The kinetics of the reduction of the lipophilic quinone avarone by n-alkyl-1,4-dihydronicotinamides of various lipophilicities
Kinetika redukcije lipofilnog hinona avarona n-alkyl-1,4-di -hidronikotinamidima različite lipofilnosti
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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 protic ...medium.
Sintetisano je nekoliko N-alkil-1,4-dihidronikotinamida, model-jedinjenja
NADH, od kojih neki imaju amfifilne osobine, i proučavana je kinetika njihove
reakcije sa biološkim aktivnim, lipofilnim hinonom avaronom u protinom
rastvaraču u prisustvu katjonskih, anjonskih ili nejonskih površinski aktivnih supstanci i bez njh.Bez dodatih micelarnih agenasa, N-dodecil-derivat 3 (derivat srednje
dužine niza) i dugolančani N-heptadecil-derivat 4 pokazuju značajno povećanje brzine
reakcije u poređenju sa drugim model-jedinjenjima, usled stabilizacije semihinonskih
intermedijera. Anjonski površinski aktivni agensi usporavaju reakciju, nejonski
agensi dovode do slabog ubrzanja sa derivatima kratkog alkilniza, a usporavaju reak
ciju sa derivatima srednjeg i dugog niza, dok katjonski agensi ubrzavaju reakciju sa svim
derivatima, sem sa dugolančanim 4. Rezultati ukazuju na mehanizam e-p-e redukcije
lipofilnih hinona modelima NADH u protičnom medijumu.
Keywords:
Avarone / Kinetics / NADH models / Quinone / SurfactantsSource:
Journal of the Serbian Chemical Society, 1999, 64, 11, 647-654Publisher:
- Belgrade : Serbian Chemical Society
DOI: 10.2298/JSC9911647Z
ISSN: 0352-5139; 1820-7421
WoS: 000083803100001
Scopus: 2-s2.0-0033263339
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IHTMTY - JOUR AU - Zlatović, Mario AU - Gašić, Miroslav J. AU - Sladić, Dušan PY - 1999 UR - https://cer.ihtm.bg.ac.rs/handle/123456789/4398 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. AB - Sintetisano je nekoliko N-alkil-1,4-dihidronikotinamida, model-jedinjenja NADH, od kojih neki imaju amfifilne osobine, i proučavana je kinetika njihove reakcije sa biološkim aktivnim, lipofilnim hinonom avaronom u protinom rastvaraču u prisustvu katjonskih, anjonskih ili nejonskih površinski aktivnih supstanci i bez njh.Bez dodatih micelarnih agenasa, N-dodecil-derivat 3 (derivat srednje dužine niza) i dugolančani N-heptadecil-derivat 4 pokazuju značajno povećanje brzine reakcije u poređenju sa drugim model-jedinjenjima, usled stabilizacije semihinonskih intermedijera. Anjonski površinski aktivni agensi usporavaju reakciju, nejonski agensi dovode do slabog ubrzanja sa derivatima kratkog alkilniza, a usporavaju reak ciju sa derivatima srednjeg i dugog niza, dok katjonski agensi ubrzavaju reakciju sa svim derivatima, sem sa dugolančanim 4. Rezultati ukazuju na mehanizam e-p-e redukcije lipofilnih hinona modelima NADH u protičnom medijumu. PB - Belgrade : Serbian Chemical Society 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 T1 - Kinetika redukcije lipofilnog hinona avarona n-alkyl-1,4-di -hidronikotinamidima različite lipofilnosti VL - 64 IS - 11 SP - 647 EP - 654 DO - 10.2298/JSC9911647Z ER -
@article{ author = "Zlatović, Mario and Gašić, Miroslav J. and Sladić, Dušan", 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., Sintetisano je nekoliko N-alkil-1,4-dihidronikotinamida, model-jedinjenja NADH, od kojih neki imaju amfifilne osobine, i proučavana je kinetika njihove reakcije sa biološkim aktivnim, lipofilnim hinonom avaronom u protinom rastvaraču u prisustvu katjonskih, anjonskih ili nejonskih površinski aktivnih supstanci i bez njh.Bez dodatih micelarnih agenasa, N-dodecil-derivat 3 (derivat srednje dužine niza) i dugolančani N-heptadecil-derivat 4 pokazuju značajno povećanje brzine reakcije u poređenju sa drugim model-jedinjenjima, usled stabilizacije semihinonskih intermedijera. Anjonski površinski aktivni agensi usporavaju reakciju, nejonski agensi dovode do slabog ubrzanja sa derivatima kratkog alkilniza, a usporavaju reak ciju sa derivatima srednjeg i dugog niza, dok katjonski agensi ubrzavaju reakciju sa svim derivatima, sem sa dugolančanim 4. Rezultati ukazuju na mehanizam e-p-e redukcije lipofilnih hinona modelima NADH u protičnom medijumu.", publisher = "Belgrade : Serbian Chemical Society", 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, Kinetika redukcije lipofilnog hinona avarona n-alkyl-1,4-di -hidronikotinamidima različite lipofilnosti", volume = "64", number = "11", pages = "647-654", doi = "10.2298/JSC9911647Z" }
Zlatović, M., Gašić, M. J.,& Sladić, D.. (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 Belgrade : Serbian Chemical Society., 64(11), 647-654. https://doi.org/10.2298/JSC9911647Z
Zlatović M, Gašić MJ, Sladić D. 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. doi:10.2298/JSC9911647Z .
Zlatović, Mario, Gašić, Miroslav J., Sladić, Dušan, "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://doi.org/10.2298/JSC9911647Z . .