DNA İLE BAĞLANABİLEN SUDA ÇÖZÜNÜR SÜLFONATO KALİKS[8]AREN SENTEZİ VE ANTİMİKROBİYAL AKTİVİTESİ

Bu çalışmada; biyolojik fonksiyonları taklit edebilen veya etkileyen reseptörlerin tasarımı ve sentezi için çok yönlü moleküller olarak bilinen kaliksarenlerin suda çözünür bir türevi sentezlenmiştir. Sentezlenen sülfonato kaliks[8]aren (sCLX8) türevinin yapısı FT-IR ve 1H-NMR gibi spektroskopik yöntemlerle aydınlatılmıştır. Yapısı aydınlatılan sülfonato kaliks[8]aren molekülünün B.subtilis gibi gram pozitif ve E.coli gibi gram negatif özellikteki bakteri hatları üzerine disk difüzyon testi ile antibakteriyel aktivitesi incelenmiştir. Yine fonksiyonel hale getirilmiş suda çözünür kaliksaren iskeletinin, makromoleküllere karşı bağlanma davranışını görebilmek için çift zincirli DNA (dsDNA) ile olan muhtemel etkileşimi agaroz jel elektroforezi ve UV-Vis spektrofotometresi ile çalışılmıştır.

Anahtar Kelimeler:

Sülfonato kaliks, 8, aren, DNA, Disk difüzyon, B. Subtilis, E. Coli

SYNTHESIS AND ANIMICROBIAL ACTIVITY OF WATER-SOLUBLE SULFONATO CALIX[8]AREN BINDING WITH DNA

In this study; it was synthesized a water soluble calixarene derivative so-called as versatile molecules for the design and synthesis of receptors having mimic properties or affect biological functions. The structure of the synthesized sulfonato calix[8]arene (sCLX8) derivative was clarified by spectroscopic methods such as FT-IR and 1H-NMR. Antibacterial activity of the sulfonate calix[8]arene molecule was investigated by disk diffusion test on gram-positive and gram-negative bacterial lines such as B. subtilis and E. coli, respectively. Furthermore, possible interaction between the double-stranded DNA (dsDNA) and calixarene was studied by agarose gel electrophoresis and UV-Vis spectrophotometry in order to see the binding behavior of the functionalized water-soluble calixarene skeleton toward macromolecules.

Keywords:

Sulphonato calix, 8, aren, DNA, Disc diffusion, B. Subtilis, E. Coli,

PDF

___

[1] AKCEYLAN E., Faz Transfer Katalizörü Olabilecek Kaliksaren Türevlerinin Sentezi Ve Seçilmiş Reaksiyonlarda Uygulamaları, Selçuk Üniversitesi Fen Bilimleri Entitüsü, Konya, Türkiye, 2011.
[2] CHEN, L., SUN, S., Lİ, J., FANG, Z., ‘’Modifying a composite based on silica molecul arsieve and a Ru (II)-basedprobewith Fe 3 O 4 particles: Construction and oxygen sensing performance’’ Inorganica Chimica Acta, 446, 24-31, 2016.
[3] RULLAUD, V., SİRAGUSA, M., CUMBO, A., GYGAX, D., SHAHGALDİAN, P., ‘’DNA surface coating of calixarene-based nanoparticles: a sequence-dependent binding mechanism ‘’, Chemical Communications, 48(100),12186-12188, 2012.
[4] KARAKUŞ G., ‘’Bazı maleik anhidrit içeren kopolimerlerin amin yapılı ilaç etken maddeleri ile türevlendirilmesi, yapısal karakterizasyonu ve biyolojik aktiviteleri’’, Marmara Pharmaceutical Journal, 19, 121-125, 2015.
[5] NİMSE, S.B., KİM, T., ‘’Biological applications of functionalized calixarenes’’ Chemical Society Reviews, 42(1), 366-386, 2013.
[6] SHİVA, K.L., SHİVA P.K., REVANASİDDAPPA H.D., ‘’Synthesis, characterization, antioxidant, antimicrobial, DNA binding and cleavage studies of mononuclear Cu (II) and Co (II) complexes of 3-hydroxy-N'-(2-hydroxybenzylidene)-2-naphthohydrazide’’ European Journal of Chemistry, 2(3), 394-403, 2011.
[7] WANG, Q,.YANG, L., WU, J., WANG, H., SONG, J., TANG, X., ‘’Fourmono nuclear platinum (II) complexes: synthesis, DNA/BSA binding, DNA cleavage and cytotoxicity’’ BioMetals, 30(1),17-26, 2017.
[8] GALİNDO, M.A., OLEA, D., ROMERO, M.A., GÓMEZ, J., DEL CASTİLLO, P., HANNON, M.J., NAVARRO, J.A., ‘’Design and Non-Covalent DNA Binding of Platinum (II) Metallacalix [4] arenes’’ Chemistry-A European Journal, 13(18), 5075-5081, 2007.
[9] SRİNİVASAN, S., ANNARAJ, J., ATHAPPAN, P.R., ‘’Spectral and redox studies on mixed ligand complexes of cobalt (III) phenan throline/bipyridyl and benzoyl hydrazones, their DNA binding and antimicrobial activity’’ Journal of Inorganic Biochemistry, 99(3), 876-882, 2005.
[10] FENG, L., GAO, M., TAO, D., CHEN, Q., WANG, H., DONG, Z., LİU, Z., ‘’Cisplatin-prodrug-constructed liposomes as a versatil ether anostic nano platform for bimodal imaging guided combination cancer therapy’’ Advanced Functional Materials, 26(13), 2207-2217, 2016.
[11] GUTSCHE, C.D., LİN, L.G., ‘’Calixarenes 12: the synthesis of functionalized calixarenes’’ Tetrahedron, 42(6), 1633-1640, 1986.
[12] FRAŇO, M., DŽUGANOVÁ, K., KOİŠ, P., MASÁR, M., ‘’DNA fragment separations by on line combination of capillary isotachophoresis–capillary zone electrophoresis with UV detection’’ Electrophoresis, 37(23-24), 3084-3088, 2016.
[13] CAİ, J., ROSENZWEİG, B.A., HAMİLTON, A.D., ‘’Inhibition of chymotrypsin by a self assembled DNA quadruplex functionalized with cyclic peptide binding fragments’’ Chemistry-A European Journal, 15(2), 328-332, 2009.
[14] YENİŞEHİRLİ G., YENİŞEHİRLİ A., BULUT Y., BULUT N., ‘’Metisilin Dirençli Staphylococcus Aureus İzolatlarının Vankomisin, Teikoplanin, Linezolid, Kinupristin-Dalfopristin Ve Daptomisine İn Vitro Duyarlılıkları’’ Ankem Derg, 29(1), 21-25, 2015.
[15] BAŞER, F., Ülkemizde doğal yayılışa sahip karayosunlarından Sphagnumcentrale CEO Jensen ve S. Capillifolium (Ehrh.) Hedw'un (Bryophyta) anti-mikrobiyal aktivitesinin belirlenmesi, Adnan Menderes Üniversitesi Fen Bilimleri Enstitüsü, Aydın, Türkiye, 2016.
[16] RAJAVELU, K., RAJAKUMAR, P., ‘’Synthesis and photophysical, electrochemical, antibacterial, and DNA binding studies of triazinocalix [2] arenes’’ Journal of Materials Chemistry B, 3(16), 3340-3350, 2015.
[17] DAWN, A., CHANDRA, H., ADE-BROWNE, C., YADAV, J., KUMARİ, H., Multi faceted Supramolecular Interactions from C-Methylresorcin[4]arene Leadto an Enhancement in In Vitro Antibacterial Activity of Gatifloxacin’’ Chemistry-A European Journal, 2017.