Synthesis, antinociceptive and anti-inflammatory effects of porphyrins

Alonso-Castro, Ángel Josabad; Zapata-Morales, Juan Ramón; Hernández-Munive, Abigail; Campos-Xolalpa, Nimsi; Pérez-Gutiérrez, Salúd; Pérez-González, Cuaúhtemoc

doi:10.1016/j.bmc.2015.03.043

Cited by 9 publications

(4 citation statements)

References 26 publications

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“…Serum was also obtained from mice and the levels of TNF-α, IL-1β and IL-6, PGE2 and NO were measured, the results show that these porphyrins decreased the levels of proinflammatory mediators PGE2 and NO. These results, taken together, further support the potential of porphyrins as anti-inflammatory drug alternatives for the treatment of inflammatory diseases [58].…”

Section: Tetraphenyl Based Porphyrinssupporting

confidence: 65%

“…In a recent report four phenylporphyrin derivatives, namely 5,10,15,20-tetraphenylporphyrin (TPP), 5,10,15,20-tetra(4 ′ -fluorophenyl)porphyrin (TpFPP), 5,10,15,20-tetra(4 ′ -chlorophenyl)porphyrin (TpClPP) and 5,10,15,20-tetra(4 ′ -bromophenyl)porphyrin (TpBrPP), were synthesized and assessed for their potential anti-inflammatory and analgesic biological activities (Figure 11) [58]. More specifically, evaluation of heat-induced hemolysis showed that all porphyrin derivatives inhibited hemolysis with a potency comparable to naproxen (NPX).…”

Section: Tetraphenyl Based Porphyrinsmentioning

confidence: 99%

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Anti-Inflammatory and Antithrombotic Potential of Metal-Based Complexes and Porphyrins

Tsoupras,

Pafli,

Stylianoudakis

et al. 2024

Compounds

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Inflammation and thrombosis are implicated in several chronic disorders. Recent studies have outlined the way in which several compounds can offer protection against inflammation. Within this comprehensive review the so-far reported anti-inflammatory health-promoting effects of several metal-based complexes, both in vitro and in vivo, are thoroughly presented. These metal-based compounds usually interfere with various biochemical processes associated with the inflammatory response and thrombus formation and become capable of inhibiting these biochemical pathways with proposed health benefits. Emphasis is given to the multifaceted actions of metal-based complexes that have exhibited potent anti-inflammatory and antithrombotic activities against the inflammatory mediator, platelet-activating factor (PAF), and its thrombo-inflammatory signaling, as well as on their anti-platelet and antitumor health promoting properties. Furthermore, the enhancement of the anti-inflammatory potency of well-established bioactive compounds by their incorporation as ligands in several metal-based complexes is discussed. Metal-based complexes bearing natural anti-inflammatory bioactives are also outlined. Characteristic examples of both free and metal-based porphyrins are explored. These compounds are recognized to have anti-inflammatory and antithrombotic assets, in addition to other pleiotropic advantages including antibacterial or anticancer actions. Additionally, applications of metal complexes in various models of inflammatory and thrombotic complications are demonstrated. The combined results of this study show that further research is required towards the preparation of several metal-based complexes with improved pharmacological profiles. Finally, restrictions on the application of these metal-based compounds are also covered, along with their prospects for the future and the need for additional study in order to improve their efficacy and safety.

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Section: Tetraphenyl Based Porphyrinssupporting

confidence: 65%

Section: Tetraphenyl Based Porphyrinsmentioning

confidence: 99%

Anti-Inflammatory and Antithrombotic Potential of Metal-Based Complexes and Porphyrins

Tsoupras,

Pafli,

Stylianoudakis

et al. 2024

Compounds

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“…Furthermore, we also conducted the nitrobenzene hydrogenation in the presence of a related soluble cobalt tetrakis(4‐ tert ‐butyl)porphyrine complex which was synthesized according to a published procedure [28] and strikingly, this compound was completely inactive under the standard reaction conditions. Hence, we conclude that the ligating macrocycle effectively prohibits the reduction of the metal cation to cobalt (nano)particles that are effective hydrogenation catalysts in their own right [29]…”

Section: Resultsmentioning

confidence: 99%

Selective and Additive‐Free Hydrogenation of Nitroarenes Mediated by a DMSO‐Tagged Molecular Cobalt Corrole Catalyst

2021

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We report on the first cobalt corrole that effectively mediates the homogeneous hydrogenation of structurally diverse nitroarenes to afford the corresponding amines. The given catalyst is easily assembled prior to use from 4-tert-butylbenzaldehyde and pyrrole followed by metalation of the resulting corrole macrocycle with cobalt(II) acetate. The thus-prepared complex is self-contained in that the hydrogenation protocol is free from the requirement for adding any auxiliary reagent to elicit the catalytic activity of the applied metal complex. Moreover, a containment system is not required for the assembly of the hydrogenation reaction set-up as both the autoclave and the reaction vessels are readily charged under a regular laboratory atmosphere.

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“…In our study, C communities have higher abundance in genes in the subcategory of tetrapyrrole that includes pathways in porphyrins (heme), corrinoids (cobalamin) and chlorophyll metabolism. Selected porphyrins have shown to have anti-inflammatory effects [ 57 , 58 ]. In contrast, coproporphyrin III, the most abundant extracellular porphyrin produced by human skin commensal Propionibacterium spp was shown to stimulate expression of the pro-inflammatory cytokine IL-8 by keratinocyte [ 59 ].…”

Section: Discussionmentioning

confidence: 99%

Immune-modulatory genomic properties differentiate gut microbiota of infants with and without eczema

Yap

Hong

et al. 2017

PLoS ONE

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Gut microbiota play an important role in human immunological processes, potentially affecting allergic diseases such as eczema. The diversity and structure of gut microbiota in infants with eczema have been previously documented. This study aims to evaluate by comparative metagenomics differences in genetic content in gut microbiota of infants with eczema and their matched controls. Stools were collected at the age of one month old from twelve infants from an at risk birth cohort in a case control manner. Clinical follow up for atopic outcomes were carried out at the age of 12 and 24 months. Microbial genomic DNA were extracted from stool samples and used for shotgun sequencing. Comparative metagenomic analysis showed that immune-regulatory TCAAGCTTGA motifs were significantly enriched in the six healthy controls (C) communities compared to the six eczema subjects (E), with many encoded by Bifidobacterium (38% of the total motifs in the C communities). Draft genomes of five Bifidobacterium species populations (B. longum, B. bifidum, B. breve, B. dentium, and B. pseudocatenulatum) were recovered from metagenomic datasets. The B. longum BFN-121-2 genome encoded more TCAAGCTTGA motifs (4.2 copies per one million genome sequence) than other Bifidobacterium genomes. Additionally, the communities in the stool of controls (C) were also significantly enriched in functions associated with tetrapyrrole biosynthesis compared to those of eczema (E). Our results show distinct immune-modulatory genomic properties of gut microbiota in infants associated with eczema and provide new insights into potential role of gut microbiota in affecting human immune homeostasis.

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Synthesis, antinociceptive and anti-inflammatory effects of porphyrins

Cited by 9 publications

References 26 publications

Anti-Inflammatory and Antithrombotic Potential of Metal-Based Complexes and Porphyrins

Anti-Inflammatory and Antithrombotic Potential of Metal-Based Complexes and Porphyrins

Selective and Additive‐Free Hydrogenation of Nitroarenes Mediated by a DMSO‐Tagged Molecular Cobalt Corrole Catalyst

Immune-modulatory genomic properties differentiate gut microbiota of infants with and without eczema

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