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Article ; Online: Antitumor Activity of Rutaecarpine in Human Colorectal Cancer Cells by Suppression of Wnt/β-Catenin Signaling.

Byun, Woong Sub / Bae, Eun Seo / Kim, Won Kyung / Lee, Sang Kook

2022 Volume 85, Issue 5, Page(s) 1407–1418

Abstract: Alkaloids derived from natural products have been traditionally used to treat various diseases, including cancers. Rutaecarpine ( ...

Abstract	Alkaloids derived from natural products have been traditionally used to treat various diseases, including cancers. Rutaecarpine (
MeSH term(s)	Animals ; Apoptosis ; Cell Line, Tumor ; Cell Proliferation ; Colorectal Neoplasms/drug therapy ; Humans ; Indole Alkaloids ; Mice ; Quinazolines ; Wnt Signaling Pathway ; beta Catenin
Chemical Substances	Indole Alkaloids ; Quinazolines ; beta Catenin ; rutecarpine (8XZV289PRY)
Language	English
Publishing date	2022-05-11
Publishing country	United States
Document type	Journal Article ; Review ; Research Support, Non-U.S. Gov't
ZDB-ID	304325-3
ISSN	1520-6025 ; 0163-3864
ISSN (online)	1520-6025
ISSN	0163-3864
DOI	10.1021/acs.jnatprod.2c00224
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Article: Antitumor Activity of Rutaecarpine in Human Colorectal Cancer Cells by Suppression of Wnt/β-Catenin Signaling

Byun, Woong Sub / Bae, Eun Seo / Kim, Won Kyung / Lee, Sang Kook

Journal of natural products. 2022 May 11, v. 85, no. 5

2022

Abstract: Alkaloids derived from natural products have been traditionally used to treat various diseases, including cancers. Rutaecarpine (1), a β-carboline-type alkaloid obtained from Evodia rutaecarpa, has been previously reported as an anti-inflammatory agent. ... ...

Abstract	Alkaloids derived from natural products have been traditionally used to treat various diseases, including cancers. Rutaecarpine (1), a β-carboline-type alkaloid obtained from Evodia rutaecarpa, has been previously reported as an anti-inflammatory agent. Nonetheless, its anticancer activity and the underlying molecular mechanisms remain to be explored. In the procurement of Wnt/β-catenin inhibitors from natural alkaloids, 1 was found to exhibit activity against the Wnt/β-catenin-response reporter gene. Since the abnormal activation of Wnt/β-catenin signaling is highly involved in colon carcinogenesis, the antitumor activity and molecular mechanisms of 1 were investigated in colorectal cancer (CRC) cells. The antiproliferative activity of 1 was associated with the suppression of the Wnt/β-catenin-mediated signaling pathway and its target gene expression in human CRC cells. 1 also induced G₀/G₁ cell cycle arrest and apoptotic cell death, and the antimigration and anti-invasion potential of 1 was confirmed through epithelial–mesenchymal transition biomarker inhibition by the regulation of Wnt signaling. The antitumor activity of 1 was supported in an Ls174T-implanted xenograft mouse model via Wnt target gene regulation. Overall, these findings suggest that targeting the Wnt/β-catenin signaling pathway by 1 is a promising therapeutic option for the treatment of human CRC harboring β-catenin mutation.
Keywords	Euodia ; alkaloids ; anti-inflammatory agents ; antineoplastic activity ; apoptosis ; biomarkers ; carcinogenesis ; cell cycle checkpoints ; colon ; colorectal neoplasms ; gene expression ; humans ; mice ; mutation ; reporter genes ; xenotransplantation
Language	English
Dates of publication	2022-0511
Size	p. 1407-1418.
Publishing place	American Chemical Society and American Society of Pharmacognosy
Document type	Article
ZDB-ID	304325-3
ISSN	1520-6025 ; 0163-3864
ISSN (online)	1520-6025
ISSN	0163-3864
DOI	10.1021/acs.jnatprod.2c00224
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Article ; Online: Design, Synthesis, and Biological Activity of Marinacarboline Analogues as STAT3 Pathway Inhibitors for Docetaxel-Resistant Triple-Negative Breast Cancer.

Byun, Woong Sub / Lim, Hyewon / Hong, Junhwa / Bae, Eun Seo / Lee, Seok Beom / Kim, Younggwan / Lee, Jeeyeon / Lee, Sang Kook / Hong, Suckchang

Journal of medicinal chemistry

2023 Volume 66, Issue 4, Page(s) 3106–3133

Abstract: Metastatic triple-negative breast cancer (mTNBC) is a fatal type of breast cancer (BC), and signal transducer and activator of transcription 3 (STAT3) has emerged as an effective target for mTNBC. In the present study, ... ...

Abstract	Metastatic triple-negative breast cancer (mTNBC) is a fatal type of breast cancer (BC), and signal transducer and activator of transcription 3 (STAT3) has emerged as an effective target for mTNBC. In the present study, compound
MeSH term(s)	Humans ; Animals ; Mice ; Docetaxel/therapeutic use ; Triple Negative Breast Neoplasms/drug therapy ; STAT3 Transcription Factor/metabolism ; Apoptosis ; Xenograft Model Antitumor Assays ; Cell Line, Tumor ; Cell Proliferation ; Antineoplastic Agents/pharmacology
Chemical Substances	Docetaxel (15H5577CQD) ; STAT3 Transcription Factor ; Antineoplastic Agents ; STAT3 protein, human
Language	English
Publishing date	2023-02-14
Publishing country	United States
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	218133-2
ISSN	1520-4804 ; 0022-2623
ISSN (online)	1520-4804
ISSN	0022-2623
DOI	10.1021/acs.jmedchem.2c01115
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Article ; Online: Synthesis and biological evaluation of atropisomeric tetrahydroisoquinolines overcoming docetaxel resistance in triple-negative human breast cancer cells.

Song, Jayoung / Kim, Ahreum / Hong, Intaek / Kim, Sangji / Byun, Woong Sub / Lee, Hyun Soo / Kim, Hyung Sik / Lee, Sang Kook / Kwon, Yongseok

Bioorganic chemistry

2023 Volume 137, Page(s) 106573

Abstract: Herein, atropisomeric 8-aryltetrahydroisoquinolines have been synthesized and biologically evaluated. Based on our structure-activity relationship study, a highly bioactive racemic compound has been produced, and it exhibited high antiproliferative ... ...

Abstract	Herein, atropisomeric 8-aryltetrahydroisoquinolines have been synthesized and biologically evaluated. Based on our structure-activity relationship study, a highly bioactive racemic compound has been produced, and it exhibited high antiproliferative activities against various cancer cell lines, including docetaxel-resistant breast cancer cell lines. Each enantiomer can be synthesized in an enantioselective manner by employing the chiral phosphoric acid-catalyzed atroposelective Pictet-Spengler cyclization. An axially (R)-configured enantiomer showed a higher biological activity compared with the axially (S)-configured enantiomer. Further biological studies suggested that the (R)-enantiomer overcomes docetaxel resistance via the downregulation of signal transducer and activator of transcription 3 activation and consequently induces cellular apoptosis in docetaxel-resistant triple-negative breast cancer cell lines.
MeSH term(s)	Humans ; Docetaxel/pharmacology ; Tetrahydroisoquinolines ; Triple Negative Breast Neoplasms/drug therapy ; Triple Negative Breast Neoplasms/metabolism ; Apoptosis ; Cell Line, Tumor
Chemical Substances	Docetaxel (15H5577CQD) ; Tetrahydroisoquinolines
Language	English
Publishing date	2023-04-29
Publishing country	United States
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	120080-x
ISSN	1090-2120 ; 0045-2068
ISSN (online)	1090-2120
ISSN	0045-2068
DOI	10.1016/j.bioorg.2023.106573
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Zs.A 4207: Show issues

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Article: Inhibition of DOT1L by Half-Selenopsammaplin A Analogs Suppresses Tumor Growth and EMT-Mediated Metastasis in Triple-Negative Breast Cancer.

Byun, Woong Sub / Lee, Gyu Ho / Park, Hyeung-Geun / Lee, Sang Kook

Pharmaceuticals (Basel, Switzerland)

2020 Volume 14, Issue 1

Abstract: Due to a lack of hormone receptors, current treatment strategies for triple-negative breast cancer (TNBC) are limited with frequent disease recurrence and metastasis. Recent findings have suggested that aberrant methylation of histone H3 lysine 79 ... ...

Abstract	Due to a lack of hormone receptors, current treatment strategies for triple-negative breast cancer (TNBC) are limited with frequent disease recurrence and metastasis. Recent findings have suggested that aberrant methylation of histone H3 lysine 79 residue (H3K79me) by the histone methyltransferase disruptor of telomeric silencing 1-like (DOT1L) is a potential therapeutic target for TNBC clinical management. Therefore, we developed DOT1L inhibitors as potential antitumor agents against TNBC cells. We reveal that a synthetic half-selenopsammaplin A analog 9l (subsequently known as 9l) exhibited inhibitory activity against DOT1L-mediated H3K79 methylation, and showed antitumor activity in TNBC cells. The analog 9l also significantly inhibited TNBC invasion and migration via the modulation of epithelial-mesenchymal transition (EMT) markers, including N-cadherin and vimentin downregulation and E-cadherin upregulation. In an MDA-MB-231/Luc-implanted orthotopic mouse metastasis model, treatment with 9l effectively inhibited tumor growth and lung metastasis via DOT1L regulatory activity and EMT processes. Taken together, these findings highlight the potential of 9l as a novel therapeutic candidate for treating metastatic TNBC via DOT1L modulation.
Language	English
Publishing date	2020-12-28
Publishing country	Switzerland
Document type	Journal Article
ZDB-ID	2193542-7
ISSN	1424-8247
ISSN	1424-8247
DOI	10.3390/ph14010018
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Article: Antitumor Activity of Asperphenin B by Induction of Apoptosis and Regulation of Glyceraldehyde-3-phosphate Dehydrogenase in Human Colorectal Cancer Cells

Byun, Woong Sub / Bae, Eun Seo / Park, Sung Chul / Kim, Won Kyung / Shin, Jongheon / Lee, Sang Kook

Journal of natural products. 2021 Jan. 05, v. 84, no. 3

2021

Abstract: Colorectal cancer (CRC) is a common and intractable malignancy with a high mortality risk. Conventional chemotherapeutics are effective for patients with early stage CRC, but the majority of deaths of CRC patients are linked to acquired drug resistance ... ...

Abstract	Colorectal cancer (CRC) is a common and intractable malignancy with a high mortality risk. Conventional chemotherapeutics are effective for patients with early stage CRC, but the majority of deaths of CRC patients are linked to acquired drug resistance or metastasis occurrence. Asperphenin B (1), a lipopeptidyl benzophenone isolated from a marine-derived Aspergillus sp. fungus, reportedly possesses antiproliferative activity against cancer cells. However, its antitumor activity and the underlying molecular mechanisms remain unexplored. In this study, 1 induced G₂/M phase cell cycle arrest and subsequent apoptotic cell death and inhibited tumor growth in a xenograft model. The 1-induced G₂/M phase arrest was associated with the regulation of checkpoint proteins, including Chk1/2 and Cdc25c. The 1-induced apoptosis was correlated with an upregulation of p53 and cleaved caspases and a downregulation of survivin. Further experiments revealed that 1-mediated suppression of migration and invasion of metastatic HCT116 cells was partially associated with the downregulation of glyceraldehyde-3-phosphate dehydrogenase (GAPDH) expression. The antimetastatic potential of 1 was also confirmed by E-cadherin upregulation and N-cadherin and Snail downregulation, which were in turn associated with the GAPDH regulation. These findings highlight the potential use of 1 as a novel candidate for treating metastatic CRC with the modulation of GAPDH function.
Keywords	Aspergillus ; antineoplastic activity ; apoptosis ; benzophenones ; cadherins ; caspases ; cell cycle checkpoints ; colorectal neoplasms ; drug resistance ; drug therapy ; fungi ; glyceraldehyde-3-phosphate dehydrogenase ; humans ; metastasis ; models ; mortality ; pro-apoptotic proteins ; risk ; xenotransplantation
Language	English
Dates of publication	2021-0105
Size	p. 683-693.
Publishing place	American Chemical Society and American Society of Pharmacognosy
Document type	Article
Note	NAL-AP-2-clean
ZDB-ID	304325-3
ISSN	1520-6025 ; 0163-3864
ISSN (online)	1520-6025
ISSN	0163-3864
DOI	10.1021/acs.jnatprod.0c01155
Database	NAL-Catalogue (AGRICOLA)

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Article ; Online: Periplocin exerts antitumor activity by regulating Nrf2-mediated signaling pathway in gemcitabine-resistant pancreatic cancer cells.

Bae, Eun Seo / Byun, Woong Sub / Ock, Chae Won / Kim, Won Kyung / Park, Hyen Joo / Lee, Sang Kook

Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie

2022 Volume 157, Page(s) 114039

Abstract: Although gemcitabine-based chemotherapy is common and effective for pancreatic cancer (PC), acquired drug resistance is one of the major reasons for treatment failure. Therefore, a novel therapeutic approach for gemcitabine-resistant PC is required. ... ...

Abstract	Although gemcitabine-based chemotherapy is common and effective for pancreatic cancer (PC), acquired drug resistance is one of the major reasons for treatment failure. Therefore, a novel therapeutic approach for gemcitabine-resistant PC is required. Nuclear factor erythroid 2-related factor 2 (Nrf2) is an oxidative stress-responsive transcription factor regulating antioxidant responses and plays a crucial role in chemoresistance. In the present study, the antitumor activity of periplocin, a natural cardiac glycoside, was evaluated in an established gemcitabine-resistant PC cell line (PANC-GR). Nrf2 was overexpressed in gemcitabine-resistant cells, and Nrf2 knockdown recovered gemcitabine sensitivity in PANC-GR cells. The antiproliferative activity of periplocin was highly associated with Nrf2 downregulation and Nrf2-mediated signaling pathways in PANC-GR cells. Periplocin also increased reactive oxygen species production inducing G
MeSH term(s)	Humans ; Mice ; Animals ; Gemcitabine ; Deoxycytidine/pharmacology ; Deoxycytidine/therapeutic use ; Drug Resistance, Neoplasm ; Cell Line, Tumor ; Pancreatic Neoplasms/pathology ; Signal Transduction ; Apoptosis ; Xenograft Model Antitumor Assays ; Pancreatic Neoplasms
Chemical Substances	Gemcitabine ; Deoxycytidine (0W860991D6)
Language	English
Publishing date	2022-11-21
Publishing country	France
Document type	Journal Article
ZDB-ID	392415-4
ISSN	1950-6007 ; 0753-3322 ; 0300-0893
ISSN (online)	1950-6007
ISSN	0753-3322 ; 0300-0893
DOI	10.1016/j.biopha.2022.114039
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Article: Discovery of CRBN-dependent WEE1 Molecular Glue Degraders from a Multicomponent Combinatorial Library.

Razumkov, Hlib / Jiang, Zixuan / Baek, Kheewoong / You, Inchul / Geng, Qixiang / Donovan, Katherine A / Tang, Michelle T / Metivier, Rebecca J / Mageed, Nada / Seo, Pooreum / Li, Zhengnian / Byun, Woong Sub / Hinshaw, Stephen M / Sarott, Roman C / Fischer, Eric S / Gray, Nathanael S

bioRxiv : the preprint server for biology

2024

Abstract: Small molecules promoting protein-protein interactions produce a range of therapeutic outcomes. Molecular glue degraders exemplify this concept due to their compact drug-like structures and ability to engage targets without reliance on existing cognate ... ...

Abstract	Small molecules promoting protein-protein interactions produce a range of therapeutic outcomes. Molecular glue degraders exemplify this concept due to their compact drug-like structures and ability to engage targets without reliance on existing cognate ligands. While Cereblon molecular glue degraders containing glutarimide scaffolds have been approved for treatment of multiple myeloma and acute myeloid leukemia, the design of new therapeutically relevant monovalent degraders remains challenging. We report here an approach to glutarimide-containing molecular glue synthesis using multicomponent reactions as a central modular core-forming step. Screening the resulting library identified HRZ-01 derivatives that target casein kinase 1 alpha (CK1α) and Wee-like protein kinase (WEE1). Further medicinal chemistry efforts led to identification of selective monovalent WEE1 degraders that provide a potential starting point for the eventual development of a selective chemical degrader probe. The structure of the hit WEE1 degrader complex with CRBN-DDB1 and WEE1 provides a model of the protein-protein interface and a rationale for the observed kinase selectivity. Our findings suggest that modular synthetic routes combined with in-depth structural characterization give access to selective molecular glue degraders and expansion of the CRBN-degradable proteome.
Language	English
Publishing date	2024-05-05
Publishing country	United States
Document type	Preprint
DOI	10.1101/2024.05.04.592550
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Article ; Conference proceedings: Antitumour activity of a natural cardiac glycoside, periplocin, by regulating Nrf2-mediated signalling pathway in gemcitabine-resistant pancreatic cancer cells

Lee, Sang Kook / Bae, Eun Seo / Byun, Woong Sub / Ock, Chae Won / Kim, Won Kyung / Park, Hyen Joo

Planta Medica

2023 Volume 89, Issue 14

Event/congress	71st International Congress and Annual Meeting of the Society for Medicinal Plant and Natural Product Research (GA), Trinity College Dublin Ireland, 2023-07-02
Language	English
Publishing date	2023-11-01
Publisher	Georg Thieme Verlag KG
Publishing place	Stuttgart ; New York
Document type	Article ; Conference proceedings
ZDB-ID	123545-x
ISSN	1439-0221 ; 0032-0943
ISSN (online)	1439-0221
ISSN	0032-0943
DOI	10.1055/s-0043-1774237
Database	Thieme publisher's database

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Article ; Online: Proteomics-Based Discovery of First-in-Class Chemical Probes for Programmed Cell Death Protein 2 (PDCD2).

Ji, Wenzhi / Byun, Woong Sub / Lu, Wenchao / Zhu, Xijun / Donovan, Katherine A / Dwyer, Brendan G / Che, Jianwei / Yuan, Linjie / Abulaiti, Xianmixinuer / Corsello, Steven M / Fischer, Eric S / Zhang, Tinghu / Gray, Nathanael S

Angewandte Chemie (International ed. in English)

2023 Volume 62, Issue 43, Page(s) e202308292

Abstract: Chemical probes are essential tools for understanding biological systems and for credentialing potential biomedical targets. Programmed cell death 2 (PDCD2) is a member of the B-cell lymphoma 2 (Bcl-2) family of proteins, which are critical regulators of ...

Abstract	Chemical probes are essential tools for understanding biological systems and for credentialing potential biomedical targets. Programmed cell death 2 (PDCD2) is a member of the B-cell lymphoma 2 (Bcl-2) family of proteins, which are critical regulators of apoptosis. Here we report the discovery and characterization of 10 e, a first-in-class small molecule degrader of PDCD2. We discovered this PDCD2 degrader by serendipity using a chemical proteomics approach, in contrast to the conventional approach for making bivalent degraders starting from a known binding ligand targeting the protein of interest. Using 10 e as a pharmacological probe, we demonstrate that PDCD2 functions as a critical regulator of cell growth by modulating the progression of the cell cycle in T lymphoblasts. Our work provides a useful pharmacological probe for investigating PDCD2 function and highlights the use of chemical proteomics to discover selective small molecule degraders of unanticipated targets.
MeSH term(s)	Humans ; Apoptosis Regulatory Proteins/metabolism ; Proteomics ; Apoptosis ; Lymphoma, B-Cell ; Cell Proliferation
Chemical Substances	Apoptosis Regulatory Proteins ; PDCD2 protein, human
Language	English
Publishing date	2023-09-15
Publishing country	Germany
Document type	Journal Article ; Research Support, N.I.H., Extramural
ZDB-ID	2011836-3
ISSN	1521-3773 ; 1433-7851
ISSN (online)	1521-3773
ISSN	1433-7851
DOI	10.1002/anie.202308292
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