Synthesis and In Vitro Evaluation of Inherent Properties of L-Glutamic Acid Based Dendritic Lipopeptide Oligomers
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RESEARCH ARTICLE
Synthesis and In Vitro Evaluation of Inherent Properties of L-Glutamic Acid Based Dendritic Lipopeptide Oligomers Namita Hegde 1
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Kapil Juvale 1
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Bala Prabhakar 1
# Springer Science+Business Media, LLC, part of Springer Nature 2020
Abstract Purpose The present study reports synthesis, characterization and in vitro evaluation of physicochemical and biological properties of dendritic lipopeptide oligomers comprising L-glutamic acid dendrons and myristoyl tails such that termini of the molecules carry carboxylic ester, carboxylic acid or alcohol functions, which account for nonpolar neutral, polar anionic and polar neutral surfaces, respectively. Methods Reactions adopted in the current work were fairly rapid, moderately simplified and required fewer coupling reagents. As inherent physicochemical and biological properties depend upon structural details, synthesized compounds were tested for the presence of foaming, nanoparticle formation, antibacterial and anticancer potential, if any. Results The synthesized nonpolar molecule demonstrated potential to form self-assembled polymeric nanoparticles, whereas the polar molecules demonstrated surfactant-like properties. None of the synthesized molecules demonstrated any inherent antibacterial activity against gram-positive as well as gram-negative bacterial strains, but compound with hydroxyl termini showed anticancer activity hint as a result of preliminary screening. Conclusion The synthesized molecules demonstrate potential for their application as drug delivery materials and hold scope for further investigations. Keywords Dendron . Myristoyl . Nanoparticle . Peptide . Self-assemble
Introduction Dendritic molecular assemblies form oligomeric dendrons at lower generations (G) and polymeric dendrimers at higher generations. Dendrons as well as dendrimers are monodispersed large molecules of specific molecular weights, owing to their stepwise synthesis. Such branched polymeric structures are synthesized in a highly controlled manner, i.e. propagating generations of divalent monomers are attached Electronic supplementary material The online version of this article (https://doi.org/10.1007/s12247-020-09493-7) contains supplementary material, which is available to authorized users. * Kapil Juvale [email protected] * Bala Prabhakar [email protected] 1
Shobhaben Pratapbhai Patel School of Pharmacy & Technology Management, SVKM’s NMIMS, V. L. Mehta Road, Vile Parle (W), Mumbai 400056, India
stepwise to a common central core. Synthesis of dendritic molecules is called convergent if it propagates from the periphery towards the central core, and divergent if the propagation is vice versa [1]. Shape of the lower generation oligomeric dendrons appears conical due to its spread growing only towards one side. Dendrons gradually form a spherical dendrimer structure if bonded covalently and a supramolecular selfassembly if bonded non-covalently, as depicted schematically in Fig. 1. These dendritic systems are often utilized as drug delivery carriers. Dr
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