title: Chemometric analysis of correlations between electronic absorption characteristics and structural and/or physicochemical parameters for ampholytic substances of biological and pharmaceutical relevance.
abstract: Forty ampholytic compounds of biological and pharmaceutical relevance were subjected to chemometric analysis based on unsupervised and supervised learning algorithms. This enabled relations to be found between empirical spectral characteristics derived from electronic absorption data and structural and physicochemical parameters predicted by quantum chemistry methods or phenomenological relationships based on additivity rules. It was found that the energies of long wavelength absorption bands are correlated through multiparametric linear relationships with parameters reflecting the bulkiness features of the absorbing molecules as well as their nucleophilicity and electrophilicity. These dependences enable the quantitative analysis of spectral features of the compounds, as well as a comparison of their similarities and certain pharmaceutical and biological features. Three QSPR models to predict the energies of long-wavelength absorption in buffers with pH=2.5 and pH=7.0, as well as in methanol, were developed and validated in this study. These models can be further used to predict the long-wavelength absorption energies of untested substances (if they are structurally similar to the training compounds).
authors.affiliation: Faculty of Chemistry, University of Gdańsk, Wita Stwosza 63, 80-308 Gdańsk, Poland; Research Laboratory, Polpharma S.A., Pelplińska 19, 80-200 Starogard Gdański, Poland.
authors.forename: U
authors.initials: U
authors.lastname: Judycka-Proma
authors.affiliation: Research Laboratory, Polpharma S.A., Pelplińska 19, 80-200 Starogard Gdański, Poland.
authors.forename: L
authors.initials: L
authors.lastname: Bober
authors.affiliation: Faculty of Chemistry, University of Gdańsk, Wita Stwosza 63, 80-308 Gdańsk, Poland.
authors.forename: A
authors.initials: A
authors.lastname: Gajewicz
authors.affiliation: Faculty of Chemistry, University of Gdańsk, Wita Stwosza 63, 80-308 Gdańsk, Poland. Electronic address: tomasz.puzyn@ug.edu.pl.
authors.forename: T
authors.initials: T
authors.lastname: Puzyn
authors.affiliation: Faculty of Chemistry, University of Gdańsk, Wita Stwosza 63, 80-308 Gdańsk, Poland. Electronic address: jerzy.blazejowski@ug.edu.pl.
authors.forename: J
authors.initials: J
authors.lastname: Błażejowski
mesh_terms: D065966:Absorption, Physicochemical; D002021:Buffers; D004583:Electrons; D006863:Hydrogen-Ion Concentration; D008958:Models, Molecular; D004364:Pharmaceutical Preparations / Q000737:chemistry*; D025341:Principal Component Analysis; D021281:Quantitative Structure-Activity Relationship; D013223:Statistics as Topic
chemical_list: D002021:Buffers; D004364:Pharmaceutical Preparations
keywords: Ampholytes of biological and pharmaceutical relevance; Chemometric analysis; Quantitative Structure–Property Relationships; Similarity analysis; Spectral (experimental) versus physicochemical (predicted) molecular characteristics