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254027.pdf (1.61 MB)

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2022-11-12

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cc-by-nc-nd (c) Elsevier B.V., 2022
Si us plau utilitzeu sempre aquest identificador per citar o enllaçar aquest document: https://hdl.handle.net/2445/214806

Synthesis and biological properties of palladium(II) cyclometallated compounds derived from ( E )-2-((4-hydroxybenzylidene)amino)phenol

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( E )-2-((4-hydroxybenzylidene)amino)phenol (iminophenol a ) reacted with Pd(OAc) 2 giving place to com- pound 1a , in which the iminophenol was bonded to palladium(II) in a κ3 - C ortho ,N,O ortho tridentate chelat- ing mode. Thus, 1a was formed by neutral mononuclear units of schematic formula Pd(C,N,O), consisting of two fused five-membered metallacycles. Self-assembly of the Pd(C,N,O) units gave place to the polynu- clear structure of 1a . Treatment of 1a with PPh 3 or PPh 2 CH 2 CH 2 PPh 2 in molar ratio Pd(II)/PPh 3 = 1/1 or Pd(II)/PPh 2 CH 2 CH 2 PPh 2 = 2/1 produced the mononuclear or dinuclear compound of schematic formula [Pd(C,N,O)(PPh 3 )] ( 2a ) or {[P d (C,N,O)] 2 ( μ2 -PPh 2 CH 2 CH 2 PPh 2 )} ( 3a ), respectively. Compounds a were char- acterized by elemental analysis, high resolution ESI-( + ) mass spectrometry, IR, and NMR. In addition, the crystal structure of the adducts 2a ·2(CH 2 Cl-CH 2 Cl) and 3a ·5(dmso) was determined by single crystal X- ray diffraction analysis. Most compounds a were noncytotoxic or poorly cytotoxic. Nonetheless, 2a was moderately cytotoxic against the MCF-7 breast and HCT-116 colon human cancer cell lines, and presented very low cytotoxicity towards normal skin human BJ cells. Compounds a showed moderate antibacterial activity against some Gram-positive ( B. subtilis and S. aureus ) and Gram-negative ( E. coli ) bacterial strains, and displayed also moderate antioxidant activity, producing 3a the best antioxidant activity. 1a changed the electrophoretic mobility of the pBluescript SK + plasmid DNA. This change followed the pattern of cisplatin , but it started at a concentration twenty times higher than with cisplatin . Moreover, compounds 1a - 3a inhibited topoisomerase IIα at concentrations of 10, 50 and 25 μM, respectively.

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Matèries

Pal·ladi (Element químic), Antioxidants, ADN

Matèries (anglès)

Palladium, Antioxidants, DNA

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Articles publicats en revistes (Bioquímica i Fisiologia)
Articles publicats en revistes (Institut de Biomedicina (IBUB))

Citació

ALBERT MACH, Joan, AL JANABI, Basma, GRANELL SANVICENTE, Jaime ramón, SADAT HASHEMI, Mojdeh, SAINZ GARCÍA, Daniel, KHOSA, M. kaleem, CALVIS, Carme, MESSEGUER, Ramon, BALDOMÀ LLAVINÉS, Laura, BADÍA PALACÍN, Josefa, FONT BARDIA, Ma. mercedes. Synthesis and biological properties of palladium(II) cyclometallated compounds derived from ( E )-2-((4-hydroxybenzylidene)amino)phenol. _Journal of Organometallic Chemistry_. 2022. Vol. 983, núm. 1-11. [consulta: 26 de novembre de 2025]. ISSN: 0022-328X. [Disponible a: https://hdl.handle.net/2445/214806]

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