title: Study of the Chemical Space of Selected Bacteriostatic Sulfonamides from an Information Theory Point of View.
abstract: The relative structural location of a selected group of 27 sulfonamide-like molecules in a chemical space defined by three information theory quantities (Shannon entropy, Fisher information, and disequilibrium) is discussed. This group is composed of 15 active bacteriostatic molecules, 11 theoretically designed ones, and para-aminobenzoic acid. This endeavor allows molecules that share common chemical properties through the molecular backbone, but with significant differences in the identity of the chemical substituents, which might result in bacteriostatic activity, to be structurally classified and characterized. This is performed by quantifying the structural changes on the electron density distribution due to different functional groups and number of electrons. The macroscopic molecular features are described by means of the entropy-like notions of spatial electronic delocalization, order, and uniformity. Hence, an information theory three-dimensional space (IT-3D) emerges that allows molecules with common properties to be gathered. This space witnesses the biological activity of the sulfonamides. Some structural aspects and information theory properties can be associated, as a result of the IT-3D chemical space, with the bacteriostatic activity of these molecules. Most interesting is that the active bacteriostatic molecules are more similar to para-aminobenzoic acid than to the theoretically designed analogues.
authors.affiliation: Departamento de Fsica Aplicada II, Universidad de Sevilla, 41012, Sevilla, Spain.|Instituto Carlos I de Fsica Teórica y Computacional, Universidad de Granada, 18071, Granada, Spain.
authors.forename: Sheila
authors.identifier: http://orcid.org/0000-0002-7667-8462
authors.initials: S
authors.lastname: López-Rosa
authors.affiliation: Departamento de Química, Universidad Autónoma Metropolitana, 09340-, Mexico City, México.
authors.forename: Moyocoyani
authors.initials: M
authors.lastname: Molina-Espíritu
authors.affiliation: Instituto Carlos I de Fsica Teórica y Computacional, Universidad de Granada, 18071, Granada, Spain.|Departamento de Química, Universidad Autónoma Metropolitana, 09340-, Mexico City, México.
authors.forename: Rodolfo O
authors.initials: RO
authors.lastname: Esquivel
authors.affiliation: Química Computacional, FES-Zaragoza, Universidad Nacional Autónoma de México, 09230-, Iztapalapa, Mexico City, México.
authors.forename: Catalina
authors.initials: C
authors.lastname: Soriano-Correa
authors.affiliation: Instituto Carlos I de Fsica Teórica y Computacional, Universidad de Granada, 18071, Granada, Spain.|Departamento de Fsica Atómica, Molecular y Nuclear, Universidad de Granada, 18071, Granada, Spain.
authors.forename: Jésus S
authors.initials: JS
authors.lastname: Dehesa
mesh_terms: D000900:Anti-Bacterial Agents / Q000737:chemistry* / Q000494:pharmacology; D001419:Bacteria / Q000187:drug effects; D019277:Entropy; D008826:Microbial Sensitivity Tests; D011789:Quantum Theory; D013449:Sulfonamides / Q000737:chemistry* / Q000494:pharmacology
chemical_list: D000900:Anti-Bacterial Agents; D013449:Sulfonamides
keywords: chemical space; electronic structure; information theory; structure-activity relationships; sulfonamides