Antibakteriyel ve Antikanser Özellikleri Gösteren Piridin ve Kinolin Temelli Schiff Bazı Türevlerinin Sensör Özellikleri Öz

Year 2021, Volume: 10 Issue: 4, 1260 - 1271, 31.12.2021

Pelin Yeşildaş , Bahar Yılmaz , Mevlüt Bayrakcı

https://doi.org/10.17798/bitlisfen.901941

Abstract

Bu çalışmada, literatürdeki güncel sentez yöntemleri izlenerek, piridin ve kinolin grupları içeren Schiff bazı tipinde üç farklı molekül (P-1, P-2 ve P-3) başarıyla sentezlendi. Sentezlenen bileşiklerin yapısal karakterizasyonu spektrofotometrik yöntemler kullanılarak aydınlatıldı. Spektrofotometrik çalışmalarda, P-1 molekülü civaya karşı seçimli bir bağlanma gösterirken, P-2 molekülünün alüminyuma karşı seçimli bir bağlanma sergilediği görüldü. Ayrıca, sentezlenen tüm bileşiklerin antikanser aktivitesi, in vitro koşullarda insan meme kanseri hücresi (MCF-7) ve normal insan embriyonik böbrek hücresi (HEK 293) üzerinde Alamar mavisi testi kullanılarak değerlendirildi. Antikanser aktivite sonuçlarına göre, moleküllerin MCF-7 kanser hücre hattı üzerinde daha fazla ölüme neden olduğu görüldü. Dahası, P-1, P-2 ve P-3 moleküllerinin antibakteriyel çalışmaları disk difüzyon yöntemi kullanılarak gram-pozitif (B. subtilis) ve gram-negatif (E. coli) bakteri hatları üzerinde başarılı bir şekilde yapıldı. Bu sonuçlar, P-1 ve P-2'nin canlı hücrelerde sağlıklı hücrelere zarar vermeden mükemmel floresans probları olarak kullanılabileceğini gösterdi. Ayrıca, bu bileşikler Schiff baz moleküllerinin antikanser ve antibakteriyel uygulamaları ile ilgili yeni çalışmalar için ilham kaynağı olabilir.

Keywords

Antibakteriyel, Antikanser, Floresans, Sensör, Schiff bazı

Thanks

Bu çalışma Karamanoğlu Mehmetbey Üniversitesi yüksek lisans öğrencisi Pelin Yeşildaş’ın tez çalışmasının bir parçasıdır.

Sensor Properties of Pyridine and Quinoline Based Schiff Bases Derivatives Showing Antibacterial and Anticancer Properties

Abstract

Keywords

Antibacterial, Anticancer, Fluorescence, Sensor, Schiff base

References

• [1] Zishen W., Ziqi G., Zhenhuan Y. 1990. Synthesis, characterization and anticancer activity of L-alanine Schiff base complexes of copper (II), zinc (II), nickel (II) and cobalt (II). Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry, 20(3), 335-344.
• [2] Wang Y., Ma Z.Y., Zhang D.L., Deng J.L., Chen X., Xie C.Z., Xu J.Y. 2018. Highly selective and sensitive turn-on fluorescent sensor for detection of Al3+ based on quinoline-base Schiff base. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 195, 157-164.
• [3] Abd El‐Halim H.F., Mohamed G.G., Anwar M.N. 2018. Antimicrobial and anticancer activities of Schiff base ligand and its transition metal mixed ligand complexes with heterocyclic base. Applied Organometallic Chemistry, 32, e3899.
• [4] Tahlan S., Narasimhan B., Lim S.M., Ramasamy K., Mani V., Shah S.A.A. 2019. 2-Mercaptobenzimidazole Schiff Bases: Design, Synthesis, Antimicrobial Studies and Anticancer Activity on HCT-116 Cell Line. Mini reviews in medicinal chemistry, 19, 1080-1092.
• [5] Kennedy C.D., Gonsalves F.A.N. 1987. The action of divalent zinc, cadmium, mercury, copper and lead on the trans-root potential and efflux of excised roots. J.Exp. Bot., 38, 800-817.
• [6] Wang T., Yue W. 2017. Carbon nanotubes heavy metal detection with stripping voltammetry: a review paper. Electroanalysis, 29, 2178-2189.
• [7] Vasanthi L.A., Revathi P., Rajendran R.B., Munuswamy N. 2017. Detection of metal induced cytopathological alterations and DNA damage in the gills and hepatopancreas of green mussel Perna viridis from Ennore Estuary, Chennai, India. Marine pollution bulletin, 117, 41-49.
• [8] Djurišić A.B., Leung Y.H., Ng A.M., Xu X.Y., Lee P.K., Degger N., Wu R.S.S. 2015. Toxicity of metal oxide nanoparticles: mechanisms, characterization, and avoiding experimental artefacts. Small, 11, 26-44.
• [9] Priyadarshini E., Pradhan N. 2017. Gold nanoparticles as efficient sensors in colorimetric detection of toxic metal ions: a review. Sensors and Actuators B: Chemical, 238, 888-902.
• [10] Mahmoud W.H., Deghadi R.G., Mohamed G.G. 2016. Novel Schiff base ligand and its metal complexes with some transition elements. Synthesis, spectroscopic, thermal analysis, antimicrobial and in vitro anticancer activity. Applied Organometallic Chemistry, 30, 221-230.
• [11] Malik M.A., Dar O.A., Gull P., Wani M.Y., Hashmi A.A. 2018. Heterocyclic Schiff base transition metal complexes in antimicrobial and anticancer chemotherapy. Med. Chem. Comm., 9, 409-436.
• [12] Choi Y.W., Park G.J., Na Y.J., Jo H.Y., Lee S.A., You G.R., Kim C. 2014. A single schiff base molecule for recognizing multiple metal ions: a fluorescence sensor for Zn (II) and Al (III) and colorimetric sensor for Fe (II) and Fe (III). Sensors and Actuators B: Chemical, 194, 343-352.
• [13] You G.R., Park G.J., Lee S.A., Ryu K.Y., Kim C. 2015. Chelate-type Schiff base acting as a colorimetric sensor for iron in aqueous solution. Sensors and Actuators B: Chemical, 215, 188-195.
• [14] Amali I.B., Kesavan M.P., Vijayakumar V., Gandhi N.I., Rajesh J., Rajagopal G. 2019. Structural analysis, antimicrobial and cytotoxic studies on new metal (II) complexes containing N2O2 donor Schiff base ligand. Journal of Molecular Structure, 1183, 342-350.
• [15] Patel V.K., Jejurkar C.R. 1989. Synthesis of mixed schiff base complexes of Cu (II) and Ni (II) and their spectral, magnetic and antifungal studies.
• [16] Bontidean I., Ahlqvist J., Mulchandani A., Chen W., Bae W., Mehra R.K., Csöregi E. 2003. Novel synthetic phytochelatin-based capacitive biosensor for heavy metal ion detection. Biosensors and Bioelectronics, 18, 547-553.
• [17] Stresty T.V.S., Madhava Rao K.V. 1999. Ultrastructural alterations in response to zinc and nickel stress in the root cell of pigeonpea. Environ. Exp Bot., 41, 3-13.
• [18] Fathima S.S.A., Meeran M.M.S., Nagarajan E.R. 2019. Synthesis of novel (E)-2-((anthracen-9-ylmethylene) amino) pyridin-3-ol and its transition metal complexes: Multispectral characterization, biological evaluation and computational studies. Journal of Molecular Liquids, 279, 177-189.
• [19] O'brien J., Wilson I., Orton T., Pognan F. 2000. Investigation of the Alamar Blue (resazurin) fluorescent dye for the assessment of mammalian cell cytotoxicity. European journal of biochemistry, 267, 5421-5426.
• [20] Hudzicki J. 2009. Kirby-Bauer disk diffusion susceptibility test protocol. American Society for Microbiology.
• [21] Uysal A., Durak Y. 2012. Pulsed-field gel electrophoresis typing, antibiotic resistance, and plasmid profiles of Escherichia coli strains isolated from foods. Canadian journal of microbiology, 58, 1278-1287.
• [22] Yilmaz B., Bayrakci M. 2018. Macrocyclic anthracene-anchored calix [4] arene as a sensitive and selective fluorescent chemosensor for ytterbium ions. Journal of Macromolecular Science, Part A, 55, 513-518.
• [23] Keskin S., Bayrakci M. 2019. A Simple and Highly Sensitive Turn-on Schiff Base Type Naked-eye Fluorescent Sensor for Aluminum Ion in Living Cells. Acta Chimica Slovenica, 66, 792-801.
• [24] Yilmaz B., Bayraç A. T., Bayrakci M. 2020. Evaluation of anticancer activities of novel facile synthesized calix [n] arene sulfonamide analogs. Applied biochemistry and biotechnology, 190(4), 1484-1497.
• [25] Yilmaz B., Keskinates M., Bayrakci M. 2021. Novel integrated sensing system of calixarene and rhodamine molecules for selective colorimetric and fluorometric detection of Hg2+ ions in living cells. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 245, 118904.
• [26] Bayrakcı M., Yılmaz B. 2019. DNA İle Bağlanabilen Suda Çözünür Sülfonato Kaliks[8]aren Sentezi Ve Antimikrobiyal Aktivitesi. Ömer Halisdemir Üniversitesi Mühendislik Bilimleri Dergisi, 8, 615-620.
• [27] Bayrakci M., Keskinates M., Yilmaz B. 2021. Antibacterial, thermal decomposition and in vitro time release studies of chloramphenicol from novel PLA and PVA nanofiber mats. Materials Science and Engineering: C, 122, 111895.