Cyclic Anhydrides as Powerful Tools for Bioconjugation and Smart Delivery

Spanedda, Maria Vittoria; Bourel-Bonnet, Line

doi:10.1021/acs.bioconjchem.1c00023

Cited by 21 publications

(30 citation statements)

References 149 publications

(281 reference statements)

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“…In this figure, is detailed the chemical structure of the original polymer, DDSA and one possible reaction product with the aim to illustrate chitosan acylation. It is worth noting that free amine groups of chitosan could also be involved 21 . On the other hand, the other carboxyl group exposed after the anhydride ring is open, could further react with other close OH groups, increasing the polymer cross‐linking.…”

Section: Resultsmentioning

confidence: 99%

Dodecenylsuccinic anhydride modified chitosan hydrogels for the sustained delivery of hydrophobic drugs. The case of thymol buccal delivery

Echazú

Antona

Perna

et al. 2021

J of Applied Polymer Sci

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Chitosan polymer as a bioactive carrier has an emerging importance due to its great versatility. Many strategies are reported for enhancing its properties. Herein, chitosan hydrogels modified by dodecenylsuccinic anhydride (DDSA) are prepared, characterized by SEM, FTIR, 13C NMR while their mechanical properties and cytotoxicity are assessed. Chitosan modification was studied by FTIR and 13C NMR. According to rheological measurements, modified chitosan hydrogels present a predominantly elastic behavior and exert a higher compressive strength than chitosan hydrogels. Furthermore, this work evaluates thymol incorporation, its release profile as well as its in vivo performance in a periodontitis rat model. In vitro studies reveal that thymol‐loaded‐DDSA‐chitosan hydrogels possess antimicrobial activity against Staphylococcus aureus and Pseudomonas aeruginosa for 2 days and antioxidant activity for 5 days. The incorporation of hydrophobic chains improves thymol release profile; however, DDSA‐chitosan hydrogels cytotoxicity is greater when compared to chitosan hydrogels. Finally, in a preliminary in vivo study, the local application of thymol‐loaded hydrogels is evaluated during a one‐week period. The histomorphometric measurements indicate that periodontal damage is lower when thymol is administrated in chitosan hydrogels in comparison to DDSA‐chitosan hydrogels. Nevertheless, DDSA‐chitosan hydrogels could still be useful for the sustained local delivery of hydrophobic drugs.

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Section: Resultsmentioning

confidence: 99%

Dodecenylsuccinic anhydride modified chitosan hydrogels for the sustained delivery of hydrophobic drugs. The case of thymol buccal delivery

Echazú

Antona

Perna

et al. 2021

J of Applied Polymer Sci

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“…A linker or spacer such as succinic acid is used to facilitate this conjugation (Irby et al, 2017;Palko-Łabuz et al, 2021). Another helpful linker to lead the conjugation is a succinic anhydride moiety due to being functionalized (Muthu et al, 2015;Spanedda and Bourel-Bonnet, 2021).…”

Section: Nanoparticles Based On Liposomes As the Carrier In Drug Deli...mentioning

confidence: 99%

Chemical Conjugation in Drug Delivery Systems

Eras

Castillo²,

Suárez³

et al. 2022

Front. Chem.

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Cancer is one of the diseases with the highest mortality rate. Treatments to mitigate cancer are usually so intense and invasive that they weaken the patient to cure as dangerous as the own disease. From some time ago until today, to reduce resistance generated by the constant administration of the drug and improve its pharmacokinetics, scientists have been developing drug delivery system (DDS) technology. DDS platforms aim to maximize the drugs’ effectiveness by directing them to reach the affected area by the disease and, therefore, reduce the potential side effects. Erythrocytes, antibodies, and nanoparticles have been used as carriers. Eleven antibody–drug conjugates (ADCs) involving covalent linkage has been commercialized as a promising cancer treatment in the last years. This review describes the general features and applications of DDS focused on the covalent conjugation system that binds the antibody carrier to the cytotoxic drug.

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“…[1][2][3][4] The 2-methylenesuccinic anhydride, which is also known as itaconic anhydride (ITA) is a derivative of itaconic acid and presents elevated reactivity. 5 The main production of itaconic acid is by the fermentation of carbohydrates. [6][7][8][9] Therefore, it is considered a bio-based chemical.…”

Section: Introductionmentioning

confidence: 99%

Effect of Isomerization and Copolymerization of Itaconic Anhydride During the Synthesis of Renewable Monomers Using Vegetable Oils

Gaglieri¹,

Alarcon²,

Moura³

et al. 2023

J. Braz. Chem. Soc.

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Vegetable oils are alternatives to producing renewable monomers since they are biomass. It is possible to react them with anhydrides by heating to provide monomers with high reactivity. However, after the reaction of grape seed oil with itaconic anhydride, it was observed the occurrence of parallel reactions that had not been observed when the same oil was reacted with maleic anhydride. Some articles in the literature have reported that temperature and bases can isomerize itaconic anhydride into citraconic anhydride, which is more stable at room temperature. However, they have not focused on completely understanding how this phenomenon occurred nor studied it in processes that involve microwave irradiation. Therefore, this paper presents a complete characterization and investigation about the thermal behavior of itaconic anhydride and how it can affect the monomer synthesis performed under heating.

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Cyclic Anhydrides as Powerful Tools for Bioconjugation and Smart Delivery

Cited by 21 publications

References 149 publications

Dodecenylsuccinic anhydride modified chitosan hydrogels for the sustained delivery of hydrophobic drugs. The case of thymol buccal delivery

Dodecenylsuccinic anhydride modified chitosan hydrogels for the sustained delivery of hydrophobic drugs. The case of thymol buccal delivery

Chemical Conjugation in Drug Delivery Systems

Effect of Isomerization and Copolymerization of Itaconic Anhydride During the Synthesis of Renewable Monomers Using Vegetable Oils

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