Anthranilic acids from isatin: an efficient, versatile and environmentally friendly method

Rio, Gabriel Freitas do; Silva, Bárbara V.; Martinez, Sabrina T.; Pinto, Ângelo C.

doi:10.1590/0001-3765201520140289

Cited by 9 publications

(2 citation statements)

References 23 publications

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“…Anthranilate-related compounds have been recognized as having biologic activities, in particular, anticancer, -platelet, -bacterial, and -inflammatory activities (16)(17)(18). The 2 anthranilate derivatives-(E)-4-(N-{2- [1-(hydroxyimino)ethyl]phenyl}sulfamoyl)phenyl pivalate (HFP031) and butyl 2-[2-(2-fluorophenyl)acetamido] benzoate (HFP034)-have been reported to have antiinflammatory potency.…”

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confidence: 99%

Topical application of anthranilate derivatives ameliorates psoriatic inflammation in a mouse model by inhibiting keratinocyte‐derived chemokine expression and neutrophil infiltration

et al. 2018

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Psoriasis is an inflammatory autoimmune skin disorder possessing a complex etiology related to genetic and environmental triggers. Keratinocytes show a potential role for the origin of psoriasis. In this study, we estimated the efficiency of 2 anthranilate derivatives-(E)-4-( N-{2-[1-(hydroxyimino)ethyl]phenyl}sulfamoyl)phenyl pivalate (HFP031) and butyl 2-[2-(2-fluorophenyl)acetamido]benzoate (HFP034)-on psoriasis amelioration in a mouse model. The results showed that topical treatment with both compounds could attenuate epidermal thickness and scaling in an imiquimod (IMQ)-induced psoriasis mouse model via decreased expression of cytokines and chemokines [C-X-C chemokine ligand (CXCL)1 and CXCL2], leading to the reduction of neutrophilic abscess in the skin. The in vivo cutaneous absorption of HFP034 was 7.6-fold greater than that of HFP031. Both compounds caused negligible irritation on healthy mouse skin. In addition, we examined the effect of the anthranilate derivatives on chemokine expression in IMQ-treated HaCaT keratinocytes. Our results elucidated a mechanism for anti-inflammatory activity of HFP034 that involved the elevation of intracellular cAMP concentration, suppression of NF-κB activity, and attenuation of neutrophil chemoattractant expression. These results suggest that HFP034 could increase the cutaneous concentration of cAMP to suppress neutrophil infiltration into the skin. Topically applied HFP034 may demonstrate a potential for future clinical application as a novel therapy for psoriasis treatment.-Lin, Z.-C., Hsieh, P.-W., Hwang, T.-L., Chen, C.-Y., Sung, C. T., Fang, J.-Y. Topical application of anthranilate derivatives ameliorates psoriatic inflammation in a mouse model by inhibiting keratinocyte-derived chemokine expression and neutrophil infiltration.

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confidence: 99%

Topical application of anthranilate derivatives ameliorates psoriatic inflammation in a mouse model by inhibiting keratinocyte‐derived chemokine expression and neutrophil infiltration

et al. 2018

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“…These enzymes transfer electrons to the dye to obtain statin, and after decarboxylation occurs the anthranilic acid is produced, as shown in Figure 2. The anthranilic acid is an amino acid also known as vitamin L1 for its performance as coenzyme in the production of breast milk (Rio et al, 2015). Ligninolytic enzymes could biodegrade chromophore dye compounds in sterile and non-sterile environments.…”

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confidence: 99%

Bioremediation potential of industrial laundry effluent by agaricomycetes from brazilian tropical dry forest

Barrera

Neto

Oliveira

et al. 2022

RSD

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Mycotic bioremediation of effluents from industrial jeans laundries is a necessary biotechnological treatment to prevent contamination of water bodies. In phase I, the discoloration of Indigo Carmine Dye (ICD) and Textile Effluent (TE) by seven species of Agaricomycetes from the brazilian tropical dry forest (Caatinga) was evaluated. First, nutritional stress was caused by Nitrogen Limitation (NL) at three experimental times, T1 (1 day). T2 (4 days) and T3 (7 days). In phase II, microorganisms were cultivated in the initial growth times Gi1 (10 days) and Gi2 (25 days), Without Addition of Nutrients (WAN) and stress was induced by NL (T1). Subsequently, ICD and TE discoloration tests continued for 28 days. In the ecotoxic analysis, the biotreated samples in phase II were tested on nauplii of Artemia HIGH 5 without the addition of food. In phase I, the percentages of ICD and TE discoloration were greater than 55% using fungi F1, F2, F5 and F6 for 10 days without sterility. In phase II, the best percentages of discoloration were found for TE in Gi1 and for ICD in Gi2, with F1 and F5 (identified by molecular biology). The results showed that Gi1 (WAN) increased the biodegradation of TE and Gi2 (WAN) favored the biodegradation of ICD, in T1 (NL) without sterility. The best enzymatic activity of laccase and lignin peroxidase was presented in F5. The enzyme extracts had a Michaelis-Menten kinetic behavior. All samples of TE bioremediated in phase II no showed toxicity on Artemia sp. in 48 hours of experimentation.

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Physio-somatic symptoms in schizophrenia: association with depression, anxiety, neurocognitive deficits and the tryptophan catabolite pathway

et al. 2017

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To investigate the frequency of physio-somatic symptoms (PS) symptoms in schizophrenia and their relation to positive, negative and affective symptoms; neurocognitive deficits and impairments in the tryptophan catabolite (TRYCAT) pathway. Eighty four patients with schizophrenia and 40 healthy controls were assessed using the 12 item Fibromyalgia and Chronic Fatigue Syndrome Rating scale (FF) and scales for negative and positive symptoms, depression and anxiety. Cognitive functioning was tested using the Cambridge Neuropsychological Test Automated Battery (CANTAB). Other assessments included: immunoglobulin (Ig)A and IgM responses to tryptophan catabolites (TRYCATs), namely quinolinic (QA), 3-OH-kynurenine (3HK), picolinic (PA), xanthurenic (XA) and kynurenic acid (KA) and anthranilic acid (AA). More than 50% of the patients studied had elevated levels of physio-somatic (PS) symptoms, significantly co-occurring with depression and anxiety, but not with negative or positive symptoms. PS symptoms were significantly associated with IgA/IgM responses to TRYCATs, including increased IgA responses to 3 HK, PA and XA, and lowered IgA to QA and AA. Fatigue, muscle pain and tension, autonomic and cognitive symptoms and a flu-like malaise were strongly associated with cognitive impairments in spatial planning and working memory, paired associative learning, visual sustained attention and attention set shifting. PS symptoms in schizophrenia aggregate with depression and anxiety symptoms and may be driven by TRYCAT patterning of IgA/IgM-responses, with IgA indicating mucosal-mediated changes and IgM indicating regulatory functions. As such, the patterning of IgA/IgM responses to TRYCATs may indicate differential TRYCATs regulation of neuronal and glia activity that act to regulate PS signalling in schizophrenia.

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Anthranilic acids from isatin: an efficient, versatile and environmentally friendly method

Cited by 9 publications

References 23 publications

Topical application of anthranilate derivatives ameliorates psoriatic inflammation in a mouse model by inhibiting keratinocyte‐derived chemokine expression and neutrophil infiltration

Topical application of anthranilate derivatives ameliorates psoriatic inflammation in a mouse model by inhibiting keratinocyte‐derived chemokine expression and neutrophil infiltration

Bioremediation potential of industrial laundry effluent by agaricomycetes from brazilian tropical dry forest

Physio-somatic symptoms in schizophrenia: association with depression, anxiety, neurocognitive deficits and the tryptophan catabolite pathway

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