Anti-inflammatory effect of thalidomide dithiocarbamate and dithioate analogs

Talaat, Roba M.; Elsayed, Waheba; Agwa, Hussein S.; Gamal‐Eldeen, Amira M.; Moawia, Shaden; Zahran, M. A.

doi:10.1016/j.cbi.2015.05.017

Cited by 20 publications

(17 citation statements)

References 73 publications

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“…1 H and 13 C NMR spectra for all synthesized compounds were recorded on a Bruker 400 MHz spectrometer for 1 H and 100 MHz for 13 C, with TMS as an internal standard for 1 H NMR, chemical shifts are reported in parts per million (ppm) relative to the respective deuterated solvent peak CDCl3 (δ 7.27 ppm), DMSOd6 (δ 2.50 ppm) for 1 H and CDCl3 (δ 77.00 ppm), DMSO-d6 (δ 39.51 ppm) for 13 C NMR. MALDI mass spectra of synthesized compounds were recorded on JEOL JMS-700N for electron ionization or on JEOL JMS-T100TD for electro-spray ionization using α-cyano-4-hydroxycinnamic acid (CHCA) as a matrix (m/z 189.17) (Nagasaki University, Japan).…”

Section: Instrumentationmentioning

confidence: 99%

“…The structures of amines applied in this reaction protocol are given in Table 1. The chemical structures of the synthesized compounds were confirmed by IR, 1 H NMR, 13 C NMR, and Electrospray ionization high resolution mass spectra (ESI-HRMS). The IR spectra of phthalimide dithiocarbamate derivatives 8a-j, 9a-e and 9g-j supported the expected structures and showed absorption bands in the region 1704-1776 cm -1 as two peaks owing to asymmetric and symmetric stretching vibrations of the two carbonyls of phthalimide.…”

Section: Chemistrymentioning

confidence: 99%

“…Based on these results and assumption, new series of phthalimide derivatives were synthesized and evaluated as potential antitumor drug candidates [6,7]. Recently, our group reported the potency of the thalidomide dithiocarbamate analogs as novel antitumor derivatives [8][9][10][11][12][13][14]. On the other hand, dithiocarbamic acid esters have drawn a great attention due to their cancer chemopreventive and antitumor activities [15,16].…”

Section: Introductionmentioning

confidence: 99%

“…On the other hand, dithiocarbamic acid esters have drawn a great attention due to their cancer chemopreventive and antitumor activities [15,16]. Some molecules that incorporated dithiocarbamic acid ester functionality, as a linker between different pharmacophores, showed significant anticancer activities, such as TH derivatives [8][9][10][11][12][13][14], chromones [17], quinazolinones [18] and naphthalimide derivatives [19].…”

Section: Introductionmentioning

confidence: 99%

“…Our research interest is still existing in development of TH analogs and potential antitumor compounds [8][9][10][11][12][13][14][20][21][22]. So, we herein describe the design, synthesis and biological evaluation of novel dithiocarbamate analogs connected either through methylene or ethylene bridges to phthalimide pharmacophoric core.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and biological evaluation of phthalimide dithiocarbamate and dithioate derivatives as anti-proliferative and anti-angiogenic agents-I

et al. 2017

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A facile synthesis of new phthalimide dithiocarbamate and dithioate analogs 8a-j, 9a-e and 9g-j were achieved by the reaction of N-chloromethyl and N-bromoethylphthalimide with carbon disulfide (CS2) and various amines. The structures of the synthesized analogs were elucidated by spectroscopic methods, including IR, 1 H NMR and 13 C NMR, and ESI-HRMS techniques. The antiproliferative activity of the newly synthesized compounds was also evaluated against various human cancer cell lines. The compound 9e and 9i exhibited the highest activity against human breast adenocarcinoma MCF-7 and hepatocellular carcinoma HepG2 cells. Compound 8f showed better antiproliferative effect against colon carcinoma HCT-116 and cervical carcinoma HeLa compared to thalidomide. The binding affinity to vascular endothelial growth factor receptor (VEGFR) of some compounds was assessed in addition to molecular docking study. Compounds 9e and 9i showed high docking score values and they significantly declined the concentration of VEGFR. KEYWORDS

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Section: Instrumentationmentioning

confidence: 99%

Section: Chemistrymentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Synthesis and biological evaluation of phthalimide dithiocarbamate and dithioate derivatives as anti-proliferative and anti-angiogenic agents-I

et al. 2017

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Synthesis and Evaluation of Thalidomide and Phthalimide Esters as Antitumor Agents

Zahran

Abdin

Osman

et al. 2014

Archiv der Pharmazie

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A series of thalidomide and phthalimide ester analogs were efficiently synthesized from N-chloromethylthalidomide, N-chloromethylphthalimide, and N-(2-bromoethyl)phthalimide derivatives with various biologically important carboxylic acids. The synthesized compounds were purified and characterized by various chromatographic and spectroscopic techniques. The antitumor activity of all the synthesized compounds was screened against human liver and breast cancer cells, which showed that phthalimide ester 6a was the best cytotoxic compound against MCF7 cells, while all of the tested compounds showed a non-cytotoxic effect against HepG2 cells. Compounds 5a, 6a, and 7a possess immunosuppressant effect, while compounds 5c, 5d, 6c, 6d, 7c, and 7d showed an immunostimmulatory effect. Meanwhile, estimation of the binding affinity for all the synthesized compounds toward the vascular endothelial growth factor receptor (VEGFR) showed that compounds 5a, 5b, and 7d were the most potent inhibitors.

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Thalidomide interaction with inflammation in idiopathic pulmonary fibrosis

et al. 2023

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The “Thalidomide tragedy” is a landmark in the history of the pharmaceutical industry. Despite limited clinical trials, there is a continuous effort to investigate thalidomide as a drug for cancer and inflammatory diseases such as rheumatoid arthritis, lepromatous leprosy, and COVID-19. This review focuses on the possibilities of targeting inflammation by repurposing thalidomide for the treatment of idiopathic pulmonary fibrosis (IPF). Articles were searched from the Scopus database, sorted, and selected articles were reviewed. The content includes the proven mechanisms of action of thalidomide relevant to IPF. Inflammation, oxidative stress, and epigenetic mechanisms are major pathogenic factors in IPF. Transforming growth factor-β (TGF-β) is the major biomarker of IPF. Thalidomide is an effective anti-inflammatory drug in inhibiting TGF-β, interleukins (IL-6 and IL-1β), and tumour necrosis factor-α (TNF-α). Thalidomide binds cereblon, a process that is involved in the proposed mechanism in specific cancers such as breast cancer, colon cancer, multiple myeloma, and lung cancer. Cereblon is involved in activating AMP-activated protein kinase (AMPK)-TGF-β/Smad signalling, thereby attenuating fibrosis. The past few years have witnessed an improvement in the identification of biomarkers and diagnostic technologies in respiratory diseases, partly because of the COVID-19 pandemic. Hence, investment in clinical trials with a systematic plan can help repurpose thalidomide for pulmonary fibrosis. Graphical Abstract

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Anti-inflammatory effect of thalidomide dithiocarbamate and dithioate analogs

Cited by 20 publications

References 73 publications

Synthesis and biological evaluation of phthalimide dithiocarbamate and dithioate derivatives as anti-proliferative and anti-angiogenic agents-I

Synthesis and biological evaluation of phthalimide dithiocarbamate and dithioate derivatives as anti-proliferative and anti-angiogenic agents-I

Synthesis and Evaluation of Thalidomide and Phthalimide Esters as Antitumor Agents

Thalidomide interaction with inflammation in idiopathic pulmonary fibrosis

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