title: Lipophilicity of porphyrins and their retention in IAM, C8-C18 and HILIC chromatographic systems.
abstract: Porphyrins are a class of photosensitizers used in photodynamic therapy (PDT). Understanding the interaction of porphyrins with membrane cells components is important in order to improve this therapy. Many analytical methods can be used for this aim. High performance liquid chromatography (HPLC) was used for the separation of porphyrins on RP and HILIC stationary phases as well as on a biomimetic membrane IAM phase. Twenty-six tetraphenyl porphyrins (TPP) were successfully separated on an IAM column, a C18 Gravity RP column, a C8 Gravity RP column, a PolarTec RP column and a HILIC column. Stationary phases were chosen as the most appropriate to cover the study of different types of interactions. Elution was performed with a 45 min linear gradient. Obtained gradient retention times were converted to gradient chromatography hydrophobicity index (CHI) and to an apparent retention factor (kapp). The partition coefficients (logP) of the 26 compounds were measured in a 2-octanol/PBS system and estimated in silico. Correlation between kapp values was studied. Moreover, a multivariate analysis was performed to explain columns relationships. Obtained results show that porphyrins are separated mainly according to hydrophobic interactions that are relative to their structure (sugar number and the disposition around the porphyrin macrocycle).
authors.affiliation: Lipides, Systèmes Analytiques et Biologiques, ex EA4041, Faculté de Pharmacie, Univ. Paris-Sud, 92296 Châtenay Malabry Cedex, France. Electronic address: donia.essaid@u-psud.fr.
authors.forename: D
authors.initials: D
authors.lastname: Essaid
authors.affiliation: Lipides, Systèmes Analytiques et Biologiques, ex EA4041, Faculté de Pharmacie, Univ. Paris-Sud, 92296 Châtenay Malabry Cedex, France.
authors.forename: P
authors.initials: P
authors.lastname: Chaminade
authors.affiliation: Institut Curie, Centre de Recherche, Centre Universitaire, Univ. Paris-Sud, F-91405 Orsay, France; CNRS, INSERM, UMR 9187-U 1196, Centre Universitaire, Univ. Paris-Sud, F-91405 Orsay, France.
authors.forename: Ph
authors.initials: P
authors.lastname: Maillard
authors.affiliation: Lipides, Systèmes Analytiques et Biologiques, ex EA4041, Faculté de Pharmacie, Univ. Paris-Sud, 92296 Châtenay Malabry Cedex, France.
authors.forename: A
authors.initials: A
authors.lastname: Kasselouri
mesh_terms: D000465:Algorithms; D032701:Biomimetics; D002138:Calibration; D002853:Chromatography, Liquid / Q000379:methods; D057927:Hydrophobic and Hydrophilic Interactions; D016014:Linear Models; D008567:Membranes, Artificial; D015999:Multivariate Analysis; D000442:Octanols / Q000737:chemistry; D010743:Phospholipids / Q000737:chemistry; D010778:Photochemotherapy / Q000379:methods; D011166:Porphyrins / Q000032:analysis / Q000737:chemistry*; D025341:Principal Component Analysis; D012984:Software
chemical_list: D008567:Membranes, Artificial; D000442:Octanols; D010743:Phospholipids; D011166:Porphyrins
keywords: HILIC; HPLC-gradient elution; IAM; Lipophilicity; Porphyrin; RP-LC