Vibrational spectra of captopril (SQ 14,225: 1-(D-3-mercapto-2-methylpropionyl)-L-proline) and the synthesis of the 1:1 coordination compound of captopril with Zn(II) and its characterization by vibrational spectra

Bukovec, Peter; Milićev, S.; Bukovec, N.; Čepon, Marko

doi:10.1016/s0020-1693(00)81163-9

Cited by 16 publications

(4 citation statements)

References 15 publications

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“…At pH < 6 the Zn(II) ion is coordinated by three sites (carbonyl, carboxyl and thiol groups), whereas at pH>6 the complex formation involves only two atoms (carbonyl oxygen and sulphur). [40,41] …”

Section: Raman Spectramentioning

confidence: 99%

Free radical scavenging and copper chelation: A potentially beneficial action of captopril

Tamba¹,

Torreggiani²

2000

Free Radical Research

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Captopril (CpSH), an angiotensin converting enzyme (ACE) inhibitor, is reported to provide protection against free-radical mediated damage. The purpose of this study was to investigate, by means of pulse radiolysis technique, the behaviour of CpSH towards radiation-induced radicals in the absence and in the presence of copper(II) ions, which can play a relevant role in the metal catalysed generation of reactive oxygen species. The results indicate that the -SH group is crucial in determining the radical scavenging action of CpSH and the nature of the resulting CpSH transient products in the absence or in the presence of oxygen. In the presence of Cu(II), the -SH group is still involved in the biological action of the molecule participating both in the one-electron reduction of Cu(II) with formation of CpSSCp, and in Cu(I) chelation. This conclusion is supported by the Raman spectroscopic data which allow to identify the CpSH sites involved in the copper complex at different pH. These results suggest that CpSH may potentially inhibit oxidative damage both through free radical scavenging and metal chelation. Considering the low CpSH concentration in vivo, the metal chelation mechanism, more than the direct radical scavenging, could play the major role in moderating the toxicological effects of free radicals.

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Section: Raman Spectramentioning

confidence: 99%

Free radical scavenging and copper chelation: A potentially beneficial action of captopril

Tamba¹,

Torreggiani²

2000

Free Radical Research

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“…The IR bands of captopril in Nujol have been assigned in detail as was done with the Zn/captopril (1:1) complex [6]. The IR spectrum of captopril in KBr was about the same as that in Nujol, and of interest to this discussion is that the -COOH and amide I bands at 1748 and 1588 cm −1 had the same, very strong, intensities.…”

Section: Spectral Properties Of Captopril Of Commercementioning

confidence: 95%

“…The amide I (of equal intensity to that of COOH) was at 1608 cm −1 compared to 1588 cm −1 of free captopril probably indicating a weakening of the hydrogen-bonding to the C = O oxygen [6]. The anhydrous complex A had a more complex IR spectrum in the 2000-400 cm −1 region from either captopril or the hydrated complex B.…”

Section: Spectral Properties Of Tris(captoprilato)arsenic·xh 2 O (X =mentioning

confidence: 97%

“…Its interaction with trace metal ions in the plasma is deemed to be responsible for its side effects. Therefore complexes of captopril have been isolated with Zn(II) [3,5,6], Cu(I) [5], Cu(II) [5,9,26], Ni(II) [26], Fe(III) [26], Sn(II) [26], Me 2 Sn(IV) [20], VO 2+ [31], or studied in solution with Zn(II), Cd(II), Pb(II) [14], Cu(II) and Fe(III) [12]. In all cases coordination is achieved via the -S − and amide oxygen (giving a six-membered ring) and -COO − (giving either dimers or polymers).…”

Section: Introductionmentioning

confidence: 99%

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Thiolates of arsenic(III) and Bi(III) with the anti-hypertensive drug captopril

Ioannou

Tsivgoulis

2013

Main Group Chemistry

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Arsenic trioxide, but not bismuth trioxide, reacted with the oral anti-hypertensive drug captopril giving the anhydrous (and in one case the dihydrated) tris(captoprilato)arsenic in good yields. Bismuth(III) nitrate pentahydrate reacted with 1, 2, 3 equivalents of captopril giving solutions containing the corresponding thiolato complexes and nitric acid. Their 1 H NMR spectra in CD 3 OD showed that both major and minor captoprilato conformers existed and the more captoprilato ligands are coordinated to Bi(III) the more up field the CH 2 S protons resonate. Addition of a calculated amounts of NaOH to the solutions of Bi(III)/captopril 1:1 and 1:2 gave solids insoluble in methanol or DMSO, the structures of which could not be reliably established by IR. The IR spectra of the isolated tris(captoprilato)arsenic and bismuth showed two νC=O bands for the COOH groups implying a complex hydrogen bonding network. These two complexes have sufficient solubility in water to be studied for biochemical or biological activities.

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In vivo toxicological effects and spectral studies of organotin(IV)N-maleoylglycinates

Khan

Baloch

Ashfaq

et al. 2005

Appl. Organometal. Chem.

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Vibrational spectra of captopril (SQ 14,225: 1-(D-3-mercapto-2-methylpropionyl)-L-proline) and the synthesis of the 1:1 coordination compound of captopril with Zn(II) and its characterization by vibrational spectra

Cited by 16 publications

References 15 publications

Free radical scavenging and copper chelation: A potentially beneficial action of captopril

Free radical scavenging and copper chelation: A potentially beneficial action of captopril

Thiolates of arsenic(III) and Bi(III) with the anti-hypertensive drug captopril

In vivo toxicological effects and spectral studies of organotin(IV)N-maleoylglycinates

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