Impact of 1,5-disubstituted tetrazole ring on chelating ability of δ-selective opioid peptide

Łodyga-Chruścińska, Elżbieta; Ołdziej, Stanisław; Micera, Giovanni; Sanna, Daniele; Chruściński, Longin; Olczak, Jacek; Zabrocki, Janusz

doi:10.1016/j.jinorgbio.2003.11.011

Cited by 13 publications

(5 citation statements)

References 31 publications

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“…These additional peaks were clearly due to the charge transfer between N amide and Cu(II) and Cu(II) d−d transition. – It was also found that the CD spectra of (3b,c)−Cu(II) themselves exhibited distinct intensity. For instance, the positive peaks at ca.…”

Section: Resultsmentioning

confidence: 90%

“…540 nm. Accordingly, N-terminal Pro residue of a peptide is also capable of taking part in Cu(II) complexes following a coordination model of {NH, 2N − , CO}, which is supported by the N/Cu(II) charge transfer transition at 310 nm and the d−d transitions at ca. 550 nm.…”

Section: Resultsmentioning

confidence: 98%

“…550 nm in the CD spectra (Figure ), the [M−H] + of MS, and the Pro residue at the N-terminus into account, the binding mode of Cu(II) and 3a−f was postulated as {NH, N − , 2CO}. , The structures of (3a−f)−Cu(II) corresponding to this coordination model were optimized using the QSAR module of Cerius 2 and are summarized in Figure .…”

Section: Resultsmentioning

confidence: 99%

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Coordination of Thrombolytic Pro-Ala-Lys peptides with Cu (II): Leading to Nanoscale Self-assembly, Increase of Thrombolytic Activity and Additional Vasodilation

et al. 2008

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Vasodilation is one of the biologically important properties for thrombolytic agents because of it may help thrombolysis via dilating blood vessels. Aimed at discovering agents with the dual-action of vasodilative and thrombolytic activities, H-Pro-Ala-Lys (PAK, 3a) and five novel analogs H-Pro-Ala-AA ( 2b-f, AA = Val, Phe, Ser, Glu, and His) were coordinated with Cu(II) to form Cu(II)-Pro-Ala-AA [( 3a-f) -Cu(II)]. The coordination chemistry was confirmed by the d-d transition occurred in their UV and circular dichroism (CD) spectra and the molecular ion in their electrospray ionization mass spectrometry (ESI-MS) spectra. The particle size tests of their solution and powders revealed that the coordination generally resulted in nanoscale self-assembly. Zeta potential and half-peak width tests indicated that the formed nanoparticles were sufficiently stable during the monitored 8 days. The bioassays implied that comparing to the PAK peptides themselves and CuCl 2 the coordination led to a 3000-fold increase of the in vitro thrombolytic activity, a 10-fold increase of the in vivo thrombolytic activity, and especially an additional vasodilation. Thus Cu(II)-peptide coordination indeed is a way for thrombolytic peptide design.

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Section: Resultsmentioning

confidence: 90%

Section: Resultsmentioning

confidence: 98%

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Coordination of Thrombolytic Pro-Ala-Lys peptides with Cu (II): Leading to Nanoscale Self-assembly, Increase of Thrombolytic Activity and Additional Vasodilation

et al. 2008

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“…13 The investigations of complexes of Cu 2+ and peptide have been correlated with nanoscale self-assembly, bioactivity, and with positron emission tomography (PET) images of arterial thrombosis. [14][15][16][17][18][19][20][21] Recently, three Cu(II)-complexes, Cu(II)-Arg-Gly-Asp-Ser-Arg-Gly-Asp-Ser (Cu(II)-4a), Cu(II)-Arg-Gly-Asp-Val-Arg-Gly-Asp-Val (Cu(II)-4b), and Cu(II)-Arg-Gly-Asp-Phe-Arg-Gly-Asp-Phe (Cu(II)-4c), were synthesized, 22 consisting of octapeptides with two repeated RGD-peptides; among the three, it was revealed that Cu(II)-4a and Cu(II)-4c possessed the highest in vitro and in vivo activities, respectively. Besides Cu(II)-4c can form nanoparticles.…”

Section: Cumentioning

confidence: 99%

Cu2+-RGDFRGDS: exploring the mechanism and high efficacy of the nanoparticle in antithrombotic therapy

Wu¹,

Wang²,

Wang³

et al. 2015

IJN

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Thrombosis disease has been the leading cause of morbidity and mortality worldwide. In the discovery of antithrombotic agents, three complexes of Cu 2+ and repetitive arginine- -FS activity in decreasing glycoprotein IIb/IIIa, P-selectin, and IL-8 was responsible for the antithrombotic action. Finally, adherence onto the surface and entry into the cytoplasm were considered the steps of a two-step model for the blocking of platelet activation by Cu 2+ -FS nanoparticles. Findings indicated that the antiplatelet aggregation activity of Cu 2+ -FS was 10-52 times higher than that of RGDFRGDS, while the effective dose for antithrombotic action was 5,000 times lower than that of RGDFRGDS.

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“…7 In medical chemistry, tetrazoles are considered lipophilic spacers and metabolically stable surrogates for carboxylic acid. 8 In addition, tetrazoles have been used in organometallic chemistry as effective stabilizers of metal peptide structures, as peptide chelating agents 9,10 and as ligands with different coordination modes in coordination chemistry. 11,12 Tetrazoles have also been used as plant growth regulators, herbicides and fungicides.…”

Section: Introductionmentioning

confidence: 99%

Highly Active and Reusable Cu/C Catalyst for Synthesis of 5-Substituted 1H-Tetrazoles Starting from Aromatic Aldehydes

Khalifeh

Rastegar

Khalili

2020

ACSi

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A new, efficient and convenient method for the synthesis of 5-substituted 1H-tetrazole derivatives with a wide range of substituents in good to excellent yields has been developed. The synthesis was performed by the one-pot three-component [3+2]cycloaddition reaction between aldehyde, hydroxylamine and sodium azide in the presence of Cu/C. The reaction probably proceeds by the in situ formation of nitriles followed by successive [3+2]cycloaddition with sodium azide. A variety of aldehydes were used to obtain the corresponding tetrazoles. The catalyst was recovered by simple filtration and reused at least five times without significant loss of catalytic activity. The use of this method offers additional advantages for the synthesis of 5-substituted 1H-tetrazole derivatives, including the easy availability of starting materials, mild conditions, experimental simplicity and good yields.

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Impact of 1,5-disubstituted tetrazole ring on chelating ability of δ-selective opioid peptide

Cited by 13 publications

References 31 publications

Coordination of Thrombolytic Pro-Ala-Lys peptides with Cu (II): Leading to Nanoscale Self-assembly, Increase of Thrombolytic Activity and Additional Vasodilation

Coordination of Thrombolytic Pro-Ala-Lys peptides with Cu (II): Leading to Nanoscale Self-assembly, Increase of Thrombolytic Activity and Additional Vasodilation

Cu2+-RGDFRGDS: exploring the mechanism and high efficacy of the nanoparticle in antithrombotic therapy

Highly Active and Reusable Cu/C Catalyst for Synthesis of 5-Substituted 1H-Tetrazoles Starting from Aromatic Aldehydes

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Impact of 1,5-disubstituted tetrazole ring on chelating ability of δ-selective opioid peptide

Cited by 13 publications

References 31 publications

Coordination of Thrombolytic Pro-Ala-Lys peptides with Cu (II): Leading to Nanoscale Self-assembly, Increase of Thrombolytic Activity and Additional Vasodilation

Coordination of Thrombolytic Pro-Ala-Lys peptides with Cu (II): Leading to Nanoscale Self-assembly, Increase of Thrombolytic Activity and Additional Vasodilation

Cu2+-RGDFRGDS: exploring the mechanism and&nbsp;high efficacy of the nanoparticle in antithrombotic therapy

Highly Active and Reusable Cu/C Catalyst for Synthesis of 5-Substituted 1H-Tetrazoles Starting from Aromatic Aldehydes

Contact Info

Product

Resources

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Cu2+-RGDFRGDS: exploring the mechanism and high efficacy of the nanoparticle in antithrombotic therapy