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Nicotinic acid and derivatives as multifunctional pharmacophores for medical applications

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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.

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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

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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.).

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None.

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

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Authors and Affiliations

  1. Department of Clinical Microbiology and Applied Technology, Faculty of Medical Technology, Mahidol University, Bangkok, 10700, Thailand

    Nujarin Sinthupoom, Veda Prachayasittikul & Virapong Prachayasittikul

  2. Center of Data Mining and Biomedical Informatics, Faculty of Medical Technology, Mahidol University, Bangkok, 10700, Thailand

    Supaluk Prachayasittikul

  3. Laboratory of Medicinal Chemistry, Chulabhorn Research Institute and Chulabhorn Graduate Institute, Bangkok, 10210, Thailand

    Somsak Ruchirawat

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  1. Nujarin Sinthupoom
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  2. Veda Prachayasittikul
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  5. Virapong Prachayasittikul
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Correspondence to Supaluk Prachayasittikul or Virapong Prachayasittikul.

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Sinthupoom, N., Prachayasittikul, V., Prachayasittikul, S. et al. Nicotinic acid and derivatives as multifunctional pharmacophores for medical applications. Eur Food Res Technol 240, 1–17 (2015). https://doi.org/10.1007/s00217-014-2354-1

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  • DOI: https://doi.org/10.1007/s00217-014-2354-1

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