Epoxide‐derived mixed‐mode chromatographic stationary phases for separation of active substances in fixed‐dose combination drugs

Zhang, Shuanghong; Wan, Qian-Hong; Li, Yan

doi:10.1002/jssc.201900307

Cited by 9 publications

(3 citation statements)

References 22 publications

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“…The different organic compounds [9–11], such as acridine derivatives [12], ethylene‐bridged hybrid C18 [13], imidazolium derivatives [14–16], benzimidazole [17], 2‐methylindole [18], quinolinium [19], epoxide‐derived [20], calix[4]arene‐derivatives [21, 22], tetra‐proline‐modified calix[4]arene [23], types of biomolecules [24], and amide and amine groups [25–27], can be bonded on silica surface to design MM stationary phases. Moreover, to improve the retention, many polar groups have been embedded on the alkyl hydrocarbon chain of stationary phases, such as amide [28–31], carbamate [32], ether, ammonium [33], urea [34], and poly(ionic liquid) [35].…”

Section: Introductionmentioning

confidence: 99%

Preparation of two amide‐bonded stationary phases and comparative evaluation under mixed‐mode chromatography

Hosseini

Heydar

2021

J of Separation Science

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In this work, the conventional reactions were used to functionalize the silica surface with amide and hydrocarbon chain groups affording two different mixed‐mode stationary phases (Sil‐amide‐C11 and Sil‐C12‐amide). The prepared stationary phases were analyzed by elemental analysis and thermogravimetric analysis. The retention of benzene, phenol, pyridine, and aniline was investigated and compared with synthesized and commercial columns, and this led to prove the existence of different interactions on the synthesized stationary phases. The mixed‐mode stationary phases showed multiple interactions, and different chromatography modes were found under distinct chromatographic conditions. According to the type of amide group (either free or within the hydrocarbon chain), different interactions can be made on the columns. The alkylbenzenes and polycyclic aromatic hydrocarbons, as nonpolar hydrocarbons, were chromatographed under reversed‐phase liquid chromatography modes, in which amide groups on the silica could efficiently separate polar analytes under hydrophilic interaction liquid chromatography mode in both prepared stationary phases. The performance of the columns was compared by the separation of the carboxylic acid group and biological samples. The bonding method and the type of amide group showed different interactions leading to different separation and performance.

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Section: Introductionmentioning

confidence: 99%

Preparation of two amide‐bonded stationary phases and comparative evaluation under mixed‐mode chromatography

Hosseini

Heydar

2021

J of Separation Science

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“…Conventional liquid chromatography uses a monofunctional stationary phase such as reversed phase or ion exchanger to separate the mixture, and the solute retention is primarily controlled by a single mode of action based on hydrophobic or ionic interactions. In contrast, mixed-mode chromatography uses a multifunctional stationary phase to achieve separation by multivalent complexation between a multivalent compound and a multivalent stationary phase. , Recently, we reported studies of the retention behavior of divalent solutes (such as alkylanilines and alkylbenzoic acids) in mixed-mode chromatography and demonstrated that solute retention is highly dependent on the cooperative binding due to a combination of hydrophobic and ionic interactions. , Liquid chromatography can be used not only as a separation method for a range of compounds but also as a means of characterizing noncovalent interactions in porous materials. In the latter application, the porous material to be investigated is loaded into a chromatographic column and equilibrated with a mobile phase.…”

Section: Introductionmentioning

confidence: 99%

“…25,26 Recently, we reported studies of the retention behavior of divalent solutes (such as alkylanilines and alkylbenzoic acids) in mixed-mode chromatography and demonstrated that solute retention is highly dependent on the cooperative binding due to a combination of hydrophobic and ionic interactions. 27,28 Liquid chromatography can be used not only as a separation method for a range of compounds but also as a means of characterizing noncovalent interactions in porous materials. In the latter application, the porous material to be investigated is loaded into a chromatographic column and equilibrated with a mobile phase.…”

Section: ■ Introductionmentioning

confidence: 99%

Inverse Mixed-Mode Chromatography for the Evaluation of Multivalency and Cooperativity of Host–Guest Complexation in Porous Materials

2019

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A new separation-based analytical method was developed to evaluate the multivalency and cooperativity of supramolecular host−guest complexation in porous materials. The method is based on inverse mixed-mode chromatography in which a porous material with a multivalent functional group is packed into a column and bound with a complementary guest molecule to form a multivalent complex. The bound guest molecules are eluted in the mobile phase and detected by appropriate methods such as UV absorption. The retention factor of the guest molecule is determined and broken down into the contributions of noncovalent interactions between binding sites (e.g., hydrophobic and ionic components), thereby calculating the effective molarity and cooperativity factor of the complexation. Two model systems denoted as RP/SCX and RP/SAX were analyzed by the established method. On average, the RP/SCX system has an effective molarity (EM) of 0.14 M and a cooperativity factor (β) of 0.86, while the RP/SAX system has an EM value of 0.18 M and a β value of 2.3. Interestingly, experiments have shown that these values do not change with changes in the intrinsic binding strength of the constituent sites. In summary, the developed method allows for quantitative assessment of multivalency and cooperativity effects in porous materials, providing a valuable complement to the analytical toolbox for supramolecular chemists and materials scientists.

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Base‐deactivated and alkaline‐resistant chromatographic stationary phase based on functionalized polymethylsilsesquioxane microspheres

Huo

Chen

2019

J of Separation Science

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Vinyl, chloropropyl, and mercaptopropyl functionalized particles were prepared by a two‐step acidic/alkaline catalyzed co‐hydrolysis/condensation of methyltrimethoxysilane with a different silane precursor that carries chemically reactive functional group including vinyl, chloropropyl, and mercaptopropyl, respectively. The morphology, pore structure, and functional groups of the synthesized packings were studied by SEM, nitrogen adsorption‐desorption measurements, and solid‐state 13C 29Si NMR spectroscopy, respectively. The particles show ordered sphere, narrow particle size distribution, and mesoporous structure. The carbon contents of the microspheres are in the range of 17–19%, comparable to those of octadecyl‐bonded silica packings. The three‐kind of microspheres were directly used as packing materials for high‐performance liquid chromatography without size classification. The chromatographic performance of the columns was evaluated and compared with a commercially available C18 phase. The results revealed that these columns possess typical reversed‐phase chromatographic properties with increased hydrophobicity than polymethylsilsesquioxane and symmetric peaks for basic compounds. They were applied to the simultaneous separation of combination bendazol hydrochlorothiazide capsules containing polar and basic drugs with peaks identified by tandem with mass spectrometry. In general, a novel method is provided for the synthesis of different methyltrimethoxysilane‐derived microspheres for high‐performance liquid chromatography, which are advantageous for separating basic compounds.

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Epoxide‐derived mixed‐mode chromatographic stationary phases for separation of active substances in fixed‐dose combination drugs

Cited by 9 publications

References 22 publications

Preparation of two amide‐bonded stationary phases and comparative evaluation under mixed‐mode chromatography

Preparation of two amide‐bonded stationary phases and comparative evaluation under mixed‐mode chromatography

Inverse Mixed-Mode Chromatography for the Evaluation of Multivalency and Cooperativity of Host–Guest Complexation in Porous Materials

Base‐deactivated and alkaline‐resistant chromatographic stationary phase based on functionalized polymethylsilsesquioxane microspheres

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