Passive Membrane Penetration of the Serotonin Precursor 5-Hydroxytryptophan is Controlled by Its Zwitterion

Chemistry & Biodiversity
Károly Mazák, Béla Noszál

Abstract

Species-specific partition coefficients in the octanol/water system were determined for the neurotransmitter serotonin (5-HT) and its precursor 5-hydroxytryptophan (5-HTP). The pH-independent partition coefficients (p) of the individual microspecies were determined by combination of experimentally measured distribution constants and a custom-tailored evaluation method, using highly similar auxiliary compounds. Experimental microscopic partition coefficients for triprotic molecules have only been reported before for thyroxine and its derivatives. The parabolic pH-distribution profile of 5-HT shows the dominance of the lipophilic non-charged microspecies, with a log p of 0.66. However, the most lipophilic non-charged form of 5-HTP, with a log p of 0.31, has no significant contribution to the distribution coefficient at any pH value. Instead, the less lipophilic zwitterionic protonation isomer dominates the distribution in the pH range 2.10 - 11.11. Although the non-charged microspecies of 5-HTP is 151 times more lipophilic than its zwitterionic protonation isomer, the overwhelming dominance of the zwitterionic form ensures that its contribution to the overall lipophilicity exceeds 1320 times that of the non-charged one. This fact...Continue Reading

References

Feb 20, 2002·Chemical Reviews·Alessandra PagliaraBernard Testa
Mar 20, 2002·Current Topics in Medicinal Chemistry·A Avdeef
Dec 12, 2002·Cellular and Molecular Life Sciences : CMLS·A Avdeef, B Testa
Jun 14, 2005·Biophysical Journal·Anita V ThomaeStefanie D Krämer
Jul 19, 2005·Pharmacology & Therapeutics·Erick H TurnerAaron D Blackwell
Dec 21, 2005·The Journal of Nutrition·Richard A HawkinsJuan R Viña
Mar 8, 2006·Journal of Pharmaceutical and Biomedical Analysis·Zoran Mandić, Vesna Gabelica
Nov 2, 2006·JAMA : the Journal of the American Medical Association·David S PatersonHannah C Kinney
Apr 9, 2009·Chemistry & Biodiversity·Károly MazákBéla Noszál
Nov 11, 2009·European Journal of Pharmaceutical Sciences : Official Journal of the European Federation for Pharmaceutical Sciences·Mie LarsenCarsten Uhd Nielsen
Nov 6, 2010·Pharmaceutical Research·Xiangli LiuAlfred Fahr
Feb 18, 2011·Cellular Physiology and Biochemistry : International Journal of Experimental Cellular Physiology, Biochemistry, and Pharmacology·Martina PavanettoRenzo Deana
Nov 29, 2011·European Journal of Pharmaceutical Sciences : Official Journal of the European Federation for Pharmaceutical Sciences·Károly Mazák, Béla Noszál
Jul 17, 2012·Journal of Medicinal Chemistry·Károly Mazák, Béla Noszál
Oct 3, 2012·European Journal of Pharmaceutical Sciences : Official Journal of the European Federation for Pharmaceutical Sciences·Károly MazákBéla Noszál
Jan 10, 2013·Journal of Pharmaceutical and Biomedical Analysis·Gergő TóthBéla Noszál
Oct 19, 2013·Journal of Mammary Gland Biology and Neoplasia·Aaron M MarshallNelson D Horseman
Jun 1, 2014·European Journal of Pharmaceutical Sciences : Official Journal of the European Federation for Pharmaceutical Sciences·Károly Mazák, Béla Noszál
Jul 1, 2015·European Journal of Pharmaceutical Sciences : Official Journal of the European Federation for Pharmaceutical Sciences·Károly MazákBéla Noszál
Apr 14, 2016·Journal of Pharmaceutical and Biomedical Analysis·Károly Mazák, Béla Noszál
Dec 25, 2016·Journal of Pharmaceutical and Biomedical Analysis·Károly MazákBéla Noszál

❮ Previous
Next ❯

Citations

May 21, 2020·ChemMedChem·Károly Mazák, Béla Noszál

❮ Previous
Next ❯

Related Concepts

Trending Feeds

COVID-19

Coronaviruses encompass a large family of viruses that cause the common cold as well as more serious diseases, such as the ongoing outbreak of coronavirus disease 2019 (COVID-19; formally known as 2019-nCoV). Coronaviruses can spread from animals to humans; symptoms include fever, cough, shortness of breath, and breathing difficulties; in more severe cases, infection can lead to death. This feed covers recent research on COVID-19.

Blastomycosis

Blastomycosis fungal infections spread through inhaling Blastomyces dermatitidis spores. Discover the latest research on blastomycosis fungal infections here.

Nuclear Pore Complex in ALS/FTD

Alterations in nucleocytoplasmic transport, controlled by the nuclear pore complex, may be involved in the pathomechanism underlying multiple neurodegenerative diseases including Amyotrophic Lateral Sclerosis and Frontotemporal Dementia. Here is the latest research on the nuclear pore complex in ALS and FTD.

Applications of Molecular Barcoding

The concept of molecular barcoding is that each original DNA or RNA molecule is attached to a unique sequence barcode. Sequence reads having different barcodes represent different original molecules, while sequence reads having the same barcode are results of PCR duplication from one original molecule. Discover the latest research on molecular barcoding here.

Chronic Fatigue Syndrome

Chronic fatigue syndrome is a disease characterized by unexplained disabling fatigue; the pathology of which is incompletely understood. Discover the latest research on chronic fatigue syndrome here.

Evolution of Pluripotency

Pluripotency refers to the ability of a cell to develop into three primary germ cell layers of the embryo. This feed focuses on the mechanisms that underlie the evolution of pluripotency. Here is the latest research.

Position Effect Variegation

Position Effect Variagation occurs when a gene is inactivated due to its positioning near heterochromatic regions within a chromosome. Discover the latest research on Position Effect Variagation here.

STING Receptor Agonists

Stimulator of IFN genes (STING) are a group of transmembrane proteins that are involved in the induction of type I interferon that is important in the innate immune response. The stimulation of STING has been an active area of research in the treatment of cancer and infectious diseases. Here is the latest research on STING receptor agonists.

Microbicide

Microbicides are products that can be applied to vaginal or rectal mucosal surfaces with the goal of preventing, or at least significantly reducing, the transmission of sexually transmitted infections. Here is the latest research on microbicides.

Related Papers

European Journal of Pharmaceutical Sciences : Official Journal of the European Federation for Pharmaceutical Sciences
Károly MazákBéla Noszál
European Journal of Pharmaceutical Sciences : Official Journal of the European Federation for Pharmaceutical Sciences
Károly MazákBéla Noszál
European Journal of Pharmaceutical Sciences : Official Journal of the European Federation for Pharmaceutical Sciences
Károly Mazák, Béla Noszál
Journal of Pharmaceutical and Biomedical Analysis
Károly MazákBéla Noszál
© 2022 Meta ULC. All rights reserved