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Self‐Assembled Vesicle–Carbon Nanotube Conjugate Formation through a Boronate–Diol Covalent Linkage
Author(s) -
Dinda Soumik,
Mandal Deep,
Sarkar Saheli,
Das Prasanta Kumar
Publication year - 2017
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201703452
Subject(s) - conjugate , covalent bond , diol , linkage (software) , carbon nanotube , chemistry , vesicle , nanotechnology , polymer chemistry , organic chemistry , materials science , biochemistry , gene , mathematical analysis , mathematics , membrane
A vesicle–single walled carbon nanotube (CNT) conjugate was developed by a boronic acid–diol covalent linkage between a self‐assembled vesicle and dispersed CNT. Trimesic acid based phenylboronic acid appended triple‐tailed amphiphiles ( T1 and T1S ) were synthesized that formed monolayered vesicles through H ‐aggregation in DMSO–water (2:1 v/v) and pure water, respectively. Aqueous CNT dispersion was prepared with cholesterol‐based glucose‐functionalized amphiphile ( D1 ). These two supramolecular self‐assemblies were covalently linked by using a boronic acid–diol interaction between a phenylboronic acid based T1S vesicle and 1,2‐diol moieties of glucose tethered dispersing agent ( D1 ) to develop a vesicle–CNT conjugate. Lewis acid–base chemistry was exploited to form this boronate–diol adduct between two supramolecular self‐assemblies. The formation of vesicles, CNT dispersion, and the vesicle–CNT conjugate was characterized by microscopic and spectroscopic techniques. Anticancer drug doxorubicin was encapsulated within this T1S ‐vesicle– D1 ‐CNT conjugate with a higher loading capacity compared to the individual cargo carrier (vesicle or CNT). This cytocompatible T1S ‐vesicle– D1 ‐CNT conjugate successfully delivered loaded doxorubicin within a B16F10 melanoma cell and also exhibited better cellular transportation ability compared to the drug‐loaded vesicle or CNT. This was further reflected in an enhanced killing efficiency of the cancer cells by the vesicle–CNT conjugate compared to the drug‐loaded vesicle or CNT.