Preparation and properties of 3-halopyridine--adenine dinucleotides, NAD+ analogues and model compounds.
European journal of biochemistry
confidence
Key findings
Synthesis and characterization of 3-halogenopyridine-adenine dinucleotides as NAD+ analogues; competitive inhibition of dehydrogenases; no clinical/biological endpoints.
View source on PubMed (PMID 179812) ↗
- Sample size
- Not reported
- Population
- In vitro enzymatic studies (yeast alcohol dehydrogenase, lactate dehydrogenase, malate dehydrogenase)
- Dosing
- Not reported
- Duration
- Not reported
- Route
- Not applicable (in vitro)
- Blinding
- not_reported
- Controls
- not_reported
- Drug class
- coenzyme
Full abstract
The preparation of model compounds 1-(2',6'-dichlorobenzyl)-3-halogenopyridinium and the study of their properties were achieved. Their chemical reduction to the corresponding 1,4-dihydropyridines is proved by spectroscopic analysis. 3-Iodopyridine--adenine dinucleotide was prepared by enzymic transglycosidation while the 3-chloro, 3-bromo and 3-iodo pyridine--adenine dinucleotides were synthesized from 3-amino-pyridine--adenine dinucleotide. The 3-halogenopyridine--adenine dinucleotides were proved to be active as hydrogen acceptors with alcohol as a substrate. The absorption band at 290 nm of cinnamaldehyde appeared to be a very sensitive tool for studying the enzymic reaction. With the alcohol dehydrogenase from yeast, only slight activity was detected. 3-Halogenopyridine--adenine dinucleotides are competitive inhibitors with respect to nicotinamide--adenine dinucleotide with alcohol dehydrogenase from yeast, lactate dehydrogenase and malate dehydrogenase. The use of 3-iodopyridine--adenine dinucleotide as a heavy-atom derivative for X-ray structure determination is proposed.