Investigation of the adsorption behaviour of a chiral model compound on a tartardiamide-based network-polymeric chiral stationary phase

Lindholm, Johan; Fornstedt, Torgny

doi:10.1016/j.chroma.2005.07.122

Cited by 24 publications

(8 citation statements)

References 19 publications

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“…We can also see that the ratio between the number of non-chiral and chiral sites (q s,I /q s,II ) vary very much for both protein CSPs and other CSPs, from around 3 to up to 128 times (see Table 1). Finally, the small molecule CSPs has a non-chiral capacity in average of 562 mM (Table 1) which is very similar to global capacities for conventional solutes on C18 phases [15].…”

Section: Characterization Of Preparative Chiral Separation Systemsmentioning

confidence: 91%

“…Another type of CSP, that received great early attention, is the brush-type phases introduced by Pirkle and Welch [13]. More recently developed CSPs shown to have preparative potential are tartardiamide-based network-polymeric phases (Kromasil CHI) [14,15]. Another interesting class of CSPs are the immobilized antibiotics such as macrocycles vancomycin [16], ristocetin A, teicoplanin [17] and teicoplanin aglycone [18,19].…”

Section: Introductionmentioning

confidence: 99%

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Potential of adsorption isotherm measurements for closer elucidating of binding in chiral liquid chromatographic phase systems

Samuelsson

Arnell

Fornstedt³

2009

J of Separation Science

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The human body is a chiral environment and many drugs are chiral and interact differently depending on the type of enantiomer. Therefore, the interest in analytical and preparative separations of enantiomers has steadily increased over the years. LC is today the most important technique in analytical laboratories worldwide. The key to understand the separation system lies in the adsorption isotherm, which describes the equilibrium distribution of solutes between the mobile and stationary phases. By measuring adsorption isotherms in chiral phase systems, a deeper interpenetration concerning enantioselective and non-selective binding energies and adsorption processes is possible. Furthermore, this data provides the core information needed to optimize preparative chromatographic processes for purification of single enantiomers. However, the measurement of adsorption isotherms is a delicate matter and there are many dangerous pitfalls that may produce erroneous results and even wrong mechanistic conclusions. This review summarizes the most relevant methods and a workflow will be given for avoiding the common pitfalls and obtaining reliable data. Several applications from the literature are also treated to give insight in what information can potentially be obtained from using this methodology.

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Section: Characterization Of Preparative Chiral Separation Systemsmentioning

confidence: 91%

Section: Introductionmentioning

confidence: 99%

Potential of adsorption isotherm measurements for closer elucidating of binding in chiral liquid chromatographic phase systems

Samuelsson

Arnell

Fornstedt³

2009

J of Separation Science

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“…A simultaneous recording from an optical rotation ALP detector exhibits an injection shock and signs of optical rotation of warfarin enantiomers as well as the sample purity. The unusual peak profiles prompted there was possible effect of system peak on the peak shape, which could be produced by mobile phase additive [58,61,63,67,68]. In the present mobile phase, IPA and TFA are the two additives (or strong solvents) that can be adsorbed on the stationary phase by intermolecular interaction such as hydrogen bonding, while hexane is the pure weak solvent.…”

Section: Enantiomer Peak Profiles Of Warfarin Csp1mentioning

confidence: 91%

“…Lindholm and Fornstedt observed peak deformations of 2-phenylbutyric acid enantiomers due to a co-eluting system peak of formic acid on a tartardiamide-based network-polymeric CSP [67]. Arnell et al from the same group identified the system peak of the strongly adsorbed additive and carried out varying mobile phase composition to tune the peak shapes of the two ␤-blocker enantiomers on a teicoplanin CSP (Chirobiotic T) [68].…”

Section: Introductionmentioning

confidence: 97%

Characterization of warfarin unusual peak profiles on oligoproline chiral high performance liquid chromatography columns

Lao

Gan

2010

Journal of Chromatography A

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“…Oil nano-compartments in solid lipid (fat) as exchange CSPs, complex (Pirkle-type) CSPs, crown ether CSPs, cyclodextrin CSPs and macrocyclic glycopeptide CSPs, or large molecules such as synthetic chiral polymers and naturally occurring chiral structures) [114][115][116][117]. A"three-point binding model" designed by Dalgliesh in 1952 explains that at least three different molecular interactions (i.e.…”

Section: Amorphous Lipidmentioning

confidence: 99%

Development of Mitotane Lipid Nanocarriers and Enantiomers: Two-in-One Solution to Efficiently Treat Adreno-Cortical Carcinoma

Menaa¹,

Menaa²

2012

CMC

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Adrenocortical carcinoma (ACC) is a rare but aggressive malignancy with a poor prognosis. Treatment options for advanced ACC are limited. Indeed, radical tumor resection can lead to local or metastatic recurrence, and mitotane (Lysodren(®)), the only recognized adrenolytic drug, offers modest response rates, notably due to some of its physico-chemical and pharmacological properties (i.e. hydrophobicity, low bioavailability). Meantime, high cumulative doses of Lysodren(®) usually cause systemic toxicities. To reduce adverse health effects, the search of safe and efficient mitotane nano-formulations as well as the full characterization and testing of its enantiomers can represent valuable therapeutic options. Interestingly, recent investigations showed that solid lipid nanoparticles (SLN) and nanostructured lipid carriers (NLC) could considerably improve the efficacy of mitotane (i.e. enhanced solubility and bioavailability, progressive release of the loaded drug into blood and targeted tissues) as well as its safety (i.e. lower toxicity, higher biocompatibility). These two nano-carriers for mitotane delivery and targeting are of particular interest over other polymeric particles (i.e. low-cost, efficient and simple scaling to an industrial production level following green methods). Besides, emerging studies suggested that the S-(-)- mitotane is more potent than the R-(+)-mitotane for ACC treatment. Therefore, the production of pure and active S-(-)-mitotane might offer synergic or additive benefits for ACC patients when combined to solid lipid-based nanocarriers. In this review, we first provide an updated overview of the ACC disease before emphasizing on the promising mitotane drug nano-systems, as well as on the separation, purification and production of single mitotane enantiomer using state-of-art chromatographic-based methods.

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Investigation of the adsorption behaviour of a chiral model compound on a tartardiamide-based network-polymeric chiral stationary phase

Cited by 24 publications

References 19 publications

Potential of adsorption isotherm measurements for closer elucidating of binding in chiral liquid chromatographic phase systems

Potential of adsorption isotherm measurements for closer elucidating of binding in chiral liquid chromatographic phase systems

Characterization of warfarin unusual peak profiles on oligoproline chiral high performance liquid chromatography columns

Development of Mitotane Lipid Nanocarriers and Enantiomers: Two-in-One Solution to Efficiently Treat Adreno-Cortical Carcinoma

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