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Article ; Online: A tetranuclear polypyridylruthenium(II) complex as a selective stain for extracellular vesicle penetration through brain microvascular endothelium.

Wardhani, Kartika / Levina, Aviva / Sun, Biyun / Grau, Georges E R / Keene, F Richard / Collins, J Grant / Lay, Peter A

Chemical communications (Cambridge, England)

2023 Volume 59, Issue 45, Page(s) 6877–6880

Abstract: A new photoluminescent polypyridylruthenium(II) stain for extracellular vesicles (EVs) released from lipopolysaccharide-stimulated THP-1 monocytes enabled important new insights into how the bacteria-induced immune system affects the blood-brain barrier ( ...

Abstract	A new photoluminescent polypyridylruthenium(II) stain for extracellular vesicles (EVs) released from lipopolysaccharide-stimulated THP-1 monocytes enabled important new insights into how the bacteria-induced immune system affects the blood-brain barrier (BBB). These included previously unknown aspects of EV interactions with BBB microvascular endothelial cells and the extracellular matrix relevant to human brain diseases.
MeSH term(s)	Humans ; Endothelial Cells ; Endothelium ; Brain ; Blood-Brain Barrier ; Extracellular Vesicles
Language	English
Publishing date	2023-06-01
Publishing country	England
Document type	Journal Article
ZDB-ID	1472881-3
ISSN	1364-548X ; 1359-7345 ; 0009-241X
ISSN (online)	1364-548X
ISSN	1359-7345 ; 0009-241X
DOI	10.1039/d2cc05827h
Database	MEDical Literature Analysis and Retrieval System OnLINE

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Article ; Online: Ruthenium complexes as antimicrobial agents.

Li, Fangfei / Collins, J Grant / Keene, F Richard

Chemical Society reviews

2015 Volume 44, Issue 8, Page(s) 2529–2542

Abstract: One of the major advances in medical science has been the development of antimicrobials; however, a consequence of their widespread use has been the emergence of drug-resistant populations of microorganisms. There is clearly a need for the development of ...

Abstract	One of the major advances in medical science has been the development of antimicrobials; however, a consequence of their widespread use has been the emergence of drug-resistant populations of microorganisms. There is clearly a need for the development of new antimicrobials--but more importantly, there is the need for the development of new classes of antimicrobials, rather than drugs based upon analogues of known scaffolds. Due to the success of the platinum anticancer agents, there has been considerable interest in the development of therapeutic agents based upon other transition metals--and in particular ruthenium(II/III) complexes, due to their well known interaction with DNA. There have been many studies of the anticancer properties and cellular localisation of a range of ruthenium complexes in eukaryotic cells over the last decade. However, only very recently has there been significant interest in their antimicrobial properties. This review highlights the types of ruthenium complexes that have exhibited significant antimicrobial activity and discusses the relationship between chemical structure and biological processing--including site(s) of intracellular accumulation--of the ruthenium complexes in both bacterial and eukaryotic cells.
MeSH term(s)	Animals ; Anti-Infective Agents/chemistry ; Anti-Infective Agents/pharmacology ; Bacteria/cytology ; Bacteria/drug effects ; Humans ; Ruthenium/chemistry ; Ruthenium/pharmacology
Chemical Substances	Anti-Infective Agents ; Ruthenium (7UI0TKC3U5)
Language	English
Publishing date	2015-04-21
Publishing country	England
Document type	Journal Article ; Review
ZDB-ID	1472875-8
ISSN	1460-4744 ; 0306-0012
ISSN (online)	1460-4744
ISSN	0306-0012
DOI	10.1039/c4cs00343h
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Article: Eukaryotic Cell Toxicity and HSA Binding of [Ru(Me

Sun, Biyun / Musgrave, Ian F / Day, Anthony I / Heimann, Kirsten / Keene, F Richard / Collins, J Grant

Frontiers in chemistry

2018 Volume 6, Page(s) 595

Abstract: The toxicity ( ... ...

Abstract	The toxicity (IC
Language	English
Publishing date	2018-11-30
Publishing country	Switzerland
Document type	Journal Article
ZDB-ID	2711776-5
ISSN	2296-2646
ISSN	2296-2646
DOI	10.3389/fchem.2018.00595
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Article ; Online: Synthesis and biological properties of tetranuclear ruthenium complexes containing the bis[4(4'-methyl-2,2'-bipyridyl)]-1,7-heptane ligand.

Sun, Biyun / Sundaraneedi, Madhu K / Southam, Hannah M / Poole, Robert K / Musgrave, Ian F / Keene, F Richard / Collins, J Grant

Dalton transactions (Cambridge, England : 2003)

2019 Volume 48, Issue 38, Page(s) 14505–14515

Abstract: Linear and non-linear tetranuclear ruthenium(ii) complexes containing the bridging ligand bis[4(4'-methyl-2,2'-bipyridyl)]-1,7-heptane have been synthesised and their biological properties examined. The minimum inhibitory concentrations (MIC) and the ... ...

Abstract	Linear and non-linear tetranuclear ruthenium(ii) complexes containing the bridging ligand bis[4(4'-methyl-2,2'-bipyridyl)]-1,7-heptane have been synthesised and their biological properties examined. The minimum inhibitory concentrations (MIC) and the minimum bactericidal concentrations (MBC) of the ruthenium(ii) complexes were determined against six strains of bacteria: Gram-positive Staphylococcus aureus (S. aureus) and methicillin-resistant S. aureus (MRSA); and the Gram-negative Escherichia coli (E. coli) strains MG1655, APEC, UPEC and Pseudomonas aeruginosa (P. aeruginosa). The results showed that both tetranuclear complexes had significant antimicrobial activity, with the non-linear (branched) species (Rubb
MeSH term(s)	2,2'-Dipyridyl/chemistry ; 2,2'-Dipyridyl/pharmacology ; Anti-Bacterial Agents/chemical synthesis ; Anti-Bacterial Agents/chemistry ; Anti-Bacterial Agents/pharmacology ; Antineoplastic Agents/chemical synthesis ; Antineoplastic Agents/chemistry ; Antineoplastic Agents/pharmacology ; Caco-2 Cells ; Cell Proliferation/drug effects ; Coordination Complexes/chemical synthesis ; Coordination Complexes/chemistry ; Coordination Complexes/pharmacology ; Drug Screening Assays, Antitumor ; Gram-Negative Bacteria/drug effects ; Gram-Positive Bacteria/drug effects ; Hep G2 Cells ; Heptanes/chemistry ; Heptanes/pharmacology ; Humans ; Ligands ; Pyridines/chemistry ; Ruthenium/chemistry ; Ruthenium/pharmacology
Chemical Substances	Anti-Bacterial Agents ; Antineoplastic Agents ; Coordination Complexes ; Heptanes ; Ligands ; Pyridines ; bis(4(4'-methyl-2,2'-bipyridyl))-1,7-heptane ; 2,2'-Dipyridyl (551W113ZEP) ; Ruthenium (7UI0TKC3U5)
Language	English
Publishing date	2019-09-18
Publishing country	England
Document type	Journal Article
ZDB-ID	1472887-4
ISSN	1477-9234 ; 1364-5447 ; 0300-9246 ; 1477-9226
ISSN (online)	1477-9234 ; 1364-5447
ISSN	0300-9246 ; 1477-9226
DOI	10.1039/c9dt03221e
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Article ; Online: Biological processing of dinuclear ruthenium complexes in eukaryotic cells.

Li, Xin / Heimann, Kirsten / Dinh, Xuyen Thi / Keene, F Richard / Collins, J Grant

Molecular bioSystems

2016 Volume 12, Issue 10, Page(s) 3032–3045

Abstract: The biological processing - mechanism of cellular uptake, effects on the cytoplasmic and mitochondrial membranes, intracellular sites of localisation and induction of reactive oxygen species - of two dinuclear polypyridylruthenium(ii) complexes has been ... ...

Abstract	The biological processing - mechanism of cellular uptake, effects on the cytoplasmic and mitochondrial membranes, intracellular sites of localisation and induction of reactive oxygen species - of two dinuclear polypyridylruthenium(ii) complexes has been examined in three eukaryotic cells lines. Flow cytometry was used to determine the uptake of [{Ru(phen)2}2{μ-bb12}](4+) (Rubb12) and [Ru(phen)2(μ-bb7)Ru(tpy)Cl](3+) {Rubb7-Cl, where phen = 1,10-phenanthroline, tpy = 2,2':6',2''-terpyridine and bbn = bis[4(4'-methyl-2,2'-bipyridyl)]-1,n-alkane} in baby hamster kidney (BHK), human embryonic kidney (HEK-293) and liver carcinoma (HepG2) cell lines. The results demonstrated that the major uptake mechanism for Rubb12 and Rubb7-Cl was active transport, although with a significant contribution from carrier-assisted diffusion for Rubb12 and passive diffusion for Rubb7-Cl. Flow cytometry coupled with Annexin V/TO-PRO-3 double-staining was used to compare cell death by membrane damage or apoptosis. Rubb12 induced significant direct membrane damage, particularly with HepG2 cells, while Rubb7-Cl caused considerably less membrane damage but induced greater levels of apoptosis. Confocal microscopy, coupled with JC-1 assays, demonstrated that Rubb12 depolarises the mitochondrial membrane, whereas Rubb7-Cl had a much smaller affect. Cellular localisation experiments indicated that Rubb12 did not accumulate in the mitochondria, whereas significant mitochondrial accumulation was observed for Rubb7-Cl. The effect of Rubb12 and Rubb7-Cl on intracellular superoxide dismutase activity showed that the ruthenium complexes could induce cell death via a reactive oxygen species-mediated pathway. The results of this study demonstrate that Rubb12 predominantly kills eukaryotic cells by damaging the cytoplasmic membrane. As this dinuclear ruthenium complex has been previously shown to exhibit greater toxicity towards bacteria than eukaryotic cells, the results of the present study suggest that metal-based cationic oligomers can achieve selective toxicity against bacteria, despite exhibiting a non-specific membrane damage mechanism of action.
MeSH term(s)	Adenosine Triphosphate/biosynthesis ; Animals ; Apoptosis ; Biological Transport ; Cation Transport Proteins/antagonists & inhibitors ; Cation Transport Proteins/metabolism ; Cell Line ; Cell Membrane/metabolism ; Cell Membrane Permeability ; Eukaryotic Cells/drug effects ; Eukaryotic Cells/metabolism ; Flow Cytometry ; Humans ; Membrane Potential, Mitochondrial ; Molecular Structure ; Reactive Oxygen Species/metabolism ; Ruthenium/chemistry ; Ruthenium/metabolism ; Temperature
Chemical Substances	Cation Transport Proteins ; Reactive Oxygen Species ; Ruthenium (7UI0TKC3U5) ; Adenosine Triphosphate (8L70Q75FXE)
Language	English
Publishing date	2016-10-20
Publishing country	England
Document type	Journal Article
ZDB-ID	2188635-0
ISSN	1742-2051 ; 1742-206X
ISSN (online)	1742-2051
ISSN	1742-206X
DOI	10.1039/c6mb00431h
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Article ; Online: Synthesis, isomerisation and biological properties of mononuclear ruthenium complexes containing the bis[4(4'-methyl-2,2'-bipyridyl)]-1,7-heptane ligand.

Sun, Biyun / Southam, Hannah M / Butler, Jonathan A / Poole, Robert K / Burgun, Alexandre / Tarzia, Andrew / Keene, F Richard / Collins, J Grant

Dalton transactions (Cambridge, England : 2003)

2018 Volume 47, Issue 7, Page(s) 2422–2434

Abstract: A series of mononuclear ruthenium(ii) complexes containing the tetradentate ligand bis[4(4'-methyl-2,2'-bipyridyl)]-1,7-heptane have been synthesised and their biological properties examined. In the synthesis of the [Ru(phen')( ... ...

Abstract	A series of mononuclear ruthenium(ii) complexes containing the tetradentate ligand bis[4(4'-methyl-2,2'-bipyridyl)]-1,7-heptane have been synthesised and their biological properties examined. In the synthesis of the [Ru(phen')(bb
Language	English
Publishing date	2018-02-13
Publishing country	England
Document type	Journal Article
ZDB-ID	1472887-4
ISSN	1477-9234 ; 1364-5447 ; 0300-9246 ; 1477-9226
ISSN (online)	1477-9234 ; 1364-5447
ISSN	0300-9246 ; 1477-9226
DOI	10.1039/c7dt04595f
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Article: Membrane Insertion of a Dinuclear Polypyridylruthenium(II) Complex Revealed by Solid-State NMR and Molecular Dynamics Simulation: Implications for Selective Antibacterial Activity

Weber, Daniel K / Collins J. Grant / Downton Matthew T / Keene F. Richard / Sani Marc-Antoine / Separovic Frances

Journal of the American Chemical Society. 2016 Nov. 23, v. 138, no. 46

2016

Abstract: Dinuclear polypyridylruthenium(II) complexes bridged by a flexible methylene linker have received considerable interest as potential antibacterial agents. Their potency and uptake into bacterial cells is directly modulated by the length of the bridging ... ...

Abstract	Dinuclear polypyridylruthenium(II) complexes bridged by a flexible methylene linker have received considerable interest as potential antibacterial agents. Their potency and uptake into bacterial cells is directly modulated by the length of the bridging linker, which has implicated membrane interactions as an essential feature of their mechanism of action. In this work, a combination of molecular dynamics (MD) simulations and solid-state NMR was used to present an atomistic model of a polypyridylruthenium(II) complex bound and incorporated into a bacterial membrane model. The results of Â³Â¹P, Â²H, Â¹H, and Â¹Â³C NMR studies revealed that the antibacterial [{Ru(phen)â}â(Î¼-bbââ)]â´âº complex (Rubbââ), where phen = 1,10-phenanthroline and bbââ = bis[4(4â²-methyl-2,2â²-bipyridyl)]-1,12-dodecane), incorporated into a negatively charged model bacterial membrane, but only associated with the surface of a charge-neutral model of a eukaryotic membrane. Furthermore, an inactive [{Ir(phen)â}â(Î¼-bbââ)]â¶âº (Irbbââ) analogue, which is not taken up by bacterial cells, maintained only a surface-bound association with both bacterial and eukaryotic model membranes according to Â³Â¹P and Â²H NMR. The effects of Rubbââ on Â³Â¹P chemical shift anisotropy and Â²H acyl chain order parameters for negatively charged membranes correlated with a membrane-spanning state of the complex according to MD simulationâin which the metal centers embed in the lipid head group region and the central void, created by the biconic shape of the complex, resulting in increasing disorder of lipid acyl chains and membrane-thinning. A transbilayer mechanism and membrane-spanning may be essential for the cellular uptake and antibacterial activity of this class of compounds.
Keywords	antibacterial properties ; antibiotics ; bacteria ; deuterium ; lipids ; mechanism of action ; models ; molecular dynamics ; nuclear magnetic resonance spectroscopy ; phosphorus ; stable isotopes
Language	English
Dates of publication	2016-1123
Size	p. 15267-15277.
Publishing place	American Chemical Society
Document type	Article
ZDB-ID	3155-0
ISSN	1520-5126 ; 0002-7863
ISSN (online)	1520-5126
ISSN	0002-7863
DOI	10.1021%2Fjacs.6b09996
Database	NAL-Catalogue (AGRICOLA)

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Article ; Online: Binding of pixantrone to DNA at CpA dinucleotide sequences and bulge structures.

Konda, Shyam K / Wang, Haiqiang / Cutts, Suzanne M / Phillips, Don R / Collins, J Grant

Organic & biomolecular chemistry

2015 Volume 13, Issue 21, Page(s) 5972–5982

Abstract: The binding of the anti-cancer drug pixantrone to three oligonucleotide sequences, d(TCATATGA)2, d(CCGAGAATTCCGG)2 {double bulge = DB} and the non-self complementary d(TACGATGAGTA) : d(TACCATCGTA) {single bulge = SB}, has been studied by NMR spectroscopy ...

Abstract	The binding of the anti-cancer drug pixantrone to three oligonucleotide sequences, d(TCATATGA)2, d(CCGAGAATTCCGG)2 {double bulge = DB} and the non-self complementary d(TACGATGAGTA) : d(TACCATCGTA) {single bulge = SB}, has been studied by NMR spectroscopy and molecular modelling. The upfield shifts observed for the aromatic resonances of pixantrone upon addition of the drug to each oligonucleotide confirmed the drug bound by intercalation. For the duplex sequence d(TCATATGA)2, NOEs were observed from the pixantrone aromatic H7/8 and aliphatic Ha/Hb protons to the H6/H8 and H1' protons of the C2, A3, T6 and G7 nucleotides, demonstrating that pixantrone preferentially binds at the symmetric CpA sites. However, weaker NOEs observed to various protons from the T4 and A5 residues indicated alternative minor binding sites. NOEs from the H7/H8 and Ha/Hb protons to both major (H6/H8) and minor groove (H1') protons indicated approximately equal proportions of intercalation was from the major and minor groove at the CpA sites. Intermolecular NOEs were observed between the H7/H8 and H4 protons of pixantrone and the A4H1' and G3H1' protons of the oligonucleotide that contains two symmetrically related bulge sites (DB), indicative of binding at the adenine bulge sites. For the oligonucleotide that only contains a single bulge site (SB), NOEs were observed from pixantrone protons to the SB G7H1', A8H1' and G9H1' protons, confirming that the drug bound selectively at the adenine bulge site. A molecular model of pixantrone-bound SB could be constructed with the drug bound from the minor groove at the A8pG9 site that was consistent with the observed NMR data. The results demonstrate that pixantrone preferentially intercalates at adenine bulge sites, compared to duplex DNA, and predominantly from the minor groove.
MeSH term(s)	Antineoplastic Agents/pharmacology ; Base Sequence ; Binding Sites ; DNA/chemistry ; Intercalating Agents/pharmacology ; Isoquinolines/pharmacology ; Molecular Docking Simulation ; Nucleic Acid Conformation
Chemical Substances	Antineoplastic Agents ; Intercalating Agents ; Isoquinolines ; DNA (9007-49-2) ; pixantrone (F5SXN2KNMR)
Language	English
Publishing date	2015-06-07
Publishing country	England
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	2097583-1
ISSN	1477-0539 ; 1477-0520
ISSN (online)	1477-0539
ISSN	1477-0520
DOI	10.1039/c5ob00526d
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Article ; Online: DNA condensation in live E. coli provides evidence for transertion.

Gorle, Anil K / Bottomley, Amy L / Harry, Elizabeth J / Collins, J Grant / Keene, F Richard / Woodward, Clifford E

Molecular bioSystems

2017 Volume 13, Issue 4, Page(s) 677–680

Abstract: Condensation studies of chromosomal DNA in E. coli with a tetranuclear ruthenium complex are carried out and images obtained with wide-field fluorescence microscopy. Remarkably different condensate morphologies resulted, depending upon the treatment ... ...

Abstract	Condensation studies of chromosomal DNA in E. coli with a tetranuclear ruthenium complex are carried out and images obtained with wide-field fluorescence microscopy. Remarkably different condensate morphologies resulted, depending upon the treatment protocol. The occurrence of condensed nucleoid spirals in live bacteria provides evidence for the transertion hypothesis.
MeSH term(s)	Chromosomes, Bacterial/drug effects ; DNA, Bacterial/drug effects ; Escherichia coli/drug effects ; Escherichia coli/genetics ; Escherichia coli/metabolism ; Microscopy, Fluorescence ; Organometallic Compounds/chemistry ; Organometallic Compounds/pharmacology ; Ribosomes/metabolism ; Ruthenium/chemistry
Chemical Substances	DNA, Bacterial ; Organometallic Compounds ; Ruthenium (7UI0TKC3U5)
Language	English
Publishing date	2017-03-28
Publishing country	England
Document type	Journal Article
ZDB-ID	2188635-0
ISSN	1742-2051 ; 1742-206X
ISSN (online)	1742-2051
ISSN	1742-206X
DOI	10.1039/c6mb00753h
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Article: Multi-nuclear platinum drugs: a new paradigm in chemotherapy.

Wheate, Nial J / Collins, J Grant

Current medicinal chemistry. Anti-cancer agents

2005 Volume 5, Issue 3, Page(s) 267–279

Abstract: The initial report of the therapeutic anticancer properties of a di-nuclear platinum complex in 1988 started a new paradigm in platinum based chemotherapy. Several multi-nuclear platinum complexes have entered clinical trials in recent years, with ... ...

Abstract	The initial report of the therapeutic anticancer properties of a di-nuclear platinum complex in 1988 started a new paradigm in platinum based chemotherapy. Several multi-nuclear platinum complexes have entered clinical trials in recent years, with varying results. This group of charged complexes, consisting of di- and tri-nuclear compounds linked by aliphatic ligands, many with hydrogen bonding functionality, are able to overcome cisplatin and carboplatin resistance in many important human cancer cell lines. The adducts they form with DNA--which are, to some extent, affected by their pre-covalent association--are the reason for their increased cytotoxicity, and are distinctly different from those formed by cisplatin. Multi-nuclear platinum DNA adducts are broadly defined as flexible, non-directional and mainly interstrand cross-links. These complexes are also able to induce conformational changes in DNA, particularly the conversion from B-type to Z- and A-type. While these complexes are much more cytotoxic than cisplatin, they are also highly toxic. The maximum tolerated doses range from 0.006 to 1.1 mg/m(2) which is 10 to 100 fold lower than cisplatin. BBR3464 has shown in vivo activity at its MTD in several pre-clinical and clinical trials; however, recent phase II trials have shown that BBR3464, and other multi-nuclear platinum drugs, did not yield results substantially different from cisplatin, possibly due to their binding and degradation by human plasma proteins. This review will look at the success, and limitations, of multi-nuclear platinum drugs, and discuss their future potential as anti-cancer agents.
MeSH term(s)	Animals ; Antineoplastic Agents/chemistry ; Antineoplastic Agents/pharmacology ; Antineoplastic Agents/therapeutic use ; Cell Line, Tumor ; Cell Survival/drug effects ; DNA Adducts/metabolism ; Humans ; Molecular Structure ; Neoplasms/drug therapy ; Neoplasms/metabolism ; Neoplasms/pathology ; Organoplatinum Compounds/chemistry ; Organoplatinum Compounds/pharmacology ; Organoplatinum Compounds/therapeutic use ; Structure-Activity Relationship
Chemical Substances	Antineoplastic Agents ; DNA Adducts ; Organoplatinum Compounds
Language	English
Publishing date	2005-05
Publishing country	Netherlands
Document type	Journal Article ; Review
ZDB-ID	2064844-3
ISSN	1875-5968 ; 1568-0118
ISSN (online)	1875-5968
ISSN	1568-0118
DOI	10.2174/1568011053765994
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