Synthesis of n-squalenoyl cytarabine and evaluation of its affinity with phospholipid bilayers and monolayers

Lipophilic prodrug of paclitaxel: Interaction with a dimyristoylphosphatidylcholine monolayer

“…(2012) suggested that the stronger interaction of SQ-paclitaxel/ DMPC with respect to paclitaxel/DMPC could be due to its increased lipophilicity that increases the affinity for the phospholipid bilayers (in the case of calorimetric measurements) or monolayers as shown in our work. This behavior could be due to the inclusion of squalene moiety among the phospholipid molecules (Sarpietro et al, 2011). From these results a possible localization of SQ-COOH, paclitaxel and SQ-paclitaxel in the DMPC monolayer can be hypothesized.…”

Interaction of β-caryophyllene and β-caryophyllene oxide with phospholipid bilayers: Differential scanning calorimetry study

“…The non perturbative technique of differential scanning calorimetry (DSC) was applied for measuring the effect of the molecules on the thermotropic behaviour of DMPC MLV [21,22]. Experiments were also carried out in order to characterize the interference of the aqueous or lipid medium with the uptake of the test substances through the biomembrane model [23].…”

Lipid prodrug nanocarriers in cancer therapy

“…Classification of the anticancer drugs, lipids used for their derivatization and the nanoscale drug delivery system based on these prodrugs are reported in Table 1. A C C E P T E D M A N U S C R I P T Liposomes [37][38][39] Stearic acid C18 (stearoyl) Liposomes [36][37][38][39] Micelles [40,41] Polymer nanoparticles [42] Solid lipid nanoparticles [43][44][45][46] Self-assembled nanoparticles [47] Squalene Nanoparticles [50][51][52][53] [54-57, 59-63, 66, 67] Isoprenoids (monoisoprenoyl, geranyl farnesyl,polyisoprenoyl) Nanoparticles [68,69] Squalene Liposomes [58] Gemcitabine monofosfate Squalene Nanoparticles [64,65] Cytosine arabinoside Oleic acid Palmitic acid Liposomes [73] Cholesterol Liposomes [74] Glycerol substituted Liposomes [75] Phospholipids Thioether lipids (1-Salkylthioglycerols) Micelles [76] Squalene Liposomes [77][78] 5-fluorouracil Stearic acid Solid lipid nanoparticles [79] Floxuridine Octanoic acid; palmitic acid Liposomes [80][81][82] Octanoic acid; Solid lipid nanoparticles [84] Capecitabine Palmitic acid, Phytic acid,Oleic acid, Stearic acid, Linoleic acid, Linolenic acid Solid lipid nanoparticles, cubosomes, gyroids, double diamonds [85][86]…”

“…6). Physicochemical investigation revealed its enhanced affinity compared to the free drug for multi-lamellar vesicles of dimyristoylphosphatidylcholine (DMPC) thus opening the way to the use of SQCytarabine-loaded liposomes for drug delivery purposes [77]. In addition, this prodrug displayed behaviour analogy with other squalenoyl derivatives [49] and the capacity of self-assemble into nanoparticles without the use of any carrying and/or surface active material [78].…”

“…Adapted with permission from ref. [77] Although to a lesser extent, the prodrug approach has been applied to fluoropyrimidine 5-fluorouracil (5-FU), a drug widely used in the treatment of advanced colorectal and breast cancers [30], and its analogue floxuridine (5-fluoro-2'-deoxyuridine, FUdR).…”