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European Food Research and Technology

, Volume 240, Issue 1, pp 1–17 | Cite as

Nicotinic acid and derivatives as multifunctional pharmacophores for medical applications

  • Nujarin Sinthupoom
  • Veda Prachayasittikul
  • Supaluk PrachayasittikulEmail author
  • Somsak Ruchirawat
  • Virapong PrachayasittikulEmail author
Review Article

Abstract

Cardiovascular disease is one of the major health problems worldwide. It is a vascular condition known as an atherosclerosis referring to the accumulation of immune cells and lipids in vascular walls that finally obstructs blood flow to trigger heart attack. To prevent and treat the atherosclerosis is to control blood lipid level. Diverse classes of lipid-lowering drug have been used. Nicotinic acid (niacin or vitamin B3) is the first drug that has been used for over five decades. Nicotinic acid and its derivatives play important role as multifunctional pharmacophores exerting a variety of biological activities. This review focuses on the redox and non-redox reactions as well as antioxidant activity of nicotinic acid derivatives and drugs acting on nicotinic acid receptor including therapeutic and cosmetic applications. Structure–activity relationship of nicotinic acid derivatives has been discussed. This article could provide insight into the rational design and development of novel bioactive compounds with therapeutic potential.

Graphical Abstract

Keywords

Niacin Nicotinic acid derivatives Nicotinic acid receptor Pharmacophore Antioxidant Structure–activity relationships 

Abbreviations

VLDL

Very-low-density lipoprotein

IDL

Intermediate-density lipoprotein

LDL

Low-density lipoprotein

HDL

High-density lipoprotein

FDA

Food and Drug Administration

NAD+

Nicotinamide adenine dinucleotide

NADP+

Nicotinamide adenine dinucleotide phosphate

DNA

Deoxyribonucleic acid

SAR

Structure–activity relationship

FAD

Flavin adenine dinucleotide

ATP

Adenosine triphosphate

Acetyl CoA

Acetyl coenzyme A

TCA

Tricarboxylic acid

ROS

Reactive oxygen species

CYP450

Cytochrome P450

PARP

Poly ADP-ribose polymerase

PARG

Poly ADP-ribose glycohydrolase

cAMP

Cyclic adenosine monophosphate

PKA

Protein kinase A

HSL

Hormone-sensitive lipase

FFA

Free fatty acid

GPR

G-protein-coupled receptors

Gi-PRs

Inhibitory G-protein-coupled receptors

TMH

Transmembrane helices

ECL

Extracellular loop

PLA2

Phospholipase A2

HOMO

Highest occupied molecular orbital

LUMO

Lowest unoccupied molecular orbital

IP

Ionization potential

µ

Dipole moment

QSAR

Quantitative structure–activity relationships

MIC

Minimum inhibitory concentration

EA

Electron affinity

Notes

Acknowledgments

This project is supported by the Office of the Higher Education Commission, Mahidol University under the National Research Universities Initiative and Annual Government Grant of Mahidol University (2556–2558 B.E.).

Conflict of interest

None.

Compliance with Ethics Requirements

This article does not contain any studies with human or animal subjects.

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Copyright information

© Springer-Verlag Berlin Heidelberg 2014

Authors and Affiliations

  • Nujarin Sinthupoom
    • 1
  • Veda Prachayasittikul
    • 1
  • Supaluk Prachayasittikul
    • 2
    Email author
  • Somsak Ruchirawat
    • 3
  • Virapong Prachayasittikul
    • 1
    Email author
  1. 1.Department of Clinical Microbiology and Applied Technology, Faculty of Medical TechnologyMahidol UniversityBangkokThailand
  2. 2.Center of Data Mining and Biomedical Informatics, Faculty of Medical TechnologyMahidol UniversityBangkokThailand
  3. 3.Laboratory of Medicinal ChemistryChulabhorn Research Institute and Chulabhorn Graduate InstituteBangkokThailand

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