NOVEL IMIDAZOLYL DERIVATIVES OF 1, 8-ACRIDINEDIONE AS POTENTIAL DNA-INTERCALATING AGENTS

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JAMALIAN A.; SHAFIEE A.; HEMMATEENEJAD B.; KHOSHNEVISZADEH M.; MIRI R.; MADADKAR SOBHANI A.; BATHAIE S.Z.; MOOSAVI MOVAHEDI A.A.

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Journal: JOURNAL OF THE IRANIAN CHEMICAL SOCIETY(JICS) Year:2011 | Volume:8 | Issue:4 Page(s): 1098-1112

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Title

NOVEL IMIDAZOLYL DERIVATIVES OF 1, 8-ACRIDINEDIONE AS POTENTIAL DNA-INTERCALATING AGENTS

Author(s)

Keywords

DNA-INTERCALATION

IMIDAZOLYL-1

8-ACRIDINEDIONE

CIRCULAR DICHROISM

DOCKING

QSAR

Abstract

The effect of twelve novel imidazolyl derivatives of 1, 8-ACRIDINEDIONE (ligands) on calf thymus DNA was studied applying different biophysical techniques including UV-Vis spectrophotometry, CD spectropolarimetry and fluorimetric methods to gain deeper insights into the mechanism of interaction of the ligands with DNA. The binding parameters such as C50, Kapp, DGo(H2O) andm -value, followed by Scatchard analysis, indicate that among the tested ligands, four compounds; 12b, 13b, 12f and 13f, containing nitro and benzyl imidazole substituents, revealed uncompetitive intercalative mode of interaction with DNA. UV-Vis studies imply that the compounds bind cooperatively to DNA at the concentration range of 100-200 mM. Based on biophysical data, QSAR analysis, and DOCKING simulations, we propose that in cytotoxic 1, 8-ACRIDINEDIONEs, the imidazole moiety is essential for pharmacological activity and the introduction of more flexible and electron-withdrawing substituents on the imidazole ring serves to enhance their DNA intercalating ability.

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APA: Copy

JAMALIAN, A., SHAFIEE, A., HEMMATEENEJAD, B., KHOSHNEVISZADEH, M., MIRI, R., MADADKAR SOBHANI, A., BATHAIE, S.Z., & MOOSAVI MOVAHEDI, A.A.. (2011). NOVEL IMIDAZOLYL DERIVATIVES OF 1, 8-ACRIDINEDIONE AS POTENTIAL DNA-INTERCALATING AGENTS. JOURNAL OF THE IRANIAN CHEMICAL SOCIETY(JICS), 8(4), 1098-1112. SID. https://sid.ir/paper/282620/en

Vancouver: Copy

JAMALIAN A., SHAFIEE A., HEMMATEENEJAD B., KHOSHNEVISZADEH M., MIRI R., MADADKAR SOBHANI A., BATHAIE S.Z., MOOSAVI MOVAHEDI A.A.. NOVEL IMIDAZOLYL DERIVATIVES OF 1, 8-ACRIDINEDIONE AS POTENTIAL DNA-INTERCALATING AGENTS. JOURNAL OF THE IRANIAN CHEMICAL SOCIETY(JICS)[Internet]. 2011;8(4):1098-1112. Available from: https://sid.ir/paper/282620/en

IEEE: Copy

A. JAMALIAN, A. SHAFIEE, B. HEMMATEENEJAD, M. KHOSHNEVISZADEH, R. MIRI, A. MADADKAR SOBHANI, S.Z. BATHAIE, and A.A. MOOSAVI MOVAHEDI, “NOVEL IMIDAZOLYL DERIVATIVES OF 1, 8-ACRIDINEDIONE AS POTENTIAL DNA-INTERCALATING AGENTS,” JOURNAL OF THE IRANIAN CHEMICAL SOCIETY(JICS), vol. 8, no. 4, pp. 1098–1112, 2011, [Online]. Available: https://sid.ir/paper/282620/en

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