Molecular lipophilicity determination of a huperzine series by HPLC: comparison of C18 and IAM stationary phases.

J Pharm Biomed Anal

Equipe des Sciences Séparatives et Biopharmaceutiques (2SB, EA/3924), Laboratoire de Chimie Analytique et de Chimie Thérapeutique, Faculté de Médecine et de Pharmacie, Place Saint-Jacques, 25030 Besançon cedex, France.

Published: April 2006

Two hydrophobic parameters (logkw-C18 and logkw-IAM, respectively) of a huperzine A series were extrapolated by high performance liquid chromatography (HPLC) using both C18 and immobilised artificial membrane (IAM) columns. A mathematical correlation between C18 and IAM hydrophobic parameters was completed, suggesting a similar behaviour on both columns. This behaviour was principally led by hydrophobic forces. The theoretical lipophilicity (logP) of each compound was computed using Pallas software and compared to experimental values, showing a similar lipophilic behaviour. Finally, the huperzine logkw-IAM and logkw-C18 values were correlated with the relative bound percentage of huperzine in human serum albumin, confirming that hydrophobic forces are predominant in the huperzine-HSA binding mechanism.

Download full-text PDF

Source
http://dx.doi.org/10.1016/j.jpba.2005.11.011DOI Listing

Publication Analysis

Top Keywords

huperzine series
8
c18 iam
8
hydrophobic parameters
8
hydrophobic forces
8
molecular lipophilicity
4
lipophilicity determination
4
huperzine
4
determination huperzine
4
series hplc
4
hplc comparison
4

Similar Publications

Design, synthesis and anti-Alzheimer's disease activity evaluation of C-3 arylated huperzine A derivatives.

Fitoterapia

September 2024

Sichuan Research Center for Drug Precision Industrial Technology, West China School of Pharmacy, Sichuan University, Chengdu 610041, PR China. Electronic address:

A series of C-3 arylated huperzine A (HPA) derivatives (1-30) were designed and synthesized in good yields via palladium-catalyzed Suzuki cross-coupling reaction. Cholinesterase inhibitory and neuroprotective activities of all 30 derivatives were evaluated. Cholinesterase inhibition results revealed that derivatives 2 and 15 exhibited dual inhibitory activity against both acetylcholinesterase (AChE inhibition: 2, IC = 1.

View Article and Find Full Text PDF
Article Synopsis
  • - Plants create a variety of alkaloids that resemble animal neurotransmitters, but many of these alkaloids come from structures with unclear biosynthetic pathways and enzymes.
  • - Researchers discovered that neofunctionalized α-carbonic anhydrases (CAHs) play a key role in the biosynthesis of Lycopodium alkaloids by facilitating important chemical reactions.
  • - The study highlights how unique enzyme actions can enhance the effectiveness of compounds like huperzine A, which inhibits acetylcholinesterase, indicating a complex interplay between enzyme function and alkaloid potency in plants.
View Article and Find Full Text PDF

N-Doped Carbon Nanotubes Supported Fe-Mn Dual-Single-Atoms Nanozyme with Synergistically Enhanced Peroxidase Activity for Sensitive Colorimetric Detection of Acetylcholinesterase and Its Inhibitor.

Anal Chem

June 2023

Key Laboratory of the Ministry of Education for Advanced Catalysis Materials, College of Chemistry and Materials Science, College of Geography and Environmental Sciences, Zhejiang Normal University, Jinhua 321004, China.

Monitoring acetylcholinesterase (AChE) and its inhibitors is of importance for early diagnosis and therapy of neurological diseases. Herein, N-doped carbon nanotubes supported Fe-Mn dual-single-atoms (FeMn DSAs/N-CNTs) were fabricated by a simple pyrolysis, as thoroughly figured out by a series of the characterization techniques. The peroxidase-like activity of FeMn DSAs/N-CNTs was investigated by catalytic oxidation of 3,3',5,5'-tetramethylbenzidine (TMB) to generate rich hydroxyl radicals (·OH) in the HO system, which effectively catalyzed colorless TMB oxidation to blue oxidized TMB (ox-TMB).

View Article and Find Full Text PDF

Palladium-catalyzed synthesis and acetylcholinesterase inhibitory activity evaluation of 1-arylhuperzine A derivatives.

J Asian Nat Prod Res

November 2023

Sichuan Engineering Research Center for Biomimetic Synthesis of Natural Drugs, School of Life Science and Engineering, Southwest Jiaotong University, Chengdu 610031, China.

A series of arylated huperzine A (HPA) derivatives (-) were efficiently synthesized in good yields (45-88% yields) through the late-stage modification of structurally complex natural anti-Alzheimer's disease (AD) drug huperzine A (HPA), using the palladium-catalyzed Suzuki-Miyaura cross-coupling reaction. The acetylcholinesterase (AChE) inhibitory activity of all synthesized compounds was evaluated to screen the potential anti-AD bioactive molecules. The results showed that introducing the aryl groups to C-1 position of HPA resulted in the unsatisfactory AChE inhibitory activity.

View Article and Find Full Text PDF

The complete chloroplast genome of the medical plant Huperzia crispata from the Huperziaceae family: structure, comparative analysis, and phylogenetic relationships.

Mol Biol Rep

December 2022

Key Laboratory of Plant Secondary Metabolism Regulation in Zhejiang Province, College of Life Sciences and Medicine, Zhejiang Sci-Tech University, Hangzhou, 310018, Zhejiang, China.

Background: Huperzia crispata, belonging to the Huperziaceae family, is one of the most essential resources of huperzine A for candidate drugs to treat Alzheimer's diseases. However, there is very limited information about H. crispat, and its taxonomic status and interspecific relationships between Huperzia species are still unclear.

View Article and Find Full Text PDF

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!