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
Oncology Letters
Join Editorial Board Propose a Special Issue
Print ISSN: 1792-1074 Online ISSN: 1792-1082
Journal Cover
June-2017 Volume 13 Issue 6

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
June-2017 Volume 13 Issue 6

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
Article

Design and synthesis of novel N(4)-substituted thiosemicarbazones bearing a pyrrole unit as potential anticancer agents

  • Authors:
    • Taofeng Zhu
    • Shanshan Shen
    • Qin Lu
    • Xingpei Ye
    • Weiliang Ding
    • Ruhua Chen
    • Jing Xie
    • Wenjiao Zhu
    • Jun Xu
    • Lei Jia
    • Weina Wu
    • Tieliang Ma
  • View Affiliations / Copyright

    Affiliations: Department of Respiratory Disease, The First Affiliated Hospital of Soochow University, Suzhou, Jiangsu 215006, P.R. China, Department of Gastroenterology, The Affiliated Drum Tower Hospital of Nanjing University Medical School, Nanjing, Jiangsu 210008, P.R. China, Department of Physics and Chemistry, College of Chemistry and Chemical Engineering, Henan Polytechnic University, Jiaozuo, Henan 454000, P.R. China, Central Laboratory, The Affiliated Yixing Hospital of Jiangsu University, Yixing, Jiangsu 214200, P.R. China, Department of Geriatrics, The Affiliated Yixing Hospital of Jiangsu University, Yixing, Jiangsu 214200, P.R. China
  • Pages: 4493-4500
    |
    Published online on: April 5, 2017
       https://doi.org/10.3892/ol.2017.5995
  • 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

A series of N(4)-substituted thiosemicarbazones (TSCs) bearing pyrrole unit (1a‑1e) were synthesized and fully characterized by elemental analyses, infrared spectra, 1H nuclear magnetic resonance and single crystal X‑ray diffraction. The compounds were assessed as potential chemotherapeutic agents. All newly synthesized compounds were screened for their anticancer activity against lung cancer PC‑9, esophageal cancer Eca‑109 and gastric cancer SGC‑7901 cell lines. The results of MTT, Terminal deoxynucleotidyl transferase dUTP nick end labeling and fluorescence-activated cell sorting assays indicated that all the prepared compounds exhibited cytotoxicity against PC-9, Eca-109 and SGC-7901 cells in vitro. All the compounds significantly induced cancer cell apoptosis accompanied by increasing the Bax/Bcl‑2 ratio and activation of caspase‑3. The structure‑activity association was discussed and the potential pre‑clinical trials may be conducted. The present findings have a great potential in biomedical applications of novel N(4)‑substituted TSCs.
View Figures

Figure 1

Figure 2

Figure 3

Figure 4

Figure 5

View References

1 

Huang H, Chen Q, Ku X, Meng L, Lin L, Wang X, Zhu C, Wang Y, Chen Z, Li M, et al: A series of alpha-heterocyclic carboxaldehyde thiosemicarbazones inhibit topoisomerase IIalpha catalytic activity. J Med Chem. 53:3048–3064. 2010. View Article : Google Scholar : PubMed/NCBI

2 

Jansson PJ, Sharpe PC, Bernhardt PV and Richardson DR: Novel thiosemicarbazones of the ApT and DpT series and their copper complexes: Identification of pronounced redox activity and characterization of their antitumor activity. J Med Chem. 53:5759–5769. 2010. View Article : Google Scholar : PubMed/NCBI

3 

Soares MA, Lessa JA, Mendes IC, Da Silva JG, Dos Santos RG, Salum LB, Daghestani H, Andricopulo AD, Day BW, Vogt A, et al: N(4)-Phenyl-substituted 2-acetylpyridine thiosemicarbazones: Cytotoxicity against human tumor cells, structure-activity relationship studies and investigation on the mechanism of action. Bioorg Med Chem. 20:3396–3409. 2012. View Article : Google Scholar : PubMed/NCBI

4 

Enyedy ÉA, Primik MF, Kowol CR, Arion VB, Kiss T and Keppler BK: Interaction of Triapine and related thiosemicarbazones with iron (III)/(II) and gallium (III): A comparative solution equilibrium study. Dalton Trans. 40:5895–5905. 2011. View Article : Google Scholar : PubMed/NCBI

5 

Kowol CR, Trondl R, Arion VB, Jakupec MA, Lichtscheidl I and Keppler BK: Fluorescence properties and cellular distribution of the investigational anticancer drug triapine (3-aminopyridine-2-carboxaldehyde thiosemicarbazone) and its zinc (II) complex. Dalton Trans. 39:704–706. 2010. View Article : Google Scholar : PubMed/NCBI

6 

Zeglis BM, Divilov V and Lewis JS: Role of metalation in the topoisomerase IIα inhibition and antiproliferation activity of a series of α-heterocyclic-N4-substituted thiosemicarbazones and their Cu (II) complexes. J Med Chem. 54:2391–2398. 2011. View Article : Google Scholar : PubMed/NCBI

7 

Ramachandran E, Thomas SP, Poornima P, Kalaivani P, Prabhakaran R, Padma VV and Natarajan K: Evaluation of DNA binding, antioxidant and cytotoxic activity of mononuclear Co (III) complexes of 2-oxo-1,2-dihydrobenzo [h] quinoline-3-carbaldehyde thiosemicarbazones. Eur J Med Chem. 50:405–415. 2012. View Article : Google Scholar : PubMed/NCBI

8 

Raja DS, Paramaguru G, Bhuvanesh NS, Reibenspies JH, Renganathan R and Natarajan K: Effect of terminal N-substitution in 2-oxo-1,2-dihydroquinoline-3-carbaldehyde thiosemicarbazones on the mode of coordination, structure, interaction with protein, radical scavenging and cytotoxic activity of copper (II) complexes. Dalton Trans. 40:4548–4559. 2011. View Article : Google Scholar : PubMed/NCBI

9 

Li MX, Zhang LZ, Yang M, Niu JY and Zhou J: Synthesis, crystal structures, in vitro biological evaluation of zinc (II) and bismuth (III) complexes of 2-acetylpyrazine N(4)-phenylthiosemicarbazone. Bioorg Med Chem Lett. 22:2418–2423. 2012. View Article : Google Scholar : PubMed/NCBI

10 

Li MX, Zhang LZ, Zhang D, Ji BS and Zhao JW: Synthesis, crystal structures, and biological evaluation of manganese (II) and nickel (II) complexes of 4-cyclohexyl-1-(1-(pyrazin-2-yl)ethylidene)thiosemicarbazide. Eur J Med Chem. 46:4383–4390. 2011. View Article : Google Scholar : PubMed/NCBI

11 

Li MX, Zhang D, Zhang LZ and Niu JY: Synthesis, crystal structures, and biological activities of 2-thiophene N(4)-methylthiosemicarbazone and its unusual hexanuclear silver(I) cluster. Inorg Chem Commun. 13:1268–1271. 2010. View Article : Google Scholar

12 

Matesanz AI, Leitao I and Souza P: Palladium (II) and platinum (II) bis (thiosemicarbazone) complexes of the 2,6-diacetylpyridine series with high cytotoxic activity in cisplatin resistant A2780cisR tumor cells and reduced toxicity. J Inorg Biochem. 125:26–31. 2013. View Article : Google Scholar : PubMed/NCBI

13 

Matesanz AI and Souza P: Unprecedented Pt(II) complex of an asymmetric 2,6-diacetylpyridine bis(4N-substituted thiosemicarbazone) ligand. Inorg Chem Commun. 27:5–8. 2013. View Article : Google Scholar

14 

Palanimuthu D, Shinde SV, Somasundaram K and Samuelson AG: In vitro and in vivo anticancer activity of copper bis (thiosemicarbazone) complexes. J Med Chem. 56:722–734. 2013. View Article : Google Scholar : PubMed/NCBI

15 

Ilies DC, Pahontu E, Shova S, Gulea A and Rosu T: Synthesis, characterization and crystal structures of nickel(II), palladium(II) and copper(II) complexes with 2-furaldehyde-4-phenylthiosemicarbazone. Polyhedron. 51:307–315. 2013. View Article : Google Scholar

16 

Vine KL, Matesic L, Locke JM, Ranson M and Skropeta D: Cytotoxic and anticancer activities of isatin and its derivatives: A comprehensive review from 2000–2008. Anticancer Agents Med Chem. 9:397–414. 2009. View Article : Google Scholar : PubMed/NCBI

17 

Ye XP, Zhu TF, Wu WN, Ma TL, Zhang ZP, Wang Y and Jia L: Syntheses, characterizations and biological activities of two Cu(II) complexes with acylhydrazone ligand bearing pyrrole unit. Inorg Chem Commun. 47:60–62. 2014. View Article : Google Scholar

18 

Wang Y, Yang ZY and Chen ZN: Synthesis, characterization and DNA-binding properties of four Zn (II) complexes with bis (pyrrol-2-yl-methyleneamine) ligands. Bioorg Med Chem Lett. 18:298–303. 2008. View Article : Google Scholar : PubMed/NCBI

19 

Sheldrick GM: SADABS, program for empirical absorption correction of area detector data. University of Göttingen; Germany: 1996

20 

Sheldrick GM: SHELX-97, program for crystal structure solution and refinement. University of Göttingen; Germany: 1997

21 

Yang M, Lu YL, Li MX, Xu XW and Chen L: Synthesis, crystal structures and biological evaluation of 2-benzoylpyridine N(4)-cyclohexylthiosemicarbazone and its binuclear copper(II) complex. Inorg Chem Commun. 35:117–121. 2013. View Article : Google Scholar

22 

Nouri K and Yazdanparast R: Proliferation inhibition, cell cycle arrest and apoptosis induced in HL-60 cells by a natural diterpene ester from Daphne mucronata. Daru. 19:145–153. 2011.PubMed/NCBI

23 

Farnebo M, Bykov VJ and Wiman KG: The p53 tumor suppressor: A master regulator of diverse cellular processes and therapeutic target in cancer. Biochem Biophys Res Commun. 396:85–89. 2010. View Article : Google Scholar : PubMed/NCBI

24 

Shu D, Qing Y, Tong Q, He Y, Xing Z, Zhao Y, Li Y, Wei Y, Huang W and Wu X: Deltonin isolated from Dioscorea zingiberensis inhibits cancer cell growth through inducing mitochondrial apoptosis and suppressing Akt and mitogen activated protein kinase signals. Biol Pharm Bull. 34:1231–1239. 2011. View Article : Google Scholar : PubMed/NCBI

25 

Cory S and Adams JM: The Bcl2 family: Regulators of the cellular life-or-death switch. Nat Rev Cancer. 2:647–656. 2002. View Article : Google Scholar : PubMed/NCBI

26 

Nagaraj NS, Anilakumar KR and Singh OV: Diallyl disulfide causes caspase-dependent apoptosis in human cancer cells through a Bax-triggered mitochondrial pathway. J Nutr Biochem. 21:405–412. 2010. View Article : Google Scholar : PubMed/NCBI

27 

Han YH, Kim SZ, Kim SH and Park WH: Pyrogallol inhibits the growth of lung cancer Calu-6 cells via caspase-dependent apoptosis. Chem Biol Interact. 177:107–114. 2009. View Article : Google Scholar : PubMed/NCBI

Related Articles

  • Abstract
  • View
  • Download
  • Twitter
Copy and paste a formatted citation
Spandidos Publications style
Zhu T, Shen S, Lu Q, Ye X, Ding W, Chen R, Xie J, Zhu W, Xu J, Jia L, Jia L, et al: Design and synthesis of novel N(4)-substituted thiosemicarbazones bearing a pyrrole unit as potential anticancer agents. Oncol Lett 13: 4493-4500, 2017.
APA
Zhu, T., Shen, S., Lu, Q., Ye, X., Ding, W., Chen, R. ... Ma, T. (2017). Design and synthesis of novel N(4)-substituted thiosemicarbazones bearing a pyrrole unit as potential anticancer agents. Oncology Letters, 13, 4493-4500. https://doi.org/10.3892/ol.2017.5995
MLA
Zhu, T., Shen, S., Lu, Q., Ye, X., Ding, W., Chen, R., Xie, J., Zhu, W., Xu, J., Jia, L., Wu, W., Ma, T."Design and synthesis of novel N(4)-substituted thiosemicarbazones bearing a pyrrole unit as potential anticancer agents". Oncology Letters 13.6 (2017): 4493-4500.
Chicago
Zhu, T., Shen, S., Lu, Q., Ye, X., Ding, W., Chen, R., Xie, J., Zhu, W., Xu, J., Jia, L., Wu, W., Ma, T."Design and synthesis of novel N(4)-substituted thiosemicarbazones bearing a pyrrole unit as potential anticancer agents". Oncology Letters 13, no. 6 (2017): 4493-4500. https://doi.org/10.3892/ol.2017.5995
Copy and paste a formatted citation
x
Spandidos Publications style
Zhu T, Shen S, Lu Q, Ye X, Ding W, Chen R, Xie J, Zhu W, Xu J, Jia L, Jia L, et al: Design and synthesis of novel N(4)-substituted thiosemicarbazones bearing a pyrrole unit as potential anticancer agents. Oncol Lett 13: 4493-4500, 2017.
APA
Zhu, T., Shen, S., Lu, Q., Ye, X., Ding, W., Chen, R. ... Ma, T. (2017). Design and synthesis of novel N(4)-substituted thiosemicarbazones bearing a pyrrole unit as potential anticancer agents. Oncology Letters, 13, 4493-4500. https://doi.org/10.3892/ol.2017.5995
MLA
Zhu, T., Shen, S., Lu, Q., Ye, X., Ding, W., Chen, R., Xie, J., Zhu, W., Xu, J., Jia, L., Wu, W., Ma, T."Design and synthesis of novel N(4)-substituted thiosemicarbazones bearing a pyrrole unit as potential anticancer agents". Oncology Letters 13.6 (2017): 4493-4500.
Chicago
Zhu, T., Shen, S., Lu, Q., Ye, X., Ding, W., Chen, R., Xie, J., Zhu, W., Xu, J., Jia, L., Wu, W., Ma, T."Design and synthesis of novel N(4)-substituted thiosemicarbazones bearing a pyrrole unit as potential anticancer agents". Oncology Letters 13, no. 6 (2017): 4493-4500. https://doi.org/10.3892/ol.2017.5995
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