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Benzophenone Maleimide

Benzophenone maleimide is an excellent building block for developing benzophenone-based photoaffinity probes. It readily reacts with a biological molecule that has a thiol group such as proteins, peptides, thiol-modified oligos. Benzophenones were introduced as photocrosslinkers in the 1970s and have since become one of the most popular photocrosslinkers since they are more selective and has high affinity towards methionine. Benzophenone is converted into an active diradical upon activation by relatively long (350–365 nm) wavelengths. Early work demonstrated that Benzophenone was more suitable for biological applications than other simple aryl ketones (e.g., acetophenones) because the conditions required for photolysis are less damaging to the protein primary structure. Benzophenone generates a triplet ketyl biradical that can react with protein functional groups via a sequential abstraction–recombination mechanism.

References

View all 50 references: Citation Explorer
Self-assembly of benzophenone-diphenylalanine conjugate into a nanostructured photocatalyst.
Authors: Adorinni, Simone and Goti, Giulio and Rizzo, Lorenzo and Grassi, Federica and Kralj, Slavko and Matroodi, Fatima and Natali, Mirco and De Zorzi, Rita and Marchesan, Silvia and Dell'Amico, Luca
Journal: Chemical communications (Cambridge, England) (2023): 7619-7622
Electronic and Photochemical Passivation by a Classic Sunscreen Material Leading to Reduced Voc Losses and Enhanced Stability in Organic Solar Cells.
Authors: Xu, Zhuo and Islam, Md Moidul and Meitzner, Rico and Anand, Aman and Djoumessi, Aurelien Sokeng and Stumpf, Steffi and Hoeppener, Stephanie and Neumann, Christof and Turchanin, Andrey and Schubert, Ulrich S and Hoppe, Harald
Journal: ACS applied materials & interfaces (2023): 45146-45157
Fluorogenic Photo-Crosslinking of Glycan-Binding Protein Recognition Using a Fluorinated Azido-Coumarin Fucoside.
Authors: Bousch, Cécile and Vreulz, Brandon and Kansal, Kartikey and El-Husseini, Ali and Cecioni, Samy
Journal: Angewandte Chemie (International ed. in English) (2023): e202314248
Benzophenone: A Small Molecule Additive for Enhanced Performance and Stability of Inverted Perovskite Solar Cells.
Authors: Elbohy, Hytham and Suzuki, Hiroo and Nishikawa, Takeshi and Htun, Thiri and Tsutsumi, Kosei and Nakano, Chiyu and Kyaw, Aung Ko Ko and Hayashi, Yasuhiko
Journal: ACS applied materials & interfaces (2023): 45177-45189
Degradable Anti-Biofouling Polyester Coatings with Controllable Lifetimes.
Authors: Mu, Gaoyan and Genzer, Jan and Gorman, Christopher B
Journal: Langmuir : the ACS journal of surfaces and colloids (2022): 1488-1496
Page updated on December 17, 2024

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Physical properties

Molecular weight

277.28

Solvent

DMSO

Storage, safety and handling

H-phraseH303, H313, H333
Hazard symbolXN
Intended useResearch Use Only (RUO)
R-phraseR20, R21, R22

Storage

Freeze (< -15 °C); Minimize light exposure

CAS

92944-71-3
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