New chiral stationary phases based on xanthone derivatives for liquid chromatography.

Six chiral derivatives of xanthones (CDXs) were covalently bonded to silica, yielding the corresponding xanthonic chiral stationary phases (XCSPs). The new XCSPs were packed into stainless-steel columns with 150 x 4.6 mm i.d. Moreover, the greening of the chromatographic analysis by reducing the internal diameter (150 x 2.1 mm i.d.) of the liquid chromatography (LC) columns was also investigated. The enantioselective capability of these phases was evaluated by LC using different chemical classes of chiral compounds, including several types of drugs. A library of CDXs was evaluated in order to explore the principle of reciprocity as well as the chiral self-recognition phenomenon. The separation of enantiomeric mixtures of CDXs was investigated under multimodal elution conditions. The XCSPs provided high specificity for the enantiomeric mixtures of CDXs evaluated mainly under normal-phase elution conditions. Furthermore, two XCSPs were prepared with both enantiomers of the same xanthonic selector in order to confirm the inversion order elution.

[1]  S. Cravo,et al.  New Cyclotetrapeptides and a New Diketopiperzine Derivative from the Marine Sponge-Associated Fungus Neosartorya glabra KUFA 0702 , 2016, Marine drugs.

[2]  M. Pinto,et al.  Chiral enantioresolution of cathinone derivatives present in “legal highs”, and enantioselectivity evaluation on cytotoxicity of 3,4-methylenedioxypyrovalerone (MDPV) , 2016, Forensic Toxicology.

[3]  I. Ahmad,et al.  Recent Insight into the Biological Activities of Synthetic Xanthone Derivatives , 2016 .

[4]  Y. Okamoto,et al.  Efficient Separation of Enantiomers Using Stereoregular Chiral Polymers. , 2016, Chemical reviews.

[5]  S. Cravo,et al.  A New Cyclic Hexapeptide and a New Isocoumarin Derivative from the Marine Sponge-Associated Fungus Aspergillus similanensis KUFA 0013 , 2015, Marine drugs.

[6]  P. Castro,et al.  Dispersive liquid–liquid microextraction and HPLC to analyse fluoxetine and metoprolol enantiomers in wastewaters , 2015, Environmental Chemistry Letters.

[7]  Weihua Tang,et al.  Recent development of cationic cyclodextrins for chiral separation , 2015 .

[8]  A. R. Ribeiro,et al.  Enantioseparation of chiral pharmaceuticals in biomedical and environmental analyses by liquid chromatography: an overview. , 2014, Journal of chromatography. B, Analytical technologies in the biomedical and life sciences.

[9]  M. Pinto,et al.  Xanthones from Marine‐Derived Microorganisms: Isolation, Structure Elucidation and Biological Activities , 2014 .

[10]  E. Sousa,et al.  New chiral derivatives of xanthones: synthesis and investigation of enantioselectivity as inhibitors of growth of human tumor cell lines. , 2014, Bioorganic & medicinal chemistry.

[11]  M. Pinto,et al.  Multidimensional optimization of promising antitumor xanthone derivatives. , 2013, Bioorganic & medicinal chemistry.

[12]  M. Pinto,et al.  Small Molecules as Chromatographic Tools for HPLC Enantiomeric Resolution: Pirkle-Type Chiral Stationary Phases Evolution , 2013, Chromatographia.

[13]  A. Palmeira,et al.  Enantioresolution of chiral derivatives of xanthones on (S,S)-Whelk-O1 and L-phenylglycine stationary phases and chiral recognition mechanism by docking approach for (S,S)-Whelk-O1. , 2013, Chirality.

[14]  M. Pinto,et al.  Resolution and determination of enantiomeric purity of new chiral derivatives of xanthones using polysaccharide-based stationary phases. , 2012, Journal of chromatography. A.

[15]  B. Chankvetadze.  Recent developments on polysaccharide-based chiral stationary phases for liquid-phase separation of enantiomers. , 2012, Journal of chromatography. A.

[16]  Shulin Zhuang,et al.  Development of chiral stationary phases for high-performance liquid chromatographic separation , 2012 .

[17]  P. Correia‐de‐Sá,et al.  Synthesis of new chiral xanthone derivatives acting as nerve conduction blockers in the rat sciatic nerve. , 2012, European journal of medicinal chemistry.

[18]  V. Kairys,et al.  Enantioseparation and chiral recognition mechanism of new chiral derivatives of xanthones on macrocyclic antibiotic stationary phases. , 2012, Journal of chromatography. A.

[19]  E. Tesařová,et al.  Recentchiral selectors for separation in HPLC and CE , 2012 .

[20]  S. Bräse,et al.  Xanthones from fungi, lichens, and bacteria: the natural products and their synthesis. , 2012, Chemical reviews.

[21]  T. Ward,et al.  Chiral separations: a review of current topics and trends. , 2012, Analytical chemistry.

[22]  Nicola Marchetti,et al.  Recent applications in chiral high performance liquid chromatography: a review. , 2011, Analytica chimica acta.

[23]  D. A. Engebretson,et al.  Assessing chiral self-recognition using chiral stationary phases , 2011 .

[24]  F. Carvalho,et al.  Polysulfated xanthones: multipathway development of a new generation of dual anticoagulant/antiplatelet agents. , 2011, Journal of medicinal chemistry.

[25]  M. Lämmerhofer.  Chiral recognition by enantioselective liquid chromatography: mechanisms and modern chiral stationary phases. , 2010, Journal of chromatography. A.

[26]  E. Sousa,et al.  Bromoalkoxyxanthones as promising antitumor agents: synthesis, crystal structure and effect on human tumor cell lines. , 2009, European journal of medicinal chemistry.

[27]  S. Cravo,et al.  Improved methodologies for synthesis of prenylated xanthones by microwave irradiation and combination of heterogeneous catalysis (K10 clay) with microwave irradiation , 2009 .

[28]  M. E. Sousa,et al.  Multimilligram enantioresolution of low-solubility xanthonolignoids on polysaccharide chiral stationary phases using a solid-phase injection system. , 2006, Journal of chromatography. A.

[29]  M. E. Sousa,et al.  Xanthone derivatives: new insights in biological activities. , 2005, Current medicinal chemistry.

[30]  L. Gales,et al.  Xanthones--a structural perspective. , 2005, Current medicinal chemistry.

[31]  E. Sousa,et al.  Isomeric Kielcorins and Dihydroxyxanthones: Synthesis, Structure Elucidation, and Inhibitory Activities of Growth of Human Cancer Cell Lines and on the Proliferation of Human Lymphocytes In Vitro , 2002 .

[32]  T. Hobo,et al.  Influence of the method of preparation of chiral stationary phases on enantiomer separations in high-performance liquid chromatography , 1995 .

[33]  C. Welch,et al.  Improved chiral stationary phase for ß-blocker enantioseparations , 1995 .

[34]  C. Welch.  Evolution of chiral stationary phase design in the Pirkle laboratories , 1994 .

[35]  C. Welch,et al.  An Improved Chiral Stationary Phase for the Chromatographic Separation of Underivatized Naproxen Enantiomers , 1992 .

[36]  K. Maher,et al.  Chiral separations by high-performance liquid chromatography , 1992 .

[37]  T. Pochapsky,et al.  Considerations of Chiral Recognition Relevant to the Liquid Chromatographic Separation of Enantiomers , 1989 .

[38]  William H. Pirkle,et al.  Considerations of chiral recognition relevant to the liquid chromatography separation of enantiomers , 1989 .

[39]  J. Finn,et al.  CHIRAL HIGH-PRESSURE LIQUID CHROMATOGRAPHIC STATIONARY PHASES. 3. GENERAL RESOLUTION OF ARYLALKYLCARBINOLS , 1981 .

[40]  J. Finn,et al.  Broad spectrum resolution of optical isomers using chiral high-performance liquid chromatographic bonded phases , 1980 .

[41]  S. Bocian,et al.  Amino acids, peptides, and proteins as chemically bonded stationary phases--A review. , 2016, Journal of separation science.

[42]  S. Bräse,et al.  Xanthone dimers: a compound family which is both common and privileged. , 2015, Natural product reports.

[43]  D. Raynie,et al.  The Greening of the Chromatography Laboratory , 2011 .

[44]  W. H. Pirkle,et al.  Reciprocity in Chiral Recognition : Comparison of several chiral stationary phases , 1987 .