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Comparative LC Enantioseparation of Novel PPAR Agonists on Cellulose- and Amylose-Based Chiral Stationary Phases

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Abstract

The LC enantiomeric separation of several dual PPARα/γ agonists on the commercially available Chiralcel OD and Chiralpak AD columns has been evaluated in normal phase mode using a mobile phase consisting in a mixture of n-hexane, 2-propanol and trifluoroacetic acid at constant volume ratio. Most compounds were separated as underivatized acids without requiring time consuming analysis. Some complementary selectivity was evidenced on the two investigated chiral stationary phases related to the different accessibility of the active sites of the helical cavities. Additional information on the chiral recognition mechanism were deduced from the chromatographic behaviour of some selected methyl esters.

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References

  1. Issemann I, Green S (1990) Nature 347:645–650. doi:10.1038/347645a0

    Article  CAS  Google Scholar 

  2. Berger J, Moller DE (2002) Annu Rev Med 53:409–435. doi:10.1146/annurev.med.53.082901.104018

    Article  CAS  Google Scholar 

  3. Berger JP, Akiyama TE, Meinke PT (2005) Trends Pharmacol Sci 26:244–251. doi:10.1016/j.tips.2005.03.003

    Article  CAS  Google Scholar 

  4. Kliewer SA, Umesono K, Noonan DJ, Heyman RA, Evans RM (1992) Nature 358:771–774. doi:10.1038/358771a0

    Article  CAS  Google Scholar 

  5. Mangelsdorf DJ, Evans RM (1995) Cell 83:841–850. doi:10.1016/0092-8674(95)90200-7

    Article  CAS  Google Scholar 

  6. Desvergne B, Wahli W (1999) Endocr Rev 20:649–688

    Article  CAS  Google Scholar 

  7. Renaud JP, Moras D (2000) Cell Mol Life Sci 57:1748–1769

    Article  CAS  Google Scholar 

  8. Nagy L, Schwabe JW (2004) Trends Biochem Sci 29:317–324. doi:10.1016/j.tibs.2004.04.006

    Article  CAS  Google Scholar 

  9. Nettles KW, Greene GL (2005) Annu Rev Physiol 67:309–333. doi:10.1146/annurev.physiol.66.032802.154710

    Article  CAS  Google Scholar 

  10. Issemann I, Prince RA, Tugwood JD, Green S (1993) J Mol Endocrinol 11:37–47

    Article  CAS  Google Scholar 

  11. Staels B, Dallongeville J, Auwerx J, Schoonjans K, Leitersdorf E, Fruchart J-C (1998) Circulation 98:2088–2093

    CAS  Google Scholar 

  12. Pinelli A, Godio C, Laghezza A, Mitro N, Fracchiolla G, Tortorella V, Lavecchia A, Novellino E, Fruchart J-C, Staels B, Crestani M, Loiodice F (2005) J Med Chem 48:5509–5519. doi:10.1021/jm0502844

    Article  CAS  Google Scholar 

  13. Fracchiolla G, Laghezza A, Piemontese L, Carbonara G, Lavecchia A, Tortorella P, Crestani M, Novellino E, Loiodice F (2007) ChemMedChem 2:641–654. doi:10.1002/cmdc.200600307

    Article  CAS  Google Scholar 

  14. Yashima E, Okamoto Y (1997) Chiral recognition mechanisms of polysaccharide stationary phases. In: Aboul-Enein HY, Wainer IW (eds) The impact of stereochemistry on drug development and use, chemical analysis series. Wiley, New York, pp 403–419

  15. Okamoto Y, Yashima E (1998) Angew Chem Int Ed 37:1020–1043. doi:10.1002/(SICI)1521-3773(19980504)

    Article  Google Scholar 

  16. Aboul-Enein HY, Ali I (2003) Polysaccharide-based chiral stationary phases. In: Cazes (ed) Chiral separations by liquid chromatography and related technologies. Marcel Dekker, New York, pp. 21–88

  17. Aboul-Enein HY, Ali I (2004) Applications of polysaccharide-based chiral stationary phases for resolution of different compound classes. In: Methods Mol Biol, Gübitz G, Schmid MG (eds), Humana Press, Totowa, NJ, pp 186–187

  18. Yamamoto C, Okamoto Y (2004) Bull Chem Soc Jpn 77:227–257. doi:10.1246/bcsj.77.227

    Article  CAS  Google Scholar 

  19. Vogt U, Zugenmaier P (1985) Ber Bunsenges Phys Chem 89:1217–1224

    CAS  Google Scholar 

  20. Azzolina O, Collina S, Ghislandi V (1993) Il Farmaco 48:1401–1416

    CAS  Google Scholar 

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Correspondence to Fulvio Loiodice.

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Piemontese, L., Faliti, S., Carbonara, G. et al. Comparative LC Enantioseparation of Novel PPAR Agonists on Cellulose- and Amylose-Based Chiral Stationary Phases. Chroma 70, 1327–1333 (2009). https://doi.org/10.1365/s10337-009-1323-5

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