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Exploring the cellular uptake and localisation of phosphorescent rhenium fac-tricarbonyl metallosurfactants as a function of lipophilicity

Exploring the cellular uptake and localisation of phosphorescent rhenium fac-tricarbonyl metallosurfactants as a function of lipophilicity
Exploring the cellular uptake and localisation of phosphorescent rhenium fac-tricarbonyl metallosurfactants as a function of lipophilicity

A systematic study of the cellular uptake of emissive complexes as a function of their lipophilicity is presented. Here a series of amphiphilic rhenium fac-tricarbonyl bisimine complexes bearing axial substituted imidazole or thiazole ligands, [Re(bpy)(CO)3(ImCnHm)]+ {n = 1 m = 3 (1+), n = 4 m = 9 (2+), n = 8 m = 17 (3+), n = 12 m = 25 (4+), n = 16 m = 33 (5+), n = 2 m = 3 (6+); bpy = 2,2'-bipyridine, Im = imidazole} and [Re(bpy)(CO)3(L)]+ {L = 1-mesitylimidazole, ImMes (7+), 4,5-dimethylthiazole, dmt (8+) and 4-methyl-5-thiazole-ethanol, mte (9+)} is reported. The X-ray crystal structures of 2+, 8+ and 9+ confirm the geometry and expected distribution of ligands and indicated that the plane of the imidazole/thiazole ring is approximately parallel to the long axis of the bipy ligand. Luminescence studies revealed excellent properties for their use in cell imaging with visible excitation and broad emission profiles. Their uptake in two distinct species has been examined by fluorescence imaging of the diplomonad fish parasite Spironucleus vortens (S. vortens) and rod-shaped yeast Schizosaccharomyces pombe (Schiz. pombe) as a function of their lipophilicity. The uptake of the complexes was highest for the more lipophilic 2+-5+ in both S. vortens and Schiz. pombe in which the long alkyl chain aids in crossing bilipid membranes. However, the increased lipophilicity of longer chains also resulted in greater toxicity. Localisation over the whole cell varied with differing alkyl chain lengths with complex 2+ preferentially locating to the nucleus of S. vortens, 3+ showing enhanced nuclear partitioning in Schiz. pombe, and 4+ for the remaining cell wall bound in the case of S. vortens. Interestingly, complexes of intermediate lipophilicity such as 7+ and 8+ showed reasonable uptake, proved to be non-toxic, and were capable of crossing exterior cell walls and localising in the organelles of the cells.

0300-9246
14241-14253
Hallett, Andrew J.
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Placet, Emeline
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Prieux, Roxane
ec42db27-df05-41f1-b324-1ad1b59a1eae
McCafferty, Danielle
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Platts, James A.
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Lloyd, David
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Isaacs, Marc
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Hayes, Anthony J.
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Coles, Simon J.
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Pitak, Mateusz B.
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Marchant, Sarah
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Marriott, Stephen N.
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Allemann, Rudolf K.
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Dervisi, Athanasia
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Fallis, Ian A.
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Hallett, Andrew J.
36cc4f6a-74d4-4894-8a65-8dd9d7803593
Placet, Emeline
e718347f-4af2-4da4-99ff-6407b9e0f8ef
Prieux, Roxane
ec42db27-df05-41f1-b324-1ad1b59a1eae
McCafferty, Danielle
311aca27-74c4-4fc9-af80-b3f841e4ee84
Platts, James A.
2df1575c-ebd8-4dac-af9e-1590b47f0a73
Lloyd, David
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Isaacs, Marc
581415d1-5ee1-4394-b56b-a881c2e7493d
Hayes, Anthony J.
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Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Pitak, Mateusz B.
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Marchant, Sarah
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Marriott, Stephen N.
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Allemann, Rudolf K.
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Dervisi, Athanasia
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Fallis, Ian A.
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Hallett, Andrew J., Placet, Emeline, Prieux, Roxane, McCafferty, Danielle, Platts, James A., Lloyd, David, Isaacs, Marc, Hayes, Anthony J., Coles, Simon J., Pitak, Mateusz B., Marchant, Sarah, Marriott, Stephen N., Allemann, Rudolf K., Dervisi, Athanasia and Fallis, Ian A. (2018) Exploring the cellular uptake and localisation of phosphorescent rhenium fac-tricarbonyl metallosurfactants as a function of lipophilicity. Dalton transactions (Cambridge, England : 2003), 47 (40), 14241-14253. (doi:10.1039/c8dt00669e).

Record type: Article

Abstract

A systematic study of the cellular uptake of emissive complexes as a function of their lipophilicity is presented. Here a series of amphiphilic rhenium fac-tricarbonyl bisimine complexes bearing axial substituted imidazole or thiazole ligands, [Re(bpy)(CO)3(ImCnHm)]+ {n = 1 m = 3 (1+), n = 4 m = 9 (2+), n = 8 m = 17 (3+), n = 12 m = 25 (4+), n = 16 m = 33 (5+), n = 2 m = 3 (6+); bpy = 2,2'-bipyridine, Im = imidazole} and [Re(bpy)(CO)3(L)]+ {L = 1-mesitylimidazole, ImMes (7+), 4,5-dimethylthiazole, dmt (8+) and 4-methyl-5-thiazole-ethanol, mte (9+)} is reported. The X-ray crystal structures of 2+, 8+ and 9+ confirm the geometry and expected distribution of ligands and indicated that the plane of the imidazole/thiazole ring is approximately parallel to the long axis of the bipy ligand. Luminescence studies revealed excellent properties for their use in cell imaging with visible excitation and broad emission profiles. Their uptake in two distinct species has been examined by fluorescence imaging of the diplomonad fish parasite Spironucleus vortens (S. vortens) and rod-shaped yeast Schizosaccharomyces pombe (Schiz. pombe) as a function of their lipophilicity. The uptake of the complexes was highest for the more lipophilic 2+-5+ in both S. vortens and Schiz. pombe in which the long alkyl chain aids in crossing bilipid membranes. However, the increased lipophilicity of longer chains also resulted in greater toxicity. Localisation over the whole cell varied with differing alkyl chain lengths with complex 2+ preferentially locating to the nucleus of S. vortens, 3+ showing enhanced nuclear partitioning in Schiz. pombe, and 4+ for the remaining cell wall bound in the case of S. vortens. Interestingly, complexes of intermediate lipophilicity such as 7+ and 8+ showed reasonable uptake, proved to be non-toxic, and were capable of crossing exterior cell walls and localising in the organelles of the cells.

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Accepted/In Press date: 10 May 2018
e-pub ahead of print date: 23 May 2018
Published date: 16 October 2018

Identifiers

Local EPrints ID: 425639
URI: http://eprints.soton.ac.uk/id/eprint/425639
ISSN: 0300-9246
PURE UUID: 2ca5ea92-b4c8-4760-bb1c-9f1e4c96acb8
ORCID for Simon J. Coles: ORCID iD orcid.org/0000-0001-8414-9272
ORCID for Mateusz B. Pitak: ORCID iD orcid.org/0000-0002-3680-7100

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Date deposited: 30 Oct 2018 17:30
Last modified: 18 Feb 2021 16:53

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Contributors

Author: Andrew J. Hallett
Author: Emeline Placet
Author: Roxane Prieux
Author: Danielle McCafferty
Author: James A. Platts
Author: David Lloyd
Author: Marc Isaacs
Author: Anthony J. Hayes
Author: Simon J. Coles ORCID iD
Author: Mateusz B. Pitak ORCID iD
Author: Sarah Marchant
Author: Stephen N. Marriott
Author: Rudolf K. Allemann
Author: Athanasia Dervisi
Author: Ian A. Fallis

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