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Chemical Compound Review:

ETHYLDIMETHYLAMINOPROPYL CARBODIIMIDE 3- (ethyliminomethylideneamino)- N,N...

Synonyms: EDAC, AG-E-38147, ACMC-209esd, ANW-23435, CCG-36290, ...

Martin, B.M. et al., Northwood, I.C. et al., Jenkins, M.K. et al., Applegate, D. et al., Willing, A. et al., et al.

Jorge-Herrero, Fernández, Turnay, Olmo, Calero, García, Freile, Castillo-Olivares,

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Disease relevance of ETHYLDIMETHYLAMINOPROPYL CARBODIIMIDE

The Fe-protein and the MoFe-protein of the Azotobacter vinelandii nitrogenase complex can be chemically cross-linked by 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (Willing, A., Georgiadis, M.M., Rees, D. C., and Howard, J. B. (1989) J. Biol. Chem. 264, 8499-8503) [1].
The electrostatically stabilized complex between Anabaena variabilis ferredoxin--NADP+ reductase and Azotobacter vinelandii flavodoxin has been covalently cross-linked by treatment with 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide [2].
The interaction between horse heart cytochrome c and Chromatium vinosum flavocytochrome c-552 was studied using the water-soluble reagent 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC) [3].

High impact information on ETHYLDIMETHYLAMINOPROPYL CARBODIIMIDE

Exposure of normal interleukin 2 (IL-2)-producing helper T-cell clones to antigen and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide-treated antigen-presenting cells results in proliferative unresponsiveness to subsequent stimulation with antigen and normal antigen-presenting cells [4].
However, treatment of PEDF with 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide abolished it, implicating the PEDF aspartic and/or glutamic acid residues in its interaction with collagen I [5].
Small, acid-soluble spore proteins (SASP) of the alpha/beta-type from several Bacillus species were cross-linked into homodimers, heterodimers and homooligomers with 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC) in the presence of linear plasmid DNA [6].
This domain was cross-linked to BDNF through a 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide coupling reaction [7].
In order to identify the ferredoxin binding region on CODH, the ferredoxin and CODH were cross-linked by using 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide [8].

Biological context of ETHYLDIMETHYLAMINOPROPYL CARBODIIMIDE

1 mM K+ reduces the ADP binding to the high affinity nucleotide binding site to the same extent in normal and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide-treated enzyme and Na+ counteracts this effect [9].
Investigation of the in vitro autophosphorylation of receptor monomers and dimers cross-linked with 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide demonstrated that the treatment of cells with PMA caused an inhibition of the tyrosine phosphorylation of both monomeric and dimeric EGF receptors [10].
The structure of the actin-myosin complex during ATP hydrolysis was studied by covalently crosslinking myosin subfragment 1 (S1) to F-actin in the presence of nucleotides (especially ATP) using 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide [11].
The same held true for 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC, IC50 500 microM) and diethyl pyrocarbonate (DEPC, IC50 20 microM), two reagents known to modify carboxylic or histidinyl side-chains, respectively [12].

Anatomical context of ETHYLDIMETHYLAMINOPROPYL CARBODIIMIDE

We have used the zero-length cross-linker 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC) to examine protein-protein associations within purified outer arm dynein and axonemes from Chlamydomonas flagella [13].
The sarcoplasmic reticulum Ca(2+)-ATPase loses hydrolytic activity and the ability to be phosphorylated by Pi following incubation with EDC [1-ethyl-3-(3-dimethylaminopropyl)carbodiimide] [14].
Liposome surfaces were modified with normal rabbit IgG or rabbit anti-sheep erythrocyte IgG by adsorption or by coupling with a water soluble cross-linking reagent, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDCI) [15].
Treatment with EDAC was much less protective than the other two chemical reagents (43.28 +/- 17.4 and 55.85 +/- 14.57 nmol amino acid/mg dry tissue for pericardium and collagen, respectively) [16].
To probe the effect of nucleotide on the formation of ionic contacts between actin and the 567-578 residue loop of the heavy chain of rabbit skeletal muscle myosin subfragment 1 (S1), the complexes between F-actin and proteolytic derivatives of S1 were submitted to chemical cross-linking with 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide [17].

Associations of ETHYLDIMETHYLAMINOPROPYL CARBODIIMIDE with other chemical compounds

The treatment of the different proteins with 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide and N-hydroxysuccinimide revealed that carboxylate residues from Fd and lysine residues from Delta9D contribute to cross-linking [18].
Fatty acids were separated by reversed-phase high-performance liquid chromatography after derivatization with 2-nitrophenylhydrazine hydrochloride in the presence of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride [19].
A water soluble carbodiimide, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC), has been used to crosslink horse heart cytochrome c and trypsin-solubilized bovine liver microsomal cytochrome b5 [20].
Pig phospholipase A2, pig iso-phospholipase A2 and bovine pancreatic phospholipase A2 were reacted in solution with 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide, in the presence of N-hydroxysulfosuccinimide, at pH 7 [21].
Stearic acid (SA) grafted chitosan oligosaccharide (CSO) (CSO-SA), which was synthesized by an 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC)-mediated coupling reaction, was demonstrated to form micelle like structure by self-aggregation in aqueous solution [22].

Gene context of ETHYLDIMETHYLAMINOPROPYL CARBODIIMIDE

Using 1-ethyl 3-(3-dimethylaminopropyl)carbodiimide, we observed erythropoietin cross-linking with a protein of 66 kDa in addition to the 100- and 85-kDa proteins [23].
Modification of bovine adrenodoxin with 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC) dramatically inhibited the reaction with adrenodoxin reductase (EC 1.18.1.2) [24].
A covalent complex between purified rat liver microsomal NADPH-cytochrome P-450 reductase and horse cytochrome c was formed through cross-linking studies with 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide at low ionic strength [25].
Chitinase isolated from Zea mays seeds is inactivated by 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC) in the absence of exogenous nucleophiles [26].
Adrenodoxin interaction with adrenodoxin reductase and cytochrome P-450scc. Cross-linking of protein complexes and effects of adrenodoxin modification by 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide [27].

Analytical, diagnostic and therapeutic context of ETHYLDIMETHYLAMINOPROPYL CARBODIIMIDE

Unstained frozen hydrated samples of myosin subfragment 1 (S-1) cross-linked to actin with the zero-length cross-linker 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide have been examined by electron microscopy in an effort to probe structural states of the attached cross-bridge [28].

References

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The use of a water-soluble carbodiimide to study the interaction between Chromatium vinosum flavocytochrome c-552 and cytochrome c. Vieira, B., Davidson, M., Knaff, D., Millett, F. Biochim. Biophys. Acta (1986) [Pubmed]
Molecular events in the induction of a nonresponsive state in interleukin 2-producing helper T-lymphocyte clones. Jenkins, M.K., Pardoll, D.M., Mizuguchi, J., Chused, T.M., Schwartz, R.H. Proc. Natl. Acad. Sci. U.S.A. (1987) [Pubmed]
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Probing the active site of the reconstituted aspartate/glutamate carrier from bovine heart mitochondria: carbodiimide-catalyzed acylation of a functional lysine residue. Dierks, T., Stappen, R., Salentin, A., Krämer, R. Biochim. Biophys. Acta (1992) [Pubmed]
The Mr 78,000 intermediate chain of Chlamydomonas outer arm dynein interacts with alpha-tubulin in situ. King, S.M., Wilkerson, C.G., Witman, G.B. J. Biol. Chem. (1991) [Pubmed]
Sarcoplasmic reticulum calcium ATPase. Labeling of a putative Mg2+ site by reaction with a carbodiimide and a spin-label. Coan, C., Jakobs, P., Ji, J.Y., Murphy, A.J. FEBS Lett. (1993) [Pubmed]
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Influence of different chemical cross-linking treatments on the properties of bovine pericardium and collagen. Jorge-Herrero, E., Fernández, P., Turnay, J., Olmo, N., Calero, P., García, R., Freile, I., Castillo-Olivares, J.L. Biomaterials (1999) [Pubmed]
Effect of nucleotide on interaction of the 567-578 segment of myosin heavy chain with actin. Martin, B.M., Karczewska, E., Pliszka, B. Biochim. Biophys. Acta (2006) [Pubmed]
Identification of the binding region of the [2Fe-2S] ferredoxin in stearoyl-acyl carrier protein desaturase: insight into the catalytic complex and mechanism of action. Sobrado, P., Lyle, K.S., Kaul, S.P., Turco, M.M., Arabshahi, I., Marwah, A., Fox, B.G. Biochemistry (2006) [Pubmed]
Improved method of determination of biologically important C10:0-C22:6 fatty acids as their 2-nitrophenylhydrazides by reversed-phase high-performance liquid chromatography. Miwa, H., Yamamoto, M. J. Chromatogr. (1986) [Pubmed]
Crosslinking of cytochrome c and cytochrome b5 with a water-soluble carbodiimide. Reaction conditions, product analysis and critique of the technique. Mauk, M.R., Mauk, A.G. Eur. J. Biochem. (1989) [Pubmed]
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Structure of the murine erythropoietin receptor complex. Characterization of the erythropoietin cross-linked proteins. Mayeux, P., Lacombe, C., Casadevall, N., Chretien, S., Dusanter, I., Gisselbrecht, S. J. Biol. Chem. (1991) [Pubmed]
Identification of specific carboxylate groups on adrenodoxin that are involved in the interaction with adrenodoxin reductase. Geren, L.M., O'Brien, P., Stonehuerner, J., Millett, F. J. Biol. Chem. (1984) [Pubmed]
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Identification of an essential tyrosine residue in the catalytic site of a chitinase isolated from Zea mays that is selectively modified during inactivation with 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide. Verburg, J.G., Smith, C.E., Lisek, C.A., Huynh, Q.K. J. Biol. Chem. (1992) [Pubmed]
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