Fabrication of branched polyethylenimin/alginic acid/poly(cyclohexane-1,4-diyl acetone dimethylene ketal as a nano size carrier for controlled release of 5-fluorouracil

Chen, Pochung; Yii, Doris; Tsai, Hsieh‐Chih; Parasuraman, Vijaya Rohini; Prasannan, Adhimoorthy; Kao, Chen‐Yu; Lai, Juin‐Yih

doi:10.1016/j.reactfunctpolym.2019.03.006

Cited by 3 publications

(9 citation statements)

References 45 publications

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“…Again, the increased strengthening of −CO bond may be the consequence of increased steric hindrance and a bigger molecular size of coformer also proposed in Figure . This is also proved true after the peak at 1179.10 cm –1 (−C–O) in the 5-FU spectrum diminished in the cocrystal spectrum due to vanished single bond properties of the carbonyl groups in the course of cocrystal formation.…”

Section: Results and Discussionmentioning

confidence: 66%

“…Moreover, the absorption frequencies of −C−O were also observed at almost same positions: 1179.10 cm −1 (5-FU) and 1174.75 cm −1 (5-FU-Sc). 42 This suggests the efficient involvement of carbonyl groups of coformer in the development of hydrogen bonding interaction as compared to 5-FU. This may be the result of more steric hindrance of the cyclic structure of 5-FU than the aliphatic structure of succinic acid as depicted in Figure 4.…”

Section: Resultsmentioning

confidence: 98%

“…In the IR spectrum of unsubstituted or nonderivatized 5-FU, a rounded peak at 3409.02 cm −1 can be accredited to the absorption frequency of (N−H) group (stretching), and a wide sharp band of high intensity at wavenumber 1647.77 cm −1 can be assigned to v(CO) groups (stretching). 42,43 3.1.1. 5-FU-Cinnamic acid (5-FU-Cn).…”

Section: Resultsmentioning

confidence: 99%

“…Absorption frequencies of 5-FU, all coformers, and cocrystals are represented in Table . In the IR spectrum of unsubstituted or nonderivatized 5-FU, a rounded peak at 3409.02 cm –1 can be accredited to the absorption frequency of (N–H) group (stretching), and a wide sharp band of high intensity at wavenumber 1647.77 cm –1 can be assigned to v (CO) groups (stretching). , …”

Section: Results and Discussionmentioning

confidence: 99%

“…This observed trend is also affirmed by the observation of −C−O absorption frequencies of API and cocrystals at a shift of less than 10 cm −1 (nonsignificant), 1179.10 cm −1 (5-FU), and 1080.89 cm −1 (5-FU−Ml). 42 This suggests the strong disturbance and involvement of carbonyl groups of coformer molecules while the very less involvement of carbonyl groups of API in the formation of noncovalent interactions between API and coformer for the development of cocrystals. This could be explained by the bigger molecular size of malic acid that generates high steric hindrance while forming hydrogen bonds with the consecutive NH−CO−NH groups of 5-FU as manifested in Figure 6.…”

Section: -Fu−maleic Acid (5-fu-ml)mentioning

confidence: 99%

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Synthesis of 5-Fluorouracil Cocrystals with Novel Organic Acids as Coformers and Anticancer Evaluation against HCT-116 Colorectal Cell Lines

Jubeen

Liaqat

Amjad

et al. 2020

Crystal Growth & Design

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5-Fluorouracil (5-FU) being a mainstream anticancer drug is under keen and detailed investigation for prodrugs formulations in order to minimize the associated side effects. Cocrystallization of 5-FU is an innovative technique for the synthesis of 5-FU prodrugs to improve its anticancer effectiveness. The present study is based on the synthesis of 5-FU supramolecular synthons with four coformers: succinic acid, cinnamic acid, malic acid, and benzoic acid utilizing acetone as a solvent. Solid state grinding followed by a slow evaporation solution method was applied. Colorless clear crystals were obtained in all the cases. The cocrystal formation was supported with the help of Fourier transform infrared (FTIR) spectroscopy and powder X-ray diffraction (PXRD). Through FTIR, the main peaks of interest in the spectrum of 5-FU were N–H (3409.02 cm–1) and carbonyl group (1647.80 cm–1), which were prominently shifted in all spectra of the cocrystals demonstrating the replacement as well as the development of already present interactions with the new ones. For 5-FU–cinnamic acid cocrystals, the anticipated peaks were observed at 1673.13 cm–1 (−CO) and 3566.89 cm–1 (N–H) manifesting a significant change in comparison to 5-FU. Furthermore, with the help of PXRD characterization, the representative peak of 5-FU was recorded at 2θ = 28.80°. The shifting of this specific peak and development of many new ones in the spectra of cocrystals proved the development of new structural entities. Finally, the anticancer activity of all cocrystals was evaluated in comparison to that of API. All cocrystals manifest significantly greater growth inhibition potential than the main active pharmaceutical ingredient. 5-FU–Cinnamic acid (3C) was the one that proved to be the most potent anticancer agent at all four concentrations: 4.82% (12 μg/mL), 34.21% (25 μg/mL), 55.08% (50 μg/mL), and 67.29% (100 μg/mL). In short, this study proved to be a true example to enhance the anticancer potential of 5-FU following fairly easy fabrication requirements of the cocrystallization phenomenon. After the successful synthesis of these supramolecular synthons and subsequent enhancement of growth inhibition potential of 5-FU, these cocrystals can further be evaluated for in vivo trials and membrane crossing potentials in the future.

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Section: Results and Discussionmentioning

confidence: 66%

Section: Resultsmentioning

confidence: 98%

Section: Resultsmentioning

confidence: 99%

Section: Results and Discussionmentioning

confidence: 99%

Section: -Fu−maleic Acid (5-fu-ml)mentioning

confidence: 99%

See 3 more Smart Citations

Synthesis of 5-Fluorouracil Cocrystals with Novel Organic Acids as Coformers and Anticancer Evaluation against HCT-116 Colorectal Cell Lines

Jubeen

Liaqat

Amjad

et al. 2020

Crystal Growth & Design

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Chitosan based hybrid hydrogels for drug delivery: Preparation, biodegradation, thermal, and mechanical properties

Kamacı

Kaya

2022

Polymers for Advanced Techs

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In the present paper, biodegradable hybrid hydrogels were prepared by using chitosan as a natural polymer and polyurethane containing azomethine as a synthetic polymer for the drug delivery application for 5‐fluorouracil. The fabricated hydrogels were characterized via FT‐IR and SEM analysis. Besides, the thermal, mechanical, and wettability properties, water uptake, biodegradation, protein absorption, drug loading, and release behaviors of the hybrid hydrogels were studied. The obtained results indicated that the fabricated hybrid hydrogels have exhibited good mechanical, hydrophilic, water uptake, and biodegradation behaviors. The hybrid hydrogels also showed 50% drug release amounts and they could be a good candidate for the controlled delivery of 5‐FU due to these properties.

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Polyketal-based nanocarriers: A new class of stimuli-responsive delivery systems for therapeutic applications

Rajagopal

Jayandharan

Krishnan

2022

European Polymer Journal

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Fabrication of branched polyethylenimin/alginic acid/poly(cyclohexane-1,4-diyl acetone dimethylene ketal as a nano size carrier for controlled release of 5-fluorouracil

Cited by 3 publications

References 45 publications

Synthesis of 5-Fluorouracil Cocrystals with Novel Organic Acids as Coformers and Anticancer Evaluation against HCT-116 Colorectal Cell Lines

Synthesis of 5-Fluorouracil Cocrystals with Novel Organic Acids as Coformers and Anticancer Evaluation against HCT-116 Colorectal Cell Lines

Chitosan based hybrid hydrogels for drug delivery: Preparation, biodegradation, thermal, and mechanical properties

Polyketal-based nanocarriers: A new class of stimuli-responsive delivery systems for therapeutic applications

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