio, Samanta, Lee, Jae Wook, Horikoshi, Naoki, Kam, Sharon, Ng, Andrew A., Edwards, Jeffrey, Butler, Tae-León, Chan, Justin, Lee, Yvonne, Potter, Garrett, Capece, Mark C., Liu, Corey W., Wakatsuki, Soichi, Smith, Mark, & Sakamoto, Kathleen M. SAR optimization studies on modified salicylamides as a potential treatment for acute myeloid leukemia through inhibition of the CREB pathway. United States. https://doi.org/10.1016/j.bmcl.2019.06.023
Chae, Hee-Don, Cox, Nick, Capolicchio, Samanta, Lee, Jae Wook, Horikoshi, Naoki, Kam, Sharon, Ng, Andrew A., Edwards, Jeffrey, Butler, Tae-León, Chan, Justin, Lee, Yvonne, Potter, Garrett, Capece, Mark C., Liu, Corey W., Wakatsuki, Soichi, Smith, Mark, and Sakamoto, Kathleen M. Wed .
"SAR optimization studies on modified salicylamides as a potential treatment for acute myeloid leukemia through inhibition of the CREB pathway". United States. https://doi.org/10.1016/j.bmcl.2019.06.023. https://www.osti.gov/servlets/purl/1560676.
@article{osti_1560676,
title = {SAR optimization studies on modified salicylamides as a potential treatment for acute myeloid leukemia through inhibition of the CREB pathway},
author = {Chae, Hee-Don and Cox, Nick and Capolicchio, Samanta and Lee, Jae Wook and Horikoshi, Naoki and Kam, Sharon and Ng, Andrew A. and Edwards, Jeffrey and Butler, Tae-León and Chan, Justin and Lee, Yvonne and Potter, Garrett and Capece, Mark C. and Liu, Corey W. and Wakatsuki, Soichi and Smith, Mark and Sakamoto, Kathleen M.},
abstractNote = {Disruption of cyclic adenosine monophosphate response element binding protein (CREB) provides a potential new strategy to address acute leukemia, a disease associated with poor prognosis, and for which conventional treatment options often carry a significant risk of morbidity and mortality. In this paper, we describe the structure-activity relationships (SAR) for a series of XX-650-23 derived from naphthol AS-E phosphate that disrupts binding and activation of CREB by the CREB-binding protein (CBP). Through the development of this series, we identified several salicylamides that are potent inhibitors of acute leukemia cell viability through inhibition of CREB-CBP interaction. Among them, a biphenyl salicylamide, compound 71, was identified as a potent inhibitor of CREB-CBP interaction with improved physicochemical properties relative to previously described derivatives of naphthol AS-E phosphate.},
doi = {10.1016/j.bmcl.2019.06.023},
journal = {Bioorganic and Medicinal Chemistry Letters},
number = 16,
volume = 29,
place = {United States},
year = {Wed Jun 19 00:00:00 EDT 2019},
month = {Wed Jun 19 00:00:00 EDT 2019}
}
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