5453-51-0Relevant articles and documents
Anti-inflammatory potential of invasive sun corals (Scleractinia: Tubastraea spp.) from Brazil: alternative use for management?
Carpes, Raphael de Mello,Coelho, Marsen Garcia Pinto,Creed, Joel Christopher,Felzenszwalb, Israel,Fleury, Beatriz Grosso,Garden, Simon John,Corrêa Fernandes, Daniele
, (2020)
Aim: The objective was to analyse the anti-inflammatory potential of the invasive coral species Tubastraea coccinea and Tubastraea tagusensis. Methods: Methanolic extracts, fractions and synthesized compounds were evaluated for their anti-inflammatory ability, and their composition was elucidated through chemical analysis. Key findings: The genus Tubastraea (Order Scleractinia, Family Dendrophylliidae) (known as sun corals) presents compounds with pharmacological value. The introduction of these azooxanthellate hard corals into Brazil, initially in Rio de Janeiro state, occurred through their fouling of oil and gas platforms from the Campos oil Basin. The two invasive species have successfully expanded along the Brazilian coast and threaten endemic species and biodiversity. The HPLC-MS and GC-MS data suggest the presence of aplysinopsin analogues (alkaloids). Anti-inflammatory activity was observed in all samples tested in in-vivo assays, especially in T. coccinea. The ethyl acetate fraction from this sample was more effective in in-vitro assays for anti-inflammatory activity. Depending on the concentration, this fraction showed cytotoxic responses. Conclusions: These species have potential pharmacological use, and considering their invasive nature, this study presents a potential alternative use, which may enhance the management of this biological invasion.
The indole-hydantoin derivative exhibits anti-inflammatory activity by preventing the transactivation of NF-κB through the inhibition of NF-κB p65 phosphorylation at Ser276
Lin, Xin,Tago, Kenji,Okazaki, Nozomi,So, Takanori,Takahashi, Kyoko,Mashino, Tadahiko,Tamura, Hiroomi,Funakoshi-Tago, Megumi
, (2021/09/02)
Indole- and hydantoin-based derivatives both exhibit anti-inflammatory activity, suggesting that the structures of indole and hydantoin are functional for this activity. In the present study, we synthesized two types of indole-hydantoin derivatives, IH-1 (5-(1H-indole-3-ylmethylene) imidazolidine-2,4-dione) and IH-2 (5-(1H-indole-3-ylmethyl) imidazolidine-2,4-dione) and examined their effects on LPS-induced inflammatory responses in murine macrophage-like RAW264.7 cells. LPS-induced inflammatory responses were not affected by indole, hydantoin, or IH-2. In contrast, IH-1 significantly inhibited the LPS-induced production of nitric oxide (NO) and secretion of CCL2 and CXCL1 by suppressing the mRNA expression of inducible NO synthase (iNOS), CCL2, and CXCL1. IH-1 markedly inhibited the LPS-induced activation of NF-κB without affecting the degradation of IκBα or nuclear translocation of NF-κB. IH-1 markedly attenuated the transcriptional activity of NF-κB by suppressing the LPS-induced phosphorylation of the NF-κB p65 subunit at Ser276. Furthermore, IH-1 prevented the LPS-induced interaction of NF-κB p65 subunit with a transcriptional coactivator, cAMP response element-binding protein (CBP). Collectively, these results revealed the potential of the novel indole-hydantoin derivative, IH-1 as an anti-inflammatory drug.
Privileged scaffolds or promiscuous binders: A comparative study on rhodanines and related heterocycles in medicinal chemistry
Mendgen, Thomas,Steuer, Christian,Klein, Christian D.
supporting information; experimental part, p. 743 - 753 (2012/03/11)
Rhodanines and related five-membered heterocycles with multiple heteroatoms have recently gained a reputation of being unselective compounds that appear as "frequent hitters" in screening campaigns and therefore have little value in drug discovery. However, this judgment appears to be based mostly on anecdotal evidence. Having identified various rhodanines and related compounds in screening campaigns, we decided to perform a systematic study on their promiscuity. An amount of 163 rhodanines, hydantoins, thiohydantoins, and thiazolidinediones were synthesized and tested against several targets. The compounds were also characterized with respect to aggregation and electrophilic reactivity, and the binding modes of rhodanines and related compounds in published X-ray cocrystal structures were analyzed. The results indicate that the exocyclic, double bonded sulfur atom in rhodanines and thiohydantoins, in addition to other structural features, offers a particularly high density of interaction sites for polar interactions and hydrogen bonds. This causes a promiscuous behavior at concentrations in the "screening range" but should not be regarded as a general knockout criterion that excludes such screening hits from further development. It is suggested that special criteria for target affinity and selectivity are applied to these classes of compounds and that their exceptional and potentially valuable biomolecular binding properties are consequently exploited in a useful way.
