A new synthetic methodology for the preparation of biocompatible and organo-soluble barbituric- and thiobarbituric acid based chitosan derivatives for biomedical applications

Shahzad, Sohail Anjum; Shahzadi, Lubna; Mahmood, Nasir; Siddiqi, Saadat Anwar; Manzoor, Faisal; Chaudhry, Aqif Anwar; Rehman, Ihtesham Ur; Yar, Muhammad

doi:10.1016/j.msec.2016.04.056

Cited by 32 publications

(31 citation statements)

References 46 publications

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“…In recent years, functional biological materials have been studied extensively in drug delivery systems, due to their low price and excellent biocompatibility and they have shown great promise [12][13][14]. Glucose-responsive delivery systems based on biological materials have rarely been reported [15][16][17][18].…”

Section: Introductionmentioning

confidence: 99%

Phenylboronic acid-diol crosslinked 6-O-vinylazeloyl-d-galactose nanocarriers for insulin delivery

Bremner

et al. 2017

Materials Science and Engineering: C

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A new block polymer named poly 3-acrylamidophenylboronic acid-b-6-O-vinylazeloyl-d-galactose (p(AAPBA-b-OVZG)) was prepared using 3-acrylamidophenylboronic acid (AAPBA) and 6-O-vinylazeloyl-d-galactose (OVZG) via a two-step procedure involving S-1-dodecyl-S-(α', α'-dimethyl-α″-acetic acid) trithiocarbonate (DDATC) as chain transfer agent, 2,2-azobisisobutyronitrile (AIBN) as initiator and dimethyl formamide (DMF) as solvent. The structures of the polymer were examined by Fourier transform infrared spectroscopy (FT-IR) and H NMR and the thermal stability was determined by thermal gravimetric analysis (TG/DTG). Transmission electron microscopy (TEM) and dynamic light scattering (DLS) were utilized to evaluate the morphology and properties of the p(AAPBA-b-OVZG) nanoparticles. The cell toxicity, animal toxicity and therapeutic efficacy were also investigated. The results indicate the p(AAPBA-b-OVZG) was successfully synthesized and had excellent thermal stability. Moreover, the p(AAPBA-b-OVZG) nanoparticles were submicron in size and glucose-sensitive in phosphate-buffered saline (PBS). In addition, insulin as a model drug had a high encapsulation efficiency and loading capacity and the release of insulin was increased at higher glucose levels. Furthermore, the nanoparticles showed a low-toxicity in cell and animal studies and they were effective at decreasing blood glucose levels of mice over 96h. These p(AAPBA-b-OVZG) nanoparticles show promise for applications in diabetes treatment using insulin or other hypoglycemic proteins.

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Section: Introductionmentioning

confidence: 99%

Phenylboronic acid-diol crosslinked 6-O-vinylazeloyl-d-galactose nanocarriers for insulin delivery

Bremner

et al. 2017

Materials Science and Engineering: C

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“…The orderly arrangement of polymer chains and crystallinity in the structure were attributed to the hydrogen bonding within and between the chains. We also observed that CS–DETBA had no peak around a 2θ of 10°, a new peak at a 2θ of 13.05°, and a peak at a 2θ of 20.47° with a much decreased intensity compared to that of CS . A very low intensity peak at a 2θ of 13.05° indicated a new crystalline domain in the structure.…”

Section: Resultsmentioning

confidence: 55%

“…There was also a slight shift in the peak for COC at 1060 cm −1 (for CS) to 1063 cm −1 (for CS–DETBA). The presence of a band at 1670 cm −1 indicated CO (a ketonic group in conjugated system) of the DETBA . There was a slight shift in the peak from 1590 to 1598 cm −1 with increasing intensity for amide II–NH deformation.…”

Section: Resultsmentioning

confidence: 98%

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Synthesis of a novel organosoluble, biocompatible, and antibacterial chitosan derivative for biomedical applications

Rizwan

Yahya

Hassan

et al. 2017

J of Applied Polymer Sci

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Electrospun materials have a number of applications in the tissue engineering field. However, the limited solubility of chitosan (CS), especially in organic solvents, makes its electrospinning with other synthetic organosoluble polymers impossible. In this article, we report the synthesis of a novel organosoluble derivative of CS through the application of a simple synthetic methodology. CS was reacted with 1,3‐diethyl‐2‐thiobarbituric acid (DETBA) with triethylorthoformate in the presence of methanol and acetic acid (4:1). The functional groups in the synthesized materials were confirmed by Fourier transform infrared and solid‐state NMR spectroscopy, whereas X‐ray diffraction revealed the level of crystallinity. The CS derivative (CS–DETBA) was tested for its cytotoxic effects on human gastric adenocarcinoma AGS cells and was found to be nontoxic. The prepared derivative showed a much enhanced inhibitory effect on the growth of three bacterial strains, Escherichia coli, Pseudomonas aeruginosa, and Staphylococcus aureus, over that of CS itself. Overall, CS–DETBA showed good solubility in a range of organic solvents, such as dimethyl sulfoxide and N,N‐dimethylformamide, and was blended with polycaprolactone (PCL) to form films and electrospun nanofibers. The morphologies of the synthesized materials were analyzed by field emission scanning electron microscopy, and the fiber diameter was 360 nm under optimum conditions. This study demonstrated that the CS–DETBA–PCL blend could be a potential material for tissue engineering and biomedical applications. © 2017 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2018, 135, 45905.

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“…Barbituric acid is an organic compound based on a pyrimidine heterocyclic skeleton and was first discovered by the German chemist Adolf von Baeyer in 1864 (Baeyer, 1864). Although barbituric acid is not pharmacologically active, it can form a large variety of derivatives called barbiturates that have been used in many ways (Shahzad et al, 2016). Barbituric acid derivatives possess different biological activities, such as hypnotic (Shonle and Moment, 1923;Wisner, 1925), sedative (Kliethermes et al, 2004), anticonvulsant (Srivastava and Kumar, 2004), antimicrobial (Dhorajiya et al, 2014), antiviral (Marecki et al, 2019), anti-inflammatory (Xu et al, 2016), anticancer, and antitumor properties (Singh et al, 2009;Penthala et al, 2015;Laxmi et al, 2016).…”

Section: Introductionmentioning

confidence: 99%

Antifibrotic Effects of a Barbituric Acid Derivative on Liver Fibrosis by Blocking the NF-κB Signaling Pathway in Hepatic Stellate Cells

et al. 2020

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A new synthetic methodology for the preparation of biocompatible and organo-soluble barbituric- and thiobarbituric acid based chitosan derivatives for biomedical applications

Cited by 32 publications

References 46 publications

Phenylboronic acid-diol crosslinked 6-O-vinylazeloyl-d-galactose nanocarriers for insulin delivery

Phenylboronic acid-diol crosslinked 6-O-vinylazeloyl-d-galactose nanocarriers for insulin delivery

Synthesis of a novel organosoluble, biocompatible, and antibacterial chitosan derivative for biomedical applications

Antifibrotic Effects of a Barbituric Acid Derivative on Liver Fibrosis by Blocking the NF-κB Signaling Pathway in Hepatic Stellate Cells

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