Coordinating properties of the amide bond. Stability and structure of metal ion complexes of peptides and related ligands

Sigel, Helmut; Martin, R. Bruce

doi:10.1021/cr00050a003

Cited by 1,558 publications

(1,227 citation statements)

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“…This complex is supposed to be at the lower end of stability for this group of complexes, as it doesn't present inter-ligand interactions. For the complexes included in this work stability constants of the ternary complexes are expected to be higher (they were not measured) based on literature data of related compounds, due to dipeptide side chain-phenanthroline interactions (such as those observed in solid state) [13,43]. Therefore a higher, significant, percentage of ternary species is expected in the bioassay conditions.…”

Section: Cytotoxic Activitymentioning

confidence: 99%

Synthesis, structural characterization and cytotoxic activity of ternary copper(II)–dipeptide–phenanthroline complexes. A step towards the development of new copper compounds for the treatment of cancer

Iglesias¹,

Álvarez²,

Torre³

et al. 2014

Journal of Inorganic Biochemistry

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Section: Cytotoxic Activitymentioning

confidence: 99%

Synthesis, structural characterization and cytotoxic activity of ternary copper(II)–dipeptide–phenanthroline complexes. A step towards the development of new copper compounds for the treatment of cancer

Iglesias¹,

Álvarez²,

Torre³

et al. 2014

Journal of Inorganic Biochemistry

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“…On top of the perturbation of solvation energy on the electron transfer reaction, the heterogeneity of the precursor ions might also play an important role in governing the resulting spectral features of these Group IIB metal ion [63][64][65][66] and generate different forms of zwitterions. To get additional insights into the effect of Group IIB metal ions coordination on the deprotonation reaction of amide group, theoretical calculation using Nmethyl glycyl-glycinamide as a truncated peptide model was investigated.…”

Section: The Role Of Precursor Ion Heterogeneitymentioning

confidence: 99%

Formation of Peptide Radical Cations (M^+·) in Electron Capture Dissociation of Peptides Adducted with Group IIB Metal Ions

Chen

Chan

Wong

et al. 2011

J. Am. Soc. Mass Spectrom.

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Peptides adducted with different divalent Group IIB metal ions (Zn 2+ , Cd 2+ , and Hg 2+ ) were found to give very different ECD mass spectra. ECD of Zn 2+ adducted peptides gave series of c-/z-type fragment ions with and without metal ions. ECD of Cd 2+ and Hg 2+ adducted model peptides gave mostly a-type fragment ions with M +• and fragment ions corresponding to losses of neutral side chain from M +• . No detectable a-ions could be observed in ECD spectra of Zn 2+ adducted peptides. We rationalized the present findings by invoking both proton-electron recombination and metal-ion reduction processes. . The relative population of these precursor ions depends largely on the acidity of the metal-ion peptide complexes. Peptides adducted with divalent metal-ions of small ionic radii (i.e., Zn 2+ ) would form predominantly species (b) and (c); whereas peptides adducted with metal ions of larger ionic radii (i.e., Hg 2+ ) would adopt predominantly species (a). Species (b) and (c) are believed to be essential for proton-electron recombination process to give c-/z-type fragments via the labile ketylamino radical intermediates. Species (c) is particularly important for the formation of non-metalated c-/z-type fragments. Without any mobile protons, species (a) are believed to undergo metal ion reduction and subsequently induce spontaneous electron transfer from the peptide moiety to the charge-reduced metal ions. Depending on the exothermicity of the electron transfer reaction, the peptide radical cations might be formed with substantial internal energy and might undergo further dissociation to give structural related fragment ions.

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“…Serine forms, in addition to the previously mentioned complexes the [Cu(PA) (LH -1 )] species. This complex is formed through induced ionization of the β-alcohol group, as mentioned in the literature [20]. Ornithine and lysine are α-amino acids having an extra amino group, which may be protonated.…”

Section: Ternary Complex Formation Equilibria Involving Amino Acids Amentioning

confidence: 96%

Complex Formation Equilibria of Ternary Complexes of Cu(II) Involving Pyridine-2-Carboxylic Acid and Various Biologically Relevant Ligands

Shoukry¹,

Hosny²,

Amin³

et al. 2016

Int. J. Curr. Res. Chem. Pharm. Sci

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Binary and ternary complexes of Cu 2+ involving pyridine-2-carboxylic acid (picolinic acid; PA) and amino acids, peptides or DNA constituents(HL) have been investigated. Ternary complexes of amino acids or peptides are formed by simultaneous reactions. Amino acids form the [Cu(PA)L] complex, whereas peptides form [Cu(PA)L] and [Cu(PA)(LH -1 )]. The ternary complexes of Cu 2+ with picolinic acid and DNA are formed in a stepwise process, whereby binding of Cu 2+ to picolinic acid is followed by ligation of the DNA constituents. The stability of the ternary complexes is compared with the stabilities of the corresponding binary complexes. DNA constituents form both 1:1 and 1:2 complexes with[Cu(PA)] + . The concentration distribution of the complexes in solution was evaluated. Probable mode of chelation with picolinic acid and various biologically relevant ligands was discussed. Absorption spectra of the binary and ternary complexes of Cu 2+ were also investigated. The isolated metal chelates, [Cu(PA)(Cl2)(H2O)2] and [Cu(PA)2(Cl2)], are characterized by elemental analysis and infrared measurements.

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Coordinating properties of the amide bond. Stability and structure of metal ion complexes of peptides and related ligands

Cited by 1,558 publications

References 135 publications

Synthesis, structural characterization and cytotoxic activity of ternary copper(II)–dipeptide–phenanthroline complexes. A step towards the development of new copper compounds for the treatment of cancer

Synthesis, structural characterization and cytotoxic activity of ternary copper(II)–dipeptide–phenanthroline complexes. A step towards the development of new copper compounds for the treatment of cancer

Formation of Peptide Radical Cations (M^+·) in Electron Capture Dissociation of Peptides Adducted with Group IIB Metal Ions

Complex Formation Equilibria of Ternary Complexes of Cu(II) Involving Pyridine-2-Carboxylic Acid and Various Biologically Relevant Ligands

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Coordinating properties of the amide bond. Stability and structure of metal ion complexes of peptides and related ligands

Cited by 1,558 publications

References 135 publications

Synthesis, structural characterization and cytotoxic activity of ternary copper(II)–dipeptide–phenanthroline complexes. A step towards the development of new copper compounds for the treatment of cancer

Synthesis, structural characterization and cytotoxic activity of ternary copper(II)–dipeptide–phenanthroline complexes. A step towards the development of new copper compounds for the treatment of cancer

Formation of Peptide Radical Cations (M+·) in Electron Capture Dissociation of Peptides Adducted with Group IIB Metal Ions

Complex Formation Equilibria of Ternary Complexes of Cu(II) Involving Pyridine-2-Carboxylic Acid and Various Biologically Relevant Ligands

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Formation of Peptide Radical Cations (M^+·) in Electron Capture Dissociation of Peptides Adducted with Group IIB Metal Ions