Jump to main content
Jump to site search
SCHEDULED MAINTENANCE Close the message box

Maintenance work is planned for Monday 16 August 2021 from 07:00 to 23:59 (BST).

Website performance may be temporarily affected and you may not be able to access some PDFs or images. If this does happen, refreshing your web browser should resolve the issue. We apologise for any inconvenience this might cause and thank you for your patience.


Issue 15, 2016

Mitochondrial selectivity and remarkable photocytotoxicity of a ferrocenyl neodymium(iii) complex of terpyridine and curcumin in cancer cells

Author affiliations

Abstract

A series of four novel neodymium(III) complexes of the formulation [Nd(R-tpy)(OO)(NO3)2] (1–4), where R-tpy is 4′-phenyl-2,2′:6′,2′′-terpyridine (Ph-tpy; 1, 2) and 4′-ferrocenyl-2,2′:6′,2′′-terpyridine (Fc-tpy; 3, 4); OO is the conjugate base of acetylacetone (Hacac; 1, 3) or curcumin (Hcurc; 2, 4), are synthesized and characterized. The single crystal structure of 1 shows that the complex is a discrete mononuclear species with the Nd(III) centre in a nine coordinate environment provided by a set of O6N3 donor atoms. Complexes 1 and 3 having the simple acac ligand are prepared as control compounds. Complex 4, possessing an appended ferrocenyl (Fc) and the curcumin moiety, is remarkably photocytotoxic to HeLa and MCF-7 cancer cells in visible light giving respective IC50 values of 0.7 μM and 2.1 μM while being significantly less toxic to MCF-10A normal cells (IC50 = 34 μM) and in the dark (IC50 > 50 μM). The phenyl appended complex 2, lacking a ferrocenyl moiety, is significantly less toxic to both the cell lines when compared with 4. Complexes 1 and 3, lacking the photoactive curcumin moiety, do not show any apparent toxicity both in light and in the dark. The cell death is apoptotic in nature and is mediated by the light-induced formation of reactive oxygen species (ROS). Fluorescence imaging experiment with HeLa cells reveals mitochondrial accumulation of complex 4 within 4 h of incubation. The complexes bind to calf thymus (ct) DNA with moderate affinity giving Kb values in the range of 104–105 M−1. The curcumin complexes 2 and 4 cleave plasmid supercoiled DNA to its nicked circular form in visible light via1O2 and ˙OH pathways. The presence of the ferrocenyl moiety is likely to be responsible for the enhanced cellular uptake and photocytotoxicity of complex 4. Thus, the mitochondria targeting complex 4, being remarkably cytotoxic in light but non-toxic in the dark and to normal cells, is a potential candidate for photochemotherapeutic applications.

Graphical abstract: Mitochondrial selectivity and remarkable photocytotoxicity of a ferrocenyl neodymium(iii) complex of terpyridine and curcumin in cancer cells

Supplementary files

Article information


Submitted
07 Dec 2015
Accepted
23 Feb 2016
First published
23 Feb 2016

Dalton Trans., 2016,45, 6424-6438
Article type
Paper
Author version available

Mitochondrial selectivity and remarkable photocytotoxicity of a ferrocenyl neodymium(III) complex of terpyridine and curcumin in cancer cells

T. Sarkar, S. Banerjee, S. Mukherjee and A. Hussain, Dalton Trans., 2016, 45, 6424 DOI: 10.1039/C5DT04775G

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.


Social activity

Search articles by author

Spotlight

Advertisements