Structure activity analysis of the pro-apoptotic, antitumor effect of nitrostyrene adducts and related compounds

Kaap, S.; Quentin, Iris; Tamiru, Dereje; Shaheen, Mohammed; Eger, Kurt; Steinfelder, Hans Jürgen

doi:10.1016/s0006-2952(02)01618-0

Cited by 70 publications

(48 citation statements)

References 29 publications

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“…Here, we have identified MNS as a novel inhibitor of NLRP3 inflammasome activation. Previously MNS was reported to inhibit platelet aggregation, tumor cell growth, and apoptosis (45)(46)(47). Effects of nitrostyrene on tyrosine kinases, protein phosphatases, and telomerase activity have been suggested to account for those inhibitions.…”

Section: Resultsmentioning

confidence: 99%

3,4-Methylenedioxy-β-nitrostyrene Inhibits NLRP3 Inflammasome Activation by Blocking Assembly of the Inflammasome

Varadarajan

Muñoz-Planillo

et al. 2014

Journal of Biological Chemistry

231

197

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Background:The NLRP3 inflammasome is a critical component of the innate immune system, and its malfunction contributes to the pathogenesis of inflammatory diseases. Results: Nitrostyrene specifically inhibits NLRP3 activation. Conclusion: Nitrostyrene blocks the assembly of NLRP3 inflammasome by inhibiting NLRP3 ATPase activity. Significance: We identify a novel chemical probe for studying the molecular mechanism of NLRP3 inflammasome activation.

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Section: Resultsmentioning

confidence: 99%

3,4-Methylenedioxy-β-nitrostyrene Inhibits NLRP3 Inflammasome Activation by Blocking Assembly of the Inflammasome

Varadarajan

Muñoz-Planillo

et al. 2014

Journal of Biological Chemistry

231

197

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“…Trans--nitrostyrene (TBNS) is a byproduct in the synthesis of methamphetamine and there is evidence to suggest that it induces apoptosis in cancer cell lines via inhibition of PTP 40,45 .…”

Section: Insert Figmentioning

confidence: 99%

Synthesis and serotonin transporter activity of 1,3-bis(aryl)-2-nitro-1-propenes as a new class of anticancer agents

McNamara¹,

Cloonan²,

Knox³

et al. 2011

Bioorganic & Medicinal Chemistry

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Synthesis and serotonin transporter activity of 1,3-bis(aryl)-2-nitro-1-propenes as a new class of anticancer agents, Bioorganic & Medicinal Chemistry (2010), doi: 10.1016/j.bmc.2010 This is a PDF file of an unedited manuscript that has been accepted for publication. As a service to our customers we are providing this early version of the manuscript. The manuscript will undergo copyediting, typesetting, and review of the resulting proof before it is published in its final form. Please note that during the production process errors may be discovered which could affect the content, and all legal disclaimers that apply to the journal pertain. derived cell lines, whilst having no effect on 'normal' peripheral blood mononuclear cells. Such effects appear to be independent of the serotonin transporter, a high affinity target for amphetamines and independent of protein tyrosine phosphatases and tubulin dynamics both of which have been previously associated with nitrostyrene-induced cell death. We demonstrate that a number of these compounds induce caspase activation, PARP cleavage, chromatin condensation and membrane blebbing in a Burkitt's lymphoma-derived cell line, consistent with these compounds inducing apoptosis in vitro. Although no specific target has yet been identified for the action of these compounds, the cell death elicited is potent, selective and worthy of further investigation.

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“…These compounds are found to be important because of their biological activities, such as insecticidal [4,5], fungicidal [5][6][7][8], bactericidal [9,10], and antitumor effects [11], including pharmacologically valuable substances [6][7][8][9]. They have proved to be valuable precursors for a wide variety of target molecules.…”

Section: Introductionmentioning

confidence: 99%

Does a fluorinated Lewis acid catalyst change the molecular mechanism of the decomposition process of nitroethyl carboxylates?

2017

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The molecular mechanism of the decomposition reaction of nitroethyl benzoates catalyzed by Lewis acids based on boron element-BH 3 and BF 3 -was studied using density functional theory methods. These reactions take place much faster than the uncatalyzed process. However, the presence of fluorinated Lewis acids has a unique influence on the molecular mechanism. In the case of BF 3 , a change from a one-step mechanism to a two-step one involving a zwitterionic intermediate is observed.

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Structure activity analysis of the pro-apoptotic, antitumor effect of nitrostyrene adducts and related compounds

Cited by 70 publications

References 29 publications

3,4-Methylenedioxy-β-nitrostyrene Inhibits NLRP3 Inflammasome Activation by Blocking Assembly of the Inflammasome

3,4-Methylenedioxy-β-nitrostyrene Inhibits NLRP3 Inflammasome Activation by Blocking Assembly of the Inflammasome

Synthesis and serotonin transporter activity of 1,3-bis(aryl)-2-nitro-1-propenes as a new class of anticancer agents

Does a fluorinated Lewis acid catalyst change the molecular mechanism of the decomposition process of nitroethyl carboxylates?

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