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Molecules 2016, 21(2), 194; doi:10.3390/molecules21020194

Cellular Uptake and Photo-Cytotoxicity of a Gadolinium(III)-DOTA-Naphthalimide Complex “Clicked” to a Lipidated Tat Peptide

1
Monash Institute of Pharmaceutical Sciences, Monash University, Parkville VIC 3163, Australia
2
Department of Chemistry, University of Zurich, Winterthurerstrasse 190, Zurich CH-8057, Switzerland
3
School of Chemistry, Monash University, Clayton VIC 3800, Australia
These authors contributed equally to this work.
*
Authors to whom correspondence should be addressed.
Academic Editor: Wiktor Szymański
Received: 12 December 2015 / Revised: 1 February 2016 / Accepted: 2 February 2016 / Published: 5 February 2016
(This article belongs to the Special Issue Photoresponsive Drugs)
View Full-Text   |   Download PDF [2002 KB, uploaded 5 February 2016]   |  

Abstract

A new bifunctional macrocyclic chelator featuring a conjugatable alkynyl-naphthalimide fluorophore pendant group has been prepared and its Gd(III) complex coupled to a cell-penetrating lipidated azido-Tat peptide derivative using Cu(I)-catalysed “click” chemistry. The resulting fluorescent conjugate is able to enter CAL-33 tongue squamous carcinoma cells, as revealed by confocal microscopy, producing a very modest anti-proliferative effect (IC50 = 93 µM). Due to the photo-reactivity of the naphthalimide moiety, however, the conjugate’s cytotoxicity is significantly enhanced (IC50 = 16 µM) upon brief low-power UV-A irradiation. View Full-Text
Keywords: cell-penetrating peptide; fluorescence; gadolinium complex; photo-cytotoxicity; theranostic cell-penetrating peptide; fluorescence; gadolinium complex; photo-cytotoxicity; theranostic
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

O’Malley, W.I.; Rubbiani, R.; Aulsebrook, M.L.; Grace, M.R.; Spiccia, L.; Tuck, K.L.; Gasser, G.; Graham, B. Cellular Uptake and Photo-Cytotoxicity of a Gadolinium(III)-DOTA-Naphthalimide Complex “Clicked” to a Lipidated Tat Peptide. Molecules 2016, 21, 194.

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