Spandidos Publications Logo
  • About
    • About Spandidos
    • Aims and Scopes
    • Abstracting and Indexing
    • Editorial Policies
    • Reprints and Permissions
    • Job Opportunities
    • Terms and Conditions
    • Contact
  • Journals
    • All Journals
    • Oncology Letters
      • Oncology Letters
      • Information for Authors
      • Editorial Policies
      • Editorial Board
      • Aims and Scope
      • Abstracting and Indexing
      • Bibliographic Information
      • Archive
    • International Journal of Oncology
      • International Journal of Oncology
      • Information for Authors
      • Editorial Policies
      • Editorial Board
      • Aims and Scope
      • Abstracting and Indexing
      • Bibliographic Information
      • Archive
    • Molecular and Clinical Oncology
      • Molecular and Clinical Oncology
      • Information for Authors
      • Editorial Policies
      • Editorial Board
      • Aims and Scope
      • Abstracting and Indexing
      • Bibliographic Information
      • Archive
    • Experimental and Therapeutic Medicine
      • Experimental and Therapeutic Medicine
      • Information for Authors
      • Editorial Policies
      • Editorial Board
      • Aims and Scope
      • Abstracting and Indexing
      • Bibliographic Information
      • Archive
    • International Journal of Molecular Medicine
      • International Journal of Molecular Medicine
      • Information for Authors
      • Editorial Policies
      • Editorial Board
      • Aims and Scope
      • Abstracting and Indexing
      • Bibliographic Information
      • Archive
    • Biomedical Reports
      • Biomedical Reports
      • Information for Authors
      • Editorial Policies
      • Editorial Board
      • Aims and Scope
      • Abstracting and Indexing
      • Bibliographic Information
      • Archive
    • Oncology Reports
      • Oncology Reports
      • Information for Authors
      • Editorial Policies
      • Editorial Board
      • Aims and Scope
      • Abstracting and Indexing
      • Bibliographic Information
      • Archive
    • Molecular Medicine Reports
      • Molecular Medicine Reports
      • Information for Authors
      • Editorial Policies
      • Editorial Board
      • Aims and Scope
      • Abstracting and Indexing
      • Bibliographic Information
      • Archive
    • World Academy of Sciences Journal
      • World Academy of Sciences Journal
      • Information for Authors
      • Editorial Policies
      • Editorial Board
      • Aims and Scope
      • Abstracting and Indexing
      • Bibliographic Information
      • Archive
    • International Journal of Functional Nutrition
      • International Journal of Functional Nutrition
      • Information for Authors
      • Editorial Policies
      • Editorial Board
      • Aims and Scope
      • Abstracting and Indexing
      • Bibliographic Information
      • Archive
    • International Journal of Epigenetics
      • International Journal of Epigenetics
      • Information for Authors
      • Editorial Policies
      • Editorial Board
      • Aims and Scope
      • Abstracting and Indexing
      • Bibliographic Information
      • Archive
    • Medicine International
      • Medicine International
      • Information for Authors
      • Editorial Policies
      • Editorial Board
      • Aims and Scope
      • Abstracting and Indexing
      • Bibliographic Information
      • Archive
  • Articles
  • Information
    • Information for Authors
    • Information for Reviewers
    • Information for Librarians
    • Information for Advertisers
    • Conferences
  • Language Editing
Spandidos Publications Logo
  • About
    • About Spandidos
    • Aims and Scopes
    • Abstracting and Indexing
    • Editorial Policies
    • Reprints and Permissions
    • Job Opportunities
    • Terms and Conditions
    • Contact
  • Journals
    • All Journals
    • Biomedical Reports
      • Information for Authors
      • Editorial Policies
      • Editorial Board
      • Aims and Scope
      • Abstracting and Indexing
      • Bibliographic Information
      • Archive
    • Experimental and Therapeutic Medicine
      • Information for Authors
      • Editorial Policies
      • Editorial Board
      • Aims and Scope
      • Abstracting and Indexing
      • Bibliographic Information
      • Archive
    • International Journal of Epigenetics
      • Information for Authors
      • Editorial Policies
      • Editorial Board
      • Aims and Scope
      • Abstracting and Indexing
      • Bibliographic Information
      • Archive
    • International Journal of Functional Nutrition
      • Information for Authors
      • Editorial Policies
      • Editorial Board
      • Aims and Scope
      • Abstracting and Indexing
      • Bibliographic Information
      • Archive
    • International Journal of Molecular Medicine
      • Information for Authors
      • Editorial Policies
      • Editorial Board
      • Aims and Scope
      • Abstracting and Indexing
      • Bibliographic Information
      • Archive
    • International Journal of Oncology
      • Information for Authors
      • Editorial Policies
      • Editorial Board
      • Aims and Scope
      • Abstracting and Indexing
      • Bibliographic Information
      • Archive
    • Medicine International
      • Information for Authors
      • Editorial Policies
      • Editorial Board
      • Aims and Scope
      • Abstracting and Indexing
      • Bibliographic Information
      • Archive
    • Molecular and Clinical Oncology
      • Information for Authors
      • Editorial Policies
      • Editorial Board
      • Aims and Scope
      • Abstracting and Indexing
      • Bibliographic Information
      • Archive
    • Molecular Medicine Reports
      • Information for Authors
      • Editorial Policies
      • Editorial Board
      • Aims and Scope
      • Abstracting and Indexing
      • Bibliographic Information
      • Archive
    • Oncology Letters
      • Information for Authors
      • Editorial Policies
      • Editorial Board
      • Aims and Scope
      • Abstracting and Indexing
      • Bibliographic Information
      • Archive
    • Oncology Reports
      • Information for Authors
      • Editorial Policies
      • Editorial Board
      • Aims and Scope
      • Abstracting and Indexing
      • Bibliographic Information
      • Archive
    • World Academy of Sciences Journal
      • Information for Authors
      • Editorial Policies
      • Editorial Board
      • Aims and Scope
      • Abstracting and Indexing
      • Bibliographic Information
      • Archive
  • Articles
  • Information
    • For Authors
    • For Reviewers
    • For Librarians
    • For Advertisers
    • Conferences
  • Language Editing
Login Register Submit
  • This site uses cookies
  • You can change your cookie settings at any time by following the instructions in our Cookie Policy. To find out more, you may read our Privacy Policy.

    I agree
Search articles by DOI, keyword, author or affiliation
Search
Advanced Search
presentation
Biomedical Reports
Join Editorial Board Propose a Special Issue
Print ISSN: 2049-9434 Online ISSN: 2049-9442
Journal Cover
January-2025 Volume 22 Issue 1

Full Size Image

Sign up for eToc alerts
Recommend to Library

Journals

International Journal of Molecular Medicine

International Journal of Molecular Medicine

International Journal of Molecular Medicine is an international journal devoted to molecular mechanisms of human disease.

International Journal of Oncology

International Journal of Oncology

International Journal of Oncology is an international journal devoted to oncology research and cancer treatment.

Molecular Medicine Reports

Molecular Medicine Reports

Covers molecular medicine topics such as pharmacology, pathology, genetics, neuroscience, infectious diseases, molecular cardiology, and molecular surgery.

Oncology Reports

Oncology Reports

Oncology Reports is an international journal devoted to fundamental and applied research in Oncology.

Experimental and Therapeutic Medicine

Experimental and Therapeutic Medicine

Experimental and Therapeutic Medicine is an international journal devoted to laboratory and clinical medicine.

Oncology Letters

Oncology Letters

Oncology Letters is an international journal devoted to Experimental and Clinical Oncology.

Biomedical Reports

Biomedical Reports

Explores a wide range of biological and medical fields, including pharmacology, genetics, microbiology, neuroscience, and molecular cardiology.

Molecular and Clinical Oncology

Molecular and Clinical Oncology

International journal addressing all aspects of oncology research, from tumorigenesis and oncogenes to chemotherapy and metastasis.

World Academy of Sciences Journal

World Academy of Sciences Journal

Multidisciplinary open-access journal spanning biochemistry, genetics, neuroscience, environmental health, and synthetic biology.

International Journal of Functional Nutrition

International Journal of Functional Nutrition

Open-access journal combining biochemistry, pharmacology, immunology, and genetics to advance health through functional nutrition.

International Journal of Epigenetics

International Journal of Epigenetics

Publishes open-access research on using epigenetics to advance understanding and treatment of human disease.

Medicine International

Medicine International

An International Open Access Journal Devoted to General Medicine.

Journal Cover
January-2025 Volume 22 Issue 1

Full Size Image

Sign up for eToc alerts
Recommend to Library

  • Article
  • Citations
    • Cite This Article
    • Download Citation
    • Create Citation Alert
    • Remove Citation Alert
    • Cited By
  • Similar Articles
    • Related Articles (in Spandidos Publications)
    • Similar Articles (Google Scholar)
    • Similar Articles (PubMed)
  • Download PDF
  • Download XML
  • View XML

  • Supplementary Files
    • Supplementary_Data1.pdf
    • Supplementary_Data2.pdf
Article Open Access

Design, synthesis, biological and in silico evaluation of 3‑carboxy‑coumarin sulfonamides as potential antiproliferative agents targeting HDAC6

  • Authors:
    • José L. Madrigal‑Angulo
    • Gustavo A. Hernández‑Fuentes
    • Hortensia Parra‑Delgado
    • Marycruz Olvera‑Valdéz
    • Itzia I. Padilla‑Martínez
    • Ariana Cabrera‑Licona
    • Alexandra S. Espinosa‑Gil
    • Ivan Delgado‑Enciso
    • Francisco J. Martínez‑Martínez
  • View Affiliations / Copyright

    Affiliations: Faculty of Chemical Sciences, University of Colima, Coquimatlán 28400, Mexico, Department of Molecular Medicine, School of Medicine, University of Colima, Colima 28040, Mexico, Laboratorio de Química Supramolecular y Nanociencias, Unidad Profesional Interdisciplinaria de Biotecnología, Instituto Politécnico Nacional, Ciudad de México 07340, Mexico, State Cancerology Institute of Colima, Health Services of The Mexican Social Security Institute for Welfare (IMSS‑BIENESTAR), Colima 28085, Mexico
    Copyright: © Madrigal‑Angulo et al. This is an open access article distributed under the terms of Creative Commons Attribution License.
  • Article Number: 6
    |
    Published online on: October 30, 2024
       https://doi.org/10.3892/br.2024.1884
  • Expand metrics +
Metrics: Total Views: 0 (Spandidos Publications: | PMC Statistics: )
Metrics: Total PDF Downloads: 0 (Spandidos Publications: | PMC Statistics: )
Cited By (CrossRef): 0 citations Loading Articles...

This article is mentioned in:



Abstract

Breast cancer (BC) is the most common cancer and the main cause of mortality due to cancer in women around the World. Histone deacetylase 6 (HDAC6) is a promising target for the treatment of BC. In the present study, a series of novel 3‑carboxy‑coumarin sulfonamides, analogs of belinostat, targeting HDAC6 were designed and synthesized. The compounds were synthesized and purified through open‑column chromatography. Characterization was performed using spectroscopic techniques, including 1H and 13C NMR, homonuclear and heteronuclear correlation experiments, IR and UV. Molecular docking was carried out using AutoDock Vina implemented in UCSF Chimera version 1.16 against the HDAC6 protein structure (PDB: 5EDU). 2D protein‑ligand interaction diagrams were generated with Maestro, and validation was conducted by redocking trichostatin A into the HDAC6 active site. Additionally, the compounds were evaluated in cancer cell lines (MDA‑MB‑231, MCF‑7 and NIH/3T3), and healthy cells using lymphocytes from healthy volunteers. In the in vitro experiments, the compounds evaluated showed cytotoxic activity against the BC cell lines MCF‑7 and MDA‑MB‑231 and the non‑malignant cells 3T3/NIH. Compounds 5, 8a‑c exhibited antiproliferative activity comparable to that of cisplatin and doxorubicin. Molecular docking studies showed that compounds with the 3‑benzoylcoumarin scaffold had favorable affinity with catalytic domain of HDAC6 and whose interactions are similar to those found in belinostat. Compounds 5, 8b, 8c, 4c, and 8a exhibited higher viability against nonmalignant cells (leukocytes), with percentages ranging from 73‑87%, demonstrating 3‑4‑fold lower potency than belinostat against healthy cells.
View Figures

Figure 1

Figure 2

Figure 3

Figure 4

Figure 5

Figure 6

Figure 7

Figure 8

View References

1 

Lüönd F, Tiede S and Christofori G: Breast cancer as an example of tumour heterogeneity and tumour cell plasticity during malignant progression. Br J Cancer. 125:164–175. 2021.PubMed/NCBI View Article : Google Scholar

2 

Akram M, Iqbal M, Daniyal M and Khan AU: Awareness and current knowledge of breast cancer. Biol Res. 50(33)2017.PubMed/NCBI View Article : Google Scholar

3 

van den Boogaard WMC, Komninos DSJ and Vermeij WP: Chemotherapy side-effects: Not All DNA damage is equal. Cancers (Basel). 14(627)2022.PubMed/NCBI View Article : Google Scholar

4 

Eckschlager T, Plch J, Stiborova M and Hrabeta J: Histone deacetylase inhibitors as anticancer drugs. Int J Mol Sci. 18(1414)2017.PubMed/NCBI View Article : Google Scholar

5 

Ružić D, Đoković N, Nikolić K and Vujić Z: Medicinal chemistry of histone deacetylase inhibitors. Arh Farm. 71:73–100. 2021.

6 

Yang H, Salz T, Zajac-Kaye M, Liao D, Huang S and Qiu Y: Overexpression of histone deacetylases in cancer cells is controlled by interplay of transcription factors and epigenetic modulators. FASEB J. 28:4265–4279. 2014.PubMed/NCBI View Article : Google Scholar

7 

Sakamoto KM and Aldana-Masangkay GI: The role of HDAC6 in cancer. J Biomed Biotechnol. 2011(875824)2011.PubMed/NCBI View Article : Google Scholar

8 

Matthews GM, Newbold A and Johnstone RW: Intrinsic and extrinsic apoptotic pathway signaling as determinants of histone deacetylase inhibitor antitumor activity. Adv Cancer Res. 116:165–197. 2012.PubMed/NCBI View Article : Google Scholar

9 

Bondarev AD, Attwood MM, Jonsson J, Chubarev VN, Tarasov VV and Schiöth HB: Recent developments of HDAC inhibitors: Emerging indications and novel molecules. Br J Clin Pharmacol. 87:4577–4597. 2021.PubMed/NCBI View Article : Google Scholar

10 

Campbell P and Thomas CM: Belinostat for the treatment of relapsed or refractory peripheral T-cell lymphoma. J Oncol Pharm Pract. 23:143–147. 2017.PubMed/NCBI View Article : Google Scholar

11 

El Omari N, Bakrim S, Khalid A, Albratty M, Abdalla AN, Lee LH, Goh KW, Ming LC and Bouyahya A: Anticancer clinical efficiency and stochastic mechanisms of belinostat. Biomed Pharmacother. 165(115212)2023.PubMed/NCBI View Article : Google Scholar

12 

Han XL, Du J, Zheng YD, Dai JJ, Lin SW, Zhang BY, Zhong FB, Lin ZG, Jiang SQ, Wei W and Fang ZY: CXCL1 clone evolution induced by the HDAC inhibitor belinostat might be a favorable prognostic indicator in triple-negative breast cancer. Biomed Res Int. 2021(5089371)2021.PubMed/NCBI View Article : Google Scholar

13 

Tuncer Z, Kurar E and Duran T: Investigation of the effect of belinostat on MCF-7 breast cancer stem cells via the Wnt, Notch, and Hedgehog signaling pathway. Saudi Med J. 45:121–127. 2024.PubMed/NCBI View Article : Google Scholar

14 

Tuncer Z, Duran T, Gunes C and Kurar E: Apoptotic effect of belinostat (PXD101) on MCF-7 cancer cells. Ann Med Res. 28:941–945. 2021.

15 

Lu P, Gu Y, Li L, Wang F, Yang X and Yang Y: Belinostat suppresses cell proliferation by inactivating Wnt/β-catenin pathway and promotes apoptosis through regulating PKC pathway in breast cancer. Artif Cells Nanomed Biotechnol. 47:3955–3960. 2019.PubMed/NCBI View Article : Google Scholar

16 

Stefanachi A, Leonetti F, Pisani L, Catto M and Carotti A: Coumarin: A natural, privileged and versatile scaffold for bioactive compounds. Molecules. 23(250)2018.PubMed/NCBI View Article : Google Scholar

17 

Flores-Morales V, Villasana-Ruíz AP, Garza-Veloz I, González-Delgado S and Martinez-Fierro ML: Therapeutic effects of coumarins with different substitution patterns. Molecules. 28(2413)2023.PubMed/NCBI View Article : Google Scholar

18 

Yang F, Zhao N, Song J, Zhu K, Jiang CS, Shan P and Zhang H: Design, synthesis and biological evaluation of novel coumarin-based hydroxamate derivatives as histone deacetylase (Hdac) inhibitors with antitumor activities. Molecules. 24(2569)2019.PubMed/NCBI View Article : Google Scholar

19 

Balbuena-Rebolledo I, Rivera-Antonio AM, Sixto-López Y, Basurto J, Rosales-Hernández MC, Mendieta-Wejebe JE, Martínez-Martínez FJ, Olivares-Corichi IM, García-Sánchez JR, Guevara-Salazar JA, et al: Dihydropyrazole-carbohydrazide derivatives with dual activity as antioxidant and anti-proliferative drugs on breast cancer targeting the HDAC6. Pharmaceuticals (Basel). 15(690)2022.PubMed/NCBI View Article : Google Scholar

20 

Calderón-Segura ME, Gómez-Arroyo S, Villalobos-Pietrini R, Martínez-Valenzuela C, Carbajal-López Y, Calderón-Ezquerro Mdel C, Cortés-Eslava J, García-Martínez R, Flores-Ramírez D, Rodríguez-Romero MI, et al: Evaluation of genotoxic and cytotoxic effects in human peripheral blood lymphocytes exposed in vitro to neonicotinoid insecticides news. J Toxicol. 2012(612647)2012.PubMed/NCBI View Article : Google Scholar

21 

Hernández-Fuentes GA, Delgado-Enciso I, Enríquez-Maldonado IG, Delgado-Machuca JJ, Zaizar-Fregoso S, Hernandez-Rangel AE, Garcia-Casillas AC, Guzman-Esquivel J, Rodriguez-Sanchez IP, Martinez-Fierro ML, et al: Antitumor effects of annopurpuricin A, an acetogenin from the roots of annona purpurea. Rev Bras Farmacogn. 34:111–121. 2024.

22 

Haji Agha Bozorgi A and Zarghi A: Search for the pharmacophore of histone deacetylase inhibitors using pharmacophore query and docking study. Iran J Pharm Res. 13:1165–1172. 2014.PubMed/NCBI

23 

Zagni C, Citarella A, Oussama M, Rescifina A, Maugeri A, Navarra M, Scala A, Piperno A and Micale N: Hydroxamic acid-based histone deacetylase (HDAC) inhibitors bearing a pyrazole scaffold and a cinnamoyl linker. Int J Mol Sci. 20(945)2019.PubMed/NCBI View Article : Google Scholar

24 

Zhang JH, Mottamal M, Jin HS, Guo S, Gu Y, Wang G and Zhao LM: Design, synthesis and evaluation of belinostat analogs as histone deacetylase inhibitors. Future Med Chem. 11:2765–2778. 2019.PubMed/NCBI View Article : Google Scholar

25 

Shen S and Kozikowski AP: Why hydroxamates may not be the best histone deacetylase inhibitors-what some may have forgotten or would rather forget? ChemMedChem. 11:15–21. 2016.PubMed/NCBI View Article : Google Scholar

26 

Zhang L, Zhang J, Jiang Q, Zhang L and Song W: Zinc binding groups for histone deacetylase inhibitors. J Enzyme Inhib Med Chem. 33:714–721. 2018.PubMed/NCBI View Article : Google Scholar

27 

Vickers CJ, Olsen CA, Leman LJ and Ghadiri MR: Discovery of HDAC inhibitors that lack an active site Zn(2+)-binding functional group. ACS Med Chem Lett. 3:505–508. 2012.PubMed/NCBI View Article : Google Scholar

28 

Traoré MDM, Zwick V, SimoÌes-Pires CA, Nurisso A, Issa M, Cuendet M, Maynadier M, Wein S, Vial H, Jamet H and Wong YS: Hydroxyl ketone-based histone deacetylase inhibitors to gain insight into class I HDAC selectivity versus that of HDAC6. ACS Omega. 2:1550–1562. 2017.PubMed/NCBI View Article : Google Scholar

29 

Yu W, Liu J, Clausen D, Yu Y, Duffy JL, Wang M, Xu S, Deng L, Suzuki T, Chung CC, et al: Discovery of zthyl ketone-based highly selective HDACs 1, 2, 3 inhibitors for HIV latency reactivation with minimum cellular potency serum shift and reduced hERG activity. J Med Chem. 64:4709–4729. 2021.PubMed/NCBI View Article : Google Scholar

30 

Osko JD and Christianson DW: Structural basis of catalysis and inhibition of HDAC6 CD1, the enigmatic catalytic domain of histone deacetylase 6. Biochemistry. 58:4912–4924. 2019.PubMed/NCBI View Article : Google Scholar

31 

Lobera M, Madauss KP, Pohlhaus DT, Wright QG, Trocha M, Schmidt DR, Baloglu E, Trump RP, Head MS, Hofmann GA, et al: Selective class IIa histone deacetylase inhibition via a nonchelating zinc-binding group. Nat Chem Biol. 9:319–325. 2013.PubMed/NCBI View Article : Google Scholar

32 

Butler KV, Kalin J, Brochier C, Vistoli G, Langley B and Kozikowski AP: Rational design and simple chemistry yield a superior, neuroprotective HDAC6 inhibitor, tubastatin A. J Am Chem Soc. 132:10842–10846. 2010.PubMed/NCBI View Article : Google Scholar

33 

Sixto-López Y, Gómez-Vidal JA, de Pedro N, Bello M, Rosales-Hernández MC and Correa-Basurto J: Hydroxamic acid derivatives as HDAC1, HDAC6 and HDAC8 inhibitors with antiproliferative activity in cancer cell lines. Sci Rep. 10(10462)2020.PubMed/NCBI View Article : Google Scholar

34 

Osko JD and Christianson DW: Structural determinants of affinity and selectivity in the binding of inhibitors to histone deacetylase 6. Bioorg Med Chem Lett. 30(127023)2020.PubMed/NCBI View Article : Google Scholar

35 

Villa-Martínez CA, Magaña-Vergara NE, Rodríguez M, Mojica-Sánchez JP, Ramos-Organillo ÁA, Barroso-Flores J, Padilla-Martínez II and Martínez-Martínez FJ: Synthesis, optical characterization in solution and solid-state, and DFT calculations of 3-acetyl and 3-(1'-(2'-phenylhydrazono)ethyl)-coumarin-(7)-substituted derivatives. Molecules. 27(3677)2022.PubMed/NCBI View Article : Google Scholar

36 

Martínez-Martínez FJ, Padilla-Martínez II and Trujillo-Ferrara J: 1H and 13C NMR assignments of 2-oxo-2H-1-benzopyran-3-acyl and -3-amide derivatives. Magn Reson Chem. 39:765–767. 2001.

37 

García-Báez EV, Martínez-Martínez FJ, Höpfl H and Padilla-Martínez II: π-Stacking Interactions and CH···X (X=O, Aryl) hydrogen bonding as directing features of the supramolecular self-association in 3-carboxy and 3-amido coumarin derivatives. Cryst Growth Des. 3:35–45. 2003.

38 

Shen S and Kozikowski AP: A patent review of histone deacetylase 6 inhibitors in neurodegenerative diseases (2014-2019). Expert Opin Ther Pat. 30:121–136. 2020.PubMed/NCBI View Article : Google Scholar

39 

Vögerl K, Ong N, Senger J, Herp D, Schmidtkunz K, Marek M, Müller M, Bartel K, Shaik TB, Porter NJ, et al: Synthesis and biological investigation of phenothiazine-based benzhydroxamic acids as selective histone deacetylase 6 inhibitors. J Med Chem. 62:1138–1166. 2019.PubMed/NCBI View Article : Google Scholar

40 

Campiani G, Cavella C, Osko JD, Brindisi M, Relitti N, Brogi S, Saraswati AP, Federico S, Chemi G, Maramai S, et al: Harnessing the role of HDAC6 in idiopathic pulmonary fibrosis: Design, synthesis, structural analysis, and biological evaluation of potent inhibitors. J Med Chem. 64:9960–9988. 2021.PubMed/NCBI View Article : Google Scholar

41 

Saraswati AP, Relitti N, Brindisi M, Osko JD, Chemi G, Federico S, Grillo A, Brogi S, McCabe NH, Turkington RC, et al: Spiroindoline-capped selective HDAC6 inhibitors: Design, synthesis, structural analysis, and biological evaluation. ACS Med Chem Lett. 11:2268–2276. 2020.PubMed/NCBI View Article : Google Scholar

42 

Xu Y, Tang H, Xu Y, Guo J, Zhao X, Meng Q and Xiao J: Design, synthesis, bioactivity evaluation, crystal structures, and in silico studies of new α-amino amide derivatives as potential histone deacetylase 6 inhibitors. Molecules. 27(3335)2022.PubMed/NCBI View Article : Google Scholar

43 

Takla FN, Bayoumi WA, El-Messery SM and Nasr MNA: Developing multitarget coumarin based anti-breast cancer agents: Synthesis and molecular modeling study. Sci Rep. 13(13370)2023.PubMed/NCBI View Article : Google Scholar

44 

Sodji QH, Kornacki JR, McDonald JF, Mrksich M and Oyelere AK: Design and structure activity relationship of tumor-homing histone deacetylase inhibitors conjugated to folic and pteroic acids. Eur J Med Chem. 96:340–359. 2015.PubMed/NCBI View Article : Google Scholar

45 

Zhang Z, Yamashita H, Toyama T, Sugiura H, Omoto Y, Ando Y, Mita K, Hamaguchi M, Hayashi S and Iwase H: HDAC6 expression is correlated with better survival in breast cancer. Clin Cancer Res. 10:6962–6968. 2004.PubMed/NCBI View Article : Google Scholar

46 

Rey M, Irondelle M, Waharte F, Lizarraga F and Chavrier P: HDAC6 is required for invadopodia activity and invasion by breast tumor cells. Eur J Cell Biol. 90:128–135. 2011.PubMed/NCBI View Article : Google Scholar

47 

Park SY, Jun JA, Jeong KJ, Heo HJ, Sohn JS, Lee HY, Park CG and Kang J: Histone deacetylases 1, 6 and 8 are critical for invasion in breast cancer. Oncol Rep. 25:1677–1681. 2011.PubMed/NCBI View Article : Google Scholar

48 

Vale N, Silva S, Duarte D, Crista DMA, Pinto da Silva L and Esteves da Silva JCG: Normal breast epithelial MCF-10A cells to evaluate the safety of carbon dots. RSC Med Chem. 12:245–253. 2020.PubMed/NCBI View Article : Google Scholar

49 

Paine TM, Soule HD, Pauley RJ and Dawson PJ: Characterization of epithelial phenotypes in mortal and immortal human breast cells. Int J Cancer. 50:463–473. 1992.PubMed/NCBI View Article : Google Scholar

50 

United Mexican States and General Health Council: 2018 Edition of the Basic Framework and Catalogue of Medicines. Official Journal of the Federation, Mexico, 2018 (In Spanish). https://www.dof.gob.mx/nota_detalle.php?codigo=5544613&fecha=23/11/2018#gsc.tab=0.

51 

Jasso L, Lifshitz A, Arrieta O, Burgos R, Campillo C, Celis MÁ, de la Llata M, Domínguez J, Halabe J, Islas S, et al: Importance of the list of essential medicines in medical prescription. Gac Med Mex. 156:598–599. 2020.PubMed/NCBI View Article : Google Scholar

52 

Romani AMP: Cisplatin in cancer treatment. Biochem Pharmacol. 206(115323)2022.PubMed/NCBI View Article : Google Scholar

53 

Nauta IH, Klausch T, van de Ven PM, Hoebers FJP, Licitra L, Poli T, Scheckenbach K, Brakenhoff RH, Berkhof J and René Leemans C: The important role of cisplatin in the treatment of HPV-positive oropharyngeal cancer assessed by real-world data analysis. Oral Oncol. 121(105454)2021.PubMed/NCBI View Article : Google Scholar

Related Articles

  • Abstract
  • View
  • Download
  • Twitter
Copy and paste a formatted citation
Spandidos Publications style
Madrigal‑Angulo JL, Hernández‑Fuentes GA, Parra‑Delgado H, Olvera‑Valdéz M, Padilla‑Martínez II, Cabrera‑Licona A, Espinosa‑Gil AS, Delgado‑Enciso I and Martínez‑Martínez FJ: Design, synthesis, biological and <em>in silico</em> evaluation of 3‑carboxy‑coumarin sulfonamides as potential antiproliferative agents targeting HDAC6. Biomed Rep 22: 6, 2025.
APA
Madrigal‑Angulo, J.L., Hernández‑Fuentes, G.A., Parra‑Delgado, H., Olvera‑Valdéz, M., Padilla‑Martínez, I.I., Cabrera‑Licona, A. ... Martínez‑Martínez, F.J. (2025). Design, synthesis, biological and <em>in silico</em> evaluation of 3‑carboxy‑coumarin sulfonamides as potential antiproliferative agents targeting HDAC6. Biomedical Reports, 22, 6. https://doi.org/10.3892/br.2024.1884
MLA
Madrigal‑Angulo, J. L., Hernández‑Fuentes, G. A., Parra‑Delgado, H., Olvera‑Valdéz, M., Padilla‑Martínez, I. I., Cabrera‑Licona, A., Espinosa‑Gil, A. S., Delgado‑Enciso, I., Martínez‑Martínez, F. J."Design, synthesis, biological and <em>in silico</em> evaluation of 3‑carboxy‑coumarin sulfonamides as potential antiproliferative agents targeting HDAC6". Biomedical Reports 22.1 (2025): 6.
Chicago
Madrigal‑Angulo, J. L., Hernández‑Fuentes, G. A., Parra‑Delgado, H., Olvera‑Valdéz, M., Padilla‑Martínez, I. I., Cabrera‑Licona, A., Espinosa‑Gil, A. S., Delgado‑Enciso, I., Martínez‑Martínez, F. J."Design, synthesis, biological and <em>in silico</em> evaluation of 3‑carboxy‑coumarin sulfonamides as potential antiproliferative agents targeting HDAC6". Biomedical Reports 22, no. 1 (2025): 6. https://doi.org/10.3892/br.2024.1884
Copy and paste a formatted citation
x
Spandidos Publications style
Madrigal‑Angulo JL, Hernández‑Fuentes GA, Parra‑Delgado H, Olvera‑Valdéz M, Padilla‑Martínez II, Cabrera‑Licona A, Espinosa‑Gil AS, Delgado‑Enciso I and Martínez‑Martínez FJ: Design, synthesis, biological and <em>in silico</em> evaluation of 3‑carboxy‑coumarin sulfonamides as potential antiproliferative agents targeting HDAC6. Biomed Rep 22: 6, 2025.
APA
Madrigal‑Angulo, J.L., Hernández‑Fuentes, G.A., Parra‑Delgado, H., Olvera‑Valdéz, M., Padilla‑Martínez, I.I., Cabrera‑Licona, A. ... Martínez‑Martínez, F.J. (2025). Design, synthesis, biological and <em>in silico</em> evaluation of 3‑carboxy‑coumarin sulfonamides as potential antiproliferative agents targeting HDAC6. Biomedical Reports, 22, 6. https://doi.org/10.3892/br.2024.1884
MLA
Madrigal‑Angulo, J. L., Hernández‑Fuentes, G. A., Parra‑Delgado, H., Olvera‑Valdéz, M., Padilla‑Martínez, I. I., Cabrera‑Licona, A., Espinosa‑Gil, A. S., Delgado‑Enciso, I., Martínez‑Martínez, F. J."Design, synthesis, biological and <em>in silico</em> evaluation of 3‑carboxy‑coumarin sulfonamides as potential antiproliferative agents targeting HDAC6". Biomedical Reports 22.1 (2025): 6.
Chicago
Madrigal‑Angulo, J. L., Hernández‑Fuentes, G. A., Parra‑Delgado, H., Olvera‑Valdéz, M., Padilla‑Martínez, I. I., Cabrera‑Licona, A., Espinosa‑Gil, A. S., Delgado‑Enciso, I., Martínez‑Martínez, F. J."Design, synthesis, biological and <em>in silico</em> evaluation of 3‑carboxy‑coumarin sulfonamides as potential antiproliferative agents targeting HDAC6". Biomedical Reports 22, no. 1 (2025): 6. https://doi.org/10.3892/br.2024.1884
Follow us
  • Twitter
  • LinkedIn
  • Facebook
About
  • Spandidos Publications
  • Careers
  • Cookie Policy
  • Privacy Policy
How can we help?
  • Help
  • Live Chat
  • Contact
  • Email to our Support Team