PREPARATION OF THE 9-cis, 13-cos-. AND ALL trans-ISOMERS OF α- AND β₂-RETINAL

Conformationally Defined Retinoic Acid Analogues. 4. Potential New Agents for Acute Promyelocytic and Juvenile Myelomonocytic Leukemias

“…The methods are nearly identical to those used to perform transcriptional assays. These studies utilized the CAT reporter gene containing TREpal with a thymidine kinase promoter [(TREpal) 2 -tk-CAT] as previously described by Vaezi et al Twenty-four hours after transfection, cells were treated with ( all-E )-RA (1−1000 nM) alone or together with the indicated UAB retinoid (100 or 1000 nM). After 24 h, cells were harvested and the transcriptional effects were measured in relative CAT activity, after correction with β-gal activity for transfection efficiency.…”

“…Each mixture was preparatively separated by HPLC on silica gel (0.5% Et 2 O, 0.1% THF in hexane for the former and 1% Et 2 O, 0.5% THF in hexane for the latter) using methods similar to those we previously described. [8][9][10][11] Individual isomers of ester 5 were then hydrolyzed to the corresponding acids in KOH, without E/Z-isomerization. 12 The isomeric purity for the final acids (>97%) was verified by NMR and reverse-phase HPLC.…”

“…12 The isomeric purity for the final acids (>97%) was verified by NMR and reverse-phase HPLC. [8][9][10][11] Experimental yields and selected data for the intermediates and products in Scheme 1 are summarized in Table 1. The UV/vis spectral data of the purified isomers are given in Table 1, and the complete 1 H NMR assignments are contained in Table 2.…”

“…Each pure isomer of 4 was olefinated as shown to provide a mixture of either (9 Z )- and (9 Z ,13 Z )- 5 or ( all-E )- and (13 Z )- 5 . Each mixture was preparatively separated by HPLC on silica gel (0.5% Et 2 O, 0.1% THF in hexane for the former and 1% Et 2 O, 0.5% THF in hexane for the latter) using methods similar to those we previously described. − Individual isomers of ester 5 were then hydrolyzed to the corresponding acids in KOH, without E / Z -isomerization − Experimental yields and selected data for the intermediates and products in Scheme are summarized in Table .…”

“…Each mixture was preparatively separated by HPLC on silica gel (0.5% Et 2 O, 0.1% THF in hexane for the former and 1% Et 2 O, 0.5% THF in hexane for the latter) using methods similar to those we previously described. − Individual isomers of ester 5 were then hydrolyzed to the corresponding acids in KOH, without E / Z -isomerization − Experimental yields and selected data for the intermediates and products in Scheme are summarized in Table . The UV/vis spectral data of the purified isomers are given in Table , and the complete 1 H NMR assignments are contained in Table .…”