A study of the properties, reactivity and anticancer activity of novel N- methylated-3-thiazolyl or 3-thienyl carbazoles and their Pd(II) and Pt(II) complexes

作者: Marta Reig , Ramón Bosque , Mercè Font-Bardía , Carme Calvis , Ramon Messeguer

DOI: 10.1016/J.JINORGBIO.2018.03.008

关键词: pBluescriptCisplatinMolecular mechanicsCarbazoleChemistryStereochemistryLigandDensity functional theoryReactivity (chemistry)Topoisomerase

摘要: Abstract The synthesis and characterization of two hybrid N-methylated carbazole derivatives containing a thiazolyl or thienyl ring is reported. derivative has been also characterised by X-ray diffraction analysis. study its reactivity in front [MCl2(dmso)2] (M = Pd Pt) Na2[PdCl4] methanol allowed us to isolate characterize complexes. However, for the analogue, formation any Pd(II) Pt(II) complex was not detected, indicating that it less prone bind M(II) ions than analogue. Density Functional Theory (DFT) Time-Dependent (TD-DFT) calculations have carried out order rationalize influence nature group on electronic delocalization. Molecular mechanics show free rotation relation requires greater energy income Studies cytotoxic activity new compounds colon (HCT116) breast (MDA-MB231 MCF7) cancer cell lines ligand are most active agents series MCF7 line their potency higher cisplatin. In non-tumoral human skin fibroblast BJ line, all were toxic Their potential ability modify electrophoretic mobility pBluescript SK+ plasmid DNA act as inhibitors Topoisomerases I IIα cathepsin B investigated.

参考文章(94)
Alexander F. Pozharskii, Alan R. Katritzky, Anatoly T. Soldatenkov, Heterocycles in Life and Society: An Introduction to Heterocyclic Chemistry, Biochemistry and Applications ,(2011)
Wilfred Louis Florio Armarego, Douglas Dalzell Perrin, D. R Perrin, Purification of laboratory chemicals ,(1966)
Ronald M. Pike, Zvi. Szafran, Mono M. Singh, Microscale inorganic chemistry J. Wiley. ,(1991)
Gautam R. Desiraju, Thomas Steiner, The Weak Hydrogen Bond: In Structural Chemistry and Biology ,(1999)
Pedro Martins, João Jesus, Sofia Santos, Luis R Raposo, Catarina Roma-Rodrigues, Pedro Viana Baptista, Alexandra R Fernandes, None, Heterocyclic Anticancer Compounds: Recent Advances and the Paradigm Shift towards the Use of Nanomedicine's Tool Box. Molecules. ,vol. 20, pp. 16852- 16891 ,(2015) , 10.3390/MOLECULES200916852
Franco M. Muggia, Andrea Bonetti, James D. Hoeschele, Marcel Rozencweig, Stephen B. Howell, Platinum Antitumor Complexes: 50 Years Since Barnett Rosenberg's Discovery. Journal of Clinical Oncology. ,vol. 33, pp. 4219- 4226 ,(2015) , 10.1200/JCO.2015.60.7481
Maryam Bashir, Afifa Bano, Abdul Ijaz, Bashir Chaudhary, Recent Developments and Biological Activities of N-Substituted Carbazole Derivatives: A Review. Molecules. ,vol. 20, pp. 13496- 13517 ,(2015) , 10.3390/MOLECULES200813496
Adile Ayati, Saeed Emami, Ali Asadipour, Abbas Shafiee, Alireza Foroumadi, Recent applications of 1,3-thiazole core structure in the identification of new lead compounds and drug discovery. European Journal of Medicinal Chemistry. ,vol. 97, pp. 699- 718 ,(2015) , 10.1016/J.EJMECH.2015.04.015
Glenn A. Crosby, James N. Demas, Measurement of photoluminescence quantum yields. Review The Journal of Physical Chemistry. ,vol. 75, pp. 991- 1024 ,(1971) , 10.1021/J100678A001