Disease relevance of CCRIS 2604

• To characterize the binding interface between E. coli flavodoxin and methionine synthase, we have employed site-directed mutagenesis and chemical cross-linking using carbodiimide and N-hydroxysuccinimide [1].
• Monoclonal antibody 4E3 directed against a glycosylated surface protein on human ovarian teratocarcinoma cells (CRL-1572 cell line) was conjugated to bovine carboxypeptidase A (CPA) using a 3400 Da polyethylene glycol chain bearing an N-hydroxysuccinimide group at both ends [2].
• Bacterial luciferase has been modified with the thiolating reagent S-acetylmercaptosuccinic anhydride and covalently crosslinked to either Staphylococcus aureus protein A or anti-human immunoglobulin G (IgG) with the heterobifunctional reagent m-maleimidobenzoic acid N-hydroxysuccinimide ester [3].
• Fluorescent bands were observed when the 22 kDa human dihydrofolate reductase and the 18 kDa folate transporter from Lactobacillus casei were treated with gamma-F-MTX (activated by N-hydroxysuccinimide) and subjected to SDS-PAGE [4].
• Total synthesis of the cyclic peptide lactone WS9326A, a potent tachykinin antagonist isolated from Streptomyces violaceoniger strain 9326, has been achieved via Cbz-Thr(Boc-allo-Thr-Asn-Ser(Bzl)-(E)delta MeTyr-Leu-D-Phe-OTce, which was cyclized (Phe and allo-Thr) using an active ester method with N-hydroxysuccinimide [5].

Psychiatry related information on CCRIS 2604

• This intermediate was then converted to N-succinimidyl 3-hydroxy-4-[131I]iodobenzoate ([131I]mSHIB) in 75% yield by reaction with N-hydroxysuccinimide and dicyclohexylcarbodiimide in a reaction time of only 10 min [6].

High impact information on CCRIS 2604

• Cross-linking reagents that contain NEM as one reactive group, and N-hydroxysuccinimide as the other, were used to study the topography of the 43 kd protein in AChR-rich membranes [7].
• Cross-linking of 125I-IL-4 at relatively low concentrations in the presence of the cross-linking agent 3,3'-dithiobis(propionic acid hydroxysuccinimide ester) resulted in the detection of the previously described 60- to 75-kDa protein [8].
• N-hydroxysuccinimide esters of saturated fatty acids ranging from C8 to C18 were reacted with recombinant human TNF [9].
• Despite the low affinity for MTX, the folate-binding protein could be specifically labeled by an N-hydroxysuccinimide ester of [3H]MTX and appeared to have a molecular weight of 44,000 as shown by sodium dodecyl sulfate-polyacrylamide gel electrophoresis [10].
• By co-expression and N-hydroxysuccinimide methotrexate (Mtx) radioaffinity labeling of hRFC TMD 1-6 and TMD 7-12 half-molecules, combined with endoproteinase GluC digestion, a substrate binding domain was previously localized to within TMDs 8-12 (Witt, T. L., Stapels, S. E., and Matherly, L. H. (2004) J. Biol. Chem. 279, 46755-46763) [11].

Chemical compound and disease context of CCRIS 2604

• K99 lectin from Escherichia coli was purified and biotinylated via the amino groups of lysine residues using N-biotinyl-6-amino-caproic acid N-hydroxysuccinimide ester (BcapNHS) [12].
• Heat-stable acetate kinase (AK) from Bacillus stearothermophilus was successfully immobilized covalently to Sepharose resin by several conventional methods including carbodiimide, hydroxysuccinimide, cyanogen bromide, and glutaraldehyde and also by a new method which utilizes a bifunctional ADP derivative as a spacer [13].
• Acetylation of Escherichia coli aspartase (L-aspartate ammonia-lyase, EC 4.3.1.1) with acetic anhydride or N-hydroxysuccinimide acetate resulted in the alteration of catalytic and regulatory properties as follows [14].

Biological context of CCRIS 2604

• An N-hydroxysuccinimide ester of [3H]methotrexate has been employed to covalently label a specific binding protein that resides in the plasma membrane of L1210 cells [15].
• Mouse strains of H-2b haplotype exhibit much weaker cytotoxic T lymphocyte (CTL) responses to haptens reactive with amino groups of cell surface (NH2-reactive haptens) compared with H-2k strains [16].
• However, acylation of 2 with 2,4-dinitrobenzoic acid N-hydroxysuccinimide ester (4b) leads to N3-[3-carboxy-3-L-(2,4-dinitrobenzamido)propyl]uridine (6) which is stable in aqueous solution [17].
• After initial aminoacylation of a tRNA pool, N-hydroxysuccinimide ester chemistry is applied to biotinylate the alpha-NH2 group of the amino acid bound to the 3'-end of a tRNA [18].
• The precursor polylysine was derivatized in a three-step, single-pot procedure, including biotinylation with biotin amidocaproic N-hydroxysuccinimide, astatination via the intermediate reagent N-succinimidyl 3-(trimethylstannyl)benzoate, and, finally, charge modification using succinic anhydride [19].

Anatomical context of CCRIS 2604

• The generation of potent anti-AED-NH2 CTL and helper T cell responses in C57BL/6N mice sharply contrasted with the failure of NH2-reactive haptens studied thus far to generate strong anti-hapten cytotoxic responses in H-2b mice [16].
• Profilin and beta/gamma-actin from calf thymus were covalently linked using the zero-length cross-linker 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide in combination with N-hydroxysuccinimide, yielding a single product with an apparent molecular mass of 60 kDa [20].
• The aim of this study was to investigate the effects of an alternative method for crosslinking of collagen, using N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide (EDC) in combination with N-hydroxysuccinimide (NHS), on various cellular functions of human umbilical vein endothelial cells (HUVECs) in vitro [21].
• Treatment with the N-hydroxysuccinimide of folic acid, which blocks FR-alpha activity, showed only a partial inhibition (about 20%) of folate internalization in all the cell lines [22].
• Synthesis and characterization of N-hydroxysuccinimide ester chemical affinity derivatives of asialoorosomucoid that covalently cross-link to galactosyl receptors on isolated rat hepatocytes [23].

Associations of CCRIS 2604 with other chemical compounds

• A bioactive biotin-containing derivative of the synthetic bovine parathyroid hormone analog [Nle8,Nle18,Tyr34]bovine parathyroid hormone-(1-34) (bPTH-(1-34] amide was prepared by reacting the peptide with N-biotinyl-epsilon-aminocaproic acid N-hydroxysuccinimide ester [24].
• Spleen cells from C3H/He or BALB.K mice immunized to the newly synthesized amino-reactive hapten 5-sulfo-1-naphthoxy acetic acid N-hydroxysuccinimide ester (AED-NH2) were stimulated in vitro with AED-NH2-modified syngeneic cells [25].
• Monoclonal antibody to the mouse histocompatibility antigen, H-2k, was derivatized with palmitic acid using an activated ester of N-hydroxysuccinimide [26].
• Derivatives of human growth hormone (hGH) of increasing size were produced by reaction with the N-hydroxysuccinimide ester of polyethylene glycol-5000 (PEG5000), a 5-kDa reagent that selectively conjugates to primary amines [27].
• Gonadotropin-releasing hormone (GnRH) and two of its analogs ([D-Lys6]GnRH and des-Gly10-[D-Trp6]-GnRH) were reacted with sulfonated N-hydroxysuccinimide esters of biotin that have been reported to react specifically with primary amino groups [28].

Gene context of CCRIS 2604

• As a prelude to developing affinity labels for studying the interaction between big ET-1 and endothelin converting enzyme (ECE), the effect on biological activity of modifying human big ET-1 with the N-hydroxysuccinimide esters of 3-(p-hydroxyphenyl)propionic acid (HPP) or S-acetylthioglycolic acid (ATG) was investigated [29].
• We have characterized the ability of DIDS and of selected N-hydroxysuccinimide cross-linking agents to increase the proportion of SDS-resistant oligomers of pig gastric AE2 and its proteolytic fragments [30].
• EGF was biotinylated with NHS-XX-biotin, where NHS = N-hydroxysuccinimide and -XX- = bis (aminohexanoyl) spacer arm [31].
• A photoaffinity antagonist of gonadotropin releasing hormone (GnRH), D pGlu-D-Phe-D-Trp-Ser-D-Lys6(N epsilon-azidobenzoyl)-Leu-Arg-Pro-Gly-NH2 (photoaffinity antagonist) was prepared by reacting [D-pGlu1, D-Phe2, D-Trp3, D-Lys6]GnRH with the N-hydroxysuccinimide ester of 4-azidobenzoic acid [32].
• Inhibition of human leukocyte elastase by derivatives of N-hydroxysuccinimide. A structure-activity-relationship study [33].

Analytical, diagnostic and therapeutic context of CCRIS 2604

• The reaction of human beta-endorphin and biotinyl N-hydroxysuccinimide with or without spacer arm, afforded a series of products that were separated by high performance liquid chromatography (HPLC) [34].
• N-hydroxysuccinimide activated Sepharose beads (HAS) were used to immobilize allotypic and idiotypic antisera for use in radioimmunoassays [35].
• Covalent immobilization of native biomolecules onto Au(111) via N-hydroxysuccinimide ester functionalized self-assembled monolayers for scanning probe microscopy [36].
• To identify which proteins possess the amine groups involved in ligation of functional Mn, we examined the difference in NHS biotinylation between PS II core complexes with and without the Mn cluster [37].
• When L. casei folate transport protein (18 kDa) was treated with gamma-F-MTX that had been activated with N-hydroxysuccinimide (NHS), the protein was readily visualized as a fluorescent band on SDS-PAGE electrophoretograms [38].

References