Bazı heterosiklik gruplar içeren kaliksarenlerin sentezi ve biyolojik özelliklerinin incelenmesi /
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Tarih
2018
Yazarlar
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Yayıncı
Selçuk Üniversitesi Fen Bilimleri Enstitüsü
Erişim Hakkı
info:eu-repo/semantics/openAccess
Özet
Bu tez çalışmasında, heterosiklik gruplar içeren bazı p-ter-bütilkaliks[4]aren türevleri sentezlenmiş ve sonrasında sentezlenen bileşiklerin bakteriyel (pBR322 plazmit DNA) ve ökaryotik DNA'ya (CT-DNA) karşı etkileri incelenmiştir. Sentez için gerçekleştirilen ilk şemada, başlangıç bileşiği p-ter-bütilkaliks[4]aren (1) sentezlenip sırasıyla dimetoksi (2) ve dialdehit (3) türevine dönüştürüldükten sonra, o-fenilendiamin ve onun bazı türevleriyle gerçekleştirilen reaksiyonlar sonucunda p-benzimidazol türevli kaliksarenler (4-7) elde edildi. İkinci şemada, N-sübstitüe benzimidazol bileşikleri sentezlenerek (8, 9) farklı yapıda p-benzimidazol türevli kaliksarenler (10 ve 11) ve 2-aminotiyofenol kullanılarak benzotiyazol gruplu kaliksaren türevi (12) elde edildi. Üçüncü sentez şemasının birinci kısmında, fenolik oksijene bağlı benzimidazol türevli kaliksaren bileşikleri sentezlemek amacıyla, benzimidazol bileşikleri (17-20) bir seri reaksiyonla sentezlendi ve daha sonra bileşik 2 ile reaksiyona sokularak O-benzimidazol türevli kaliksaren bileşikleri (21-24) elde edildi. Bu şemanın ikinci kısmında ise kaliksarenin farklı yapıdaki benzimidazol türevleri (25-27) sentezlendi. Dördüncü ve beşinci sentez şemasında ise, sırasıyla piridin gruplu iki farklı bileşik (31 ve 32) ve kinolin türevli mono yapısındaki kaliksaren bileşiği (34) sentezlendi. Son olarak altıncı sentez şeması içerisinde, Click reaksiyonu vasıtasıyla triazol türevli kaliksaren bileşiği (37) elde edildi. Sentezlenen tüm bileşiklerin yapıları FTIR, 1H NMR, 13C NMR, NOESY, HETCOR analizleri, MALDI-TOF kütle spektroskopisi, elementel analiz ve diğer basit teknikler ile (erime noktası vs.) aydınlatıldı. Sentezlenen bileşiklerin pBR322 plazmit DNA ile agaroz jel elektroforez metodu kullanılarak DNA cleavage etkileri incelendi. Ayrıca, CT-DNA'ya karşı etkileri floresans ve UV-Vis. spektrofotometresi kullanılarak araştırıldı. Floresans spektrometresinde ölçülen floresans şiddetlerinden, etkili olan bazı bileşikler için bağlanma (Kb) ve söndürme (quenching) sabitleri (Ksv) sabitleri hesaplandı. Ayrıca, EtBr ile yarışmalı bağlanma deneyleri yapılarak söndürme sabitleri (Ksv) hesaplandı.
In this thesis, some of the p-ter-butylcalix[4]arene derivatives containing heterocyclic groups were synthesized and their effects were investigated against bacterial (pBR322 plasmid DNA) and eukaryotic DNA (calf thymus DNA). In the first scheme for synthesis, firstly the starting compound p-ter-butylcalix[4]arene (1) synthesized according to the literature after that this compound converted to dimethoxy (2) and dialdehyde (3) derivatives. The obtained dialdehyde derivative of calixarene (3) was reacted with o-phenylenediamine and some of its derivatives and p-benzimidazole-derivatived calixarenes (4-7) were obtained. In the second scheme, p-benzimidazole-derivatived calixarenes (10 and 11) which have different structures and benzothiazole-derived calixarene (12) were synthesized. In the first part of the third synthesis scheme, benzimidazole compounds (17-20) were synthesized by a series reaction and then this compunds reacted with compound 2, finally O-benzimidazole-derived calixarene compounds (21-24) were obtained. In the second part of this scheme, different benzimidazole derivatives (25-27) were also synthesized. In the fourth and fifth synthesis scheme, two different compounds (31 and 32) with pyridine groups and the calixarene compound (34) in the quinoline-derived mono structure were synthesized, respectively. Finally, in the sixth synthesis scheme, triazole derived calixarene compound (37) was obtained by Click reaction. The structures of all synthesized compounds were elucidated by FTIR, 1H NMR, 13C NMR, NOESY, HETCOR analysis, MALDI-TOF mass spectroscopy, elemental analysis and other simple techniques (melting point, etc.). DNA cleavage effects of synthesized compounds were investigated using pBR322 plasmid DNA by agarose gel electrophoresis method. In addition, the effects against CT-DNA were investigated using fluorescence and UV-Vis. spectrometry. Binding constants (Kb) and quenching constants (Ksv) were calculated for some compounds which were effective in fluorescence spectrometry. Finally, competitive binding experiments with EtBr were performed and it was determined quenching constants (Ksv).
In this thesis, some of the p-ter-butylcalix[4]arene derivatives containing heterocyclic groups were synthesized and their effects were investigated against bacterial (pBR322 plasmid DNA) and eukaryotic DNA (calf thymus DNA). In the first scheme for synthesis, firstly the starting compound p-ter-butylcalix[4]arene (1) synthesized according to the literature after that this compound converted to dimethoxy (2) and dialdehyde (3) derivatives. The obtained dialdehyde derivative of calixarene (3) was reacted with o-phenylenediamine and some of its derivatives and p-benzimidazole-derivatived calixarenes (4-7) were obtained. In the second scheme, p-benzimidazole-derivatived calixarenes (10 and 11) which have different structures and benzothiazole-derived calixarene (12) were synthesized. In the first part of the third synthesis scheme, benzimidazole compounds (17-20) were synthesized by a series reaction and then this compunds reacted with compound 2, finally O-benzimidazole-derived calixarene compounds (21-24) were obtained. In the second part of this scheme, different benzimidazole derivatives (25-27) were also synthesized. In the fourth and fifth synthesis scheme, two different compounds (31 and 32) with pyridine groups and the calixarene compound (34) in the quinoline-derived mono structure were synthesized, respectively. Finally, in the sixth synthesis scheme, triazole derived calixarene compound (37) was obtained by Click reaction. The structures of all synthesized compounds were elucidated by FTIR, 1H NMR, 13C NMR, NOESY, HETCOR analysis, MALDI-TOF mass spectroscopy, elemental analysis and other simple techniques (melting point, etc.). DNA cleavage effects of synthesized compounds were investigated using pBR322 plasmid DNA by agarose gel electrophoresis method. In addition, the effects against CT-DNA were investigated using fluorescence and UV-Vis. spectrometry. Binding constants (Kb) and quenching constants (Ksv) were calculated for some compounds which were effective in fluorescence spectrometry. Finally, competitive binding experiments with EtBr were performed and it was determined quenching constants (Ksv).
Açıklama
Anahtar Kelimeler
DNA-etkileşimi, Heterosiklik Grup, Kaliksaren, Calf Thymus DNA, Calixarene, DNA-interaction
Kaynak
WoS Q Değeri
Scopus Q Değeri
Cilt
Sayı
Künye
Özkan, Ş. Ç. (2018). Bazı Heterosiklik Gruplar İçeren Kaliksarenlerin Sentezi ve Biyolojik Özelliklerinin İncelenmesi. (Doktora Tezi). Selçuk Üniversitesi, Fen Bilimleri Enstitüsü, Konya.
