Cytotoxicity of selected imidazolium-derived ionic liquids in the human Caco-2 cell line. Sub-structural toxicological interpretation through a QSAR study

Physico-Chemical Properties of Task-Specific Ionic Liquids

“…Model demonstrates that toxicity increases with the ions lipophilicty and susceptibility to hydrolytic cleavage, and that the model of concentration addition may be useful to predict the EC 50 values of not studied ILs. [157] As seen in Table 2, this model reflects the toxicity of the different anions (values double underlined) showing that toxicity may depend on the anion structure. Putting the data together, we may assume that the non evidence of anion toxicity in the earlier studies was due of the lower size and lipophilicty of selected anions.…”

“…The S σ-profile of the cation located at the non-polar region was found to correlate with the lipophilicity parameter (LogK 0 ) determined by HPLC by Ranke et al and co-workers. [157] This neural network is able to demonstrate the lower toxicity of the imidazolium cations with oxygenated side chains as a result of the charge shift of the structure toward more polarized regions. Some of the estimated values can be seen in Table 2 and they are very close to the experimental values.…”

“…[150] Garcia-Lorenzo et al (2008) has developed a new a QSAR model using the Topological Sub-structural Molecular Design (TOPS-MODE) approach, which calculates the spectral moments of the fragments constituting each molecule. [157] The software used was the MODESLAB 1.5 software. Following this approach, the spectral moment is determined by the construction of a matrix where nondiagonal entries are ones or zeros if the corresponding bonds share one atom or not and diagonal entries describe several bond weights such as bond dipole moments, bond distance, partition coefficient, polar surface area, polarizability, Gasteiger-Marsilli atomic charges, van der Waals atomic radii and molar refractivity.…”

Topological sub-structural molecular design (TOPS-MODE): a useful tool to explore key fragments of human $$\mathbf{A}_{3}$$ A 3 adenosine receptor ligands

“…Furthermore, a review of the QSAR models based on knowledge of the agonist ligands has been previously reported [12]. Many computational protocols and various 2D and 3D descriptors have been reported, including Topological sub-structural molecular design (TOPS-MODE) approach [13], and molecular descriptors which have allowed obtaining QSAR/QSPR (Quantitative Structure Property Relationships) models very useful in medicinal chemistry [14][15][16] and toxicology [17,18].…”

Ionske kapljevine – razvoj i izazovi industrijske primjene

“…[67][68][69] Istraživanja sorpcije ionskih kapljevina na tlo 70,71 ukazala su da se 1-alkil-3-metilimidazolijevi kationi mogu snažno adsorbirati na različite vrste tla i morskih sedimenata te tako postati postojani kontaminanti u okolišu, dok mnogi autori 72,73 upozoravaju na relativno slabu aerobnu biorazgradnju imidazolijevih, piridinijevih, amonijevih i fosfonijevih ionskih kapljevina. Nadalje, ispitivanja toksičnost ionskih kapljevinama na organizmima koji se nalaze na različitim razinama hranidbenog lanca 60,[74][75][76] te na različitim staničnim linijama sisavaca i riba [77][78][79] upućuju na umjerenu do visoku toksičnost ove skupine spojeva. Općenito, primijećeno je da su sorpcija, (bio)razgradnja odnosno toksičnost znatno uvjetovani strukturom ionskih kapljevina, što upućuje na nuž-nost daljnjih istraživanja i stvaranja baze podataka o utjecaju ionskih kapljevina na okoliš, s ciljem dizajniranja biorazgradivih i netoksičnih ionskih kapljevina te kreiranja smjernica za postavljanje zakonske regulative za njihovu proizvodnju i uporabu.…”