92944-71-3

Usage

Uses

Used in Photocrosslinking Applications:
BENZOPHENONE-4-MALEIMIDE is used as a sulfhydryl reactive heterobifunctional photocrosslinking reagent for generating photoactivatable conjugates from thiols. It is particularly useful in applications where stable and specific cross-linking is required.
Used in Photoinitiation:
In the field of photopolymerization, BENZOPHENONE-4-MALEIMIDE serves as a maleimide-containing photoinitiator, initiating the polymerization process upon exposure to UV light.
Used in Bioconjugation:
BENZOPHENONE-4-MALEIMIDE is used as a heterobifunctional cross-linking reagent in bioconjugation processes. It is typically coupled initially by thioether to a molecule containing a free sulfhydryl at a buffered pH of 6.8 (6.5-7.0). The second bonding occurs during UV irradiation (250 nm) via a diradical excited state, allowing for the formation of stable conjugates between biomolecules.
Used in Research and Development:
Due to its stability, specificity, and efficiency in attachment, BENZOPHENONE-4-MALEIMIDE is used in various research and development applications, particularly in the fields of chemistry, materials science, and biochemistry, for the creation and study of novel materials and molecular constructs.

InChI:InChI=1/C17H11NO3/c19-15-10-11-16(20)18(15)14-8-6-13(7-9-14)17(21)12-4-2-1-3-5-12/h1-11H

Upstream product

• 304456-51-7 C₁₇H₁₃NO₄ 
• 108-31-6 maleic anhydride 
• 1137-41-3 (4-aminophenyl)(phenyl)methanone 
• 304456-51-7 N-(4-benzoylphenyl)maleamic acid 

Downstream Products

• 1233082-70-6 C₃₂H₂₃NO₅ 
• 1233082-62-6 C₃₀H₂₁NO₅ 

Relevant academic research and scientific papers

Rational Design of Calpain Inhibitors Based on Calpastatin Peptidomimetics

Our previously reported structures of calpain bound to its endogenous inhibitor calpastatin have motivated the use of aziridine aldehyde-mediated peptide macrocyclization toward the design of cyclic peptides and peptidomimetics as calpain inhibitors. Inspired by nature's hint that a β-turn loop within calpastatin forms a broad interaction around calpain's active site cysteine, we have constructed and tested a library of 45 peptidic compounds based on this loop sequence. Four molecules have shown reproducibly low micromolar inhibition of calpain-2. Further systematic sequence changes led to the development of probes that displayed increased potency and specificity of inhibition against calpain over other cysteine proteases. Calculated Ki values were in the low micromolar range, rivaling other peptidomimetic calpain inhibitors and presenting an improved selectivity profile against other therapeutically relevant proteases. Competitive and mixed inhibition against calpain-2 was observed, and an allosteric inhibition site on the enzyme was identified for a noncompetitive inhibitor.

Design, synthesis and biochemical evaluation of novel ethanoanthracenes and related compounds to target burkitt’s lymphoma

Lymphomas (cancers of the lymphatic system) account for 12% of malignant diseases worldwide. Burkitt’s lymphoma (BL) is a rare form of non-Hodgkin’s lymphoma in which the cancer starts in the immune B-cells. We report the synthesis and preliminary studies on the antiproliferative activity of a library of 9,10-dihydro-9,10-ethanoanthracene based compounds structurally related to the antidepressant drug maprotiline against BL cell lines MUTU-1 and DG- 75. Structural modifications were achieved by Diels-Alder reaction of the core 9-(2- nitrovinyl)anthracene with number of dienophiles including maleic anhydride, maleimides, acrylonitrile and benzyne. The antiproliferative activity of these compounds was evaluated in BL cell lines EBV? MUTU-1 and EBV+ DG-75 (chemoresistant). The most potent compounds 13j, 15, 16a, 16b, 16c, 16d and 19a displayed IC50 values in the range 0.17–0.38 μM against the BL cell line EBV? MUTU-1 and IC50 values in the range 0.45–0.78 μM against the chemoresistant BL cell line EBV+ DG- 75. Compounds 15, 16b and 16c demonstrated potent ROS dependent apoptotic effects on the BL cell lines which were superior to the control drug taxol and showed minimal cytotoxicity to peripheral blood mononuclear cells (PBMCs). The results suggest that this class of compounds merits further investigation as antiproliferative agents for BL.

Compounds containing a michael-acceptor, especially maleimide or maleic acid derivatives, directly or indirectly linked to a chromophore and their use in long lasting sunscreen compositions

The present invention relates to compounds which are useful as sunscreens. The compounds persist on the skin for much longer than conventional sunscreens because they comprise a Michael acceptor linked directly or indirectly to a chromophore. The Michael acceptor is capable of undergoing a conjugate addition reaction with thiol groups present in cysteine residues of keratin and thus the compound is chemically bound to the skin and will not be removed by immersion in water.

Synthesis of New Bifunctional Maleimide Compounds for the Preparation of Chemoimmunoconjugates

Bifunctional maleimide compounds are suitable for binding small molecules to carrier proteins in that they bind to the sulfhydryl group of proteins through the double bond of the maleimide group and to molecules of low molecular weight (e.g. anticancer drugs) through a functional group X. 18 maleimide compounds of the general formula Maleimid-R-X (R = phenylene, benzyl-, methylene-, ethylene, or a m-benzoylethylamide group and X = hydroxy-, amino-, hydrazino-, carboxylic acid-, carboxylic anhydride-, carboxylic acid chloride-, carboxylic acid hydrazide-, oxycarbonylchloride-, aldehyde, keto-, or p-toluenesulfonate-group) were synthesized and characterized through 1H- and 13C-NMR-spectroscopy, elemental analysis, and mass spectrometry.