Preparation and Characterization of a Novel Aspirin Derivative with Anti-Thrombotic and Gastric Mucosal Protection Properties

Xie, Zhen; Zong, Min‐Hua; Gao, Sainan; Cao, Yonggang; Jiang, Lei; Shu-xin, Chen; Wang, Kuan; Sun, Shiqin; Peng, Haisheng; Bai, Yuhua; Li, Sen

doi:10.1371/journal.pone.0098513

Cited by 12 publications

(6 citation statements)

References 22 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…1720 cm −1 ) [ 28 , 36 ]. On the other hand, the FTIR spectra of ASA showed peaks for the -C=O stretchings (1800–1680 cm −1 ) and the OH stretching (broad peak between 3100 cm −1 and 2700 cm −1 ) [ 37 , 38 , 39 ]. Interestingly, the -C=O stretching peaks of aspirin were evident in the spectra obtained for the samples containing ASA.…”

Section: Resultsmentioning

confidence: 99%

Use of 3D Printing for the Development of Biodegradable Antiplatelet Materials for Cardiovascular Applications

et al. 2021

View full text Add to dashboard Cite

Small-diameter synthetic vascular grafts are required for surgical bypass grafting when there is a lack of suitable autologous vessels due to different reasons, such as previous operations. Thrombosis is the main cause of failure of small-diameter synthetic vascular grafts when used for this revascularization technique. Therefore, the development of biodegradable vascular grafts capable of providing a localized and sustained antithrombotic drug release mark a major step forward in the fight against cardiovascular diseases, which are the leading cause of death globally. The present paper describes the use of an extrusion-based 3D printing technology for the production of biodegradable antiplatelet tubular grafts for cardiovascular applications. For this purpose, acetylsalicylic acid (ASA) was chosen as a model molecule due to its antiplatelet activity. Poly(caprolactone) and ASA were combined for the fabrication and characterization of ASA-loaded tubular grafts. Moreover, rifampicin (RIF) was added to the formulation containing the higher ASA loading, as a model molecule that can be used to prevent vascular prosthesis infections. The produced tubular grafts were fully characterized through multiple techniques and the last step was to evaluate their drug release, antiplatelet and antimicrobial activity and cytocompatibility. The results suggested that these materials were capable of providing a sustained ASA release for periods of up to 2 weeks. Tubular grafts containing 10% (w/w) of ASA showed lower platelet adhesion onto the surface than the blank and grafts containing 5% (w/w) of ASA. Moreover, tubular grafts scaffolds containing 1% (w/w) of RIF were capable of inhibiting the growth of Staphylococcus aureus. Finally, the evaluation of the cytocompatibility of the scaffold samples revealed that the incorporation of ASA or RIF into the composition did not compromise cell viability and proliferation at short incubation periods (24 h).

show abstract

Section: Resultsmentioning

confidence: 99%

Use of 3D Printing for the Development of Biodegradable Antiplatelet Materials for Cardiovascular Applications

et al. 2021

View full text Add to dashboard Cite

show abstract

“…As consequence, its modifications with a lessened, or absent, effect are in development. A novel ASA derivative with nanohydroxyapatite (a kind of inorganic particle containing Ca 2+ ), possessing anti-thrombotic properties comparable to ASA, and having much lower gastric mucosal damage than ASA, has been described [46]. It is known that carnosine possesses an anti-ulcer effect both on its own [15] and in bound form.…”

Section: Discussionmentioning

confidence: 99%

A new derivative of acetylsalicylic acid and carnosine: synthesis, physical and chemical properties, biological activity

et al. 2020

View full text Add to dashboard Cite

Purpose The aim of this study was to create and assess biological activity of a new compound based on carnosine and acetylsalicylic acid (ASA) that will comprise antioxidant effect with antiplatelet activity, while simultaneously preventing side effects on the gastrointestinal tract. Methods Salicyl-carnosine (SC) was synthesized by condensation of ASA and carnosine. Antioxidant activity was determined by spectrophotometric and chemiluminescence methods. Antiplatelet activity was carried out by the light transmissionaggregometry method using the inductor ADP. Chronic gastric ulcer in rats was modeled using glacial acetic acid. Results Using SOD-like activity, iron-induced chemiluminescence, BaSO4-activated respiratory burst, and evaluation of red blood cell structure stabilization during oxidative damage induced by sodium hypochlorite, it was shown that SC possesses antioxidant activity analogous, or better, than that of carnosine. Antiplatelet activity of SC was evaluated in the blood of healthy individuals, and was also shown to be comparable to, or exceeding that of ASA. Also SC demonstrates high resistance to hydrolysis by tissue and serum carnosinases. Most importantly, it was shown that SC has protected the gastric mucosa against the formation of stomach ulcerative lesions and promoted their epithelization, therefore overcoming the undesirable inherent side effects of ASA. Conclusions SC preserves pharmacologically significant properties of ASA and carnosine while retaining an anti-ulcer activity and resistance to the carnosinase hydrolysis at the same time. These properties are particularly promising for the potential development of new anti-inflammatory and antithrombotic drugs. KeywordsCarnosine . Acetylsalicylic acid . Salicylic acid . Antioxidant . Antiplatelet action . Gastrointestinal ulcer Abbreviations ASA acetylsalicylic acid CL chemiluminescence COX cyclooxygenase HPLC high performance liquid chromatography HRMS high resolution mass spectrometry LP lipoproteins LPO lipid peroxidation NBT nitroblue tetrazolium NSAIDs non-steroidal anti-inflammatory drugs

show abstract

“…Several attempts were made to synthesise aspirin derivatives in order to get compounds having desired biological activities with reduced toxicities. Zhen et al 2014 [6] prepared aspirin derivatives having anti-thrombotic and gastric mucosal protection properties.…”

Section: Introductionmentioning

confidence: 99%

Effects of Solvent Polarity on Solvation Free Energy, Dipole Moment, Polarizability, Hyperpolarizability and Molecular Reactivity of Aspirin

Khan

Rashid

Faruk

et al. 2017

Int J Pharm Pharm Sci

View full text Add to dashboard Cite

Objective: The aim of the study is to explore the effects of solvent polarity on solvation free energy, dipole moment, polarizability, first order hyperpolarizability and different molecular properties like chemical hardness and softness, chemical potential, electronegativity, electrophilicity index of aspirin which may lead to better understand the reactivity and stability of aspirin in different solvent systems.Methods: Becke, 3-parameter, Lee-Yang-Parr (B3LYP) level of theory with 6-31G(d,p) basis set was employed to conduct all type of calculations for both in the gas phase and in solution. The solvation free energy, dipole moment and molecular properties were calculated by applying the Solvation Model on Density (SMD) in four solvent systems namely water, methanol, ethanol and n-octanol.Results: The solvation energies steadily increased as the dielectric constant was decreased i.e. free energy increases with decreasing polarity of the solvent. The dipole moment of aspirin was found to be increased when going from non-polar to polar solvents. The dipole moment of aspirin was higher in different solvents than that of the gas phase. The polarizability and first order hyperpolarizability were also increased with the increasing dielectric constant of the solvent. Moreover, ongoing from non-polar to polar solvent the chemical potential, electronegativity and electrophilicity index were increased except in n-octanol. The chemical potential, electronegativity and electrophilicity index of aspirin in n-octanol was higher than that of ethanol. On the other hand, chemical hardness was increased with decreasing polarity of the solvent and the inverse relation was found in the case of softness.Conclusion: The calculated solvation free energy, dipole moment, polarizability, first order hyperpolarizability and molecular properties found in this study may lead to the understanding of stability and reactivity of aspirin in different solvent systems.

show abstract

Preparation and Characterization of a Novel Aspirin Derivative with Anti-Thrombotic and Gastric Mucosal Protection Properties

Cited by 12 publications

References 22 publications

Use of 3D Printing for the Development of Biodegradable Antiplatelet Materials for Cardiovascular Applications

Use of 3D Printing for the Development of Biodegradable Antiplatelet Materials for Cardiovascular Applications

A new derivative of acetylsalicylic acid and carnosine: synthesis, physical and chemical properties, biological activity

Effects of Solvent Polarity on Solvation Free Energy, Dipole Moment, Polarizability, Hyperpolarizability and Molecular Reactivity of Aspirin

Contact Info

Product

Resources

About