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.
Similar content being viewed by others
References
Issemann I, Green S (1990) Nature 347:645–650. doi:10.1038/347645a0
Berger J, Moller DE (2002) Annu Rev Med 53:409–435. doi:10.1146/annurev.med.53.082901.104018
Berger JP, Akiyama TE, Meinke PT (2005) Trends Pharmacol Sci 26:244–251. doi:10.1016/j.tips.2005.03.003
Kliewer SA, Umesono K, Noonan DJ, Heyman RA, Evans RM (1992) Nature 358:771–774. doi:10.1038/358771a0
Mangelsdorf DJ, Evans RM (1995) Cell 83:841–850. doi:10.1016/0092-8674(95)90200-7
Desvergne B, Wahli W (1999) Endocr Rev 20:649–688
Renaud JP, Moras D (2000) Cell Mol Life Sci 57:1748–1769
Nagy L, Schwabe JW (2004) Trends Biochem Sci 29:317–324. doi:10.1016/j.tibs.2004.04.006
Nettles KW, Greene GL (2005) Annu Rev Physiol 67:309–333. doi:10.1146/annurev.physiol.66.032802.154710
Issemann I, Prince RA, Tugwood JD, Green S (1993) J Mol Endocrinol 11:37–47
Staels B, Dallongeville J, Auwerx J, Schoonjans K, Leitersdorf E, Fruchart J-C (1998) Circulation 98:2088–2093
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
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
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
Okamoto Y, Yashima E (1998) Angew Chem Int Ed 37:1020–1043. doi:10.1002/(SICI)1521-3773(19980504)
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
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
Yamamoto C, Okamoto Y (2004) Bull Chem Soc Jpn 77:227–257. doi:10.1246/bcsj.77.227
Vogt U, Zugenmaier P (1985) Ber Bunsenges Phys Chem 89:1217–1224
Azzolina O, Collina S, Ghislandi V (1993) Il Farmaco 48:1401–1416
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
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
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1365/s10337-009-1323-5