Rationally synthesized coumarin based pyrazolines ameliorate carrageenan induced inflammation through COX-2/pro-inflammatory cytokine inhibition

Chandel, Priyanka; Kumar, Anoop; Singla, Nishu; Kumar, A. S. Kiran; Singh, Gagandeep; Gill, Rupinder Kaur

doi:10.1039/c8md00457a

Cited by 20 publications

(4 citation statements)

References 60 publications

(51 reference statements)

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“…In this context, the present study aims to functionalize the fibrous PCL coating on AZ31 alloy with CM and ZnO nanoparticles. In the last years, coumarins have attracted a great interest due to their wide spectrum of pharmacological properties such as its antibacterial, antitumor, antioxidant and anti-inflammatory activity [ 79 , 80 , 81 ]. A large body of data found in the literature, suggests that CM elicits its anti-inflammatory activity by inhibiting the cyclooxygenase (COX) and lipoxygenase (LOX) pathways of the arachidonic acid metabolism [ 82 , 83 , 84 ].…”

Section: Discussionmentioning

confidence: 99%

“…It is important to note that the coatings containing ZnO nanoparticles, namely PCL-ZnO and PCL-CM-ZnO, predominantly showed a small-rounded morphology typical to unstimulated macrophages as noticed in the absence of LPS (TCPS (−)). However, even though the cellular morphology is seen as a characteristic of the inflammatory response towards the biomaterial [ 81 ], recent data revealed that a modified cell morphology does not necessarily indicate a strongly activated macrophage phenotype [ 110 ].…”

Section: Discussionmentioning

confidence: 99%

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In Vitro Macrophage Immunomodulation by Poly(ε-caprolactone) Based-Coated AZ31 Mg Alloy

Negrescu

Necula

Gebaur

et al. 2021

IJMS

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Due to its excellent bone-like mechanical properties and non-toxicity, magnesium (Mg) and its alloys have attracted great interest as biomaterials for orthopaedic applications. However, their fast degradation rate in physiological environments leads to an acute inflammatory response, restricting their use as biodegradable metallic implants. Endowing Mg-based biomaterials with immunomodulatory properties can help trigger a desired immune response capable of supporting a favorable healing process. In this study, electrospun poly(ε-caprolactone) (PCL) fibers loaded with coumarin (CM) and/or zinc oxide nanoparticles (ZnO) were used to coat the commercial AZ31 Mg alloy as single and combined formulas, and their effects on the macrophage inflammatory response and osteoclastogenic process were investigated by indirect contact studies. Likewise, the capacity of the analyzed samples to generate reactive oxygen species (ROS) has been investigated. The data obtained by attenuated total reflection Fourier-transform infrared (FTIR-ATR) and X-ray photoelectron spectroscopy (XPS) analyses indicate that AZ31 alloy was perfectly coated with the PCL fibers loaded with CM and ZnO, which had an important influence on tuning the release of the active ingredient. Furthermore, in terms of degradation in phosphate-buffered saline (PBS) solution, the PCL-ZnO- and secondary PCL-CM-ZnO-coated samples exhibited the best corrosion behaviour. The in vitro results showed the PCL-CM-ZnO and, to a lower extent, PCL-ZnO coated sample exhibited the best behaviour in terms of inflammatory response and receptor activator of nuclear factor kappa-B ligand (RANKL)-mediated differentiation of RAW 264.7 macrophages into osteoclasts. Altogether, the results obtained suggest that the coating of Mg alloys with fibrous PCL containing CM and/or ZnO can constitute a feasible strategy for biomedical applications.

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Section: Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

In Vitro Macrophage Immunomodulation by Poly(ε-caprolactone) Based-Coated AZ31 Mg Alloy

Negrescu

Necula

Gebaur

et al. 2021

IJMS

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“…Despite causing several known severe side effects, including cardiovascular, renal, and hepatic disorders, and above all gastrointestinal toxicity, NSAIDs remain the most prescribed drugs in medicine [ 11 , 12 , 13 , 14 , 15 ]. Many of their side effects are due to their mechanisms of action, being associated with inhibition of the enzymes cyclooxygenase (COX) and lipoxygenase (LOX), which directly mediate the production of prostaglandins and leukotrienes, many of which provide protective functions in the body [ 16 , 17 , 18 ].…”

Section: Introductionmentioning

confidence: 99%

Thiophene-Based Compounds with Potential Anti-Inflammatory Activity

et al. 2021

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Rheumatoid arthritis, arthrosis and gout, among other chronic inflammatory diseases are public health problems and represent major therapeutic challenges. Non-steroidal anti-inflammatory drugs (NSAIDs) are the most prescribed clinical treatments, despite their severe side effects and their exclusive action in improving symptoms, without effectively promoting the cure. However, recent advances in the fields of pharmacology, medicinal chemistry, and chemoinformatics have provided valuable information and opportunities for development of new anti-inflammatory drug candidates. For drug design and discovery, thiophene derivatives are privileged structures. Thiophene-based compounds, like the commercial drugs Tinoridine and Tiaprofenic acid, are known for their anti-inflammatory properties. The present review provides an update on the role of thiophene-based derivatives in inflammation. Studies on mechanisms of action, interactions with receptors (especially against cyclooxygenase (COX) and lipoxygenase (LOX)), and structure-activity relationships are also presented and discussed. The results demonstrate the importance of thiophene-based compounds as privileged structures for the design and discovery of novel anti-inflammatory agents. The studies reveal important structural characteristics. The presence of carboxylic acids, esters, amines, and amides, as well as methyl and methoxy groups, has been frequently described, and highlights the importance of these groups for anti-inflammatory activity and biological target recognition, especially for inhibition of COX and LOX enzymes.

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“…[25] Similarly, coumarin-based pyrazolines were evaluated for anti-inflammatory activity. [26] Also, coumarin-based pyrans possess molecular switching properties. [27] Without a doubt, heterocycles fused with coumarin/pyrrole may also display intriguing functional properties.…”

Section: Introductionmentioning

confidence: 99%

A Convenient Synthesis of Polysubstituted Coumarin‐pyrrolo[2,1‐a]isoquinoline‐1‐carbaldehydes from Isoquinoline, 2‐Bromoacetophenones and Coumarin‐β‐chlorovinyl Aldehydes

Alizadeh

Rostampoor

2021

ChemistrySelect

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In this research, a simple and efficient strategy for the straightforward synthesis of polysubstituted coumarin‐pyrrolo[2,1‐a]isoquinoline‐1‐carbaldehydes is presented by a sequential three‐component reaction of isoquinoline, 2‐bromoacetophenones and 3‐chloro‐3‐(2‐oxo‐2H‐chromen‐3‐yl)acrylaldehydes as readily available starting materials, which includes base‐mediated 1,4‐addition or [3+2] cycloaddition/intramolecular cyclization/formation two C−C bonds/aromatization tandem reaction under air. In this method, chemoselective cascade process, easily accessible starting materials, energy conserving (short reaction times at room temperature), simplicity of product purification (the products can be purified by washing with EtOH), excellent yields (75–88 %), metal‐free catalyst, green and mild conditions in one‐pot are important highlighted advantages of this protocol.

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Rationally synthesized coumarin based pyrazolines ameliorate carrageenan induced inflammation through COX-2/pro-inflammatory cytokine inhibition

Abstract: In the present work, coumarin based pyrazolines (7a–g) have been synthesized and investigated for their in vitro and in vivo anti-inflammatory potential.

Cited by 20 publications

References 60 publications

In Vitro Macrophage Immunomodulation by Poly(ε-caprolactone) Based-Coated AZ31 Mg Alloy

In Vitro Macrophage Immunomodulation by Poly(ε-caprolactone) Based-Coated AZ31 Mg Alloy

Thiophene-Based Compounds with Potential Anti-Inflammatory Activity

A Convenient Synthesis of Polysubstituted Coumarin‐pyrrolo[2,1‐a]isoquinoline‐1‐carbaldehydes from Isoquinoline, 2‐Bromoacetophenones and Coumarin‐β‐chlorovinyl Aldehydes

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