58879-90-6Relevant academic research and scientific papers
Stable and Rapid Thiol Bioconjugation by Light-Triggered Thiomaleimide Ring Hydrolysis
Kalia, Dimpy,Pawar, Sharad P.,Thopate, Jyoti S.
, p. 1885 - 1889 (2017/02/05)
Maleimide-mediated thiol-specific derivatization of biomolecules is one of the most efficacious bioconjugation approaches currently available. Alarmingly, however, recent work demonstrates that the resulting thiomaleimide conjugates are susceptible to breakdown via thiol exchange reactions. Herein, we report a new class of maleimides, namely o-CH2NHiPr phenyl maleimides, that undergo unprecedentedly rapid ring hydrolysis after thiol conjugation to form stable thiol exchange-resistant conjugates. Furthermore, we overcome the problem of low shelf lives of maleimide reagents owing to their propensity to undergo ring hydrolysis prior to bioconjugation by developing a photocaged version of this scaffold that resists ring hydrolysis. UV irradiation of thiol bioconjugates formed with this photocaged maleimide unleashes rapid thiomaleimide ring hydrolysis to yield the desired stable conjugates within 1 h under gentle, ice-cold conditions.
Coumarin-based fluorogenic agents and uses thereof for specific protein labelling
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Page/Page column 44, (2017/08/08)
There are provided fluorescent labelling agents comprising a dimaleimide core connected to a fluorophore, processes for preparation thereof, and uses thereof for labelling and/or detection of specific protein targets. Fluorescent labelling agents comprising a compound having the structure of Formula I, and salts thereof, are described.
Ring Substituent Effects on the Thiol Addition and Hydrolysis Reactions of N-Arylmaleimides
Chen, Yingche,Tsao, Kelvin,De Francesco, élise,Keillor, Jeffrey W.
, p. 12182 - 12192 (2016/01/09)
Maleimide groups are used extensively in bioconjugation reactions, but limited kinetic information is available regarding their thiol addition and hydrolysis reactions. We prepared a series of fluorogenic coumarin maleimide derivatives that differ by the
Aryloxymaleimides for cysteine modification, disulfide bridging and the dual functionalization of disulfide bonds
Marculescu, Cristina,Kossen, Hanno,Morgan, Rachel E.,Mayer, Patrick,Fletcher, Sally A.,Tolner, Berend,Chester, Kerry A.,Jones, Lyn H.,Baker, James R.
supporting information, p. 7139 - 7142 (2014/07/07)
Tuning the properties of maleimide reagents holds significant promise in expanding the toolbox of available methods for bioconjugation. Herein we describe aryloxymaleimides which represent 'next generation maleimides' of attenuated reactivity, and demonstrate their ability to enable new methods for protein modification at disulfide bonds.
Revised Structures of N-Substituted Dibrominated Pyrrole Derivatives and Their Polymeric Products. Termaleimide Models with Low Optical Band Gaps
Choi, Dong-Sook,Huang, Shenlin,Huang, Mingsheng,Barnard, Thomas S.,Adams, Richard D.,Seminario, Jorge M.,Tour, James M.
, p. 2646 - 2655 (2007/10/03)
This paper describes an unexpected rearrangement/oxidation of N-substituted 2,5-dibromopyrroles upon treatment with HNO3. The bromides migrate from the 2,5-positions to the 3,4-positions with subsequent oxidation at the 2,5-positions to afford N-substituted 3,4-dibromomaleimides; the structure was confirmed by single-crystal X-ray analysis. The maleimides were then polymerized to the poly(N-substituted-3,4-maleimide)s with copper bronze. This constitutes a revision of structure for the monomers and polymers. The propensity for the dibromide migration was further confirmed by treatment of N-benzyl-2,5-dibromopyrrole under nonoxidative acidic conditions (p-TsOH) to afford N-benzyl-3,4-dibromopyrrole; both the starting material and product structures were confirmed by single-crystal X-ray analysis. Several termaleimides were prepared from pyrrole, maleic anhydride, and citraconic anhydride. These trimeric compounds underwent enormous shifts in their optical absorbance maxima (ca. 200 nm) when bases or nucleophilic solvents were added. Therefore, the termaleimides served as excellent models for the polymeric systems that had undergone shifts of 350-400 nm upon treatment with the same additives. Ab initio Hartree-Fock and density functional theory were utilized to assess the minimum conformation of the trimeric system. Both terminal maleimides appear canted 37° relative to the central maleimide unit. As the two end maleimide units were computationally forced into closer proximity, there was a dipolar stabilization that ensued between the two terminal maleimides with the formation of a 1,3-dioxetane. However, it is unlikely that there could be the formation of an isolable 1,3-dioxetane due to the large energy difference between the canted structure and the dioxetane. A significant decrease in the HOMO-LUMO energy of 13 kcal/mol was calculated upon formation of the 1,3-dioxetane, suggesting that nucleophiles likely move the canted structure more toward a planar form via addition to the α,β-unsaturated carbonyl units.
