Introduction of Succinimide

General description 

Succinimide is a dicarboximide that is pyrrolidine which is substituted by oxo groups at positions 2 and 5. It is a pyrrolidinone and a dicarboximide. Succinimide is a natural product found in Xanthium strumarium and Panax notoginseng with data available.Succinimide, also known as succinimide or succinimide, is a colorless acicular crystal or thin solid with light brown luster. It tastes sweet. Easily soluble in water, alcohol or sodium hydroxide solution, insoluble in ether, chloroform, etc. it is irritant. Avoid inhalation and contact with skin. Main uses: organic synthesis, pharmacy, electroplating, chemical analysis, etc.

Application and Pharmacology

the influence of succinimide on formation kinetics of HEWL fibrils under thermal and acidic conditions (65°C and pH 2.0) was carefully investigated with a combined spectroscopic approach. With adding succinimide into HEWL solution, the morphologic changes of protein were observed by AFM images, whereas the ThT fluorescence assay and Far UV CD spectroscopy clarified the influence of succinimide on transformation of α-helix to organized β-sheets. fibrillation is closely associated with a series of neurodegenerative diseases. According to that the intermediate soluble oligomers and protofibrils are more toxic, reducing their concentrations in protein solutions by accelerating fibrillation is believed as a feasible strategy for treatment or remission of the diseases. Using hen egg-white lysozyme (HEWL) as a model protein, the promotion effect of succinimide was revealed from a series of experiments, e.g. atomic force microscopy (AFM), thioflavin T (ThT) fluorescence assay, Far UV circular dichroism (CD) and Raman spectroscopy, modeling the effect of succinimide-like derivative intermediates of intramolecular deamidation of backbone during amyloid fibrillation. The AFM measurement confirmed that succinimide effectively accelerated the morphological changes of HEWL, whilst, at the molecular level the accelerative transformation of protein secondary structures was also clarified by ThT fluorescence assay and Far UV CD spectroscopy. succinimide plays a “bridge” role to promote the direct transformation to organized β-sheets with skipping the intermediate random coils. As a result, the number of soluble oligomers and protofibrils with relatively high toxic level can be significantly reduced[1].

Figure 1 Schematic diagram of the “bridge” role of succinimide during amyloid fibrillation

Synthesis

It is obtained by the reaction of succinic acid with ammonia. Succinic acid and water are added into the reaction pot, and succinimide can be produced by ammonia reaction. Succinic acid can also be put into the reaction pot, drop ammonia, stir to dissolve and react, heat it to 102 ℃, evaporate the water, and then carry out vacuum distillation. When the temperature rises to 180 ℃, start collecting succinimide fraction to obtain the finished product.

A novel succinimide derivative (psi-da-zw) with side groups containing dopamine and betaine sulfonate zwitterionic groups was synthesized by biomimetic design based on the nucleophilic addition reaction of succinimide (PSI); The bionic super hydrophilic functional coating surface (psi-da-zw / glass) was prepared by oxidative self succinimide and deposition of DOPA catechol group in succinimide derivatives The chemical structure, morphology, wettability and light transmittance were characterized by X-ray photoelectron spectroscopy (XPS), scanning electron microscopy (SEM), contact angle measuring instrument and UV-Vis spectrophotometer  The results show that zwitterionic groups are successfully introduced into the surface of psi-da-zw / glass samples. The prepared biomimetic functional coating surface has nano self-assembled microstructure. Its surface water droplet contact angle is close to 0 °, underwater oil droplet contact angle is close to 180 °, and has excellent super hydrophilic and underwater oil pollution prevention characteristics; The coating has good light transmittance, and the light transmittance at 550 nm wavelength can reach 90.4%. Compared with blank glass, it shows the antireflection effect; The results of anti bacterial adhesion experiment showed that the prepared psi-da-zw / glass functional coating had obvious anti adhesion properties to Staphylococcus aureus and Escherichia coli. [2]

Figure 2 Schematic diagram of the route for the preparation of the succinimide derivatives (PSI-DA-ZW)

Safety

This product is toxic and irritating. Avoid inhalation and contact with skin when using it.

References

1.Fan W., Xing L. & Chen N. et al., "Promotion Effect of Succinimide on Amyloid Fibrillation of Hen Egg-White Lysozyme," The journal of physical chemistry. B, Vol.123, No.38(2019), pp.8057-8064.

2.Liu Yunhong, Peng Xinyan, Xu Wentao, et al. "Preparation and properties of bionic superhydrophilic surface based on polysuccinimide derivatives", Journal of polymers, No. 03, 2022, pp. 279-288.

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