Related Experiment Video
Updated: May 30, 2026
08:55
Facile Protocol for the Synthesis of Self-assembling Polyamine-based Peptide Amphiphiles (PPAs) and Related Biomaterials
Published on: June 25, 2018
Polyamines are traps for reactive intermediates in furan metabolism
Lisa A Peterson1, Martin B Phillips, Ding Lu
1Division of Environmental Health Sciences, University of Minnesota, Minneapolis, Minnesota 55455, USA. peter431@umn.edu
Chemical Research in Toxicology
|August 17, 2011
Summary
Furan exposure can lead to toxicity and cancer. This study identifies polyamines as key players in furan
Area of Science:
- Toxicology
- Carcinogenesis
- Metabolism
Background:
- Furan is a potential human carcinogen due to its toxicity in rodents.
- The exact mechanism of furan-induced toxicity and cancer remains unclear.
- Cytochrome P450 enzymes catalyze furan oxidation, producing reactive intermediates.
Purpose of the Study:
- To elucidate the chemical nature of furan's reactive intermediate.
- To investigate the role of cellular amines in furan metabolism and toxicity.
- To identify furan metabolites in hepatocytes and urine for in vivo relevance.
Main Methods:
- Incubation of furan with rat hepatocytes.
- Characterization of furan metabolites using analytical techniques.
- Detection of mercapturic acid derivatives in urine from furan-treated rats.
Main Results:
- Furan is oxidized to cis-2-butene-1,4-dial (BDA), which reacts with glutathione (GSH) to form GSH-BDA.
- GSH-BDA forms cross-links with cellular amines, including ornithine, putrescine, and spermidine.
- Mercapturic acid derivatives of spermidine cross-links were found in the urine of furan-treated rats.
Conclusions:
- Polyamines, such as spermidine, may play a significant role in furan toxicity.
- The formation of polyamine-BDA cross-links is an in vivo metabolic pathway.
- Further research is needed to fully understand the implications of these findings for human health.
Related Concept Videos
01:28Biosynthesis of Nucleic Acids
Nucleic acid biosynthesis is a fundamental biochemical process that produces the purine and pyrimidine nucleotides essential for DNA and RNA synthesis. This pathway maintains a balanced nucleotide pool, preventing imbalances that could jeopardize genetic integrity and cellular function. Given the crucial role of nucleotides, their synthesis is tightly regulated to ensure proper cellular homeostasis.Purine BiosynthesisThe biosynthesis of purine nucleotides begins with ribose-5-phosphate, a...
01:26Physical Properties of Amines
Amines with low molecular weight are usually gaseous at room temperature, while those with high molecular weight are liquid or solids in nature. Usually, low molecular weight amines have a rotten fish-like smell. Diamines typically have a pungent smell. For instance, cadaverine and putrescine, depicted in Figure 1, are two molecules responsible for decaying tissue.
01:29Amino Acid Biosynthetic Pathways
Amino acid biosynthesis is essential for cell growth, protein synthesis, and metabolic regulation. Cells generate essential and non-essential amino acids from metabolic intermediates to sustain vital biological functions. These intermediates originate from key metabolic pathways: glycolysis, the tricarboxylic acid (TCA) cycle, and the pentose phosphate pathway. Important precursors include α-ketoglutarate, pyruvate, oxaloacetate, phosphoenolpyruvate, and erythrose-4-phosphate, which provide...
01:202° Amines to N-Nitrosamines: Reaction with NaNO2
Secondary amines react with nitrous acid to form N-nitrosamines, as depicted in Figure 1. Nitrous acid, a weak and unstable acid, is formed in situ from an aqueous solution of sodium nitrite and strong acids, such as hydrochloric acid or sulfuric acid, in cold conditions. In the presence of an acid, the nitrous acid gets protonated. The subsequent loss of water results in the formation of the electrophile known as nitrosonium ion.
01:25Basicity of Heterocyclic Aromatic Amines
Heterocyclic amines, where the N atom is a part of an alicyclic system, are similar in basicity to alkylamines. Interestingly, the heterocyclic amine having a nitrogen atom as part of an aromatic ring has much less basicity than its corresponding alicyclic counterpart. For this reason, as presented in Figure 1, piperidine (pKb = 2.8) is significantly more basic than pyridine (pKb = 8.8).
01:07Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview
In the presence of an aqueous base and a halogen, primary amides can lose the carbonyl (as carbon dioxide) and undergo rearrangement to form primary amines. This reaction, called the Hofmann rearrangement, can produce primary amines (aryl and alkyl) in high yields without contamination by secondary and tertiary amines.