KFU. Card publication. Imino [4+4] cycloaddition products as exclusive and biologically relevant acrolein-amine conjugates are intermediates of 3-formyl-3,4-dehydropiperidine (FDP), an acrolein biomarker

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IMINO [4+4] CYCLOADDITION PRODUCTS AS EXCLUSIVE AND BIOLOGICALLY RELEVANT ACROLEIN-AMINE CONJUGATES ARE INTERMEDIATES OF 3-FORMYL-3,4-DEHYDROPIPERIDINE (FDP), AN ACROLEIN BIOMARKER

Form of presentation

Articles in international journals and collections

Year of publication

2014

Authors, employees of KFU

Kurbangalieva Almira Rafaelovna, author

Other authors

M. Takamatsu; K. Fukase

Bibliographic description in the original language

M. Takamatsu, K. Fukase, A. Kurbangalieva, K. Tanaka. Imino [4+4] cycloaddition products as exclusive and biologically relevant acrolein-amine conjugates are intermediates of 3-formyl-3,4-dehydropiperidine (FDP), an acrolein biomarker // Bioorg. Med. Chem. 2014. V. 22. � 22. P. 6380–6386.

Annotation

We demonstrated synthetically that the eight-membered heterocycles 2,6,9-triazabicyclo[3.3.1]nonanes and 1,5-diazacyclooctanes are the initial and exclusive products of the reaction, through an imino [4+4] cycloaddition, of biologically relevant amines with acrolein. The stabilities of the aminoacetals within the eight-membered heterocycles determined whether the product was subsequently transformed gradually into the 3-formyl-3,4-dehydropiperidine (FDP), which is widely used as an oxidative stress marker. The reactivity profiles discovered in this study suggested that some of the imino [4+4] cycloaddition products are reactive intermediates of FDP and contribute to the mechanisms underlying the oxidative stress response to acrolein.

Keywords

Acrolein, Biologically relevant amine, Biomarker, 1,5-Diazacyclooctane, 3-Formyl-3,4-dehydropiperidine (FDP), Imino [4+4] cycloaddition, 2,6,9-Triazabicyclo[3.3.1]nonane

The name of the journal

Bioorganic & Medicinal Chemistry

URL

http://www.sciencedirect.com/science/article/pii/S0968089614006993

Please use this ID to quote from or refer to the card

https://repository.kpfu.ru/eng/?p_id=94723&p_lang=2

Full metadata record

Field DC	Value	Language
dc.contributor.author	Kurbangalieva Almira Rafaelovna	ru_RU
dc.date.accessioned	2014-01-01T00:00:00Z	ru_RU
dc.date.available	2014-01-01T00:00:00Z	ru_RU
dc.date.issued	2014	ru_RU
dc.identifier.citation	M. Takamatsu, K. Fukase, A. Kurbangalieva, K. Tanaka. Imino [4+4] cycloaddition products as exclusive and biologically relevant acrolein-amine conjugates are intermediates of 3-formyl-3,4-dehydropiperidine (FDP), an acrolein biomarker // Bioorg. Med. Chem. 2014. V. 22. � 22. P. 6380–6386.	ru_RU
dc.identifier.uri	https://repository.kpfu.ru/eng/?p_id=94723&p_lang=2	ru_RU
dc.description.abstract	Bioorganic & Medicinal Chemistry	ru_RU
dc.description.abstract	We demonstrated synthetically that the eight-membered heterocycles 2,6,9-triazabicyclo[3.3.1]nonanes and 1,5-diazacyclooctanes are the initial and exclusive products of the reaction, through an imino [4+4] cycloaddition, of biologically relevant amines with acrolein. The stabilities of the aminoacetals within the eight-membered heterocycles determined whether the product was subsequently transformed gradually into the 3-formyl-3,4-dehydropiperidine (FDP), which is widely used as an oxidative stress marker. The reactivity profiles discovered in this study suggested that some of the imino [4+4] cycloaddition products are reactive intermediates of FDP and contribute to the mechanisms underlying the oxidative stress response to acrolein.	ru_RU
dc.language.iso	ru	ru_RU
dc.subject	Acrolein	ru_RU
dc.subject	Biologically relevant amine	ru_RU
dc.subject	Biomarker	ru_RU
dc.subject	1	ru_RU
dc.subject	5-Diazacyclooctane	ru_RU
dc.subject	3-Formyl-3	ru_RU
dc.subject	4-dehydropiperidine (FDP)	ru_RU
dc.subject	Imino [4+4] cycloaddition	ru_RU
dc.subject	2	ru_RU
dc.subject	6	ru_RU
dc.subject	9-Triazabicyclo[3.3.1]nonane	ru_RU
dc.title	Imino [4+4] cycloaddition products as exclusive and biologically relevant acrolein-amine conjugates are intermediates of 3-formyl-3,4-dehydropiperidine (FDP), an acrolein biomarker	ru_RU
dc.type	Articles in international journals and collections	ru_RU