130973-96-5Relevant articles and documents
Design, synthesis and evaluation of an NLRP3 inhibitor diazirine photoaffinity probe
Coll, Rebecca C.,Hill, James R.,Robertson, Avril A. B.,Schroder, Kate
, (2020)
The NLRP3 inhibitor MCC950/CRID3 ameliorates a remarkable number of inflammatory disorders in animal models. Herein we describe a trifluoromethyl phenyl diazirine (TPD) photoaffinity probe, called TPD-950-Br, to probe the molecular interactions of MCC950. We show that TPD-950-Br covalently captures proximal species upon photo-activation and inhibits IL-1β production in an NLRP3 inhibitor assay.
An improved synthesis of 3-[3-(trifluoromethyl)-3H-1,2-diazirin-3-yl]aniline: A key intermediate in the synthesis of photoaffinity probes
Wixe, Torbj?rn,Almqvist, Fredrik
, p. 3350 - 3352 (2017/08/03)
An improved synthesis of 3-[3-(trifluoromethyl)-3H-1,2-diazirin-3-yl]aniline, achieving an overall yield of 38% over seven steps is reported. Only three chromatographic separations were needed and the preparation of ～0.7?g of the target compound was demon
SULFONYLUREAS AND RELATED COMPOUNDS AND USE OF SAME
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, (2016/09/15)
ABSTRACT The present invention provides for certain sulfonyl ureas and related compounds which have advantageous properties and show useful activity in the inhibition of activation of the NLRP3 inflammasome. Such compounds are useful in the treatment of a wide range of disorders in which the inflammation process, or more specifically the NLRP3 inflammasome, have been implicated as being a key factor.
Process for the modification of surface
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Page column 8-9, (2010/02/08)
The present invention relates to a process for the modification of a material surface comprising the steps of (a1) photochemically fixing one or more different compounds of formula onto the material surface, or (a2) photochemically f
Synthesis of photoactivable inhibitors of osteoclast vacuolar ATPase
Biasotti, Barbara,Dallavalle, Sabrina,Merlini, Lucio,Farina, Carlo,Gagliardi, Stefania,Parini, Carlo,Belfiore, Pietro
, p. 2247 - 2254 (2007/10/03)
Amides of (2Z,4E)-5-[(5,6-dichloroindol-2-yl)]-2-methoxy-N-[3-[4-[3-(carboxymethoxy) phenyl)] piperazin-1-yl]propyl]-2,4-pentadienamide (1) and of 5-(5,6-dichloro-2-indolyl)-2-methoxy-2,4-pentadienoic acid (2) are strong inhibitors of the vacuolar ATPase located on the plasma membrane of osteoclasts. In order to understand which V-ATPase subunit is involved in the interaction with these novel inhibitors, analogues containing a photoactivable group and an iodine atom were designed. A series of alcohols or amines containing the photoactivable trifluoroaziridinophenyl or benzophenone moiety and an iodine atom were linked to the above acids via an ester or amide group. These compounds could be thereafter used as a radioactive photoprobe to label the protein. Whereas the compounds containing the photoactivable groups maintained good inhibitory activity, the introduction of the bulky iodine atom was generally detrimental, decreasing potency significantly. Better results were obtained by linking 3-(4-aminopiperidinomethyl)-3′-iodobenzophenone to 3-ethoxy-4-(2-(5,6-dichlorobenzimidazolyl))benzoic acid to give the corresponding amide 27, that inhibited vacuolar ATP-ase with a IC50=140 nM. The feasibility of introducing a radioactive 125I atom was ascertained by exchanging the iodine with a tributylstannyl group, that was again substituted by iodine.
Immobilisation on polystyrene of diazirine derivatives of mono- and disaccharides: Biological activities of modified surfaces
Chevolot,Martins,Milosevic,Leonard,Zeng,Malissard,Berger,Maier,Mathieu,Crout,Sigrist
, p. 2943 - 2953 (2007/10/03)
The potential of surface glycoengineering for biomaterials and biosensors originates from the importance of carbohydrate protein interactions in biological systems. The strategy employed here utilises carbene generated by illumination of diazirine to achieve covalent bonding of carbohydrates. Here, we describe the synthesis of an aryl diazirine containing a disaccharide (lac-tose). Surface analysis techniques [X-ray photoelectron spectroscopy (XPS) and time of flight secondary ion mass spectroscopy (ToF-SIMS)] demonstrate its successful surface immobilisation on polystyrene (PS). Results are compared to those previously obtained with an aryl diazirine containing a monosaccharide (galactose). The biological activity of galactose- or lactose-modified PS samples is studied using rat hepatocytes, Allo A lectin and solid-phase semi-synthesis with α-2,6-sialyltransferase. Allo A shows some binding to galactose-modified PS but none to lactose-modified surfaces. Similar results are obtained with rat hepatocytes. In contrast, sialylation of lactose-modified PS is achieved but not with galactose-modified surfaces. The different responses indicate that the biological activity depends not only on the carbohydrate per se but also on the structure and length of the spacer. Copyright
Structurally similar small molecule photoaffinity CCK-A agonists and antagonists as novel tools for directly probing 7TM receptor-ligand interactions
Darrow, James W.,Hadac, Elizabeth M.,Miller, Laurence J.,Sugg, Elizabeth E.
, p. 3127 - 3132 (2007/10/03)
Incorporation of photolabile benzoyl (2a-d) or trifluoromethyl-3H- diazirine (3a-d) substituents into 1,5-benzodiazepine ligands did not significantly impair the rat CCK-A binding affinity of either agonists or antagonists. The modified agonist ligands al
