BIOMAT Database Logo BIOMAT Database Logo

2,5-Diaziridinyl-3,6-bis(carboethoxyamino)-1,4-benzoquinone II: Isolation and characterization of degradation products. 1981

G K Poochikian, and J A Kelley

A direct high-performance liquid chromatographic (HPLC) method was applied to monitor 2,5-diaziridinyl-3,6-bis(carboethoxyamino)-1,4-benzoquinone (I) and its degradation products in pharmaceutical vehicles at 25 +/- 0.1 degrees. At the optimal pH for stability of I, an increase in buffer concentration [phosphate and tris(hydroxymethyl)-aminomethane] or ionic strength accelerated degradation. The reaction rate in the solutions studied followed pseudo-first-order kinetics. Degradation products were characterized by mass spectrometry after isolation by semipreparative HPLC. Different degradation pathways prevailed in acidic and basic media. The acid-catalyzed reaction resulted in consecutive aziridine ring opening, while the base-catalyzed reaction led to nucleophilic displacement of thie aziridine ring(s).

UI MeSH Term Description Entries
D008027 Light That portion of the electromagnetic spectrum in the visible, ultraviolet, and infrared range. Light, Visible,Photoradiation,Radiation, Visible,Visible Radiation,Photoradiations,Radiations, Visible,Visible Light,Visible Radiations
D010100 Oxygen An element with atomic symbol O, atomic number 8, and atomic weight [15.99903; 15.99977]. It is the most abundant element on earth and essential for respiration. Dioxygen,Oxygen-16,Oxygen 16
D002021 Buffers A chemical system that functions to control the levels of specific ions in solution. When the level of hydrogen ion in solution is controlled the system is called a pH buffer. Buffer
D002621 Chemistry A basic science concerned with the composition, structure, and properties of matter; and the reactions that occur between substances and the associated energy exchange.
D002851 Chromatography, High Pressure Liquid Liquid chromatographic techniques which feature high inlet pressures, high sensitivity, and high speed. Chromatography, High Performance Liquid,Chromatography, High Speed Liquid,Chromatography, Liquid, High Pressure,HPLC,High Performance Liquid Chromatography,High-Performance Liquid Chromatography,UPLC,Ultra Performance Liquid Chromatography,Chromatography, High-Performance Liquid,High-Performance Liquid Chromatographies,Liquid Chromatography, High-Performance
D006868 Hydrolysis The process of cleaving a chemical compound by the addition of a molecule of water.
D000970 Antineoplastic Agents Substances that inhibit or prevent the proliferation of NEOPLASMS. Anticancer Agent,Antineoplastic,Antineoplastic Agent,Antineoplastic Drug,Antitumor Agent,Antitumor Drug,Cancer Chemotherapy Agent,Cancer Chemotherapy Drug,Anticancer Agents,Antineoplastic Drugs,Antineoplastics,Antitumor Agents,Antitumor Drugs,Cancer Chemotherapy Agents,Cancer Chemotherapy Drugs,Chemotherapeutic Anticancer Agents,Chemotherapeutic Anticancer Drug,Agent, Anticancer,Agent, Antineoplastic,Agent, Antitumor,Agent, Cancer Chemotherapy,Agents, Anticancer,Agents, Antineoplastic,Agents, Antitumor,Agents, Cancer Chemotherapy,Agents, Chemotherapeutic Anticancer,Chemotherapy Agent, Cancer,Chemotherapy Agents, Cancer,Chemotherapy Drug, Cancer,Chemotherapy Drugs, Cancer,Drug, Antineoplastic,Drug, Antitumor,Drug, Cancer Chemotherapy,Drug, Chemotherapeutic Anticancer,Drugs, Antineoplastic,Drugs, Antitumor,Drugs, Cancer Chemotherapy
D001388 Aziridines Saturated azacyclopropane compounds. They include compounds with substitutions on CARBON or NITROGEN atoms. Ethyleneimines,Azacyclopropanes, Saturated,Dimethyleneimines,Saturated Azacyclopropanes
D001389 Azirines Unsaturated azacyclopropane compounds that are three-membered heterocycles of a nitrogen and two carbon atoms. Azacyclopropanes, Unsaturated,Unsaturated Azacyclopropanes
D013058 Mass Spectrometry An analytical method used in determining the identity of a chemical based on its mass using mass analyzers/mass spectrometers. Mass Spectroscopy,Spectrometry, Mass,Spectroscopy, Mass,Spectrum Analysis, Mass,Analysis, Mass Spectrum,Mass Spectrum Analysis,Analyses, Mass Spectrum,Mass Spectrum Analyses,Spectrum Analyses, Mass

Related Publications

G K Poochikian, and J A Kelley
Mitochondrial toxicity of 2,5-diaziridinyl-3,6-bis-(carboethoxyamino)-1,4-benzoquinone.
October 1983, Journal of the National Cancer Institute,
G K Poochikian, and J A Kelley
Intracerebral penetration and tissue distribution of 2,5-diaziridinyl 3,6-bis(carboethoxyamino) 1,4-benzoquinone (AZQ, NSC-182986).
January 1983, Journal of neuro-oncology,
G K Poochikian, and J A Kelley
Cellular activation of diaziquone [2,5-diaziridinyl-3,6-bis (carboethoxyamino)-1,4-benzoquinone] to its free radical species.
May 1985, Biochemical pharmacology,
G K Poochikian, and J A Kelley
Biochemical activation of AZQ [3,6-diaziridinyl-2,5-bis(carboethoxyamino)-1,4-benzoquinone] to its free radical species.
February 1982, Cancer treatment reports,
G K Poochikian, and J A Kelley
Alkylation of DNA by the new anticancer agent 3,6-diaziridinyl-2,5-bis(carboethoxyamino)-1,4-benzoquinone (AZQ).
February 1984, European journal of cancer & clinical oncology,
G K Poochikian, and J A Kelley
Comparison of the structural and cytotoxic activity of novel 2,5-bis(carboethoxyamino)-3,6-diaziridinyl-1,4-benzoquinone analogues.
April 1990, Cancer research,
G K Poochikian, and J A Kelley
2,5-Diaziridinyl-3,6-bis(carboethoxyamino)-1,4-benzoquinone I: Kinetics in aqueous solutions by high-performance liquid chromatography.
February 1981, Journal of pharmaceutical sciences,
G K Poochikian, and J A Kelley
Phase II and pharmacokinetic study of aziridinylbenzoquinone [2,5-diaziridinyl-3,6-bis(carboethoxyamino)-1,4-benzoquinone, diaziquone, NSC 182986] in high-grade gliomas.
December 1983, Cancer research,
G K Poochikian, and J A Kelley
Induction of DNA strand breaks and cross-links by 2,5-diaziridinyl-3,6-bis(carboethoxyamino)-1,4-benzoquinone in Chinese hamster ovary cells.
December 1984, Cancer research,
G K Poochikian, and J A Kelley
The pharmacologic fate of 2,5-diaziridinyl-3,6-bis(carboethoxyamino) 1,4-benzoquinone (AZQ NSC-182986) by intracarotid or intravenous administration in beagles.
January 1983, Journal of neuro-oncology,
Copied contents to your clipboard!