Synthesis and crystal structure of piperidinyl propanenitrile towards the preparation of piperidine based bioactive films for drug delivery applications

Abstract

Compounds containing the piperidine group are highly attractive as building blocks for designing new drugs. Functionalized piperidines are of significant interest due to their prevalence in the pharmaceutical field. Herein, 3-oxo-3-(piperidin-1-yl) propanenitrile has been synthesized, and piperidine-based sodium alginate/poly(vinyl alcohol) films have been prepared. The polymeric films display potency and potential for application to fight against microbial infections. The films could also help maintain interaction with tissue to ensure the controlled release of therapeutic molecules. Thus, they are promising in developing drug delivery systems essential in the pharmaceutical industry. The structure of the 3-oxo-3-(piperidin-1-yl)propanenitrile was confirmed via spectroscopic and single crystal x-ray diffraction techniques. A homogenous solution of sodium alginate (SA) was used to prepare the film by the casting method in the presence of poly(vinyl alcohol) (PVA) and 3-oxo-3-(piperidin-1-yl)propanenitrile (PPN). The prepared films were characterized physiochemically via FTIR, XRD, and TGA. The film morphology was studied using SEM. The antimicrobial potency of the prepared films was assessed against various species of microorganisms. The physicochemical analysis indicated that the films were bound by chemical and physical bond formation between the cyano group of 3-oxo-3-(piperidin-1-yl)propanenitrile, methylene group of PVA, and the hydroxyl group of SA. The films showed smooth, homogenous surfaces and good mechanical properties. The results revealed that the films are bioactive, as indicated by promising antimicrobial potency against P. aeruginosa, S. aureus, E. coli, B. subtilis, and C. albicans, with high potency as well as moderate activity against A. niger. Polymeric films have promising potential to be utilized in drug delivery applications.

Keywords: Antimicrobial; Bioactive films; Crystal structure; Piperidine; Sodium alginate; Synthesis.

Fig. 1

(a) PPN synthesis and (b) An Ortep representation of the molecule of compound 3 (PPN).

Fig. 2

Suggested mechanism of film formulation.

Fig. 3

FTIR spectra of SA, SA/PVA, and SA/PVA/PPN films.

Fig. 4

SEM and EDX of SA, SA/PVA and SA/PVA/PPN films.

Fig. 5

XRD of SA, SA/PVA and SA/PVA/PPN films.

Fig. 6

Mechanical properties of SA/PVA and SA/PVA/PPN films.

Fig. 7

Thermogravimetric analysis of neat SA and SA/PVA/PPN.

Fig. 8

Antimicrobial study of prepared films, antimicrobial activity via turbidimetric assay for (SA/PVA (0), SA/PVA/PPN 0.05 (1), 0.1 (2), and 0.15 g (3)) (A) and time required for killing of concentration 0.15 g PNN (B).