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Oxidative Medicine and Cellular Longevity
Volume 2017, Article ID 4069839, 15 pages
https://doi.org/10.1155/2017/4069839
Research Article

Dihydropyridine Derivatives as Cell Growth Modulators In Vitro

1Latvian Institute of Organic Synthesis, 21 Aizkraukles Str., Riga LV-1006, Latvia
2Laboratory for Oxidative Stress, Rudjer Boskovic Institute, Bijenicka 54, 10000 Zagreb, Croatia

Correspondence should be addressed to Astrida Velena; vl.iso@adirtsa and Neven Zarkovic; rh.bri@civokraz

Received 9 December 2016; Accepted 20 February 2017; Published 3 April 2017

Academic Editor: Serafina Perrone

Copyright © 2017 Imanta Bruvere et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Linked References

  1. S. Valente, P. Mellini, F. Spallotta et al., “1,4-Dihydropyridines active on the SIRT1/AMPK pathway ameliorate skin repair and mitochondrial function and exhibit inhibition of proliferation in cancer cells,” Journal of Medicinal Chemistry, vol. 59, no. 4, pp. 1471–1491, 2016. View at Publisher · View at Google Scholar · View at Scopus
  2. R. Visconti and D. Grieco, “New insights on oxidative stress in cancer,” Current Opinion in Drug Discovery and Development, vol. 12, no. 2, pp. 240–245, 2009. View at Google Scholar · View at Scopus
  3. S. Reuter, S. C. Gupta, M. M. Chaturvedi, and B. B. Aggarwal, “Oxidative stress, inflammation, and cancer: how are they linked?” Free Radical Biology and Medicine, vol. 49, no. 11, pp. 1603–1616, 2010. View at Publisher · View at Google Scholar · View at Scopus
  4. R. Novak Kujundžić, N. Žarković, and K. Gall Trošelj, “Pyridine nucleotides in regulation of cell death and survival by redox and non-redox reactions,” Critical Reviews in Eukaryotic Gene Expression, vol. 24, no. 4, pp. 287–309, 2014. View at Publisher · View at Google Scholar · View at Scopus
  5. T.-H. Leu and M.-C. Maa, “The molecular mechanisms for the antitumorigenic effect of curcumin,” Current Medicinal Chemistry - Anti-Cancer Agents, vol. 2, no. 3, pp. 357–370, 2002. View at Publisher · View at Google Scholar · View at Scopus
  6. A. Velena, N. Zarkovic, K. Gall Troselj et al., “1,4-dihydropyridine derivatives: dihydronicotinamide analogues—model compounds targeting oxidative stress,” Oxidative Medicine and Cellular Longevity, vol. 2016, Article ID 1892412, 35 pages, 2016. View at Publisher · View at Google Scholar · View at Scopus
  7. Z. Hyvönen, A. Plotniece, I. Reine, B. Chekavichus, G. Duburs, and A. Urtti, “Novel cationic amphiphilic 1,4-dihydropyridine derivatives for DNA delivery,” Biochimica et Biophysica Acta - Biomembranes, vol. 1509, no. 1-2, pp. 451–466, 2000. View at Publisher · View at Google Scholar · View at Scopus
  8. Z. Hyvönen, M. Ruponen, S. Rönkkö, P. Suhonen, and A. Urtti, “Extracellular and intracellular factors influencing gene transfection mediated by 1,4-dihydropyridine amphiphiles,” European Journal of Pharmaceutical Sciences, vol. 15, no. 5, pp. 449–460, 2002. View at Publisher · View at Google Scholar · View at Scopus
  9. A. Plotniece, K. Pajuste, D. Kaldre et al., “Oxidation of cationic 1,4-dihydropyridine derivatives as model compounds for putative gene delivery agents,” Tetrahedron, vol. 65, no. 40, pp. 8344–8349, 2009. View at Publisher · View at Google Scholar · View at Scopus
  10. K. Pajuste, Z. Hyvönen, O. Petrichenko et al., “Gene delivery agents possessing antiradical activity: self-assembling cationic amphiphilic 1,4-dihydropyridine derivatives,” New Journal of Chemistry, vol. 37, no. 10, pp. 3062–3075, 2013. View at Publisher · View at Google Scholar · View at Scopus
  11. G. Duburs, J. Zilbers, A. Velēna, A. Kumerova, and G. Tirzītis, “Multistage studies of control of peroxidation processes in biological membranes with antioxidants of 1,4-dihydropyridine series,” Izvestija Akademii Nauk Latvijskoj SSR, Serija B, vol. 7, no. 336, pp. 65–68, 1975 (Russian). View at Google Scholar
  12. B. Jansone, I. Kadish, T. Van Groen et al., “A novel 1,4-dihydropyridine derivative improves spatial learning and memory and modifies brain protein expression in wild type and transgenic APPSweDI mice,” PLoS ONE, vol. 10, no. 6, Article ID e0127686, 2015. View at Publisher · View at Google Scholar · View at Scopus
  13. B. Jansone, I. Kadish, T. van Groen et al., “Memory-enhancing and brain protein expression-stimulating effects of novel calcium antagonist in Alzheimer’s disease transgenic female mice,” Pharmacological Research, vol. 113, pp. 781–787, 2016. View at Publisher · View at Google Scholar
  14. T. Lovaković, M. Poljak-Blazi, G. Duburs et al., “Growth modulation of human cells in vitro by mild oxidative stress and 1,4-dihydropyridine derivative antioxidants,” Collegium Antropologicum, vol. 35, no. 1, pp. 137–141, 2011. View at Google Scholar · View at Scopus
  15. S. Zhou, C. M. Palmeira, and K. B. Wallace, “Doxorubicin-induced persistent oxidative stress to cardiac myocytes,” Toxicology Letters, vol. 121, no. 3, pp. 151–157, 2001. View at Publisher · View at Google Scholar · View at Scopus
  16. M. Rucins, D. Kaldre, K. Pajuste et al., “Synthesis and studies of calcium channel blocking and antioxidant activities of novel 4-pyridinium and/or N-propargyl substituted 1,4-dihydropyridine derivatives,” Comptes Rendus Chimie, vol. 17, no. 1, pp. 69–80, 2014. View at Publisher · View at Google Scholar · View at Scopus
  17. N. V. Makarova, A. Plotnietse, G. Tirzitis, I. Turovskii, and G. Dubur, “Some transformations of N-ethoxycarbonyl-methylpyridinium bromides with a pyridyl or 1,4-dihydropyridyl substituent at position 3,” Chemistry of Heterocyclic Compounds, vol. 33, no. 2, pp. 175–183, 1997. View at Publisher · View at Google Scholar · View at Scopus
  18. M. Petrova, R. Muhamadejev, B. Vigante et al., “Intramolecular C-H⋯O hydrogen bonding in 1,4-dihydropyridine derivatives,” Molecules, vol. 16, no. 9, pp. 8041–8052, 2011. View at Publisher · View at Google Scholar · View at Scopus
  19. G. Duburs, J. Klovins, I. Bruvere et al., “1,4-Dihydropyridine-4-yl pyridinyo derivatives as new agoallosteric modulators of adenosine A2A receptor,” Latvian Patent. Application demand P-13-02, 2013.
  20. A. Abdelwahed, I. Bouhlel, I. Skandrani et al., “Study of antimutagenic and antioxidant activities of Gallic acid and 1,2,3,4,6-pentagalloylglucose from Pistacia lentiscus. Confirmation by microarray expression profiling,” Chemico-Biological Interactions, vol. 165, no. 1, pp. 1–13, 2007. View at Publisher · View at Google Scholar · View at Scopus
  21. W. S. Stokes, S. Casati, J. Strickland, and M. Paris, “Neutral red uptake cytotoxicity tests for estimating starting doses for acute oral toxicity tests,” Current Protocols in Toxicology, vol. 36, pp. 20.4.1–20.4.20, 2008. View at Publisher · View at Google Scholar
  22. NIEHS (National Institute of Environmental Health Sciences), “ICCVAM test method evaluation report: in vitro cytotoxicity test methods for estimating starting doses for acute oral systemic toxicity tests,” NIH Publication no. 07-4519, NIEHS, Research Triangle Park, NC, USA, 2006, http://iccvam.niehs.nih.gov/docs/acutetox_docs/BRD_TMER/TMERmain_Nov2006.pdf. View at Google Scholar
  23. ICCVAM, Background Review Document: In Vitro Basal Cytotoxicity Test Methods for Estimating Acute Oral Systemic Toxicity, National Institute for Environmental Health Sciences, Research Triangle Park, NC, USA, 2006, http://iccvam.niehs.nih.gov/methods/acutetox/inv_nru_brd.htm.
  24. EU legislation Dangerous Substances Directive (Directive 67/548/EEC), and the Dangerous Preparations Directive (Directive 1999/45/EC).
  25. S. Sepehri, H. P. Sanchez, A. Fassihi, and A. Fassihi, “Hantzsch-type dihydropyridines and biginelli-type tetrahydropyrimidines: a review of their chemotherapeutic activities,” Journal of Pharmacy and Pharmaceutical Sciences, vol. 18, no. 1, pp. 1–52, 2015. View at Google Scholar · View at Scopus
  26. V. Calabrese, C. Cornelius, A. Trovato-Salinaro et al., “The hormetic role of dietary antioxidants in free radical-related diseases,” Current Pharmaceutical Design, vol. 16, no. 7, pp. 877–883, 2010. View at Publisher · View at Google Scholar · View at Scopus
  27. B. Poljsak and I. Milisav, “The neglected significance of ‘antioxidative stress’,” Oxidative Medicine and Cellular Longevity, vol. 2012, Article ID 480895, 12 pages, 2012. View at Publisher · View at Google Scholar · View at Scopus
  28. N. Zarkovic, Z. Ilic, M. Jurin, R. J. Schaur, H. Puhl, and H. Esterbauer, “Stimulation of HeLa cell growth by physiological concentrations of 4‐hydroxynonenal,” Cell Biochemistry and Function, vol. 11, no. 4, pp. 279–286, 1993. View at Publisher · View at Google Scholar · View at Scopus
  29. M. Jaganjac, T. Čačev, A. Čipak, S. Kapitanović, K. G. Trošelj, and N. Žarković, “Even stressed cells are individuals: second messengers of free radicals in pathophysiology of cancer,” Croatian Medical Journal, vol. 53, no. 4, pp. 304–309, 2012. View at Publisher · View at Google Scholar · View at Scopus
  30. L. Milkovic, W. Siems, R. Siems, and N. Zarkovic, “Oxidative stress and antioxidants in carcinogenesis and integrative therapy of cancer,” Current Pharmaceutical Design, vol. 20, no. 42, pp. 6529–6542, 2014. View at Publisher · View at Google Scholar · View at Scopus
  31. K. Ošiņa, E. Rostoka, J. Sokolovska et al., “1,4-dihydropyridine derivatives without Ca2+-antagonist activity up-regulate Psma6 mRNA expression in kidneys of intact and diabetic rats,” Cell Biochemistry and Function, vol. 34, no. 1, pp. 3–6, 2016. View at Publisher · View at Google Scholar · View at Scopus
  32. A. G. Patel and S. H. Kaufmann, “How does doxorubicin work?” Elife, vol. 1, Article ID e00387, 2012. View at Google Scholar
  33. G. Duburs, B. Vigante, A. Plotniece et al., “Dihydropyridine derivatives as bioprotectors,” Chimica Oggi, vol. 26, no. 2, pp. 68–70, 2008. View at Google Scholar · View at Scopus
  34. S. Borovic, G. Tirzitis, D. Tirzite et al., “Bioactive 1,4-dihydroisonicotinic acid derivatives prevent oxidative damage of liver cells,” European Journal of Pharmacology, vol. 537, no. 1–3, pp. 12–19, 2006. View at Publisher · View at Google Scholar · View at Scopus
  35. O. Dalivelya, N. Savina, T. Kuzhir, I. Buraczewska, M. Wojewódzka, and I. Szumiel, “Effects of an antimutagen of 1,4-dihydropyridine series on cell survival and DNA damage in L5178Y murine sublines,” Nukleonika, vol. 51, no. 3, pp. 141–146, 2006. View at Google Scholar · View at Scopus
  36. N. I. Ryabokon, R. I. Goncharova, G. Duburs, and J. Rzeszowska-Wolny, “A 1,4-dihydropyridine derivative reduces DNA damage and stimulates DNA repair in human cells in vitro,” Mutation Research, vol. 587, no. 1-2, pp. 52–58, 2005. View at Publisher · View at Google Scholar · View at Scopus
  37. M. Cindric, A. Cipak, J. Serly et al., “Reversal of multidrug resistance in murine lymphoma cells by amphiphilic dihydropyridine antioxidant derivative,” Anticancer Research, vol. 30, no. 10, pp. 4063–4069, 2010. View at Google Scholar · View at Scopus
  38. L. Capolongo, N. Amboldi, D. Ballinari et al., “Reversal of multidrug resistance by new dihydropyridines with low calcium antagonist activity,” Acta Oncologica, vol. 33, no. 7, pp. 787–791, 1994. View at Publisher · View at Google Scholar · View at Scopus
  39. S. Tasaka, H. Ohmori, N. Gomi et al., “Synthesis and structure-activity analysis of novel dihydropyridine derivatives to overcome multidrug resistance,” Bioorganic and Medicinal Chemistry Letters, vol. 11, no. 2, pp. 275–277, 2001. View at Publisher · View at Google Scholar · View at Scopus
  40. A. Krauze, S. Grinberga, L. Krasnova et al., “Thieno[2,3-b]pyridines—a new class of multidrug resistance (MDR) modulators,” Bioorganic and Medicinal Chemistry, vol. 22, no. 21, pp. 5860–5870, 2014. View at Publisher · View at Google Scholar · View at Scopus
  41. D. Tirzite, J. Koronova, and A. Plotniece, “Influence of some quaternised 1,4-dihydropyridine derivatives on liposomes and erythrocyte membranes,” Biochemistry and Molecular Biology International, vol. 45, no. 4, pp. 849–856, 1998. View at Google Scholar · View at Scopus
  42. I. T. Mak, P. Boehme, and W. B. Weglicki, “Protective effects of calcium channel blockers against free radical-impaired endothelial cell proliferation,” Biochemical Pharmacology, vol. 50, no. 9, pp. 1531–1534, 1995. View at Publisher · View at Google Scholar · View at Scopus
  43. J. Zou, Y. Li, H.-Q. Fan, and J.-G. Wang, “Effects of dihydropyridine calcium channel blockers on oxidized low-density lipoprotein induced proliferation and oxidative stress of vascular smooth muscle cells,” BMC Research Notes, vol. 5, article no. 168, 2012. View at Publisher · View at Google Scholar · View at Scopus
  44. S. Manabe, T. Okura, T. Fukuoka, and J. Higaki, “Antioxidative effects of azelnidipine on mesangial cell proliferation induced by highly concentrated insulin,” European Journal of Pharmacology, vol. 567, no. 3, pp. 252–257, 2007. View at Publisher · View at Google Scholar · View at Scopus
  45. C. Asma and D. M. Reda, “Evaluation of dihydropyridine calcium antagonist effects on the stress bioindicator organism Saccharomyces cerevisiae,” Annals of Biological Research, vol. 4, no. 10, pp. 40–46, 2013. View at Google Scholar
  46. J. Briede, D. Daija, E. Bisenieks et al., “Effects of some 1,4-dihydropyridine Ca antagonists on the blast transformation of rat spleen lymphocytes,” Cell Biochemistry & Function, vol. 17, no. 2, pp. 97–105, 1999. View at Publisher · View at Google Scholar · View at Scopus