33008-06-9Relevant academic research and scientific papers
Complementary Site-Selective Sulfonylation of Aromatic Amines by Superacid Activation
Bourbon, Paul,Appert, Emeline,Martin-Mingot, Agnès,Michelet, Bastien,Thibaudeau, Sébastien
supporting information, p. 4115 - 4120 (2021/06/21)
Under superacidic conditions, aniline and indole derivatives are sulfonylated at low temperature with easy-to-access arenesulfonic acids or arenesulfonyl hydrazides. By modification of the functional-group directing effect through protonation, this method allows nonclassical site functionalization by overcoming the innate regioselectivity of electrophilic aromatic substitution. This superacid-mediated sulfonylation of arenes is complementary to existing methods and can be applied, through protection by protonation, to the late-stage site-selective functionalization of natural alkaloids and active pharmaceutical ingredients.
Small molecule-mediated induction of endoplasmic reticulum stress in cancer cells
Basu, Sudipta,Biswas, Ankur,Lahiri, Mayurika,Pandey, Shalini,Sharma, Virender Kumar
supporting information, p. 1604 - 1611 (2021/10/23)
The endoplasmic reticulum (ER) is one of the crucial sub-cellular organelles controlling myriads of functions including protein biosynthesis, folding, misfolding and unfolding. As a result, dysregulation of these pathways in the ER is implicated in cancer development and progression. Subsequently, targeting the ER in cancer cells emerged as an interesting unorthodox strategy in next-generation anticancer therapy. However, development of small molecules to selectively target the ER for cancer therapy remained elusive and unexplored. To address this, herein, we have developed a novel small molecule library of sulfonylhydrazide-hydrazones through a short and concise chemical synthetic strategy. We identified a fluorescent small molecule that localized into the endoplasmic reticulum (ER) of HeLa cells, induced ER stress followed by triggering autophagy which was subsequently inhibited by chloroquine (autophagy inhibitor) to initiate apoptosis. This small molecule showed remarkable cancer cell killing efficacy in different cancer cells as mono and combination therapy with chloroquine, thus opening a new direction to illuminate ER-biology towards the development of novel anticancer therapeutics.
Ratiometric Signaling of Hypochlorite by the Oxidative Cleavage of Sulfonhydrazide-Based Rhodamine-Dansyl Dyad
Lee, Hyo Jin,Cho, Min Jeoung,Chang, Suk-Kyu
, p. 8644 - 8649 (2015/09/21)
(Figure Presented). A reaction-based probe 1 for hypochlorite signaling was designed by the conjugation of two fluorophores, rhodamine and dansyl moieties, by the reaction of rhodamine B base with dansylhydrazine. Probe 1 exhibited pronounced hypochlorite-selective chromogenic and fluorescent signaling behavior over other oxidants used in practical applications, such as hydrogen peroxide, peracetic acid, and ammonium persulfate, as well as commonly encountered metal ions and anions. Signaling was attributed to the hypochlorite-induced oxidative cleavage of the sulfonhydrazide linkage of the probe. In particular, favorable ratiometric fluorescence signaling was possible by utilizing the emissions of the two fluorophores. A detection limit of 1.13 × 10-6 M (0.058 ppm) was estimated for the determination of hypochlorite. A paper-based test strip was prepared and was used as a semiquantitative indicator for the presence of hypochlorite in aqueous solutions. The probe was also successfully applied for the determination of hypochlorite in practical tap water samples.
Analytical methodology for determination of organic aerosol functional group distributions
Kalafut-Pettibone, Alicia J,McGivern, W. Sean
, p. 3553 - 3560 (2013/05/22)
Secondary organic aerosol (SOA) particles result from the condensation of oxidized volatile organic compounds (VOC) and consist of a complex mixture that is not conducive to complete compositional analysis. We present a simple methodology for determining the quantities of aldehydes and ketones, alcohols, and carboxylic acids in such samples via derivatization and high-performance liquid chromatography (HPLC) with ultraviolet-visible absorption detection and tandem mass spectrometry (MS/MS). Useful concentration ranges are presented with an examination of the specificity of these compounds in multiply substituted systems. Such data are valuable in modeling the formation of laboratory-generated aerosols and in identifying point sources of field-collected aerosol samples. Calibration curves on standard samples, MS/MS transitions, including collisionally induced dissociation (CID) products, and a quantitative examination of the specificity of the derivatization reagents toward multiple functional groups are presented for a series of aliphatic standard samples. These methods are then applied to filter extracts from SOA derived from 1-iodooctane photolysis at 254 nm to demonstrate the methodology on a complex system. Ultimately, this methodology enables the measurement of variations in the chemical nature of the oxygen within an SOA particle, providing a distribution of functional group concentrations. This article not subject to U.S. Copyright. Published 2013 by the American Chemical Society.
N-arylsulfonyl hydrazones as inhibitors of IMP-1 metallo-β-lactamase
Siemann, Stefan,Evanoff, Darryl P.,Marrone, Laura,Clarke, Anthony J.,Viswanatha, Thammaiah,Dmitrienko, Gary I.
, p. 2450 - 2457 (2007/10/03)
Members of a family of N-arylsulfonyl hydrazones have been identified as novel inhibitors of IMP-1, a metallo-β-lactamase of increasing prevalence. Structure-activity relationship studies have indicated a requirement for bulky aromatic substituents on each side of the sulfonyl hydrazone backbone for these compounds to serve as efficient inhibitors of IMP-1. Molecular modeling has provided insight into the structural basis for the anti-metallo-β-lactamase activity exhibited by this class of compounds.
