5146-68-9

Usage

Uses

Used in Bioconjugation Chemistry:
N-hydroxymethylsuccinimide is used as a crosslinking agent for the covalent linkage of molecules such as proteins, peptides, and antibodies to other molecules or surfaces. This facilitates the development of various conjugates and immobilized systems for research and biomedical applications.
Used in Pharmaceutical Industry:
N-hydroxymethylsuccinimide is used as a key component in the preparation of antibody-drug conjugates. It enables the attachment of therapeutic agents to antibodies, enhancing the targeting of drugs to specific cells or tissues, thereby improving the efficacy and reducing the side effects of treatments.
Used in Biomedical Research:
N-hydroxymethylsuccinimide is used as a reagent for the immobilization of proteins onto solid surfaces. This allows for the study of protein interactions, enzymatic activities, and other biological processes in a controlled environment, contributing to the advancement of scientific knowledge and the development of new diagnostic and therapeutic tools.
Used in Diagnostics:
N-hydroxymethylsuccinimide is used in the development of diagnostic assays and sensors, where the immobilization of specific proteins or peptides onto surfaces is crucial for the detection and quantification of target molecules.
Used in Material Science:
N-hydroxymethylsuccinimide is employed in the functionalization of materials, such as nanoparticles or polymers, for various applications, including drug delivery, tissue engineering, and biosensing. Its ability to form stable covalent bonds with a wide range of molecules makes it a valuable asset in the design and synthesis of novel materials with specific properties and functions.

InChI:InChI=1/C5H7NO3/c7-3-6-4(8)1-2-5(6)9/h7H,1-3H2

Upstream product

• 50680-64-3 1-(2-bromomethyl)pyrrolidine-2,5-dione 
• 123-56-8 Succinimide 
• 50-00-0 formaldehyd 

Downstream Products

• 123-56-8 Succinimide 
• 134697-08-8 1-(4-Methoxy-phenoxymethyl)-pyrrolidine-2,5-dione 
• 134697-07-7 Succinimidylmethoxybenzene 
• 1026091-18-8 [1-(4-chloro-benzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]-acetic acid 2,5-dioxo-pyrrolidin-1-ylmethyl ester 
• 50-00-0 formaldehyd 
• 54135-60-3 2,2'-methylenebis(cyclohexane-1,3-dione) 
• 51532-41-3 bis(succinimidomethyl) ether 
• 39101-32-1 N-(4,5-dimethoxy-2-nitro-benzyl)-succinimide 

Relevant academic research and scientific papers

Synthesis, biological evaluation and pharmacokinetic studies of mefenamic acid - N-Hydroxymethylsuccinimide ester prodrug as safer NSAID

Background: Non steroidal anti-inflammatory drugs are the most widely prescribed drugs to manage pain and inflammatory conditions, but their long term use is associated with gastrointestinal toxicity. Objectives: The study aimed to synthesize an ester-bas

NMR study of the tautomeric behavior of N -(α-Aminoalkyl)tetrazoles

N-(α-Aminoalkyl)tetrazoles exist in solution as equilibrium mixtures of N1 and N2 tautomers. The position of equilibrium depends significantly on the polarity of the solvent and the substituents in the tetrazole ring. Interconversion between individual tautomers is shown to proceed via tight ion-pair intermediates in which intramolecular recombination is faster than the intermolecular crossover since the latter probably requires solvent separation of ion-pair intermediates.

Reaction of γ-dicarboxylic acids amides and imides with trifluoromethanesulfonamide and formaldehyde

Three-component condensation of trifluoromethanesulfonamide with paraformaldehyde and succinamide depending on the reaction conditions led alongside bis(trifluoromethanesulfonamido)methane to the formation of a substitution product, bis[(trifluoromethylsulfonyl)aminomethyl]succinamide, or to a cyclization product, N-[trifluoromethylsulfonyl)aminomethyl]succinimide. The attempt to obtain the latter by the reaction of the trifluoromethanesulfonamide sodium salt CF3SO2NHNa with N-chloromethylsuccinimide unexpectedly resulted in N,N-bis(succinimidomethyl)-trifluoromethanesulfonamide. Analogously the reaction of CF3SO2NHNa with N-chloromethyl-phthalimide gave N,N-bis(phthalimidomethyl)trifluoromethanesulfonamide. The reaction of CF3SO2NHNa with succinimide and phthalimide in water and alcohol solution resulted in the ring opening and further transformation of the formed monosubstituted N-(trifluoromethylsulfonyl)amides of succinic and phthalic acids.

Synthesis of soft alkyl phenolic ether prodrugs using Mitsunobu chemistry

The synthesis of soft alkyl phenolic ether prodrugs in excellent yields has been reported by coupling a phenol with a hydroxymethylimide using Mitsunobu chemistry. The imides used in this study include saccharin, phthalimide, succinimide and two other compounds containing acidic imide-like N-H groups, benzotriazole, and imidazole.

Cyclic amide derivatives as potential prodrugs II: N- hydroxymethylsuccinimide- / isatin esters of some NSAIDs as prodrugs with an improved therapeutic index

Ester prodrugs of aspirin la, ibuprofen 1b, naproxen 1c and indomethacin 1d were synthesized using N-Hydroxymethylsuccinimide (HMSI) 3 and N- hydroxymethylisatin (HMIS) 4 as promoieties to reduce their gastrointestinal toxicity and improve bioavailability. Additionally, the kinetics of hydrolysis of the synthesized prodrugs 5a-d and 6a-d were studied at 37°C in non-enzymatic simulated gastric fluid (SGF; hydrochloric acid buffer pH = 1.2); 0.02 M phosphate buffer (pH = 7.4); 80% human plasma and 10% rat liver homogenate. The results indicate higher chemical stability of the ester prodrugs in non-enzymatic SGF (t(1/2) ? 6.5-18.6 h) and rapid conversion to the parent drugs in 80% human plasma (t(1/2) ? 11.4-235 min) as well as in 10% rat liver homogenates (t(1/2) ? 12.0-90.0 min). As a general pattern, the HMSI esters 5a-d revealed higher chemical stability than the corresponding HMIS analogues 6a-d. The pH-rate profile of 5c and 6a indicated maximum stability of the former at pH = 1.2-8.0 and of the latter at pH = 1.2-4.0. The distribution coefficient (D7.4) values of the prodrugs 5a-d, 6a-d and the parent drugs 1a-d in an n-octanol/phosphate buffer (pH =7.4) system indicated enhanced lipophilic properties of the prodrugs. Furthermore, the HMIS ester prodrugs 6a-d are more lipophilic than the corresponding HMSI derivatives 5a-d. In vivo ulcerogenicity studies using scanning electron microscopy on stomach specimens of rats treated with an oral dose for 4 d revealed that the synthesized ester prodrugs are significantly less irritating to gastric mucosa than the parent drugs. These results suggested HMSI and/or HMIS esters possess good potential as prodrugs with an improved therapeutic index for oral delivery of NSAIDs.

Mechanism of Hydrolysis of O-Imidomethyl Derivatives of Phenols

Three series of O-imidomethyl derivatives of para-substituted phenolic compounds were synthesized and their rates of hydrolysis were studied.Saccharin, phthalimide, and succinimide served as the imide portions of the derivatives.Their rates of hydrolysis were found to be first order with respect to hydroxide from pH 7.0 to 10 or 11 and dependent on the acidity (leaving group potential) of both the imide and the phenol portions.The more acidic the imide or the phenol, the faster the rate of hydrolysis.However, the rates of hydrolysis were more sensitive to the acidity of the phenol.Trapping experiments with cyanide also suggested that the phenol anion was functioning as the leaving group in what is apparently an SN2 reaction.An amide derivative was found to hydrolyze more slowly than predicted from the analogous series and the pKa of the amide.This result is apparently due partially stereoelectronic constraints in the imide series that cause the CH2-O bond to be oriented more nearly perpendicular to the plane of the C(=O)N group and hence more accessible to nucleophilic attack.