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Journals / Sakarya University Journal of Science / 2017 / Cilt: 21 Sayı: 6

Structure-Activity Relationship (SAR): The study of antiproliferative activities of brominated 8-hydroxyquinoline and phthalonitrile derivatives on several cancer cell lines

Yapı Aktivite İlişkisi (SAR): Bromlanmış 8-hidroksikinolin ve ftalonitril türevlerinin çeşitli kanser hücre hatları üzerine antiproliferatif aktivitelerinin incelenmesi

Salih ÖKTEN
Tuğba Kul KÖPRÜLÜ
Osman ÇAKMAK
Şaban TEKİN
Pages
1300–1306
Publication Date
2017-12-01
DOI
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AI Summary & Key Takeaways

AI Insight
⚡ TL;DR(Too Long; Didn't Read)

In addition, biological activity was decreased when alkyl or substituted cyclic groups bounded to OH of quinoline, and the bromination of these derivatives did not increase the antiproliferative activity.

📌 3 Key Takeaways

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Objective & Hypothesis:In this study, phthalonitriles 6, 7 and their corresponding bromo derivatives 8, 9 were synthesized from 8-hydroxyquinoline to investigate antiproliferative and cytotoxic activities on C6 (rat brain tumor), HeLa (human cervix carcinoma) and HT29 (human colon carcinoma) cancer cell lines of these molecules.
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Key Findings & Data:The antiproliferative and apoptotic effects of 7-bromo- and 5,7-dibromo-8-hydroxyquinoline derivatives (2 and 3) and phthalonitrile 6, 7 and their brominated derivatives 8, 9 were compared in terms of Structure Activity Relationship (SAR).
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Conclusion & Impact:In addition, biological activity was decreased when alkyl or substituted cyclic groups bounded to OH of quinoline, and the bromination of these derivatives did not increase the antiproliferative activity.
🔬Design:Research Article
📍Scope:Comprehensive Sample
⚙️Variables:8-hidroksikinolin · ftalonitril · yapı-aktivite ilişkisi (SAR)

Abstract

In this study, phthalonitriles 6, 7 and their corresponding bromo derivatives 8, 9 were synthesized from 8-hydroxyquinoline to investigate antiproliferative and cytotoxic activities on C6 (rat brain tumor), HeLa (human cervix carcinoma) and HT29 (human colon carcinoma) cancer cell lines of these molecules. The antiproliferative and apoptotic effects of 7-bromo- and 5,7-dibromo-8-hydroxyquinoline derivatives (2 and 3) and phthalonitrile 6, 7 and their brominated derivatives 8, 9 were compared in terms of Structure Activity Relationship (SAR). Although bromohydroxyquinoline derivatives 2 and 3 exhibited high antiproliferative activity according to literature, it has been determined that phthalonitrile compounds 6, 7 and their brominated 8, 9 derivatives are significantly reduced in antiproliferative activity. The SAR of the quinoline core at C-8 revealed that OH group lead to antiproliferative and apoptotic activity. In addition, biological activity was decreased when alkyl or substituted cyclic groups bounded to OH of quinoline, and the bromination of these derivatives did not increase the antiproliferative activity.

Özet

Bu çalışmada, 8-hidroksikinolin’den ftalonitriller 6, 7 ve bunların bromlu türevleri 8, 9 sentezlenerek bu moleküllerin C6 (sıçan glial tümör), HeLa (insan rahim ağzı kanser hücresi) ve HT29 (insan adenokarsinoma) kanser hücre hatları üzerindeki antiproliferatif ve sitotoksik aktiviteleri araştırılmıştır. 7-Bromo- ve 5,7-dibromo-8-hidroksikinolin türevleri (2 ve 3) ile ftalonitril 6, 7 ve bunların bromlu türevleri 8, 9 antiproliferatif ve apoptotik etkileri yapı aktivite ilişkisi (SAR) yönüyle karşılaştırılmıştır. Bromohidroksikinolin 2 ve 3 türevleri, literatür kayıtlarına göre yüksek antiproliferatif aktivite göstermesine rağmen, 8-hidroksikinolinden hazırlanan ftalonitril bileşikleri 6, 7 ve bromlanan 8, 9 türevlerinin antiproliferatif aktiviteyi belirgin bir biçimde azalttığı belirlenmiştir. Kinolin çekirdeğinin C-8 konumundaki yapı aktivite çalışması, antiproliferatif ve apoptotik aktivitenin OH grubunun sebep olduğu ortaya çıkartmıştır. Ayrıca kinolin halkasının OH grubuna alkil ya da sübstitüe halkalı grupların bağlanması ve bromlanması da antiproliferatif aktiviteyi düşürmüştür.

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Cite This Article

ÖKTEN, S., KÖPRÜLÜ, T. K., ÇAKMAK, O., TEKİN, Ş. (2017). Structure-Activity Relationship (SAR): The study of antiproliferative activities of brominated 8-hydroxyquinoline and phthalonitrile derivatives on several cancer cell lines. Sakarya University Journal of Science, Cilt: 21 Sayı: 6, 1300–1306. https://ajindex.com/articles/942284

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