5‐Phenyl‐1,3,4‐oxadiazole‐2‐thiol/polyamide‐montmorillonite microbicides nanocomposites as drug delivery system

Abstract

The preparation and structural characterization of polymeric microbicides consisting of 5-phenyl-1,3,4-oxadiazole-2-thiol covalently bound to polyamide based on diethyl-2,3-dihydroxysuccinate and polyoxypropylenetriamine Jeffamine (T 403 ) are described. Two different mole ratios of 5-phenyl-1,3,4oxadiazole-2-thiol was reacted with chloroacetylated diethyl-2,3dihydroxysuccinate followed by polycondensation with Jeffamine (T 403 ). The nanocomposites were prepared by modification of microbicide polyamides to yield polymers with phosphonium salt or amine hydrochloride salt followed by ion exchange process between the phosphonium salt or amine hydrochloride of the polyamides and the intermellar sodium cation of the clay mineral montmorillonite. The monomers were characterized by mass spectrum, proton nuclear magnetic resonance. The polymers showed good or moderate antimicrobial activities. Nanocomposites were characterized by Fourier transformed infrared spectroscopy, X-ray diffraction, thermal gravimetric analysis, and transmission electron microscope. The swelling behavior and release of 5-phenyl-1,3,4-oxadiazole-2-thiol in different pH values (2.3, 5.8, and 7.4) were studied. A slow release, ranging from 12% to 28% after 50 hours was recorded from nanocomposites. However, the release profile reached almost 70% from polyamides. The antimicrobial activity of the polyamides was studied against gram-negative bacteria, gram-positive bacteria, yeast, and the filamentous fungi by well diffusion method. The polyamides showed better antimicrobial activities than 5-phenyl-1,3,4-oxadiazole-2-thiol.

Polyamide/Poly(Amino Acid) Polymers for Drug Delivery

“…MMT plays an important role in the delivery of drugs due to its unique characteristics such as swelling and adsorption. Salahuddin et al has recently reported 5-phenyl-1,3,4-oxadiazole-2-thiol/polyamide-MMT microbicide nanocomposites in the field of drug delivery [77]. These MMTs with anionic polymers like alginate form a unique polymer silicate material that provides a superior capability of incorporating drug molecules within the structure.…”

Synthesis and docking studies of N‐(5‐(alkylthio)‐1,3,4‐oxadiazol‐2‐yl)methyl)benzamide analogues as potential alkaline phosphatase inhibitors

“…1,3,4-Oxadiazoles are known to be associated with a broad spectrum of biological activities (Salahuddin, Elbarbary, Allam, & Hashim, 2018).…”

“…1,3,4-Oxadiazoles are known to be associated with a broad spectrum of biological activities (Salahuddin, Elbarbary, Allam, & Hashim, 2018). 1,3,4-Oxadiazole derivatives have received considerable attention of medicinal chemists owing to their wide spectrum of useful chemical, biological, and pharmacological activities (Khan, Ahuja, & Husain, 2017).…”