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Article ; Online: Simple monocyclic pyrimidine analogs as microtubule targeting agents binding to the colchicine site.

Choudhary, Shruti / Kaku, Krishna / Robles, Andrew J / Hamel, Ernest / Mooberry, Susan L / Gangjee, Aleem

2023 Volume 82, Page(s) 117217

Abstract: Complex natural products that bind to tubulin/microtubules come under the broad category of microtubule binding agents. The design of simplified analogs of previously reported bicyclic, microtubule depolymerizer, pyrrolo[2,3-d]pyrimidine, provided ... ...

Abstract	Complex natural products that bind to tubulin/microtubules come under the broad category of microtubule binding agents. The design of simplified analogs of previously reported bicyclic, microtubule depolymerizer, pyrrolo[2,3-d]pyrimidine, provided valuable structure-activity relationship data and led to the identification of novel monocyclic pyrimidine analogs of which 12 was 47-fold more potent (EC
MeSH term(s)	Humans ; Mice ; Animals ; Colchicine/pharmacology ; Colchicine/chemistry ; Tubulin/metabolism ; Tubulin Modulators/chemistry ; Microtubules/metabolism ; Structure-Activity Relationship ; Pyrimidines/chemistry ; Antineoplastic Agents/chemistry ; Cell Line, Tumor ; Binding Sites ; Cell Proliferation
Chemical Substances	Colchicine (SML2Y3J35T) ; Tubulin ; Tubulin Modulators ; Pyrimidines ; Antineoplastic Agents
Language	English
Publishing date	2023-02-24
Publishing country	England
Document type	Journal Article ; Research Support, Non-U.S. Gov't ; Research Support, N.I.H., Extramural
ZDB-ID	1161284-8
ISSN	1464-3391 ; 0968-0896
ISSN (online)	1464-3391
ISSN	0968-0896
DOI	10.1016/j.bmc.2023.117217
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Article ; Online: Correction: Eribulin rapidly inhibits TGF-β-induced Snail expression and can induce Slug expression in a Smad4-dependent manner.

Kaul, Roma / Risinger, April L / Mooberry, Susan L

British journal of cancer

2020 Volume 124, Issue 4, Page(s) 855

Language	English
Publishing date	2020-10-15
Publishing country	England
Document type	Published Erratum
ZDB-ID	80075-2
ISSN	1532-1827 ; 0007-0920
ISSN (online)	1532-1827
ISSN	0007-0920
DOI	10.1038/s41416-020-01115-w
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Article: Eribulin and Paclitaxel Differentially Alter Extracellular Vesicles and Their Cargo from Triple-Negative Breast Cancer Cells.

Pederson, Petra J / Liang, Huiyun / Filonov, Daria / Mooberry, Susan L

Cancers

2021 Volume 13, Issue 11

Abstract: Extracellular vesicles play a central role in intercellular communication and contribute to cancer progression, including the epithelial-to-mesenchymal transition (EMT). Microtubule targeting agents (MTAs) including eribulin and paclitaxel continue to ... ...

Abstract	Extracellular vesicles play a central role in intercellular communication and contribute to cancer progression, including the epithelial-to-mesenchymal transition (EMT). Microtubule targeting agents (MTAs) including eribulin and paclitaxel continue to provide significant value in cancer therapy and their abilities to inhibit oncogenic signaling pathways, including eribulin's capacity to reverse EMT are being revealed. Because microtubules are involved in the intracellular trafficking required for the formation and cargo loading of small extracellular vesicles (sEVs), we investigated whether MTA-mediated disruption of microtubule-dependent transport would impact sEV release and their cargo. Eribulin and paclitaxel caused an intracellular accumulation of CD63, a tetraspanin component of sEVs, in late/multivesicular endosomes of triple-negative breast cancer cells, consistent with the disruption of endosomal sorting and exosome cargo loading in these cells. While the concentrations of sEVs released from MTA-treated cells were not significantly altered, levels of CD63 and the CD63-associated cargos, ILK and β-integrin, were reduced in sEVs isolated from eribulin-treated HCC1937 cells as compared to vehicle or paclitaxel-treated cells. These results show that eribulin can reduce specific sEV cargos, including ILK, a major transducer of EMT in the tumor microenvironment, which may contribute to eribulin's ability to reverse EMT to promote anticancer efficacy.
Language	English
Publishing date	2021-06-03
Publishing country	Switzerland
Document type	Journal Article
ZDB-ID	2527080-1
ISSN	2072-6694
ISSN	2072-6694
DOI	10.3390/cancers13112783
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Article ; Online: Microtubule-Targeting Drugs: More than Antimitotics.

Kaul, Roma / Risinger, April L / Mooberry, Susan L

Journal of natural products

2019 Volume 82, Issue 3, Page(s) 680–685

Abstract: Nature has yielded numerous compounds that bind to tubulin/microtubules and disrupt microtubule function. Even with the advent of targeted therapies for cancer, natural products and their derivatives that target microtubules are some of the most ... ...

Abstract	Nature has yielded numerous compounds that bind to tubulin/microtubules and disrupt microtubule function. Even with the advent of targeted therapies for cancer, natural products and their derivatives that target microtubules are some of the most effective drugs used in the treatment of solid tumors and hematological malignancies. For decades, these drugs were thought to work solely through their ability to inhibit mitosis. Accumulating evidence demonstrates that their actions are much more complex, in that they also have significant effects on microtubules in nondividing cells that inhibit a diverse range of signaling events important for carcinogenesis. The abilities of these drugs to inhibit oncogenic signaling likely underlies their efficacy, especially in solid tumors. In this review, we describe the role of microtubules in cells, the proliferation paradox of cells in culture as compared to cancers in patients, and evidence that microtubule-targeting drugs inhibit cellular signaling pathways important for tumorigenesis. The potential mechanisms behind differences in the clinical indications and efficacy of these natural-product-derived drugs are also discussed. Microtubules are an important target for structurally diverse natural products, and a fuller understanding of the mechanisms of action of these drugs will promote their optimal use.
MeSH term(s)	Antimitotic Agents/pharmacology ; Antineoplastic Agents/pharmacology ; Biological Products/pharmacology ; Humans ; Microtubules/drug effects ; Mitosis/drug effects ; Molecular Structure
Chemical Substances	Antimitotic Agents ; Antineoplastic Agents ; Biological Products
Language	English
Publishing date	2019-03-05
Publishing country	United States
Document type	Journal Article ; Research Support, Non-U.S. Gov't ; Review
ZDB-ID	304325-3
ISSN	1520-6025 ; 0163-3864
ISSN (online)	1520-6025
ISSN	0163-3864
DOI	10.1021/acs.jnatprod.9b00105
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Article ; Online: Eribulin rapidly inhibits TGF-β-induced Snail expression and can induce Slug expression in a Smad4-dependent manner.

Kaul, Roma / Risinger, April L / Mooberry, Susan L

British journal of cancer

2019 Volume 121, Issue 7, Page(s) 611–621

Abstract: Background: Evidence shows that the anticancer effects of microtubule targeting agents are not due solely to their antimitotic activities but also their ability to impair microtubule-dependent oncogenic signalling.: Methods: The effects of ... ...

Abstract	Background: Evidence shows that the anticancer effects of microtubule targeting agents are not due solely to their antimitotic activities but also their ability to impair microtubule-dependent oncogenic signalling. Methods: The effects of microtubule targeting agents on regulators of TGF-β-induced epithelial-to-mesenchymal transition (EMT) were evaluated in breast cancer cell lines using high content imaging, gene and protein expression, siRNA-mediated knockdown and chromatin immunoprecipitation. Results: Microtubule targeting agents rapidly and differentially alter the expression of Snail and Slug, key EMT-promoting transcription factors in breast cancer. Eribulin, vinorelbine and in some cases, ixabepalone, but not paclitaxel, inhibited TGF-β-mediated Snail expression by impairing the microtubule-dependent nuclear localisation of Smad2/3. In contrast, eribulin and vinorelbine promoted a TGF-β-independent increase in Slug in cells with low Smad4. Mechanistically, microtubule depolymerisation induces c-Jun, which consequently increases Slug expression in cells with low Smad4. Conclusion: These results identify a mechanism by which eribulin-mediated microtubule disruption could reverse EMT in preclinical models and in patients. Furthermore, high Smad4 levels could serve as a biomarker of this response. This study highlights that microtubule targeting drugs can exert distinct effects on the expression of EMT-regulating transcription factors and that identifying differences among these drugs could lead to their more rational use.
MeSH term(s)	Breast Neoplasms/metabolism ; Cell Line, Tumor ; Cell Nucleus/metabolism ; Chromatin Immunoprecipitation/methods ; Epithelial-Mesenchymal Transition/drug effects ; Epothilones/pharmacology ; Female ; Furans/pharmacology ; Gene Expression ; Genes, jun ; Humans ; Ketones/pharmacology ; Microtubules/drug effects ; Paclitaxel/pharmacology ; Smad2 Protein/metabolism ; Smad3 Protein/metabolism ; Smad4 Protein/metabolism ; Snail Family Transcription Factors/metabolism ; Transforming Growth Factor beta/metabolism ; Tubulin Modulators/pharmacology ; Vinorelbine/pharmacology
Chemical Substances	Epothilones ; Furans ; Ketones ; SMAD2 protein, human ; SMAD3 protein, human ; SMAD4 protein, human ; SNAI1 protein, human ; SNAI2 protein, human ; Smad2 Protein ; Smad3 Protein ; Smad4 Protein ; Snail Family Transcription Factors ; Transforming Growth Factor beta ; Tubulin Modulators ; ixabepilone (K27005NP0A) ; eribulin (LR24G6354G) ; Paclitaxel (P88XT4IS4D) ; Vinorelbine (Q6C979R91Y)
Language	English
Publishing date	2019-09-04
Publishing country	England
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	80075-2
ISSN	1532-1827 ; 0007-0920
ISSN (online)	1532-1827
ISSN	0007-0920
DOI	10.1038/s41416-019-0556-9
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Article ; Online: Eribulin Activates the cGAS-STING Pathway via the Cytoplasmic Accumulation of Mitochondrial DNA.

Fermaintt, Charles S / Takahashi-Ruiz, Leila / Liang, Huiyun / Mooberry, Susan L / Risinger, April L

Molecular pharmacology

2021 Volume 100, Issue 4, Page(s) 309–318

Abstract: Microtubule-targeting agents (MTAs), including both microtubule stabilizers and destabilizers are highly effective chemotherapeutic drugs used in the treatment of solid tumors and hematologic malignancies. In addition to the shared ability of all MTAs to ...

Abstract	Microtubule-targeting agents (MTAs), including both microtubule stabilizers and destabilizers are highly effective chemotherapeutic drugs used in the treatment of solid tumors and hematologic malignancies. In addition to the shared ability of all MTAs to block cell cycle progression, growing evidence shows that different agents of this class can also have mechanistically distinct effects on nonmitotic microtubule-dependent cellular processes, including cellular signaling and transport. Herein, we test the biologic hypothesis that MTAs used in the treatment of triple-negative breast cancer (TNBC) can differentially affect innate immune signaling pathways independent of their antimitotic effects. Our data demonstrate that the microtubule destabilizer eribulin, but not the microtubule stabilizer paclitaxel, induces cGAS-STING-dependent expression of interferon-
MeSH term(s)	Animals ; Cell Line, Tumor ; Cytoplasm/drug effects ; Cytoplasm/metabolism ; DNA, Mitochondrial/metabolism ; Furans/pharmacology ; Humans ; Immunity, Innate/drug effects ; Immunity, Innate/physiology ; Ketones/pharmacology ; Membrane Proteins/metabolism ; Mice ; Mice, Inbred BALB C ; Mice, Inbred C57BL ; Mice, Transgenic ; Microtubules/drug effects ; Microtubules/metabolism ; Nucleotidyltransferases/metabolism ; Signal Transduction/drug effects ; Signal Transduction/physiology
Chemical Substances	DNA, Mitochondrial ; Furans ; Ketones ; Membrane Proteins ; STING1 protein, human ; Nucleotidyltransferases (EC 2.7.7.-) ; cGAS protein, human (EC 2.7.7.-) ; eribulin (LR24G6354G)
Language	English
Publishing date	2021-07-26
Publishing country	United States
Document type	Journal Article ; Research Support, N.I.H., Extramural ; Research Support, Non-U.S. Gov't
ZDB-ID	124034-1
ISSN	1521-0111 ; 0026-895X
ISSN (online)	1521-0111
ISSN	0026-895X
DOI	10.1124/molpharm.121.000297
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Zs.A 525: Show issues

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Article: The Microtubule Destabilizer Eribulin Synergizes with STING Agonists to Promote Antitumor Efficacy in Triple-Negative Breast Cancer Models.

Takahashi-Ruiz, Leila / Fermaintt, Charles S / Wilkinson, Nancy J / Chan, Peter Y W / Mooberry, Susan L / Risinger, April L

Cancers

2022 Volume 14, Issue 23

Abstract: Eribulin is a microtubule destabilizer used in the treatment of triple-negative breast cancer (TNBC). Eribulin and other microtubule targeted drugs, such as the taxanes, have shared antimitotic effects, but differ in their mechanism of microtubule ... ...

Abstract	Eribulin is a microtubule destabilizer used in the treatment of triple-negative breast cancer (TNBC). Eribulin and other microtubule targeted drugs, such as the taxanes, have shared antimitotic effects, but differ in their mechanism of microtubule disruption, leading to diverse effects on cellular signaling and trafficking. Herein, we demonstrate that eribulin is unique from paclitaxel in its ability to enhance expression of the immunogenic cytokine interferon beta (IFNβ) in combination with STING agonists in both immune cells and TNBC models, including profound synergism with ADU-S100 and E7766, which are currently undergoing clinical trials. The mechanism by which eribulin enhances STING signaling is downstream of microtubule disruption and independent of the eribulin-dependent release of mitochondrial DNA. Eribulin did not override the requirement of ER exit for STING activation and did not inhibit subsequent STING degradation; however, eribulin significantly enhanced IRF3 phosphorylation and IFNβ production downstream of the RNA sensing pathway that converges on this transcription factor. Additionally, we found that eribulin enhanced the population of activated CD4
Language	English
Publishing date	2022-12-02
Publishing country	Switzerland
Document type	Journal Article
ZDB-ID	2527080-1
ISSN	2072-6694
ISSN	2072-6694
DOI	10.3390/cancers14235962
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Article ; Online: Design, Synthesis, and Biological Evaluation of 5,6,7,8-Tetrahydrobenzo[4,5]thieno[2,3-

Islam, Farhana / Doshi, Arpit / Robles, Andrew J / Quadery, Tasdique M / Zhang, Xin / Zhou, Xilin / Hamel, Ernest / Mooberry, Susan L / Gangjee, Aleem

Molecules (Basel, Switzerland)

2022 Volume 27, Issue 1

Abstract: A series of eleven 4-substituted 5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3- ...

Abstract	A series of eleven 4-substituted 5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-
MeSH term(s)	Cell Line, Tumor ; Cell Proliferation/drug effects ; Chemistry Techniques, Synthetic ; Drug Design ; Drug Resistance, Neoplasm ; Humans ; Models, Molecular ; Molecular Conformation ; Molecular Structure ; Protein Multimerization/drug effects ; Pyrimidines/chemical synthesis ; Pyrimidines/chemistry ; Pyrimidines/pharmacology ; Structure-Activity Relationship ; Tubulin/chemistry ; Tubulin/metabolism ; Tubulin Modulators/chemical synthesis ; Tubulin Modulators/chemistry ; Tubulin Modulators/pharmacology
Chemical Substances	Pyrimidines ; Tubulin ; Tubulin Modulators
Language	English
Publishing date	2022-01-05
Publishing country	Switzerland
Document type	Journal Article
ZDB-ID	1413402-0
ISSN	1420-3049 ; 1431-5165 ; 1420-3049
ISSN (online)	1420-3049
ISSN	1431-5165 ; 1420-3049
DOI	10.3390/molecules27010321
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Article ; Online: Correction: Regulation of E-cadherin localization by microtubule targeting agents: rapid promotion of cortical E-cadherin through p130CAS/Src inhibition by eribulin.

Dybdal-Hargreaves, Nicholas F / Risinger, April L / Mooberry, Susan L

Oncotarget

2019 Volume 10, Issue 45, Page(s) 4719–4720

Abstract: This corrects the article DOI: 10.18632/oncotarget.23798.]. ...

Abstract	[This corrects the article DOI: 10.18632/oncotarget.23798.].
Language	English
Publishing date	2019-07-23
Publishing country	United States
Document type	Published Erratum
ZDB-ID	2560162-3
ISSN	1949-2553 ; 1949-2553
ISSN (online)	1949-2553
ISSN	1949-2553
DOI	10.18632/oncotarget.27100
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Article ; Online: Recent progress with microtubule stabilizers: new compounds, binding modes and cellular activities.

Rohena, Cristina C / Mooberry, Susan L

Natural product reports

2014 Volume 31, Issue 3, Page(s) 335–355

Abstract: Nature has yielded numerous classes of chemically distinct microtubule stabilizers. Several of these, including paclitaxel (Taxol) and docetaxel (Taxotere), are important drugs used in the treatment of cancer. New microtubule stabilizers and novel ... ...

Abstract	Nature has yielded numerous classes of chemically distinct microtubule stabilizers. Several of these, including paclitaxel (Taxol) and docetaxel (Taxotere), are important drugs used in the treatment of cancer. New microtubule stabilizers and novel formulations of these agents continue to provide advances in cancer therapy. In this review we cover recent progress in the chemistry and biology of these diverse microtubule stabilizers focusing on the wide range of organisms that produce these compounds, their mechanisms of inhibiting microtubule-dependent processes, mechanisms of drug resistance, and their interactions with tubulin including their distinct binding sites and modes. A new potential role for microtubule stabilizers in neurodegenerative diseases is reviewed.
MeSH term(s)	Antineoplastic Agents, Phytogenic/chemistry ; Antineoplastic Agents, Phytogenic/isolation & purification ; Antineoplastic Agents, Phytogenic/pharmacology ; Docetaxel ; Microtubules/drug effects ; Molecular Structure ; Paclitaxel/pharmacology ; Taxoids/pharmacology ; Tubulin Modulators/chemistry ; Tubulin Modulators/isolation & purification ; Tubulin Modulators/pharmacology
Chemical Substances	Antineoplastic Agents, Phytogenic ; Taxoids ; Tubulin Modulators ; Docetaxel (15H5577CQD) ; Paclitaxel (P88XT4IS4D)
Language	English
Publishing date	2014-01-30
Publishing country	England
Document type	Journal Article ; Research Support, N.I.H., Extramural ; Review
ZDB-ID	2002546-4
ISSN	1460-4752 ; 0265-0568
ISSN (online)	1460-4752
ISSN	0265-0568
DOI	10.1039/c3np70092e
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