Synthesis of BODIPY-labeled alkylphosphocholines with leishmanicidal activity, as fluorescent analogues of miltefosine.
Two general synthetic methods are described, by which the highly fluorescent and photostable BODIPY group can be inserted in and aligned with the alkyl backbone of linear lipids. These methods have been used to prepare strongly emitting analogues of the leishmanicidal drug miltefosine, in which the antiparasite activity in vitro of the original drug is preserved.
Hornillos
Valentín
V
Instituto de Química Orgánica, CSIC, Juan de la Cierva 3, 28006 Madrid, Spain.
Carrillo
Eugenia
E
Rivas
Luis
L
Amat-Guerri
Francisco
F
Acuña
A Ulises
AU
D000818:Animals; D000981:Antiprotozoal Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D001896:Boron Compounds / Q000138:chemical synthesis* / Q000494:pharmacology; D002626:Chemistry, Pharmaceutical / Q000379:methods*; D015195:Drug Design; D005456:Fluorescent Dyes / Q000138:chemical synthesis / Q000494:pharmacology; D006801:Humans; D007893:Leishmania donovani / Q000378:metabolism*; D008055:Lipids / Q000737:chemistry; D008956:Models, Chemical; D010767:Phosphorylcholine / Q000031:analogs & derivatives* / Q000737:chemistry* / Q000494:pharmacology; D012997:Solvents / Q000737:chemistry; D013053:Spectrophotometry / Q000379:methods
C095489:4,4-difluoro-4-bora-3a,4a-diaza-s-indacene; D000981:Antiprotozoal Agents; D001896:Boron Compounds; D005456:Fluorescent Dyes; D008055:Lipids; D012997:Solvents; D010767:Phosphorylcholine; C039128:miltefosine