G. Ferrara et al., Optical isomer separation of potential analgesic drug candidates by using capillary electrophoresis, ELECTROPHOR, 20(12), 1999, pp. 2432-2437
Using cyclodextrin capillary zone electrophoresis (CD-CZE), baseline separa
tion of synthetic potential analgesic drug diastereoisomer candidates 6,11-
dimethyl-1,2,3,4,5, 6-hexahydro-3-[(2'-methoxycarbonyl-2'-phenylcyclopropyl
)methyl]-2,6-methano-3-benzazocin-8-ol (MPCB) and 6,11-dimethyl-1,2,3,4,5,6
-hexahydro-3-{[2'-methoxycarbonyl-2'(4-chlorophenyl)cyclopropyl]methyl}-2,6
-methano-3-benzazocin-8-ol (CCB) was achieved. Among the cyclodextrins test
ed (hydroxypropyl-, carboxy-methyl- and sulfobutyl-beta-cyclodextrin (HP-be
ta-CD, CM-beta-CD and SBE-beta-CD)) SBE-beta-CD was found to be the most ef
fective complexing agent, allowing good optical isomer separation. Resoluti
on was also influenced by the CD concentration, pH of the buffet and presen
ce of organic modifier in the background electrolyte. The optimum experimen
tal conditions for the separation of studied analgesic drugs were found usi
ng 25 mM berate buffer at pH 9 containing 40 mu of SBE-beta-CD and 20% v/v
of methanol. Using the above-mentioned background electrolyte, it was also
possible to separate, in the same run, the enantiomers of normetazocine (NM
Z) as well as the optical isomers of (+/-)-cis-2-chloromethyl-1-phenyl cycl
opropancarboxylic acid methyl ester (PCE) or (+/-)-cis-2-chloromethyl-1-(4-
chlorophenyl)cyclopropancarboxylic acid methyl ester (CPCE) reagents used i
n the synthesis of the studied analgesic drugs).