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Analytical and Bioanalytical Chemistry

, Volume 394, Issue 3, pp 707–729 | Cite as

Analytical tools for the physicochemical profiling of drug candidates to predict absorption/distribution

  • Yveline Henchoz
  • Bruno Bard
  • Davy Guillarme
  • Pierre-Alain Carrupt
  • Jean-Luc Veuthey
  • Sophie MartelEmail author
Review

Abstract

The measurement of physicochemical properties at an early phase of drug discovery and development is crucial to reduce attrition rates due to poor biopharmaceutical properties. Among these properties, ionization, lipophilicity, solubility and permeability are mandatory to predict the pharmacokinetic behavior of NCEs (new chemical entities). Due to the high number of NCEs, the analytical tools used to measure these properties are automated and progressively adapted to high-throughput technologies. The present review is dedicated to experimental methods applied in the early drug discovery process for the determination of solubility, ionization constants, lipophilicity and permeability of small molecules. The principles and experimental conditions of the different methods are described, and important enhancements in terms of throughput are highlighted.

Figure

Scheme of the Drug Research Process.

Keywords

Physicochemical profiling Solubility Ionization constant Lipophilicity Permeability Experimental models 

Abbreviations

ACN

Acetonitrile

ADME

Absorption, distribution, metabolism and elimination

ADMET

Absorption, distribution, metabolism, elimination and toxicity

APCI

Atmospheric pressure chemical ionization

API

Atmospheric pressure ionization

APPI

Atmospheric pressure photoionization

b

Gradient steepness

BBB

Blood–brain barrier

CAD

Corona aerosol discharge

CAPS

3-(Cyclohexylamino)-1-propanesulfonic acid

CCD

Contactless conductivity detection

CE

Capillary electrophoresis

CNS

Central nervous system

CNS+

Compounds crossing the blood–brain barrier

CNS−

Compounds not transported into the brain

CZE

Capillary zone electrophoresis

DAD

Diode array detector

DME

Dimethyl ether

DMSO

Dimethyl sulfoxide

ELSD

Evaporating light scattering detector

EOF

Electroosmotic flow

ESI

Electrospray ionization

FaSSIF

Fasted state simulated intestinal fluid

FeSSIF

Fed state simulated intestinal fluid

HEPES

4-(2-Hydroxyethyl)piperazine-1-propanesulfonic acid

HILIC

Hydrophilic interaction liquid chromatography

HPLC

High-performance liquid chromatography

HTS

High-throughput screening

IAM

Immobilized artificial membrane

ITIES

Interface between two immiscible electrolyte solutions

k

Retention factor

ki

Retention factor at the initial gradient composition

LC

Liquid chromatography

Leff

Effective length of the capillary

LEKC

Liposome electrokinetic chromatography

log DpH

Logarithm of the distribution coefficient at a given pH

log kIAM

Logarithm of the retention factor measured on immobilized artificial membrane columns

log kw

Logarithm of the retention factor extrapolated to 100% water

log P

Logarithm of the partition coefficient

log Pa

Apparent permeability coefficient

log Pe

Effective permeability coefficient

log PI

Logarithm of the partition coefficient of an ion

log Plip

Logarithm of the partition coefficient in liposomes/water system

log Poct

Logarithm of the partition coefficient in the 1-octanol/water system

LOQ

Limit of quantification

LSER

Linear solvation free-energy relationship

LSS

Linear solvent strength

Ltot

Total length of the capillary

LYSA

Lyophilized solubility assay

MEEKC

Microemulsion electrokinetic chromatography

MEKC

Micellar electrokinetic chromatography

MeOH

Methanol

MES

2-Morpholinoethanesulfonic acid

MS

Mass spectrometry

NCE

New chemical entity

NMR

Nuclear magnetic resonance

NQAD

Nano-quantity analyte detector

ODS

Octadecyl-bonded silica

PACE

Pressure-assisted capillary electrophoresis

PAMPA

Parallel artificial membrane permeability assay

PC

Phosphatidylcholine

PC

Polycarbonate

PDMAC

Poly(diallyldimethylammonium chloride)

PK

Pharmacokinetic

pKa

Ionization constant

\({\text{p}}K^{{{\text{app}}}}_{{\text{a}}} \)

Apparent ionization constant

PVDF

Polyvinylidene fluoride

PVS

Poly(vinylsulfonate)

RI

Refractive index

RPLC

Reversed-phase liquid chromatography

SAR

Structure–activity relationship

SDS

Sodium dodecyl sulfate

t0

Column dead time

tD

System dwell time

tEOF

Migration time of the electroosmotic flow marker

tG

Gradient time

tm

Migration time

tmc

Migration time of the micelle marker

tEOF

Migration time of the EOF marker

tR

Retention time of a compound

U

Tension

UHPLC

Ultrahigh-pressure liquid chromatography

VEKC

Vesicle electrokinetic chromatography

z

Charge

Δϕ

Change in composition of the mobile phase during the gradient

μeff

Effective mobility

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Copyright information

© Springer-Verlag 2009

Authors and Affiliations

  • Yveline Henchoz
    • 1
  • Bruno Bard
    • 1
  • Davy Guillarme
    • 1
  • Pierre-Alain Carrupt
    • 1
  • Jean-Luc Veuthey
    • 1
  • Sophie Martel
    • 1
    Email author
  1. 1.School of Pharmaceutical SciencesUniversity of Geneva, University of LausanneGeneva 4Switzerland

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