Cationic Surfactants and Quaternary Derivatives for Hair and Skin Care
Randy Schueller, Perry Romanowski in Conditioning Agents for Hair and Skin, 2020
In yet another application, quaternary ammonium salts are incorporated together with indole compounds to promote sunless tanning. "It is believed that melanin is an oligomer containing several indole segments formed by cyclization and polymerization of dihydroxy phenylalanine (DOPA) caused by exposure to the sun." Schultz et al. note, therefore, that indole compounds are being investigated for their potential applications in the self-tanning industry. The main problem associated with indoles as tanning enhancers is that they facilitate a color change slowly. It has been discovered that the formation of melanin to color the skin can be catalyzed by the use of quaternary ammonium salts. Indole/quaternary salt combinations are said to impart a deep, long-lasting tan which forms on the skin within 2 hr of application and exposure to sunlight (100).
Metabolism of Chemical Carcinogens by Intestinal Tissue
Herman Autrup, Gary M. Williams in Experimental Colon Carcinogenesis, 2019
A number of nutritional and dietary components as well as xenobiotics have been shown to influence small intestinal monooxygenase activity.26 In fact, it has been suggested that this activity may entirely result from exposure to exogenous inducers.56,57 Several factors may be responsible, e.g., standard laboratory diets which contain inducing agents26 and vegetables containing indoles.58 Furthermore cholesterol59 and dietary iron31 are necessary to maintain small intestinal monooxygenase activity, and changes in the composition of dietary lipid can alter this activity.60 In general, the hepatic monooxygenases are not as sensitive to dietary alterations and exposure to xenobiotics as the small intestinal monooxygenases,61,62 e.g., fasting caused a greater decrease of monooxygenase activity in the intestine than in the liver.62
Melatonin: A “Guardian” of the Genome and Cellular Integrity for Prevention of Photocarcinogenesis
Andreia Ascenso, Sandra Simões, Helena Ribeiro in Carrier-Mediated Dermal Delivery, 2017
Melatonin is a functionally and versatile molecule, which is involved in numerous aspects of body’s biological and physiologic regulation. Its primary role and the first to be described was the regulation of circadian and circannual cycles—”circadian pacemaker” [8–10]. The role of endogenous melatonin in circadian rhythm disturbances and sleep disorders is well established but this chronobiotic is also responsible for the sexual maturation, energy expenditure or body-mass regulation [6,11]. More recently, some studies found that melatonin and its derivatives were potent free radical scavengers and broad-spectrum anti-oxidants. Accordingly, it was suggested that this indolic compound may inhibit tumors proliferation and modify immunity, the stress response, and certain aspects of the aging process [12]. Moreover, melatonin production gradually declines with age, and its loss is associated with several age-related problems, including Alzheimer’s disease and cardiovascular diseases [3,13–15].
Design, synthesis and biological evaluation of novel diarylpyridine derivatives as tubulin polymerisation inhibitors
Published in Journal of Enzyme Inhibition and Medicinal Chemistry, 2022
Shanbo Yang, Chao Wang, Lingyu Shi, Jing Chang, Yujing Zhang, Jingsen Meng, Wenjing Liu, Jun Zeng, Renshuai Zhang, Yingchun Shao, Dongming Xing
In summary, we replaced the double bond linker between the A and B rings by introducing a pyridine fragment into the CA-4 skeleton. We developed a series of diarylpyridines and evaluated their antiproliferative activity and tubulin polymerisation inhibition. Some synthesised compounds displayed moderate to potent antiproliferative activities with IC50 values at the sub-micromolar level. Among compounds, the existence of indole group was the main factor affecting the biological activity. 10t has broad-spectrum antitumor activity against all tumour cell lines tested with IC50 value of 0.19–0.33 μM. Consistent with its antiproliferative activity, 10t also exhibited potent antitubulin activity, similar to that of CA-4. Further mechanistic studies confirmed that 10t was a microtubule-destabilizing agent that induced the accumulation of cells in the G2/M phase, caused cell mitotic catastrophe and apoptosis. Additionally, the results of docking study showed that 10t may bind to colchicine binding site of tubulin. Our work not only expands the exploration of the linker modification of tubulin inhibitor CA-4 but also provides a set of rigid analogues with moderate to potent antiproliferative activity.
The contribution of gut bacterial metabolites in the human immune signaling pathway of non-communicable diseases
Published in Gut Microbes, 2021
F. Hosseinkhani, A. Heinken, I. Thiele, P. W. Lindenburg, A. C. Harms, T. Hankemeier
Indole is one of the major products of bacterial tryptophan metabolism. It has been detected in different concentrations (0.25–1.1 mM) in feces of healthy individuals, while a significant decrease (3.5 × 10−7 – 0.00110 μM/g feces) has been reported in different NCDs such as IBD, autoimmunity, neurodegeneration and diabetes.28,63,64 Exposure of human colon-cancer cell line to 1 mM indole in vitro could inhibit inflammation by up-regulating the expression of the anti-inflammatory cytokine IL-10, decreasing TNF-α-mediated activation of NF-κB, and expression of the pro-inflammatory chemokine IL-8.65 Furthermore, indole promotes epithelial barrier functions of intestinal cells by inducing increased expression of tight junction proteins between cells, thereby contributing to trans epithelial resistance to inflammation.62 Additionally, indole administration attenuated multiple deleterious effects of non-steroidal anti-inflammatory drugs (NSAIDs) on the gut in a murine model of NSAID enteropathy, by modulating neutrophilic inflammation and altering the gut microbiota composition and diversity.66 Together, these studies highlight the anti-inflammatory and beneficial effects of indole on intestinal health.
Uses, Effects and Toxicity of Synthetic Cannabinoids from the Perspective of People with Lived Experiences
Published in Journal of Psychoactive Drugs, 2020
Sulaf Assi, Danielle Marshall, Francesco Saverio Bersani, Ornella Corazza
A total of 81 different derivatives were reported from 1053 posts (Table 2). The reported derivatives belonged to seven different subclasses, among which indole and indazole-based SCs were the most common. Indole-based derivatives were the most frequently mentioned, with 46 derivatives reported 716 times. The main indole-based derivatives encountered were AM2201 (n = 125), JWH018 (n = 107) and UR144 (n = 66). Also, 22 different indazole-based derivatives were reported 220 times. The most commonly mentioned indazole-based derivatives were 5F-AKB48 (n = 63), AB-FUBINACA (n = 42) and THJ018 (n = 35). The frequency of the reports on the SC derivatives was not related to the time they have been on the market, but was rather likely attributable to the unique subjective effects associated with the SC (Table 2).
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