Effects of the Bidentate Ligand on the Photophysical Properties, Cellular Uptake, and (Photo)cytotoxicity of Glycoconjugates Based on the [Ru(tpy)(NN)(L)]2+ Scaffold

L.N. Lameijer; T.G. Brevé; V.H.S. van Rixel; S.H.C. Askes; M.A. Siegler; S. Bonnet

doi:10.1002/chem.201705388

Effects of the Bidentate Ligand on the Photophysical Properties, Cellular Uptake, and (Photo)cytotoxicity of Glycoconjugates Based on the [Ru(tpy)(NN)(L)]2+ Scaffold

L.N. Lameijer, T.G. Brevé, V.H.S. van Rixel, S.H.C. Askes, M.A. Siegler, S. Bonnet

Research output: Contribution to Journal › Article › Academic › peer-review

Abstract

© 2018 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.Ruthenium polypyridyl complexes have received widespread attention as potential chemotherapeutics in photodynamic therapy (PDT) and in photochemotherapy (PACT). Here, we investigate a series of sixteen ruthenium polypyridyl complexes with general formula [Ru(tpy)(N−N)(L)]+/2+ (tpy=2,2′:6′,2′′-terpyridine, N−N=bpy (2,2′-bipyridine), phen (1,10-phenanthroline), dpq (pyrazino[2,3-f][1,10]phenanthroline), dppz (dipyrido[3,2-a:2′,3′-c]phenazine, dppn (benzo[i]dipyrido[3,2-a:2′,3′-c]phenazine), pmip (2-(4-methylphenyl)-1H-imidazo[4,5-f][1,10]phenanthroline), pymi ((E)-N-phenyl-1-(pyridin-2-yl)methanimine), or azpy (2-(phenylazo)pyridine), L=Cl− or 2-(2-(2-(methylthio)ethoxy)ethoxy)ethyl-β-d-glucopyranoside) and their potential for either PDT or PACT. We demonstrate that although increased lipophilicity is generally related to increased uptake of these complexes, it does not necessarily lead to increased (photo)cytotoxicity. However, the non-toxic complexes are excellent candidates as PACT carriers.

Original language	English
Pages (from-to)	2709-2717
Journal	Chemistry - A European Journal
Volume	24
Issue number	11
DOIs	https://doi.org/10.1002/chem.201705388
Publication status	Published - 21 Feb 2018
Externally published	Yes

Funding

This work was supportedby the Dutch Organization for Scientific Research (NWO-CW) with a VIDI grant to S.B. The European Research Council is kindly acknowledged for a Starting Grant to S.B. Prof. E. Bouwman is gratefully acknowledged for her support and input. Fons Lefeber and Dr. Karthick Sai Sankar Gupta are acknowledged for their help with NMR spectroscopy. Gerwin Spijksma is gratefully acknowledged for performing the HRMS measurements.

Funders	Funder number
Dutch Organization for Scientific Research
NWO-CW
H2020 European Research Council
European Research Council
Nederlandse Organisatie voor Wetenschappelijk Onderzoek

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@article{5b61098c36c44c799644b676b93c589e,

title = "Effects of the Bidentate Ligand on the Photophysical Properties, Cellular Uptake, and (Photo)cytotoxicity of Glycoconjugates Based on the [Ru(tpy)(NN)(L)]2+ Scaffold",

abstract = "{\textcopyright} 2018 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.Ruthenium polypyridyl complexes have received widespread attention as potential chemotherapeutics in photodynamic therapy (PDT) and in photochemotherapy (PACT). Here, we investigate a series of sixteen ruthenium polypyridyl complexes with general formula [Ru(tpy)(N−N)(L)]+/2+ (tpy=2,2′:6′,2′′-terpyridine, N−N=bpy (2,2′-bipyridine), phen (1,10-phenanthroline), dpq (pyrazino[2,3-f][1,10]phenanthroline), dppz (dipyrido[3,2-a:2′,3′-c]phenazine, dppn (benzo[i]dipyrido[3,2-a:2′,3′-c]phenazine), pmip (2-(4-methylphenyl)-1H-imidazo[4,5-f][1,10]phenanthroline), pymi ((E)-N-phenyl-1-(pyridin-2-yl)methanimine), or azpy (2-(phenylazo)pyridine), L=Cl− or 2-(2-(2-(methylthio)ethoxy)ethoxy)ethyl-β-d-glucopyranoside) and their potential for either PDT or PACT. We demonstrate that although increased lipophilicity is generally related to increased uptake of these complexes, it does not necessarily lead to increased (photo)cytotoxicity. However, the non-toxic complexes are excellent candidates as PACT carriers.",

author = "L.N. Lameijer and T.G. Brev{\'e} and {van Rixel}, V.H.S. and S.H.C. Askes and M.A. Siegler and S. Bonnet",

year = "2018",

month = feb,

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doi = "10.1002/chem.201705388",

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Effects of the Bidentate Ligand on the Photophysical Properties, Cellular Uptake, and (Photo)cytotoxicity of Glycoconjugates Based on the [Ru(tpy)(NN)(L)]2+ Scaffold. / Lameijer, L.N.; Brevé, T.G.; van Rixel, V.H.S. et al.
In: Chemistry - A European Journal, Vol. 24, No. 11, 21.02.2018, p. 2709-2717.

Research output: Contribution to Journal › Article › Academic › peer-review

TY - JOUR

T1 - Effects of the Bidentate Ligand on the Photophysical Properties, Cellular Uptake, and (Photo)cytotoxicity of Glycoconjugates Based on the [Ru(tpy)(NN)(L)]2+ Scaffold

AU - Lameijer, L.N.

AU - Brevé, T.G.

AU - van Rixel, V.H.S.

AU - Askes, S.H.C.

AU - Siegler, M.A.

AU - Bonnet, S.

PY - 2018/2/21

Y1 - 2018/2/21

N2 - © 2018 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.Ruthenium polypyridyl complexes have received widespread attention as potential chemotherapeutics in photodynamic therapy (PDT) and in photochemotherapy (PACT). Here, we investigate a series of sixteen ruthenium polypyridyl complexes with general formula [Ru(tpy)(N−N)(L)]+/2+ (tpy=2,2′:6′,2′′-terpyridine, N−N=bpy (2,2′-bipyridine), phen (1,10-phenanthroline), dpq (pyrazino[2,3-f][1,10]phenanthroline), dppz (dipyrido[3,2-a:2′,3′-c]phenazine, dppn (benzo[i]dipyrido[3,2-a:2′,3′-c]phenazine), pmip (2-(4-methylphenyl)-1H-imidazo[4,5-f][1,10]phenanthroline), pymi ((E)-N-phenyl-1-(pyridin-2-yl)methanimine), or azpy (2-(phenylazo)pyridine), L=Cl− or 2-(2-(2-(methylthio)ethoxy)ethoxy)ethyl-β-d-glucopyranoside) and their potential for either PDT or PACT. We demonstrate that although increased lipophilicity is generally related to increased uptake of these complexes, it does not necessarily lead to increased (photo)cytotoxicity. However, the non-toxic complexes are excellent candidates as PACT carriers.

AB - © 2018 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.Ruthenium polypyridyl complexes have received widespread attention as potential chemotherapeutics in photodynamic therapy (PDT) and in photochemotherapy (PACT). Here, we investigate a series of sixteen ruthenium polypyridyl complexes with general formula [Ru(tpy)(N−N)(L)]+/2+ (tpy=2,2′:6′,2′′-terpyridine, N−N=bpy (2,2′-bipyridine), phen (1,10-phenanthroline), dpq (pyrazino[2,3-f][1,10]phenanthroline), dppz (dipyrido[3,2-a:2′,3′-c]phenazine, dppn (benzo[i]dipyrido[3,2-a:2′,3′-c]phenazine), pmip (2-(4-methylphenyl)-1H-imidazo[4,5-f][1,10]phenanthroline), pymi ((E)-N-phenyl-1-(pyridin-2-yl)methanimine), or azpy (2-(phenylazo)pyridine), L=Cl− or 2-(2-(2-(methylthio)ethoxy)ethoxy)ethyl-β-d-glucopyranoside) and their potential for either PDT or PACT. We demonstrate that although increased lipophilicity is generally related to increased uptake of these complexes, it does not necessarily lead to increased (photo)cytotoxicity. However, the non-toxic complexes are excellent candidates as PACT carriers.

U2 - 10.1002/chem.201705388

DO - 10.1002/chem.201705388

M3 - Article

SN - 0947-6539

VL - 24

SP - 2709

EP - 2717

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 11

ER -

Effects of the Bidentate Ligand on the Photophysical Properties, Cellular Uptake, and (Photo)cytotoxicity of Glycoconjugates Based on the [Ru(tpy)(NN)(L)]2+ Scaffold

Abstract

Funding

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