Synthesis and evaluation of naphthalene-based thiosemicarbazone derivatives as new anticancer agents against LNCaP prostate cancer cells

Journal of Enzyme Inhibition and Medicinal Chemistry

Volumn 31, Issue 3, 2016, Pages 410-416

  Altintop, Mehlika Dilek ^a   Sever, Belgin ^a   Özdemir, Ahmet ^a   Kuş, Gökhan ^a   Oztopcu Vatan, Pinar ^b   Kabadere, Selda ^b   Kaplancikli, Zafer Asim ^a  

^a ANADOLU UNIVERSITY   (Turkey)

^b ESKISEHIR OSMANGAZI UNIVERSITY   (Turkey)

Author keywords

Apoptosis; LNCaP cells; naphthalene; thiosemicarbazone

Indexed keywords

4 (NAPHTHALEN 1 YL) 1 (1 PHENYLETHYLIDENE)THIOSEMICARBAZIDE; 4 (NAPHTHALEN 1 YL) 1 [1 (4 BROMOPHENYL)ETHYLIDENE]THIOSEMICARBAZIDE; 4 (NAPHTHALEN 1 YL) 1 [1 (4 CHLOROPHENYL)ETHYLIDENE]THIOSEMICARBAZIDE; 4 (NAPHTHALEN 1 YL) 1 [1 (4 CYANOPHENYL)ETHYLIDENE]THIOSEMICARBAZIDE; 4 (NAPHTHALEN 1 YL) 1 [1 (4 FLUOROPHENYL)ETHYLIDENE]THIOSEMICARBAZIDE; 4 (NAPHTHALEN 1 YL) 1 [1 (4 HYDROXYPHENYL)ETHYLIDENE]THIOSEMICARBAZIDE; 4 (NAPHTHALEN 1 YL) 1 [1 (4 METHOXYPHENYL)ETHYLIDENE]THIOSEMICARBAZIDE; 4 (NAPHTHALEN 1 YL) 1 [1 (4 METHYLPHENYL)ETHYLIDENE]THIOSEMICARBAZIDE; 4 (NAPHTHALEN 1 YL) 1 [1 (4 METHYLSULFONYLPHENYL)ETHYLIDENE]THIOSEMICARBAZIDE; 4 (NAPHTHALEN 1 YL) 1 [1 (4 NITROPHENYL)ETHYLIDENE]THIOSEMICARBAZIDE; 4 (NAPHTHALEN 1 YL) 1 [1 (4 TRIFLUOROMETHOXYPHENYL)ETHYLIDENE]THIOSEMICARBAZIDE; 4 (NAPHTHALEN 1 YL) 1 [1 (4 TRIFLUOROMETHYLPHENYL)ETHYLIDENE]THIOSEMICARBAZIDE; 4 (NAPHTHALEN 1 YL) 1 [1 [4 (1 PIPERIDINYL)PHENYL]ETHYLIDENE]THIOSEMICARBAZIDE; 4 (NAPHTHALEN 1 YL) 1 [1 [4 (4 MORPHOLINYL)PHENYL]ETHYLIDENE]THIOSEMICARBAZIDE; ANTINEOPLASTIC AGENT; NAPHTHALENE DERIVATIVE; THIOSEMICARBAZONE DERIVATIVE; UNCLASSIFIED DRUG; NAPHTHALENE;

ANTINEOPLASTIC ACTIVITY; APOPTOSIS; ARTICLE; CELL DEATH; CELL VIABILITY; CONTROLLED STUDY; CYTOTOXICITY; DRUG CYTOTOXICITY; DRUG EFFECT; DRUG POTENCY; DRUG SCREENING; DRUG SYNTHESIS; FLOW CYTOMETRY; HUMAN; HUMAN CELL; IC50; LNCAP CELL LINE; MTT ASSAY; PRIORITY JOURNAL; PROSTATE CANCER; CELL PROLIFERATION; CHEMICAL STRUCTURE; CHEMISTRY; DOSE RESPONSE; DRUG EFFECTS; MALE; PATHOLOGY; PROSTATIC NEOPLASMS; STRUCTURE ACTIVITY RELATION; SYNTHESIS; TUMOR CELL CULTURE;

ANTINEOPLASTIC AGENTS; APOPTOSIS; CELL PROLIFERATION; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG SCREENING ASSAYS, ANTITUMOR; FLOW CYTOMETRY; HUMANS; MALE; MOLECULAR STRUCTURE; NAPHTHALENES; PROSTATIC NEOPLASMS; STRUCTURE-ACTIVITY RELATIONSHIP; THIOSEMICARBAZONES; TUMOR CELLS, CULTURED;

EID: 84961249306     PISSN: 14756366     EISSN: 14756374     Source Type: Journal    
DOI: 10.3109/14756366.2015.1031126     Document Type: Article

References (23)

1. Silverstein A, Silverstein V, Nunn Silverstein L. Cancer. Minneapolis (MN): Twenty-First Century Books; 2006
2. Gerritsen WR. The evolving role of immunotherapy in prostate cancer. Ann Oncol 2012; 23: 22-7
3. Culig Z. Proinflammatory cytokine interleukin-6 in prostate carcinogenesis. Am J Clin Exp Urol 2014; 2: 231-8
4. Kung HJ, Evans CP. Oncogenic activation of androgen receptor. Urol Oncol 2009; 27: 48-52
5. Suzuki H, Ueda T, Ichikawa T, Ito H. Androgen receptor involvement in the progression of prostate cancer. Endocr Relat Cancer 2003; 10: 209-16
6. Chuu CP, Kokontis JM, Hiipakka RA, et al. Androgens as therapy for androgen receptor positive castration-resistant prostate cancer. J Biomed Sci 2011; 18: 1-11
7. Culig Z, Klocker H, Bartsch G, Hobisch A. Androgen receptors in prostate cancer. Endocr Relat Cancer 2002; 9: 155-70
8. Nouri M, Ratther E, Stylianou N, et al. Androgen-targeted therapyinduced epithelial mesenchymal plasticity and neuroendocrine transdifferentiation in prostate cancer: an opportunity for intervention. Front Oncol 2014; 4: 371-6
9. Yu Y, Kalinowski DS, Kovacevic Z, et al. Thiosemicarbazones from the old to new: iron chelators that are more than just ribonucleotide reductas inhibitors. J Med Chem 2009; 52: 5271-94
10. Chapman TR, Kinsella TJ. Ribonucleotide reductase inhibitor s: a new look at an old target for radiosensitization. Front Oncol 2012; 1: 1-6
11. Moorthy NS, Cerqueira NM, Ramos MJ, Fernandes PA. Aryl-and heteroaryl-thiosemicarbazone derivatives and their metal complexes: a pharmacological template. Rec Pat Anticancer Drug Discov 2013; 8: 168-82
12. Kalinowski DS, Quach P, Richardson DR. Thiosemicarbazones: the new wave in cancer treatment. Future Med Chem 2009; 1: 1143-51
13. Álvarez C, Álvarez R, Corchete P, et al. Synthesis and biological activity of naphthalene analogues of phenstatins: naphthylphenstatins. Bioorg Med Chem Lett 2007; 17: 3417-20
14. Jiang S, Crogan-Grundy C, Drewe J, et al. Discovery of (naphthalen-4-yl)(phenyl)methanones and N-methyl-N-phenylnaphthalen-1-amines as new apoptosis inducers using a cell-and caspase-based HTS assay. Bioorg Med Chem Lett 2008; 18: 5725-8
15. Yuan JW, Wang SF, Luo ZL, et al. Synthesis and biological evaluation of compounds which contain pyrazole, thiazole and naphthalene ring as antitumor agents. Bioorg Med Chem Lett 2014; 24: 2324-8
16. Halder AK, Adhikary N, Maity MK, Jha T. Synthesis, pharmacological activity and comparative QSAR modeling of 1,5-N,N0-substituted-2-(substituted naphthalenesulphonyl)glutamamides as possible anticancer agents. Eur J Med Chem 2010; 45: 1760-71
17. Rasolofonjatovo E, Provot O, Hamze A, et al. Conformationnally restricted naphthalene derivatives type isocombretastatin A-4 and isoerianin analogues: synthesis, cytotoxicity and antitubulin activity. Eur J Med Chem 2012; 52: 22-32
18. Lokhande TN, Viswanathan CL, Joshia A, Juvekarb A. Design, synthesis and evaluation of naphthalene-2-carboxamides as reversal agents in MDR cancer. Bioorg Med Chem 2006; 14: 6022-6
19. Rajabi M, Khalilzadeh MA, Tavakolinia F, et al. Naphthalene-fused (a-alkoxycarbonyl)methylene-g-butyrolactones: antiproliferative activity and binding to bovine serum albumin and DNA. DNA Cell Biol 2012; 31: 783-9
20. Medarde M, Maya ABS, Ferez-Melero C. Naphthalene combretastatin analogues: synthesis, cytotoxicity and antitubulin activity. J Enzyme Inhib Med Chem 2004; 19: 521-40
21. Reddy GR, Kuo CC, Tan UK, et al. Synthesis and structure-activity relationships of 2-amino-1-aroylnaphthalene and 2-hydroxy-1-aroylnaphthalenes as potent antitubulin agents. J Med Chem 2008; 51: 8163-7
22. Mosmann T. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J Immunol Methods 1983; 16: 55-63
23. Van Engeland M, Nieland LJ, Ramaekers FC, et al. Annexin Vaffinity assay: a review on an apoptosis detection system based on phosphatidylserine exposure. Cytometry 1998; 31: 1-9