Anticancer activity of some polyamine derivatives on human prostate and breast cancer cell lines

  • Marta Szumilak
  • Malgorzata Galdyszynska
  • Kamila Dominska
  • Andrzej Stanczak
  • Agnieszka Wanda Piastowska-Ciesielska Department of Comparative Endocrinology, Faculty of Biomedical Sciences and Postgraduate Training, Medical University of Lodz,
Keywords: polyamine derivatives, prostate cancer, breast cancer, mitochondrial potential, cell cycle, apop-tosis

Abstract

The aim of this study was to expand our knowledge about anticancer activity of some polyamine derivatives with quinoline or chromane as terminal moieties. Tested compounds were evaluated in vitro towards metastatic human prostate adenocarcinoma (PC3), human carcinoma (DU145) and mammary gland adenocarcinoma (MCF7) cell lines. Cell viability was estimated on the basis of mitochondrial metabolic activity using watersoluble tetrazolium WST1 to establish effective concentrations of the tested compounds under experimental conditions. Cytotoxic potential of polyamine derivatives was determined by the measurement of lactate dehydrogenase activity released from damaged cells, changes in mitochondrial membrane potential, the cell cycle distribution analysis and apoptosis assay. It was revealed that the tested polyamine derivatives differed markedly in their antiproliferative activity. Bischromane derivative 5a exhibited a rather cytostatic than cytotoxic effect on the tested cells, whereas quinoline derivative 3a caused changes in cell membrane integrity, inhibited cell cycle progression, as well as induced apoptosis of prostate and breast cancer cells which suggest its potential application in cancer therapy.

References

Awadallah, El-Waei, Hanna, Abbas, Ceruso, Oz, Guler, and Supuran (4-15-2015) Synthesis, carbonic anhydrase inhibition and cytotoxic activity of novel chromone-based sulfonamide derivatives.Eur.J.Med.Chem. 96: 425-435. 10.1016/j.ejmech.2015.04.033 [doi]

Brana, Cacho, Gradillas, de Pascual-Teresa, and Ramos (2001) Intercalators as anticancer drugs.Curr.Pharm.Des 7: 1745-1780.

Budzisz, Brzezinska, Krajewska, and Rozalski (2003) Cytotoxic effects, alkylating properties and molecular modelling of coumarin derivatives and their phosphonic analogues.Eur.J.Med.Chem. 38: 597-603.

Burns, LaTurner, Ziemer, McVean, Devens, Carlson, Graminski, Vanderwerf, Weeks, and Carreon (5-6-2002) Induction of apoptosis by aryl-substituted diamines: role of aromatic group substituents and distance between nitrogens.Bioorg.Med.Chem.Lett. 12: 1263-1267.

Deady, Kaye, Finlay, Baguley, and Denny (6-20-1997) Synthesis and antitumor properties of N-[2-(dimethylamino)ethyl]carboxamide derivatives of fused tetracyclic quinolines and quinoxalines: a new class of putative topoisomerase inhibitors.J.Med.Chem. 40: 2040-2046. 10.1021/jm970044r [doi]]

Dominska, Piastowska-Ciesielska, Lachowicz-Ochedalska, and Ochedalski (2012) Similarities and differences between effects of angiotensin III and angiotensin II on human prostate cancer cell migration and proliferation.Peptides 37: 200-206.;10.1016/j.peptides.2012.07.022 [doi]

Ellem, De-Juan-Pardo, and Risbridger (12-15-2014) In vitro modeling of the prostate cancer microenvironment.Adv.Drug Deliv.Rev. 79-80: 214-221.;10.1016/j.addr.2014.04.008 [doi]

Fan, Wang, Zhao, Zhang, and Miao (5-1-2006) Chloroquine inhibits cell growth and induces cell death in A549 lung cancer cells.Bioorg.Med.Chem. 14: 3218-3222.;10.1016/j.bmc.2005.12.035 [doi]

Hansch & Verma (2007) 20-(S)-camptothecin analogues as DNA topoisomerase I inhibitors: a QSAR study.ChemMedChem. 2: 1807-1813. 10.1002/cmdc.200700138 [doi]

Jemal, Bray, Center, Ferlay, Ward, and Forman (2011) Global cancer statistics.CA Cancer J.Clin. 61: 69-90. 10.3322/caac.20107 [doi]

Latosinska & Latosinska (2013) Anticancer Drug Discovery — From Serendipity to Rational Design. Drug DiscoveryHany El-ShemyISBN 978-953-51-0906-8 http://cdn.intechopen.com/pdfs-wm/41943.pdf

Li, Li, Bai, Suo, Zhang, and Cao (2015) Matrine inhibited proliferation and increased apoptosis in human breast cancer MCF-7 cells via upregulation of Bax and downregulation of Bcl-2.Int.J.Clin.Exp.Pathol. 8: 14793-14799.

Ma & Adjei (2009) Novel agents on the horizon for cancer therapy.CA Cancer J.Clin. 59: 111-137. 10.3322/caac.20003 [doi]

Ming, Ruan, Wang, Ye, Fan, Meng, Tian, and Huang (12-1-2015) A novel chemical, STF-083010, reverses tamoxifen-related drug resistance in

breast cancer by inhibiting IRE1/XBP1.Oncotarget. 6: 40692-40703. 10.18632/oncotarget.5827 [doi]

Nawrot-Modranka, Nawrot, and Graczyk (2006) In vivo antitumor, in vitro antibacterial activity and alkylating properties of phosphorohydrazine derivatives of coumarin and chromone.Eur.J.Med.Chem. 41: 1301-1309. 10.1016/j.ejmech.2006.06.004 [doi]

Olszewska, Szymanski, Mikiciuk-Olasik, and Szymanski (4-15-2014) New cyclopentaquinoline derivatives with fluorobenzoic acid induce G1 arrest and apoptosis in human lung adenocarcinoma cells.Eur.J.Pharmacol. 729: 30-36. 10.1016/j.ejphar.2014.02.003 [doi]

Piastowska-Ciesielska, Kozlowski, Wagner, Dominska, and Ochedalski (8-30-2013) Effect of an angiotensin II type 1 receptor blocker on caveolin-1 expression in prostate cancer cells.Arch.Med.Sci. 9: 739-744. 10.5114/aoms.2012.30955 [doi]

Rescifina, Zagni, Varrica, Pistara, and Corsaro (3-3-2014) Recent advances in small organic molecules as DNA intercalating agents: synthesis, activity, and modeling.Eur.J.Med.Chem. 74: 95-115. 10.1016/j.ejmech.2013.11.029 [doi]

Sahu, Sidhar, Ghate, Advirao, Raghavan, and Giri (2013) A Novel Anticancer Agent, 8-Methoxypyrimido[4',5':4,5]thieno(2,3-) Quinoline-4(3H)-One Induces Neuro 2a Neuroblastoma Cell Death through p53-Dependent, Caspase-Dependent and -Independent Apoptotic Pathways.PLoS.One. 8: e66430-10.1371/journal.pone.0066430 [doi]

Saleh, Aljada, El-Abadelah, Sabri, Zahra, Nasr, and Aziz (2015a) The pyridone-annelated isoindigo (5'-Cl) induces apoptosis, dysregulation of mitochondria and formation of ROS in leukemic HL-60 cells.Cell Physiol Biochem. 35: 1958-1974. 000374004 [pii];10.1159/000374004 [doi]

Saleh, El-Abadelah, Aziz, Taha, Nasr, and Rizvi (6-1-2015b) Antiproliferative activity of the isoindigo 5'-Br in HL-60 cells is mediated by apoptosis, dysregulation of mitochondrial functions and arresting cell cycle at G0/G1 phase.Cancer Lett. 361: 251-261. S0304-3835(15)00193-7 [pii];10.1016/j.canlet.2015.03.013 [doi]

Sampson, Neuwirt, Puhr, Klocker, and Eder (2013) In vitro model systems to study androgen receptor signaling in prostate cancer.Endocr.Relat Cancer 20: R49-R64. ERC-12-0401 [pii];10.1530/ERC-12-0401 [doi]

Sato, Fukazawa, Suzuki, Yusa, and Tsuruo (5-1-1991) Circumvention of multidrug resistance by a newly synthesized quinoline derivative, MS-073.Cancer Res. 51: 2420-2424.

Siegel, Naishadham, and Jemal (2013) Cancer statistics, 2013.CA Cancer J.Clin. 63: 11-30. 10.3322/caac.21166 [doi]

Siegel, Miller, and Jemal (2016) Cancer statistics, 2016.CA Cancer J.Clin. 66: 7-30. 10.3322/caac.21332 [doi]

Szulawska-Mroczek, Szumilak, Szczesio, Olczak, Nazarski, Lewgowd, Czyz, and Stanczak (2013) Synthesis and biological evaluation of new bischromone derivatives with antiproliferative activity.Arch.Pharm.(Weinheim) 346: 34-43. 10.1002/ardp.201200220 [doi]

Szumilak, Szulawska-Mroczek, Koprowska, Stasiak, Lewgowd, Stanczak, and Czyz (2010) Synthesis and in vitro biological evaluation of new polyamine conjugates as potential anticancer drugs.Eur.J.Med.Chem. 45: 5744-5751. 10.1016/j.ejmech.2010.09.032 [doi]

Taher & Hegazy (2013) Synthesis of novel bis-anthraquinone derivatives and their biological evaluation as antitumor agents.Arch.Pharm.Res. 36: 573-578. 10.1007/s12272-013-0074-x [doi]

Tse & Boger (2004) Sequence-selective DNA recognition: natural products and nature's lessons.Chem.Biol. 11: 1607-1617.;10.1016/j.chembiol.2003.08.012 [doi]

Walczak & Carducci (2007) Prostate cancer: a practical approach to current management of recurrent disease.Mayo Clin.Proc. 82: 243-249. 10.4065/82.2.243 [doi]

Wojciechowska & Didkowska Illness and deaths from malignant tumors in Poland. National Cancer Registry, Cancer Centre - Institute for them. Maria Sklodowska - Curie. ISSN 0867–8251 http://onkologia.org.pl/wp-content/uploads/BIUL 2013.pdf

Xiong, Wang, Zhang, DeLa, Leon, Zhang, Zheng, Wang, and Chen (2015)

Design, Synthesis, and Evaluation of Genistein Analogues as Anti-Cancer Agents.Anticancer Agents Med.Chem. 15: 1197-1203.

Published
2017-07-11
Section
Articles