Publication

Ruthenium(II) arene PTA (RAPTA) complexes: impact of enantiomerically pure arene ligands

Paul Joseph Dyson, Catherine Marie Amélie Clavel, Kelly Joan Kilpin, Shona Cammack
2013
Journal Articles

Abstract

Organometallic ruthenium(II) arene complexes containing the PTA ligand ([Ru(eta(6)-arene)Cl-2(PTA)], PTA = 1,3,5-triaza-7-phosphatricyclo-[3.3.1.1] decane, termed RAPTA) show pharmacologically relevant antitumour properties in vitro. Two new enantiomeric pairs of RAPTA compounds, containing the chiral arene (R)- or (S)-2-phenyl-N-(1-phenylethylene) acetamide and either dichlorido or oxalato ligands were synthesised and fully characterised. The stability of the complexes towards hydrolysis was assessed and the dichlorido complexes were found to be more stable towards hydrolysis than the prototype complex RAPTA-C, ([Ru(eta(6)-p-cymene) Cl-2(PTA)]). The cytotoxicity of the compounds towards human ovarian cancer cells is moderate to good with a degree of selectivity towards the cancer cells over healthy cells. More significantly, for the first time we were able to establish the influence of a bulky, chiral group attached to the arene on the cytotoxicity of this class of compound, with the S-enantiomer being more cytotoxic than the R-enantiomer.

Official source

https://infoscience.epfl.ch/entities/publication/3ebe314d-2dd4-40fd-a350-1b589e5e7ff3

About this result

This page is automatically generated and may contain information that is not correct, complete, up-to-date, or relevant to your search query. The same applies to every other page on this website. Please make sure to verify the information with EPFL's official sources.

Paul Joseph Dyson, Catherine Marie Amélie Clavel, Kelly Joan Kilpin, Shona Cammack
2013
Journal Articles

Abstract

Official source

https://infoscience.epfl.ch/entities/publication/3ebe314d-2dd4-40fd-a350-1b589e5e7ff3

About this result

Related concepts (21)

Enantiomer

In chemistry, an enantiomer (/ɪˈnænti.əmər, ɛ-, -oʊ-/ ih-NAN-tee-ə-mər; from Ancient Greek ἐνάντιος (enántios) 'opposite', and μέρος (méros) 'part') – also called optical isomer, antipode, or optical antipode – is one of two stereoisomers that are non-superposable onto their own . Enantiomers are much like one's right and left hands, when looking at the same face, they cannot be superposed onto each other. No amount of reorientation in three spatial dimensions will allow the four unique groups on the chiral carbon (see chirality) to line up exactly.

Chirality (chemistry)

In chemistry, a molecule or ion is called chiral (ˈkaɪrəl) if it cannot be superposed on its by any combination of rotations, translations, and some conformational changes. This geometric property is called chirality (kaɪˈrælɪti). The terms are derived from Ancient Greek χείρ (cheir) 'hand'; which is the canonical example of an object with this property. A chiral molecule or ion exists in two stereoisomers that are mirror images of each other, called enantiomers; they are often distinguished as either "right-handed" or "left-handed" by their absolute configuration or some other criterion.

Enantiomeric excess

In stereochemistry, enantiomeric excess (ee) is a measurement of purity used for chiral substances. It reflects the degree to which a sample contains one enantiomer in greater amounts than the other. A racemic mixture has an ee of 0%, while a single completely pure enantiomer has an ee of 100%. A sample with 70% of one enantiomer and 30% of the other has an ee of 40% (70% − 30%). Enantiomeric excess is defined as the absolute difference between the mole fraction of each enantiomer: where In practice, it is most often expressed as a percent enantiomeric excess.

Related publications (32)

Development of cysteine cathepsin inhibitors combined with cell type-specific delivery for the treatment of B-cell lymphoma and solid tumors

Aaron Simone Petruzzella

Cysteine cathepsins proteases are enzymes that play essential physiological roles, but their activity is also associated to different aspects of cancer progression and to the development of other diseases. Therefore, cysteine cathepsins are relevant and pr ...

EPFL2024

A Cluster of Evolutionarily Recent KRAB Zinc Finger Proteins Protects Cancer Cells from Replicative Stress–Induced Inflammation

Didier Trono, Priscilla Turelli, Sandra Eloise Kjeldsen, Cyril David Son-Tuyên Pulver, Evaristo Jose Planet Letschert, Filipe Amândio Brandão Sanches Vong Martins, Olga Marie Louise Rosspopoff, Joana Carlevaro Fita, Romain Forey, Florian Huber

Heterochromatin loss and genetic instability enhance cancer progression by favoring clonal diversity, yet uncontrolled replicative stress leads to mitotic catastrophe and inflammatory responses that promote immune rejection. KRAB domain-containing zinc fin ...

2024

Exploration and modulation of mechanical cues for enhanced cancer immunotherapy

Armand Kurum

The advent of immunotherapy, such as immune checkpoint blockade (ICB) and adoptive transfer of cytotoxic lymphocytes, has transformed the clinical care of cancer. However, a significant proportion of patients are resistant to immunotherapy or experience re ...

EPFL2024