Phosphoric Acid Triester Micelles: Characterization and Self-Assembly

In this study, we analyzed the properties of amphiphilic alkyldi(methoxy poly(ethylene glycol) (MePEG)350-lactate) phosphates based on ethyl lactate, the monomethyl ether of poly(ethylene glycol)350, and alkyldichloro phosphates. Interestingly, these triesters combine two biodegradable bonds, -P(O)-...

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Bibliographic Details
Published in:Journal of Oleo Science 2023, Vol.72(10), pp.969-977
Main Authors: Yokoyama, Yuto, Makino, Kimiko, Terada, Hiroshi, Kikuchi, Akihiko, Takeuchi, Issei, Troev, Kolio
Format: Article
Language:eng ; jpn
Subjects:
Alcohols
Aqueous solutions
Doxorubicin
drug delivery
Dynamic stability
Esters
Ethyl lactate
Hydrophobicity
Micelles
Phosphates
Phospholipids
Phosphoric acid
phosphoric acid triesters
Photon correlation spectroscopy
Polyethylene glycol
Self-assembly
Solubilization
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Summary:In this study, we analyzed the properties of amphiphilic alkyldi(methoxy poly(ethylene glycol) (MePEG)350-lactate) phosphates based on ethyl lactate, the monomethyl ether of poly(ethylene glycol)350, and alkyldichloro phosphates. Interestingly, these triesters combine two biodegradable bonds, -P(O)-O-C and -C(O)-O-C-, and include hydrophilic (MePEG350-lactate) and hydrophobic (R-aliphatic chain of alcohols) moieties. The properties of these esters resemble those of phospholipids. After being placed in an aqueous solution, they self-assembled. We also determined the effects of ester composition on micelle formation, stability, and size using dynamic light scattering. Solubilization tests using Sudan III or doxorubicin hydrochloride (Dox·HCl) revealed that they could be incorporated into the hydrophobic cores of dodecyl di(MePEG350-lactate) phosphate and hexadecyl di(MePEG350-lactate) phosphate. Notably, dodecyl di(MePEG350-lactate) phosphate was stable for five days, whereas hexadecyl di(MePEG350-lactate) phosphate was stable for seven days in phosphate-buffered saline. Moreover, Dox·HCl release rates from the micelles were approximately 30-40, 70-80, and 90-100% after 1, 5, and 28 d, respectively.
ISSN:1345-8957
1347-3352
DOI:10.5650/jos.ess23108