Insights into enantioselective separations of ionic metal complexes by sub/supercritical fluid chromatography

Handlovic, Troy T.; Wahab, M. Farooq; Cole, Houston D.; Alatrash, Nagham; Ramasamy, Elamparuthi; MacDonnell, Frederick M.; McFarland, Sherri A.; Armstrong, Daniel W.

doi:10.1016/j.aca.2022.340156

Cited by 5 publications

(5 citation statements)

References 54 publications

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“…In contrast to the previous work, a reduction in retention and simultaneously preserved resolution was observed owing to the improved peak shape. This effect was independently observed and confirmed by Handlovic et al handling organic ionic ruthenium complexes . Rapid chiral baseline separations within a mere 10 min were enabled for 19 out of 20 analytes during the optimization.…”

Section: Discussionsupporting

confidence: 64%

“…This effect was independently observed and confirmed by Handlovic et al handling organic ionic ruthenium complexes. 60 Rapid chiral baseline separations within a mere 10 min were enabled for 19 out of 20 analytes during the optimization. Our new method significantly exceeds separations achieved using HPLC with respect to the number of separated chiral boron cluster compounds, time of the analyses, and resolution (Figure S9).…”

Section: ■ Conclusionmentioning

confidence: 99%

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Advanced Tool for Chiral Separations of Anionic and Zwitterionic (Metalla)carboranes: Supercritical Fluid Chromatography

et al. 2022

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The continuous expansion of research in the field of stable carboranes and their wide potential in the drug design require carrying out fundamental studies regarding their chiral separations. Although supercritical fluid chromatography (SFC) is a viable technique for fast enantioseparations, no investigation concerning boron cluster compounds has been done yet. We aimed at the development of a straightforward method enabling chiral separations of racemic mixtures of anionic cluster carboranes and metallacarboranes that represent an analytical challenge. The fast gradient screening testing nine polysaccharide-based columns was used. The key parameters affecting the selectivity were the type of chiral selector, the type of alcohol, and the base in cosolvent. Moreover, the addition of acetonitrile or water to the cosolvent was identified as an effective tool for decreasing the analysis time while preserving the resolution. After the optimization, the chiral separations of 19 out of 20 selected compounds were achieved in less than 10 min. These results demonstrate the clear advantage of SFC over chiral separations using HPLC in terms of both analysis time and structural variety of successfully separated compounds.

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Section: Discussionsupporting

confidence: 64%

Section: ■ Conclusionmentioning

confidence: 99%

Advanced Tool for Chiral Separations of Anionic and Zwitterionic (Metalla)carboranes: Supercritical Fluid Chromatography

et al. 2022

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“…We previously published the synthetic methods and structural characterization of Ru-3T and Ru-4T, 52,53 and [Ru(4,4′-btfmb) 3 ] 2+ has been reported by others. 54−57 To the best of our knowledge, all other complexes presented in this study have not been reported.…”

Section: Synthesis and Characterizationmentioning

confidence: 99%

“…The members are compared to the parent [Ru(4,4′-btfmb) 2 (LL)] 2+ complexes with LL = IP-0T, 1,10-phenanthroline (phen), or 4,4′-btfmb (Chart b). The syntheses and structural characterization of complexes Ru-3T and Ru-4T were previously published. , In this study, the photocytotoxic effects of [Ru(4,4′-btfmb) 2 (IP- n T)] 2+ ( n = 1–4) and the parent complexes without n T groups are examined on melanoma cells under various light conditions and oxygen levels. We also report on their lipophilicities, steady-state absorption and emission characteristics, excited-state properties, electronic configurations, and electrochemical profiles.…”

Section: Introductionmentioning

confidence: 99%

Ru(II) Oligothienyl Complexes with Fluorinated Ligands: Photophysical, Electrochemical, and Photobiological Properties

Cole,

Vali,

Roque

et al. 2024

Inorg. Chem.

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A series of Ru(II) complexes incorporating two 4,4′-bis(trifluoromethyl)-2,2′-bipyridine (4,4′-btfmb) coligands and thienyl-appended imidazo[4,5-f ][1,10]phenanthroline (IP-nT) ligands was characterized and assessed for phototherapy effects toward cancer cells. The [Ru(4,4′-btfmb) 2 (IP-nT)] 2+ scaffold has greater overall redox activity compared to Ru(II) polypyridyl complexes such as [Ru(bpy) 3 ] 2+ . Ru-1T−Ru-4T have additional oxidations due to the nT group and additional reductions due to the 4,4′-btfmb ligands. Ru-2T−Ru-4T also exhibit nT-based reductions. Ru-4T exhibits two oxidations and eight reductions within the potential window of −3 to +1.5 V. The lowest-lying triplets (T 1 ) for Ru-0T−2T are metal-to-ligand charge-transfer ( 3 MLCT)excited states with lifetimes around 1 μs, whereas T 1 for Ru-3T−4T is longer-lived (∼20−24 μs) and of significant intraligand charge-transfer ( 3 ILCT) character. Phototoxicity toward melanoma cells (SK-MEL-28) increases with n, with Ru-4T having a visible EC 50 value as low as 9 nM and PI as large as 12,000. Ru-3T and Ru-4T retain some of this activity in hypoxia, where Ru-4T has a visible EC 50 as low as 35 nM and PI as high as 2900. Activity over six biological replicates is consistent and within an order of magnitude. These results demonstrate the importance of lowest-lying 3 ILCT states for phototoxicity and maintaining activity in hypoxia.

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“…Among these methods, chromatographic separation techniques are common and include methods such as high-performance liquid chromatography (HPLC), [3][4][5][6][7] gas chromatography (GC), [8][9][10][11][12][13] capillary electrochromatography (CEC), [14][15][16][17][18][19] and supercritical fluid chromatography (SFC). [20][21][22][23][24][25] They are considered convenient and fast techniques for chiral separation. The key and core aspect of separating racemates is to prepare a chiral stationary phase with good stability, enantioseparation ability, and suitability for use in preparing chromatographic columns.…”

Section: Introductionmentioning

confidence: 99%

A chiral emissive porous organic cage used for high-resolution gas chromatography separations

Wang,

Tang

et al. 2024

New J. Chem.

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Insights into enantioselective separations of ionic metal complexes by sub/supercritical fluid chromatography

Cited by 5 publications

References 54 publications

Advanced Tool for Chiral Separations of Anionic and Zwitterionic (Metalla)carboranes: Supercritical Fluid Chromatography

Advanced Tool for Chiral Separations of Anionic and Zwitterionic (Metalla)carboranes: Supercritical Fluid Chromatography

Ru(II) Oligothienyl Complexes with Fluorinated Ligands: Photophysical, Electrochemical, and Photobiological Properties

A chiral emissive porous organic cage used for high-resolution gas chromatography separations

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