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Chemical Compound Review

AG-G-43475     3- (methoxycarbonimidoyl)propane- 1-thiol

Synonyms: CTK5C1742, AR-1J6301, AC1L3XK7, AC1Q1U9U, 64821-63-2, ...
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Disease relevance of methyl 4-mercaptobutyrimidate

  • The 2IT-linked immunotoxin was much more effective than the SPDP-linked immunotoxin at protecting nu/nu mice against the growth of AKR-A lymphoma cells in the peritoneal site [1].
  • We have investigated protein-rRNA cross-links formed in 30S and 50S ribosomal subunits of Escherichia coli and Bacillus stearothermophilus at the molecular level using UV and 2-iminothiolane as cross-linking agents [2].
  • Studies of the structural organization of virion proteins using the cross-linking reagent methyl-4-mercaptobutyrimidate showed only linkage of the virion envelope or core proteins to themselves [3].
  • The amine residue of NH2-C3(BHam)2 was converted to a maleimide group by reaction with N-succinimidyl-6-maleimidohexanoate, and the conjugation product was coupled to thiol groups of a monoclonal antibody against osteogenic sarcoma (OST7, IgG1) pretreated with 2-iminothiolane to prepare C3(BHam)2-OST7 [4].
  • Contact sites between protein and rRNA in 30S and 50S ribosomal subunits of Escherichia coli and Bacillus stearothermophilus were investigated at the molecular level using UV and 2-iminothiolane as cross-linkers [5].

High impact information on methyl 4-mercaptobutyrimidate

  • The 60S subunits isolated from Artemia salina ribosomes were treated with the crosslinking reagent 2-iminothiolane under mild conditions [6].
  • IT was made by crosslinking anti-CD3 to a low oligosaccharide-containing fraction of purified ricin toxin A chain (RTA; a catalytic inhibitor of protein synthesis) with a stabilized derivative of 2-iminothiolane [7].
  • 125I-Labeled HMG 17 was cross-linked to core histones using the protein-protein cross-linking reagent 2-iminothiolane [8].
  • Protein topography of the 40 S ribosomal subunit from rabbit reticulocytes shown by cross-linking with 2-iminothiolane [9].
  • Identification of proteins at the binding site for protein S1 in 70 S ribosomes and 30 S subunits by cross-linking with 2-iminothiolane [10].

Chemical compound and disease context of methyl 4-mercaptobutyrimidate


Biological context of methyl 4-mercaptobutyrimidate

  • Cytotoxicity evaluations carried out by the formazan (MTS) assay showed that the thiolated gelatin prepared with 20 mg and 40 mg of 2-iminothiolane (SHGel-20 and SHGel-40) per gram of gelatin had comparable cell viability profile to that of the unmodified gelatin [13].

Associations of methyl 4-mercaptobutyrimidate with other chemical compounds

  • To define molecular interfaces between nebulin and CaM, we thiolated lysines of CaM and ND66, a four-module cloned fragment from the C-terminus of nebulin, with 2-iminothiolane and cross-linked the complex with dibromobimane, which alkylates thiol pairs within approximately 6 A of each other to form a fluorescent adduct [14].
  • Iron oxide particles of average size 0.5-1.5 microns, covered by a silane coat carrying amino groups (Bio-Mag, Advanced Magnetics, Boston), were derivatized by reaction with N-[(gamma-maleimidobutyryl)oxy]-succinimide (GMBS), N-hydroxysuccinimidyl iodoacetate (NHIA), 2-iminothiolane (2-It), or N-succinimidyl 3-(2-pyridyldithio)propionate (SPDP) [15].
  • Chitosan was modified by the immobilization of thiol groups utilizing 2-iminothiolane in order to obtain a chitosan-4-thiobutylamidine conjugate (chitosan-TBA) [16].
  • The decay of the initial thiol adduct to an N-substituted 2-iminothiolane was confirmed for the reaction between benzylamine and 2-IT by the isolation of N-benzyl-2-iminothiolane and its characterization by elemental analysis and mass spectrometry [17].
  • Free sulfhydryl groups were introduced onto the surface of protein nanoparticles either by aldehyde quenching with cysteine or reaction of free amino groups with 2-iminothiolane [18].

Gene context of methyl 4-mercaptobutyrimidate

  • The conjugation of transferrin to liposomes was carried out using N-succinimidyl 3-(2-pyridyldithio)-propionate and 2-iminothiolane as activating agents for the liposomes and the protein [19].
  • Analysis of the two larger complexes formed by cross-linking with a reversible cross-linker (methyl-4-mercaptobutyrimidate) demonstrates that the 215,000 molecular weight complex is composed of one each of the replicase subunits, while the 135,000 molecular weight complex is composed of the two larger subunits [20].
  • Cumulated activities of peptide-linked RICs in the xenografts were as great as those of 2IT RICs, so that the therapeutic indices (tumor: liver cumulated activity ratios) were substantially better for cathepsin-degradable peptide-linked RICs [21].
  • It was converted to p-bromoacetamidobenzyl-DOTA (BAD), and conjugated to monoclonal antibody Lym-1 via 2-iminothiolane, either as the free ligand or as the 88Y chelate [22].
  • Cross-linking of elongation factor 2 to rat-liver ribosomal proteins by 2-iminothiolane [23].

Analytical, diagnostic and therapeutic context of methyl 4-mercaptobutyrimidate


  1. Comparison of two anti-Thy 1.1-abrin A-chain immunotoxins prepared with different cross-linking agents: antitumor effects, in vivo fate, and tumor cell mutants. Thorpe, P.E., Blakey, D.C., Brown, A.N., Knowles, P.P., Knyba, R.E., Wallace, P.M., Watson, G.J., Wawrzynczak, E.J. J. Natl. Cancer Inst. (1987) [Pubmed]
  2. Protein-rRNA binding features and their structural and functional implications in ribosomes as determined by cross-linking studies. Urlaub, H., Kruft, V., Bischof, O., Müller, E.C., Wittmann-Liebold, B. EMBO J. (1995) [Pubmed]
  3. Analysis of the envelope of Rauscher murine oncornavirus: in vitro labeling of glycopeptides. McLellan, W.L., August, J.T. J. Virol. (1976) [Pubmed]
  4. Bis(hydroxamamide)-based bifunctional chelating agent for 99mTc labeling of polypeptides. Xu, L.C., Nakayama, M., Harada, K., Kuniyasu, A., Nakayama, H., Tomiguchi, S., Kojima, A., Takahashi, M., Ono, M., Arano, Y., Saji, H., Yao, Z., Sakahara, H., Konishi, J., Imagawa, Y. Bioconjug. Chem. (1999) [Pubmed]
  5. Structural and functional implications in the eubacterial ribosome as revealed by protein-rRNA and antibiotic contact sites. Wittmann-Liebold, B., Uhlein, M., Urlaub, H., Müller, E.C., Otto, A., Bischof, O. Biochem. Cell Biol. (1995) [Pubmed]
  6. Topography and stoichiometry of acidic proteins in large ribosomal subunits from Artemia salina as determined by crosslinking. Uchiumi, T., Wahba, A.J., Traut, R.R. Proc. Natl. Acad. Sci. U.S.A. (1987) [Pubmed]
  7. Anti-CD3 immunotoxin prevents low-dose STZ/interferon-induced autoimmune diabetes in mouse. Vallera, D.A., Carroll, S.F., Brief, S., Blazar, B.R. Diabetes (1992) [Pubmed]
  8. High mobility group protein 17 cross-links primarily to histone H2A in the reconstituted HMG 17-nucleosome core particle complex. Cook, G.R., Yau, P., Yasuda, H., Traut, R.R., Bradbury, E.M. J. Biol. Chem. (1986) [Pubmed]
  9. Protein topography of the 40 S ribosomal subunit from rabbit reticulocytes shown by cross-linking with 2-iminothiolane. Tolan, D.R., Traut, R.R. J. Biol. Chem. (1981) [Pubmed]
  10. Identification of proteins at the binding site for protein S1 in 70 S ribosomes and 30 S subunits by cross-linking with 2-iminothiolane. Boileau, G., Sommer, A., Traut, R.R. J. Biol. Chem. (1981) [Pubmed]
  11. Disulfide cross-linking of Escherichia coli ribosomal proteins with 2-iminothiolane (methyl 4-mercaptobutyrimidate): evidence that the cross-linked protein pairs are formed in the intact ribosomal subunit. Lambert, J.M., Jue, R., Traut, R.R. Biochemistry (1978) [Pubmed]
  12. Rhenium-188-labeled anti-neural cell adhesion molecule antibodies with 2-iminothiolane modification for targeting small-cell lung cancer. Hosono, M.N., Hosono, M., Mishra, A.K., Faivre-Chauvet, A., Gautherot, E., Barbet, J., Knapp, F.F., Chatal, J.F. Annals of nuclear medicine. (2000) [Pubmed]
  13. Preparation and evaluation of thiol-modified gelatin nanoparticles for intracellular DNA delivery in response to glutathione. Kommareddy, S., Amiji, M. Bioconjug. Chem. (2005) [Pubmed]
  14. Mapping protein interfaces with a fluorogenic cross-linker and mass spectrometry: application to nebulin-calmodulin complexes. Sinz, A., Wang, K. Biochemistry (2001) [Pubmed]
  15. Hinge-thiol coupling of monoclonal antibody to silanized iron oxide particles and evaluation of magnetic cell depletion. Hermentin, P., Doenges, R., Franssen, U., Bieva, C., Vander Brugghen, F.J., Stryckmans, P., Friesen, H.J., Optaczy, B., Schneider, S., Ax, W. Bioconjug. Chem. (1990) [Pubmed]
  16. Systemic peptide delivery via the stomach: in vivo evaluation of an oral dosage form for salmon calcitonin. Guggi, D., Krauland, A.H., Bernkop-Schnürch, A. Journal of controlled release : official journal of the Controlled Release Society. (2003) [Pubmed]
  17. Formation of N-substituted 2-iminothiolanes when amino groups in proteins and peptides are modified by 2-iminothiolane. Singh, R., Kats, L., Blättler, W.A., Lambert, J.M. Anal. Biochem. (1996) [Pubmed]
  18. Preparation of avidin-labeled protein nanoparticles as carriers for biotinylated peptide nucleic acid. Langer, K., Coester, C., Weber, C., von Briesen, H., Kreuter, J. European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft für Pharmazeutische Verfahrenstechnik e.V. (2000) [Pubmed]
  19. Liposomal targeting of leukaemia HL60 cells induced by transferrin-receptor endocytosis. Sarti, P., Ginobbi, P., D'Agostino, I., Arancia, G., Lendaro, E., Molinari, A., Ippoliti, R., Citro, G. Biotechnol. Appl. Biochem. (1996) [Pubmed]
  20. Phage Q-beta ribonucleic acid replicase. Subunit relationships determined by intramolecular cross-linking. Young, R.A., Blumenthal, T. J. Biol. Chem. (1975) [Pubmed]
  21. Preclinical evaluation of cathepsin-degradable peptide linkers for radioimmunoconjugates. DeNardo, G.L., DeNardo, S.J., Peterson, J.J., Miers, L.A., Lam, K.S., Hartmann-Siantar, C., Lamborn, K.R. Clin. Cancer Res. (2003) [Pubmed]
  22. Yttrium-90-labeled monoclonal antibody for therapy: labeling by a new macrocyclic bifunctional chelating agent. Deshpande, S.V., DeNardo, S.J., Kukis, D.L., Moi, M.K., McCall, M.J., DeNardo, G.L., Meares, C.F. J. Nucl. Med. (1990) [Pubmed]
  23. Cross-linking of elongation factor 2 to rat-liver ribosomal proteins by 2-iminothiolane. Uchiumi, T., Kikuchi, M., Terao, K., Iwasaki, K., Ogata, K. Eur. J. Biochem. (1986) [Pubmed]
  24. Protein-protein cross-linking of the 50 S ribosomal subunit of Escherichia coli using 2-iminothiolane. Identification of cross-links by immunoblotting techniques. Walleczek, J., Redl, B., Stöffler-Meilicke, M., Stöffler, G. J. Biol. Chem. (1989) [Pubmed]
  25. Thiolated polymers--thiomers: synthesis and in vitro evaluation of chitosan-2-iminothiolane conjugates. Bernkop-Schnürch, A., Hornof, M., Zoidl, T. International journal of pharmaceutics. (2003) [Pubmed]
  26. Liquid secondary ion mass spectra of 2-iminothiolane derivatives. Bartlett, M.G., Busch, K.L. Biol. Mass Spectrom. (1994) [Pubmed]
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