Silibinin binding and release activities moderated by interstices of trimesoyl, tridimethyl, and tridiethyl malonate first‐tier dendrimers

Abstract

Trimesoyl 1,3,5-tridimethyl malonate (TTDMM), trimesoyl 1,3,5-tridiethyl malonate (TTDEM), trimesoyl 1,3,5-tridipropyl malonate, trimesoyl 1,3,5-tridibutyl malonate, and trimesoyl 1,3,5-tridihexyl malonate first-generation dendrimers, a complete series of dialkyl malonate esters from methyl to hexyl, were synthesized by a divergent growth approach with about a 95% yield. TTDMM and TTDEM members of this series were characterized with 500-MHz NMR and Fourier transform infrared spectroscopy. The 7.469353 and 8.435395 m 2 /g surface areas and 700.1907-and 792.6436-nm pore-average diameters of TTDMM and TTDEM, respectively, implied that they could be used as prospective drug binders. Alkyl chains from methyl to hexyl of dialkyl malonate esters had enhanced interstitial spaces to trap the drugs and toxic heavy metals for their distribution and bioremediation, respectively. Thus, the dendrimers, silibinin (SB) complexes in a 1:1 ratio with acetone, were prepared and studied with Fourier transform infrared spectroscopy, differential scanning calorimetry, dynamic light scattering, scanning electron microcopy, and atomic force microscopy. The ultraviolet-visible spectroscopy at a 330-nm lamda max (k max ) showed about 5%/h SB released in phosphate buffered saline with 10% dimethyl sulfoxide. The objective was used to investigate the capacity of dialkyl malonate terminated dendrimers to encapsulate a maximum amount of SB and anticancer drugs and the in vitro releasing activity.

Effect of increasing alkyl chain of 1st tier dendrimers on binding and release activities of methotrexate drug: An in vitro study

“…TTDMM, TTDEM and TTDPM were synthesized according to procedures reported in our previous communication [22,23]. In brief dendrimers were synthesized by TMC core and sodium dialkyl malonate salt in 1:3 molar ratio in methanol in case of TTDMM and ethanol for the rest.…”

“…Despite such extraordinary structural capabilities for MTX binding, no specific and systematic research work with TTDMM, TTDEM and TTDPM has ever been reported so far; hence our study on developing models of dendrimer-drug designing is aimed to provide an advance understanding of complexities of drug-carrier interfaces. The green method for divergent synthesis and characterization of TTDMM, TTDEM and TTDPM was reported in our previous communication [22,23]. Therefore, in this study, TTDMM, TTDEM and TTDPM with a trimesoyl chloride (TMC) core and variable dialkyl malonate esters as branching units with well-defined size were synthesized and used as drug carrier for better encapsulation of anticancer drug.…”

Ecofriendly Application of Nanomaterials: Nanobioremediation

“…Dendrimers are relatively monodispersed and highly branched macromolecules with controlled composition and architecture consisting of three components (Figure 2(a)): a central core, interior branch cells or radial symmetry, and terminal branch cell or peripheral group [23]. Dendrimers have many void spaces for their interaction of other substances Figure 2(b) [24]. Therefore, dendrimers-NPs composite can be prepared and can be used to enhance catalytic activity.…”

Dispersion and optical activities of newly synthesized magnetic nanoparticles with organic acids and dendrimers in DMSO studied with UV/vis spectrophotometry

“…So very specifically the organic acids and dendrimers containing -COOH, -OH, NCO and -CH 2 in their structures could be responsible for MNP dispersion via hydrophilic, hydrophobic, instantaneous induced dipole and electrostatic interaction. In our previous work, synthesis and characterization of 1st tier dendrimers (TTDMM, TTDEM, TTDPM, TTDBM and TTDHM) have been reported with globular structure and void spaces in their molecular framework with strong drug binding ability [29,30]. Their surface functionality and void spaces with variable dialkyl chain have initiated intermolecular interaction with MNPs.…”