The effect of hydrazine derivatives of 3-formylchromones on angiogenic basic fibroblast growth factor and fibroblast growth factor receptor -1 in human melanoma cell line WM-115.

Andrzej Łazarenkow; Marta Michalska; Marek Mirowski; Krzysztof Słomiak; Jolanta Nawrot-Modranka

doi:10.18388/abp.2017_1565

Andrzej Łazarenkow Medical University of Łódź
Marta Michalska Medical University of Łódź
Marek Mirowski Medical University of Łódź
Krzysztof Słomiak Medical University of Łódź
Jolanta Nawrot-Modranka Medical University of Łódź

DOI: https://doi.org/10.18388/abp.2017_1565

Keywords: Hydrazone derivatives of benzo-γ-pyrones, Human melanoma, Basic fibroblast growth factor, Fibroblast growth factor receptor 1, Angiogenesis

Abstract

The hydrazine derivatives of benzopyrones remain an unexplored group of chemical compounds. This preliminary study investigates the influence of A-5, CH-3 and K-2 derivatives at concentrations of 1, 10, 100 nM and 1 μM on selected biochemical factors of melanoma cell line WM-115, with regard to their potential angiogenic properties. The studied compounds were found to influence cell proliferation, as well as total protein, bFGF and FGFR1 concentration.

References

Akl MR, Nagpal P, Ayoub NM, Tai B, Prabhu SA, Capac CM, Gliksman M, Goy A, Suh KS (2016) Molecular and clinical significance of fibroblast growth factor 2 (FGF2 /bFGF) in malignancies of solid and hematological cancers for personalized therapies. Oncotarget 7: 44735-62. http://dx.doi.org/10.18632/oncotarget.8203

Baljinnyam E, Umemura M, Chuang C, De Lorenzo MS, Iwatsubo M, Chen S, Goydos JS, Ishikawa Y, Whitelock JM, Iwatsubo K (2014) Epac1 increases migration of endothelial cells and melanoma cells via FGF2-mediated paracrine signaling. Pigment Cell Melanoma Res 27: 611-20. http://dx.doi.org/10.1111/pcmr.12250

Berking C, Takemoto R, Satyamoorthy K, Elenitsas R, Herlyn M (2001) Basic fibroblast growth factor and ultraviolet B transform melanocytes in human skin. Am J Pathol 158: 943-953. http://dx.doi.org/10.1016/S0002-9440(10)64041-2

Dell’Era P, Belleri M, Stabile H, Massardi ML, Ribatti D, Presta M (2001) Paracrine and autocrine effects of fibroblast growth factor-4 in endothelial cells. Oncogene 20: 2655–2663. http://dx.doi.org/10.1038/sj.onc.1204368

Demirkesen C, Büyükpinarbaşili N, Ramazanoğlu R, Oğuz O, Mandel NM, Kaner G (2006) The correlation of angiogenesis with metastasis in primary cutaneous melanoma: a comparative analysis of microvessel density, expression of vascular endothelial growth factor and basic fibroblastic growth factor. Pathology 38: 132-137. http://dx.doi.org/10.1080/00313020600557565

Folkman J (1990) What is the evidence that tumors are angiogenesis dependent? J Natl Cancer Inst 82: 4-6.

Gartside MG, Chen H, Ibrahimi OA, Byron SA, Curtis AV, Wellens CL, Bengston A, Yudt LM, Eliseenkova AV, Ma J, Curtin JA, Hyder P, Harper UL, Riedesel E, Mann GJ, Trent JM, Bastian BC, Meltzer PS, Mohammadi M, Pollock PM (2009) Loss-of-function fibroblast growth factor receptor-2 mutations in melanoma. Mol Cancer Res 7:41-54. http://dx.doi.org/10.1158/1541-7786.MCR-08-0021

Halaban R (2000) The regulation of normal melanocyte proliferation. Pigment Cell Res 13: 4–14

Javerzat S, Auguste P, Bikfalvi A (2002) The role of fibroblast growth factors in vascular development. Trends Mol Med 8: 483–489. http://dx.doi.org/10.1016/S1471-4914(02)02394-8

Khan KA & Bicknell R (2016) Anti-angiogenic alternatives to VEGF blockade. Clin Exp Metastasis 33: 197-210. http://dx.doi.org/10.1007/s10585-015-9769-3

Khan KM, Ambreen N, Mughal UR, Jalil S, Perveen S, Choudhary MI (2010) 3-Formylchromones: potential antiinflammatory agents. Eur J Med Chem 45: 4058-4064. http://dx.doi.org/10.1016/j.ejmech.2010.05.065

Kodet O, Lacina L, Krejčí E, Dvořánková B, Grim M, Štork J, Kodetová D, Vlček Č, Šáchová J, Kolář M, Strnad H, Smetana K (2015) Melanoma cells influence the differentiation pattern of human epidermal keratinocytes. Mol Cancer 14:1. http://dx.doi.org/10.1186/1476-4598-14-1

Łazarenkow A, Nawrot-Modranka J, Brzezińska E, Krajewska U, Różalski M (2012) Synthesis, preliminary cytotoxicity evaluation of new 3-formylchromone hydrazones and phosphorohydrazone derivative of coumarin and chromone. Med Chem Res 21: 1861-1868. http://dx.doi.org/10.1007/s00044-011-9703-4

Łazarenkow A, Michalska M, Gorąca A, Mirowski M, Nawrot-Modranka J, Piechota-Polanczyk A (2013) The influence of chromone based hydrazones on lipid peroxidation and bFGF concentration in the HL-60 cell line. Acta Biochim Pol 60: 259-262.

Metzner T, Bedeir A, Held G, Peter-Vörösmarty B, Ghassemi S, Heinzle C, Spiegl-Kreinecker S, Marian B, Holzmann K, Grasl-Kraupp B, Pirker C, Micksche M, Berger W, Heffeter P, Grusch M (2011) Fibroblast growth factor receptors as therapeutic targets in human melanoma: synergism with BRAF inhibition. J Invest Dermatol 131: 2087-95. http://dx.doi.org/10.1038/jid.2011.177

Michalska M, Mirowski M, Kaplińska K, Kusztal D, Łazarenkow A, Nawrot-Modranka J (2013) Effect of phosphorohydrazone derivatives of chromone on fibrin polymerization in the presence of bFGF. Indian J Biochem Biophys 50: 227-232.

Nawrot-Modranka J, Nawrot E, Graczyk J (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. http://dx.doi.org/10.1016/j.ejmech.2006.06.004

Presta M, Dell'Era P, Mitola S, Moroni E, Ronca R, Rusnati M (2005) Fibroblast growth factor/fibroblast growth factor receptor system in angiogenesis. Cytokine Growth Factor Rev 16:159-178. http://dx.doi.org/10.1016/j.cytogfr.2005.01.004