Novel luminescent benzopyranothiophene- and BODIPY-derived aroylhydrazonic ligands and their dicopper(II) complexes: syntheses, antiproliferative activity and cellular uptake studies

Two novel unsymmetrical binucleating aroylhydrazonic ligands and four dicopper(II) complexes carrying fluorescent benzopyranothiophene (BPT) or boron dipyrromethene (BODIPY) entities were synthesized and fully characterized. Complex 1 , derived from the BPT-containing ligand H 3 L1 , had its crystal...

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Bibliographic Details
Published in:Journal of biological inorganic chemistry 2021-09, Vol.26 (6), p.675-688
Main Authors: Rada, Jesica Paola, Forté, Jérémy, Gontard, Geoffrey, Bachelet, Claude-Marie, Rey, Nicolás A., Salmain, Michèle, Corcé, Vincent
Format: Article
Language:English
Subjects:
Antineoplastic Agents - chemical synthesis
Antineoplastic Agents - metabolism
Antineoplastic Agents - pharmacology
Biochemistry
Biomedical and Life Sciences
Boron
Boron Compounds - chemistry
Breast cancer
Cancer
Cell Line, Tumor
Chemical Sciences
Coordination chemistry
Copper - chemistry
Crystal structure
Cytotoxicity
Female
Fluorescence microscopy
Humans
Inorganic chemistry
Life Sciences
Ligands
Medicinal Chemistry
Microbiology
Microscopy, Fluorescence
Mitochondria
Molecular Structure
Original Paper
Spectroscopy
Thiophenes - chemistry
Thiophenes - pharmacology
Triple Negative Breast Neoplasms
X-ray diffraction
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Summary:Two novel unsymmetrical binucleating aroylhydrazonic ligands and four dicopper(II) complexes carrying fluorescent benzopyranothiophene (BPT) or boron dipyrromethene (BODIPY) entities were synthesized and fully characterized. Complex 1 , derived from the BPT-containing ligand H 3 L1 , had its crystal structure elucidated through X-ray diffraction measurements. The absorption and fluorescence profiles of all the compounds obtained were discussed. Additionally, the stability of the ligands and complexes was monitored by UV–vis spectroscopy in DMSO and biologically relevant media. All the compounds showed moderate to high cytotoxicity towards the triple negative human breast cancer cell line MDA-MB-231. BPT derivatives were the most cytotoxic, specially H 3 L1 , reaching an IC 50 value up to the nanomolar range. Finally, fluorescence microscopy imaging studies employing mitochondria- and nucleus-staining dyes showed that the BODIPY-carrying ligand H 3 L2 was highly cell permeant and suggested that the compound preferentially accumulates in the mitochondria. Graphic abstract
ISSN:0949-8257
1432-1327
DOI:10.1007/s00775-021-01885-5