Yeni PDI tabanlı antiproliteratif kromoforlar

Yıl 2023, Cilt: 25 Sayı: 2, 761 - 769, 07.07.2023

Furkan Ozcil Hatice Yıldırım Merve Karaman Funda Yükrük

https://doi.org/10.25092/baunfbed.1277996

Öz

Çalışmanın birincil amacı, yeni sentezlenmiş ve tanımlanmış iki perilen diimidin antiproliferatif aktivitesini bulmaktır. MTT testi, PC3 prostat kanseri hücre dizisi, Panc1 pankreas kanseri hücre dizisi, Saos2 osteosarkoma hücre dizisi, Hep3B hepatoma hücre dizisi ve HUVEC kanserli olmayan insan göbek damarı endotel hücrelerine karşı antiproliteratif etkiyi araştırmak için uygulandı. PC3, Pancl ve Saos 2 hücrelerine göre, her iki bileşiğin de oldukça sitotoksik olduğu bulundu; ancak, Hep3B hücrelerinde karşılaştırılabilir bir etki görülmedi. İkinci molekül, 40,88 g/ml ile en düşük IC50 değerine sahip olarak bulundu ve diğer hücre hatlarına kıyasla PC3 hücre çoğalmasını önemli ölçüde inhibe etti.

Anahtar Kelimeler

Perilen diimid, Antiproliferatif aktivite, Sitotoksisite

Destekleyen Kurum

This work was supported by grants from Balikesir University (BAP2013/19), The Scientific and Technological Research Council of Turkey (TUBITAK-110T026) and Undersecretariat of State Planning Organization (DPT-2005-K-120-170).

Proje Numarası

BAP2013/19, TUBITAK-110T026, DPT-2005-K-120-170

Teşekkür

Bu çalışmamızda bize destek olan Balıkesir Üniversitesi, TÜBİTAK ve DPT'ye çok teşekkür ederiz.

Novel perylene diimide based antiproliferative chromophores

Öz

The primary objective of the work was to monitor the antiproliferative activity of two newly synthesized and described perylene diimides. The MTT test was used to investigate the antiproliferative effect against PC3 the prostat cancer cell line, Panc1 pancreatic cancer cell line, Saos2 osteosarcoma cell line, Hep3B hepatoma cell line and HUVEC non-cancerous human umbilical vein endothelial cells. To PC3, Panc1, and Saos 2 cells, both compounds were found to be considerably cytotoxic; however, a comparable impact was not seen in Hep3B cells. Compound 2 had the lowest IC50 value of 40,88 µg/ml and significantly inhibited PC3 cell proliferation when compared to other cell lines.

Anahtar Kelimeler

Perylene diimide, Antiproliferatif Activity, Cytotoxicity

Proje Numarası

BAP2013/19, TUBITAK-110T026, DPT-2005-K-120-170

Kaynakça

• Angadi, M.A., Gosztola, D., Wasielewski, M.R., Organic light emitting diodes using poly(phenylenevinylene) doped with perylene diimide electron acceptors, Materials Science and Engineering B, 63, 191-194, (1999).
• Ranke P., Bleyl, I., Simmerer, J., Haarer, D., Bacher, A., Schmidt, H.W., Electro- luminescence and electron transport in a perylene dye, Applied Physics Letters, 71, 1332-1334, (1997).
• Sapagovas, V.J., Gaidelis, V., Kovalevskij, V., Undzenos, A., Perylenetetracarboxylic- acid derivatives and photophysical properties, Dyes Pigments, 71, 178-187, (2016).
• Cormier, R.A., Gregg, B.A., Synthesis and characterization of liquid crystalline perylene diimides, Chemistry of Materials, 10, 1309-1319, (1998).
• Hayes R.T., Wasielewski, M.R., Gosztola, D.J., Organic dyes with excited-state Transformations, American Chemical Society, 122, 5563-5567, (2000).
• Davis, W.V., Svec, W.A., Ratner, M.A., Wasielewski, M.R., Molecular-wire behaviour in p-phenylenevinylene oligomers, Nature, 396, 60-63, (1998).
• Tornizaki K., Loewe R.S., Kirmaier, C., Schwartz, J.K., Retsek, J.L., Bocian, D.F., Holten, D., Lindsey, J.S., Synthesis and Photophysical Properties of Light- Harvesting Arrays Comprised of a Porphyrin Bearing Multiple Perylene-Accessory Pigments, Journal of Organic Chemistry, 67, 6519-6534, (2002).
• Fuller M.J., Wasielewski, M.R., Photorefractivity in Nematic Liquid Crystals Using a Donor−Acceptor Dyad with a Low-Lying Excited Singlet State for Charge Generation, The Journal of Physical Chemistry B, 105, 7216-7219, (2001).
• Fuller, M.J., Walsh, C.J., Zhao, Y., Wasielewski, .M.R., Hybrid Photorefractive Material Composed of Layered Conjugated Polymer and Dye-Doped Liquid Crystal Films, Chemistry of Materials, 14, 952-953, (2002).
• Ozcan, O., Yukruk, F., Akkaya, E.U., Uner, D., Dye sensitized artificial photosynthesis in the gas phase over thin and thick TiO2 films under UV and visible light irradiation, Applied Catalysis B: Environmental, 71, 291-297, (2006).
• Acikbas,Y.,Capan,R., Erdogan, M., Yukruk, F., Thin film characterization and vapor sensing properties of a novel perylene diimide material, Sensors & Actuators, B: Chemical, 160, 65-71, (2011).
• Gregg, B.A., Cormier, R.A., Doping Molecular Semiconductors:  n-Type Doping of a Liquid Crystal Perylene diimide, Journal of American Chemical Society, 123, 7959-7960, (2001).
• Breeze, A.J., Salomon, A., Ginley, D.S., Gregg, B.A., Tillmann, H., Horhold, H.H., Polymer—perylene diimide heterojunction solar cells, Applied Physics Letters, 81, 3085-3087, (2002).
• Sadrai, M., Hadel, L., Sauers, R.R., Husain, S., Krogh-Jespersen, K., Westbrook, J.D., Bird, F.R., Lasing action in a family of perylene derivatives: singlet absorption and emission spectra, triplet absorption and oxygen quenching constants, and molecular mechanics and semiempirical molecular orbital calculations, The Journal of Physical Chemistry, 96, 7988-7996, (1992).
• Gvishi, R., Reisfeld. R., Brushtein, Z., Spectroscopy and laser action of the “red Perylimide dye” in various solvents, Chemical Physics Letters, 213, 338-344, (1993).
• Yukruk, F., Dogan, A.L., Canpinar, H., Guc, D., Akkaya, E.U., Water soluble green perylene diimide (PDI) dyes as potential sensitizers for photodynamic therapy, Organic Letters, 7(14), 2885-2887, (2005).
• Tuna, G., Erkmen, G.K., Dalmizrak, O., Dogan, A., Ogus, I.H., Inhibition characteristics of hypericin on rat small intestine glutathione-S-transferases, Chemico-Biological Interactions, 188(1), 59–65, (2010).
• Mosmann, T., Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays, The Journal of Immunological Methods, 65, 55–63, (1983).
• Keskin, T., Isgor, B.S., Isgor, Y.G., Yukruk, F., Evaluation of Perylene diimide Derivatives for Potential Therapeutic Benefits on Cancer Chemotherapy, Chemical Biology & Drug Design, 80(5), 675-681, (2012).
• Liu, K., Xu, Z., Yin, M., Yang, W., He, B., Wie, W., Shen, J., Towards rational design of organic electron acceptors for photovoltaics: A study based on perylene diimide derivatives, Journal of Materials Chemistry, 2(15), 2093-2096, (2014).
• Abaza, M.S., Orabi, K.Y., Al-Quattan1, E., Al-Attiyah. R.J., Growth inhibitory and chemo-sensitization effects of naringenin, a natural flavanone purified from Thymus vulgaris, on human breast and colorectal cancer, Cancer Cell International, 15, 46, (2015).
• Chan, P.S., Koon, H.K., Wu, Z.G., Wong, R.N., Lung, M.L., Chang, C.K., Mak, N.K., Role of p38 MAPKs in hypericin photodynamic therapy-induced apoptosis of nasopharyngeal carcinoma cells, Photochemistry Photobiolgy, 85, 1207–1217, (2009).
• Du, H.Y., Olivo, M., Tan, B.K., Bay, B.H., Photoactivation of hypericin down-regulates glutathione S-transferase activity in nasopharyngeal cancer cells, Cancer Letters, 207, 175–181, (2004).
• Dabrowski, M.J., Maeda, D., Zebala, J., Lu, W.D., Mahajan, S., Kavanagh, T.J., Atkins,W.M., Glutathione S-transferase P1- 1 expression modulates sensitivity of human kidney 293 cells to photodynamic therapy with hypericin, Archives of Biochemistry and Biophysics, 449, 94–103, (2006).
• Chang, Y., Wang, S.J., Hypericin, the active component of St. John's wort, inhibits glutamate release in the rat cerebrocorticalsynaptosomes via a mitogen-activated protein kinase dependent pathway, European Journal of Pharmacology, 634, 53–61, (2010 ).
• Tuna, G., Erkmen, G.K., Dalmizrak, O., Dogan, A., Ogus, I.C.H., Ozer, N., Inhibition characteristics of hypericin on rat small intestine glutathione-S-transferases, Chemico-Biological Interactions, 188, 59–65, (2011).
• Taka, T., Joonlasak, .K, Huang, L., Lee, T.R., Chang, S.W.T., Tuntiwechapikul, W., Down-regulation of the human VEGF gene expression by perylenemonoimide derivatives, Bioorganic & Medicinal Chemistry Letters, 22, 518–522, (2012).
• D’Ambrosio, D., Reichenbach, P., Micheli, E., Alvino, A., Franceschin, M., Savino, M., Lingner, J., Specific binding of telomeric G-quadruplexes by hydrosoluble perylene derivatives inhibits repeat addition processivity of human telomerase, Biochimie, 94, 854-863, (2012).