Water-Solubilization by Using Symmetrically Branched Oligoglycerol Trimers

As a water-solubilizing fragment, branched glycerol trimer (BGL003) has been conjugated here with several lipophilic molecules to increase the hydrophilicity.
Alkanethiols have been chemically modified by BGL003 to develop a lipophilic-thiolate-chemisorbed “Self-assembled Monolayers” (SAM) on metal surface in an aqueous solution.
Octadecanethiol (ODT) which is used with organic solvent for depositing a molecular layer on the expensive metal surfaces. Herein, lipophilic thiols have been connected with BGL003 through succinyl residue and converted to a water-soluble derivative. The chemically modified octadecanethiol derivative has been applied for novel transition metal coating in water and the anticorrosive effect of metal piece was as high as with lipophilic thiol in organic solvent. Thus, an environmentally friendly coating method has been established from this project.
Next, a couple of branched glycerol trimers with new apex were synthesized. Using N-acyl tyrosine methylamide as a smallest model of peptides and SN38 as an antineoplastic drug, the new BGL003 was connected with side chain of tyrosine and A-ring of SN38, respectively, via one additional linker molecule. Paclitaxel and docetaxel are also a chemotherapy medication and another new BGL003 has been conjugated with 3´-debenzoylated paclitaxel and 3´-de(tert-butyloxycarbonyl) docetaxel, respectively, without any linker molecule. I believe these BGL003 modified drugs will be more hydrophilic and increase absorption amount in the human body. The efficiency (in vitro and in vivo) of these modified drugs will be tested later on.

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