The kinetics of the reduction of the lipophilic quinone avarone by n-alkyl-1,4-dihydronicotinamides of various lipophilicities
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Several NADH model compounds, N-alkyl-1,4-dihydronicotinamides, some of them possessing amphiphilic properties, have been synthesized, and the kinetics of their reaction with a biologically active liphophilic quinone, avarone, has been studied in a protic solvent both in the presence and absence of cationic, anionic or non-ionic surfactants. In the absence of micellar agents, the medium- and long-chain N-dodecyl (3) and N-heptadecyl (4) derivatives show a significant increase in the reaction rates compared to other model compounds, due to the stabilization of the semiquinone intermediate. Anionic surfactants retard the reaction, non-ionic surfactants slightly accelerate the reaction with the short-chain derivatives, and retard the reaction with the medium- and long-chain derivatives, and the cationic surfactants increase the reaction rate with all derivatives except the long-chain 4. The results support the e-p-e mechanism of the reduction of lipophilic quinones by NADH models in proti...c medium.
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avarone / quinone / NADH models / surfactants / kineticsSource:
Journal of the Serbian Chemical Society, 1999, 64, 11, 647-654Publisher:
- Serbian Chemical Soc, Belgrade
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Hemijski fakultet / Faculty of ChemistryTY - JOUR AU - Zlatović, Mario AU - Sladić, Dušan AU - Gasic, MJ PY - 1999 UR - https://cherry.chem.bg.ac.rs/handle/123456789/424 AB - Several NADH model compounds, N-alkyl-1,4-dihydronicotinamides, some of them possessing amphiphilic properties, have been synthesized, and the kinetics of their reaction with a biologically active liphophilic quinone, avarone, has been studied in a protic solvent both in the presence and absence of cationic, anionic or non-ionic surfactants. In the absence of micellar agents, the medium- and long-chain N-dodecyl (3) and N-heptadecyl (4) derivatives show a significant increase in the reaction rates compared to other model compounds, due to the stabilization of the semiquinone intermediate. Anionic surfactants retard the reaction, non-ionic surfactants slightly accelerate the reaction with the short-chain derivatives, and retard the reaction with the medium- and long-chain derivatives, and the cationic surfactants increase the reaction rate with all derivatives except the long-chain 4. The results support the e-p-e mechanism of the reduction of lipophilic quinones by NADH models in protic medium. PB - Serbian Chemical Soc, Belgrade T2 - Journal of the Serbian Chemical Society T1 - The kinetics of the reduction of the lipophilic quinone avarone by n-alkyl-1,4-dihydronicotinamides of various lipophilicities VL - 64 IS - 11 SP - 647 EP - 654 UR - https://hdl.handle.net/21.15107/rcub_cherry_424 ER -
@article{ author = "Zlatović, Mario and Sladić, Dušan and Gasic, MJ", year = "1999", abstract = "Several NADH model compounds, N-alkyl-1,4-dihydronicotinamides, some of them possessing amphiphilic properties, have been synthesized, and the kinetics of their reaction with a biologically active liphophilic quinone, avarone, has been studied in a protic solvent both in the presence and absence of cationic, anionic or non-ionic surfactants. In the absence of micellar agents, the medium- and long-chain N-dodecyl (3) and N-heptadecyl (4) derivatives show a significant increase in the reaction rates compared to other model compounds, due to the stabilization of the semiquinone intermediate. Anionic surfactants retard the reaction, non-ionic surfactants slightly accelerate the reaction with the short-chain derivatives, and retard the reaction with the medium- and long-chain derivatives, and the cationic surfactants increase the reaction rate with all derivatives except the long-chain 4. The results support the e-p-e mechanism of the reduction of lipophilic quinones by NADH models in protic medium.", publisher = "Serbian Chemical Soc, Belgrade", journal = "Journal of the Serbian Chemical Society", title = "The kinetics of the reduction of the lipophilic quinone avarone by n-alkyl-1,4-dihydronicotinamides of various lipophilicities", volume = "64", number = "11", pages = "647-654", url = "https://hdl.handle.net/21.15107/rcub_cherry_424" }
Zlatović, M., Sladić, D.,& Gasic, M.. (1999). The kinetics of the reduction of the lipophilic quinone avarone by n-alkyl-1,4-dihydronicotinamides of various lipophilicities. in Journal of the Serbian Chemical Society Serbian Chemical Soc, Belgrade., 64(11), 647-654. https://hdl.handle.net/21.15107/rcub_cherry_424
Zlatović M, Sladić D, Gasic M. The kinetics of the reduction of the lipophilic quinone avarone by n-alkyl-1,4-dihydronicotinamides of various lipophilicities. in Journal of the Serbian Chemical Society. 1999;64(11):647-654. https://hdl.handle.net/21.15107/rcub_cherry_424 .
Zlatović, Mario, Sladić, Dušan, Gasic, MJ, "The kinetics of the reduction of the lipophilic quinone avarone by n-alkyl-1,4-dihydronicotinamides of various lipophilicities" in Journal of the Serbian Chemical Society, 64, no. 11 (1999):647-654, https://hdl.handle.net/21.15107/rcub_cherry_424 .