Anti-inflammatory activity of polyamide dendrimers bearing bile acid termini synthesized via SPAAC

Garzón-Porras, Ana M.; Bertuzzi, Diego L.; Lucas, Kurt; Ornelas, Cátia

doi:10.1007/s11051-019-4672-5

Cited by 7 publications

(16 citation statements)

References 51 publications

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“…Recently, dendrimers have gained interest as potential anti-inflammatory drugs due to their intrinsic properties, and in combination with moieties with anti-inflammatory potential. − Consequently, dendrimers have been proposed to be used in the treatment of several chronic diseases, diverse types of cancer, and neurodegenerative illnesses such as Alzheimer’s disease. − …”

Section: Introductionmentioning

confidence: 99%

Nitric Oxide Releasing Polyamide Dendrimer with Anti-inflammatory Activity

Garzón-Porras

Bertuzzi

Lucas

et al. 2020

ACS Appl. Polym. Mater.

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Inflammatory processes are related to a wide variety of diseases with high global impact. Nitric oxide (NO) is an excellent candidate for the treatment of such diseases due to its important anti-inflammatory role in living systems, which is related to its concentration in the cellular medium that in turn depends directly on its release rate from NO releasing compounds. In this work, we synthesized a nitrate-terminated dendrimer and evaluated its anti-inflammatory properties. Remarkably, dendrimer bearing 18 NO-releasing groups was nontoxic, and exhibited antiinflammatory activity (13.7−27.9% of IL-8 inhibition) throughout the tested concentrations (6.50 × 10 −2 to 4.17 × 10 3 nM of dendrimer; (1.17−7.50) × 10 4 nM of NO-moiety). On the other hand, the NO-releasing monomer was pro-inflammatory at concentrations higher than 62.5 nM. Investigation of the NO-releasing profiles from monomer and dendrimer using real-time NO analyzer NOA confirmed the slow release of NO from the dendrimer. Our results suggest that the NO release from the dendrimer occurs in a controlled fashion, keeping the anti-inflammatory effect of NO even at high concentrations.

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Section: Introductionmentioning

confidence: 99%

Nitric Oxide Releasing Polyamide Dendrimer with Anti-inflammatory Activity

Garzón-Porras

Bertuzzi

Lucas

et al. 2020

ACS Appl. Polym. Mater.

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“…This strategy was used to prepare Janus dendrimers decorated with combinations of tetraethylene glycol, galactose, and the Arg‐Gly‐Asp (RGD) peptide at their periphery [118] . Ornelas and co‐workers used the SPAAC reaction to introduce bile acids at the periphery of polyamide dendrimers [119] . The bile acids were functionalized with cyclooctyne groups and coupled to 18 peripheral azides on the second generation dendrimers.…”

Section: Monodisperse Macromoleculesmentioning

confidence: 99%

“…[118] Ornelas and coworkers used the SPAAC reactiont oi ntroduce bile acids at the periphery of polyamide dendrimers. [119] The bile acids were functionalized with cyclooctyne groups and coupled to 18 peripheral azides on the second generation dendrimers.T he resulting dendrimers exhibited anti-inflammatory properties that sometimes exceeded those of the pure bile acids. Recently, Martin and co-workersd emonstrated an elegant synthesis of [60]fullerene-based dendritic structures decorated with up to 360 1,2-mannobioside units using SPAAC chemistry.…”

Section: Monodisperse Macromoleculesmentioning

confidence: 99%

A Survey of Strain‐Promoted Azide–Alkyne Cycloaddition in Polymer Chemistry

Fong

Meichsner

et al. 2021

Chemistry A European J

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Highly efficient reactions that enable the assembly of molecules into complex structures have driven extensive progress in synthetic chemistry. In particular, reactions that occur under mild conditions and in benign solvents, while producing no by‐products and rapidly reach completion are attracting significant attention. Amongst these, the strain‐promoted azide–alkyne cycloaddition, involving various cyclooctyne derivatives reacting with azide‐bearing molecules, has gained extensive popularity in organic synthesis and bioorthogonal chemistry. This reaction has also recently gained momentum in polymer chemistry, where it has been used to decorate, link, crosslink, and even prepare polymer chains. This survey highlights key achievements in the use of this reaction to produce a variety of polymeric constructs for disparate applications.

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“…49 We have also synthesized a dendrimer bearing 18 UDCA groups (Dendri-(UDCA) 18 ) and evaluated its anti-inflammatory activity. 50 Dendri-(UDCA) 18 was more than 6000 times more potent than the free UDCA when comparing with the number of UDCA molecules per dendrimer, and more than 100,000 times more potent when comparing one UDCA molecule with one dendrimer molecule. 50 To study the potential synergistic anti-inflammatory effect between the NO-releasing groups and the UDCA molecules, herein, we report the synthesis of a large well-defined bifunctional dendrimer with 108 termini bearing 54 NOreleasing groups and 54 UDCA moieties (Dendri-(NO/ UDCA) 54 ).…”

Section: Introductionmentioning

confidence: 99%

Well-Defined Bifunctional Dendrimer Bearing 54 Nitric Oxide-Releasing Moieties and 54 Ursodeoxycholic Acid Groups Presenting High Anti-Inflammatory Activity

Garzón-Porras

Bertuzzi

Lucas

et al. 2022

ACS Biomater. Sci. Eng.

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Nitric oxide (NO) and ursodeoxycholic acid (UDCA) are endogenous molecules involved in physiological processes associated with inflammation. Since inflammatory processes are present in the mechanisms of many diseases, these molecules are important for the development of new drugs. Herein, we describe the synthesis of a well-defined bifunctional dendrimer with 108 termini bearing 54 NO-releasing groups and 54 UDCA units (Dendri-(NO/UDCA)54). For comparison, a lower-generation dendrimer bearing 18 NO-releasing groups and 18 UDCA units (Dendri-(NO/UDCA)18) was also synthesized. The anti-inflammatory activity of these dendrimers was evaluated, showing that the bifunctional dendrimers have an inverse correlation between concentration and anti-inflammatory activity, with an effect dramatically pronounced for Dendri-(NO/UDCA)54 20, which at just 0.25 nM inhibited 76.1% of IL-8 secretion. Data suggest that nanomolar concentrations of these dendrimers aid in releasing NO in a safe and controlled way. This bifunctional dendrimer has great potential as a drug against multifactorial diseases associated with inflammatory processes.

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Anti-inflammatory activity of polyamide dendrimers bearing bile acid termini synthesized via SPAAC

Cited by 7 publications

References 51 publications

Nitric Oxide Releasing Polyamide Dendrimer with Anti-inflammatory Activity

Nitric Oxide Releasing Polyamide Dendrimer with Anti-inflammatory Activity

A Survey of Strain‐Promoted Azide–Alkyne Cycloaddition in Polymer Chemistry

Well-Defined Bifunctional Dendrimer Bearing 54 Nitric Oxide-Releasing Moieties and 54 Ursodeoxycholic Acid Groups Presenting High Anti-Inflammatory Activity

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