scholarly journals Predicting Reduction Rates of Energetic Nitroaromatic Compounds Using Calculated One-Electron Reduction Potentials

2015 ◽  
Vol 49 (6) ◽  
pp. 3778-3786 ◽  
Author(s):  
Alexandra J. Salter-Blanc ◽  
Eric J. Bylaska ◽  
Hayley J. Johnston ◽  
Paul G. Tratnyek
Keyword(s):  
Nitroaromatic Compounds ◽  
Reduction Potentials ◽  
Electron Reduction

scholarly journals One-Electron Reduction Potentials: Calibration of Theoretical Protocols for Morita–Baylis–Hillman Nitroaromatic Compounds in Aprotic Media

Molecules ◽  
2018 ◽  
Vol 23 (9) ◽  
pp. 2129 ◽  
Author(s):  
Amauri Francisco da Silva ◽  
Antonio João da Silva Filho ◽  
Mário Vasconcellos ◽  
Otávio Luís de Santana
Keyword(s):  
Cyclic Voltammetry ◽  
Biological Activity ◽  
Chemical Structure ◽  
Reduction Potential ◽  
Chemical Reactivity ◽  
Nitroaromatic Compounds ◽  
Reduction Potentials ◽  
Electron Reduction ◽  
The One ◽  
Antileishmanial Activities

Nitroaromatic compounds—adducts of Morita–Baylis–Hillman (MBHA) reaction—have been applied in the treatment of malaria, leishmaniasis, and Chagas disease. The biological activity of these compounds is directly related to chemical reactivity in the environment, chemical structure of the compound, and reduction of the nitro group. Because of the last aspect, electrochemical methods are used to simulate the pharmacological activity of nitroaromatic compounds. In particular, previous studies have shown a correlation between the one-electron reduction potentials in aprotic medium (estimated by cyclic voltammetry) and antileishmanial activities (measured by the IC50) for a series of twelve MBHA. In the present work, two different computational protocols were calibrated to simulate the reduction potentials for this series of molecules with the aim of supporting the molecular modeling of new pharmacological compounds from the prediction of their reduction potentials. The results showed that it was possible to predict the experimental reduction potential for the calibration set with mean absolute errors of less than 25 mV (about 0.6 kcal·mol−1).

scholarly journals Inhibition of plant fatty acid synthesis by nitroimidazoles

1981 ◽  
Vol 198 (1) ◽  
pp. 193-198 ◽  
Author(s):  
A V Jones ◽  
J L Harwood ◽  
M R Stratford ◽  
P K Stumpf
Keyword(s):  
Fatty Acid ◽  
Fatty Acid Synthesis ◽  
Soluble Fraction ◽  
Acid Synthesis ◽  
Long Chain Fatty Acids ◽  
Reduction Potentials ◽  
Marked Inhibition ◽  
Mechanism Of Inhibition ◽  
Pea Seeds ◽  
Electron Reduction

1. The effect of the addition of a number of nitroimidazoles was tested on fatty acid synthesis by germinating pea seeds, isolated lettuce chloroplasts and a soluble fraction from pea seeds. 2. All the compounds tested had a marked inhibition on stearate desaturation by lettuce chloroplasts and on the synthesis of very-long-chain fatty acids by pea seeds. 3. In contrast, the effect of the drugs on total fatty acid synthesis from [14C]acetate in chloroplasts was related to the compound's electron reduction potentials. 4. Of the compounds used, only metronidazole had a marked inhibition on palmitate elongation in the systems tested. 5. The mechanism of inhibition of plant fatty acid synthesis by nitroimidazoles is discussed and the possible relevance of these findings to their neurotoxicity is suggested.

scholarly journals Enzymatic single-electron reduction and aerobic cytotoxicity of tirapazamine and its 1-oxide and nor-oxide metabolites

Chemija ◽  
2018 ◽  
Vol 29 (4) ◽  
Author(s):  
Jonas Šarlauskas ◽  
Aušra Nemeikaitė-Čėnienė ◽  
Audronė Marozienė ◽  
Lina Misevičienė ◽  
Mindaugas Lesanavičius ◽  
...  
Keyword(s):  
Side Effects ◽  
Anticancer Agent ◽  
Redox Cycling ◽  
Nitroaromatic Compounds ◽  
Single Electron ◽  
Reductive Activation ◽  
Cell Nuclei ◽  
Electron Reduction ◽  
Phenylene Diamine

Aerobic cytotoxicity of 3-amino-1,2,4-benzotriazine-1,4-dioxide (tirapazamine, TPZ), a bioreductively activated hypoxia-specific anticancer agent, is responsible for TPZ side effects in chemotherapy. In order to clarify its mechanisms, we examined the aerobic cytotoxicity of TPZ and its main metabolites, 3-amino-1,2,4-benzotriazine-1-oxide and 3-amino-1,2,4-benzotriazine in murine hepatoma MH22a cells, and their reduction by NADPH:cytochrome P-450 reductase (P-450R) and ferredoxin:NADP+ reductase (FNR). Analogous studies of several quinones and nitroaromatic compounds with similar values of single-electron reduction midpoint potentials (E17) were carried out. In single-electron reduction by P-450R and FNR, the reactivity of TPZ and its monoxide was similar to that of quinones and nitroaromatics, and increased with an increase in their E17. The cytotoxicity of TPZ and its metabolites possessed a prooxidant character, because it was partly prevented by an antioxidant N,N’-diphenyl-p-phenylene diamine and desferrioxamine, and potentiated by 1,3-bis(2-chloroethyl)-1-nitrosourea. Importantly, the cytotoxicity of TPZ and, possibly, its 1-N-oxide, was much higher than that of quinones and nitroaromatics with similar values of E17 and redox cycling activities. A possible additional factor in the aerobic cytotoxicity of TPZ is its reductive activation in oxygen-poor cell nuclei, leading to the formation of DNA-damaging species similar to those forming under hypoxia.

One-electron Reduction Potentials of Tea Polyphenolic Compounds

1998 ◽  
Vol 14 (11) ◽  
pp. 1020-1024
Author(s):  
Wang Chao-Cun ◽  
◽  
Ha Cheng-Yong ◽  
Yao Si-De
Keyword(s):  
Polyphenolic Compounds ◽  
Reduction Potentials ◽  
Electron Reduction

scholarly journals Mutually Isomeric 2- and 4-(3-Nitro-1,2,4-triazol-1-yl)pyrimidines Inspired by an Antimycobacterial Screening Hit: Synthesis and Biological Activity against the ESKAPE Panel of Pathogens

Antibiotics ◽  
2020 ◽  
Vol 9 (10) ◽  
pp. 666
Author(s):  
Sergey Chuprun ◽  
Dmitry Dar’in ◽  
Elizaveta Rogacheva ◽  
Liudmila Kraeva ◽  
Oleg Levin ◽  
...  
Keyword(s):  
Cyclic Voltammetry ◽  
Antibacterial Activity ◽  
Reduction Potential ◽  
Gram Negative ◽  
Reduction Potentials ◽  
Apparent Correlation ◽  
Electron Reduction ◽  
Activity Loss ◽  
Eskape Pathogens ◽  
Bioactivity Profile

Starting from the structure of antimycobacterial screening hit OTB-021 which was devoid of activity against ESKAPE pathogens, we designed, synthesized and tested two mutually isomeric series of novel simplified analogs, 2- and 4-(3-nitro-1,2,4-triazol-1-yl)pyrimidines, bearing various amino side chains. These compounds demonstrated a reverse bioactivity profile being inactive against M. tuberculosis while inhibiting the growth of all ESKAPE pathogens (with variable potency patterns) except for Gram-negative P. aeruginosa. Reduction potentials (E1/2, V) measured for selected compounds by cyclic voltammetry were tightly grouped in the −1.3–−1.1 V range for a reversible single-electron reduction. No apparent correlation between the E1/2 values and the ESKAPE minimum inhibitory concentrations was established, suggesting possible significance of other factors, besides the compounds’ reduction potential, which determine the observed antibacterial activity. Generally, more negative E1/2 values were displayed by 2-(3-nitro-1,2,4-triazol-1-yl)pyrimidines, which is in line with the frequently observed activity loss on moving the 3-nitro-1,2,4-triazol-1-yl moiety from position 4 to position 2 of the pyrimidine nucleus.

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