Determination of the lipophilicity of quinolinesulfonamides by reversed-phase HPLC and theoretical calculations

Marciniec, Krzysztof; Bafeltowska, Jolanta; Maślankiewicz, Maria J.; Buszman, Ewa; Boryczka, Stanisław

doi:10.1080/10826076.2016.1234394

Cited by 10 publications

(4 citation statements)

References 29 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Parameter describing this property is lipophilicity that is defined as the partition coefficient between the an aqueous phase and the non-aqueous phase usually 1-octanol and is expressed as log P (Arnott et al, 2012). One of the best methods to determine concentration of a compound in various solvents needed to determine lipophilicity is reversed-phase high performance liquid chromatography (RP-HPLC) (Marciniec et al, 2016). Therefore, for the determination of relative lipophilicity of triazene derivatives 2a - 2i we used reversed-phase ultra-performance liquid chromatography (RP UPLC), based upon sub 3-µm porous particles.…”

Section: Resultsmentioning

confidence: 99%

Triazene salts: Design, synthesis, ctDNA interaction, lipophilicity determination, DFT calculation, and antiproliferative activity against human cancer cell lines

Cytarska

Anisiewicz

Baranowska-Łączkowska

et al. 2019

Saudi Pharmaceutical Journal

View full text Add to dashboard Cite

Synthesis, characterization and investigation of antiproliferative activity of nine triazene salts against human cancer cells lines (MV-4-11, MCF-7, JURKAT, HT-29, Hep-G2, HeLa, Du-145 and DAUDI), and normal human mammary epithelial cell line (MCF7-10A) is presented. The structures of novel compounds were determined using 1H and 13C NMR, and GC-APCI-MS analyses. Among the derivatives, compound 2c, 2d, 2e and 2f has very strong activity against biphenotypic B myelomonocytic leukemia MV4-11, with IC50 values from 5.42 to 7.69 µg/ml. The cytotoxic activity of compounds 2c-2f against normal human mammary gland epithelial cells MCF-10A is 6–11 times lower than against cancer cell lines. Our results also show that compounds 2c and 2f have very strong activity against DAUDI and HT-29 with IC50 4.91 µg/ml and 5.59 µg/ml, respectively. Their lipophilicity was determined using reversed-phase ultra-performance liquid chromatography and correlated with antiproliferative activity. Our UV–Vis spectroscopic results indicate also that triazene salts tends to interact with negatively charged DNA phosphate chain. To support the experiment, theoretical calculations of the 1H NMR shifts were carried out within the Density Functional Theory.

show abstract

Section: Resultsmentioning

confidence: 99%

Triazene salts: Design, synthesis, ctDNA interaction, lipophilicity determination, DFT calculation, and antiproliferative activity against human cancer cell lines

Cytarska

Anisiewicz

Baranowska-Łączkowska

et al. 2019

Saudi Pharmaceutical Journal

View full text Add to dashboard Cite

show abstract

“…Chromatographically determined parameters R MW and logk w are powerful lipophilicity descriptors [1]. Numerous studies have been performed in order to determine the lipophilic properties of different bioactive compounds as drugs or new drug candidates, including the new purine-2,6-dione derivatives, newly synthesized celecoxib analogues, thiosemicarbazides, quinolone sulfonamides, benzenesulfonohydrazides, 1,2,3-triazoledipyridothiazine hybrids, betulin derivatives, selected steroid derivatives, chalcones, and flavonoids, by using liquid chromatographic techniques, including RP-TLC [6][7][8][9][10][11][12][13][14][15][16][17][18][19][20]. Among various chromatographic separation methods, RP-TLC is an easy-to-use and low-cost chromatographic technique.…”

Section: Introductionmentioning

confidence: 99%

A Comparative Study of the Lipophilicity of Metformin and Phenformin

2021

View full text Add to dashboard Cite

The results presented in this paper confirm the beneficial role of an easy-to-use and low-cost thin-layer chromatography (TLC) technique for describing the retention behavior and the experimental lipophilicity parameter of two biguanide derivatives, metformin and phenformin, in both normal-phase (NP) and reversed-phase (RP) TLC systems. The retention parameters (RF, RM) obtained under different chromatographic conditions, i.e., various stationary and mobile phases in the NP-TLC and RP-TLC systems, were used to determine the lipophilicity parameter (RMW) of metformin and phenformin. This study confirms the poor lipophilicity of both metformin and phenformin. It can be stated that the optimization of chromatographic conditions, i.e., the kind of stationary phase and the composition of mobile phase, was needed to obtain the reliable value of the chromatographic lipophilicity parameter (RMW) in this study. The fewer differences in the RMW values of both biguanide derivatives were ensured by the RP-TLC system composed of RP2, RP18, and RP18W plates and the mixture composed of methanol, propan-1-ol, and acetonitrile as an organic modifier compared to the NP-TLC analysis. The new calculation procedures for logP of drugs based on topological indices 0χν, 0χ, 1χν, M, and Mν may be a certain alternative to other algorithms as well as the TLC procedure performed under optimized chromatographic conditions. The knowledge of different lipophilicity parameters of the studied biguanides can be useful in the future design of novel and more therapeutically effective metformin and phenformin formulations for antidiabetic and possible anticancer treatment. Moreover, the topological indices presented in this work may be further used in the QSAR study of the examined biguanides.

show abstract

“…Lipophilicity is a paramount descriptor which represents an essential part in design of new medications with required biological action [1]. It is also used in quantitative structure activity relationship (QSAR) investigations.…”

Section: Introductionmentioning

confidence: 99%

“…In the last few years, a great interest has been given for RP-HPLC as a tool for lipophilicity estimation and for characterization of pharmacological activity of molecules [11–13]. This is attributed to the close relationship between the retention performance of molecules in reversed phase chromatographic system and its lipophilicity [14].…”

Section: Introductionmentioning

confidence: 99%

Assessment of lipophilicity of newly synthesized celecoxib analogues using reversed-phase HPLC

et al. 2019

View full text Add to dashboard Cite

Background Lipophilicity is a physicochemical property of an essential importance in medicinal chemistry; therefore, fast and reliable measurement of lipophilicity will affect greatly the drug discovery process. Results A series of N -benzenesulfonamide-1 H -pyrazoles, oximes and hydrazones as celecoxib analogues was investigated with regard to their retention behavior using reversed-phase high performance liquid chromatography (RP-HPLC). The mobile phases employed for this study consist of a mixture of water and methanol in different proportions. In addition, the stationary phase utilized for this separation was C 18 silanized silica gel and using 200 nm as a detection wavelength. The retention behavior of the investigated compounds was determined based on practical determination of log k at different concentrations of methanol (as an organic modifier) in the mobile phase ranging from 60 to 80%. It was observed that the retention of these compounds (expressed as log k ) decreased in a linear manner with increasing the concentration of methanol. High correlation coefficients (more than 0.90 in most cases) were obtained for the relationship between the volume fraction of the organic solvent and the retention values represented as log k w . A comparative evaluation was carried out between chromatographically-obtained lipophilicity parameters (represented as lipophilicity chromatographic index log k w or isocratic chromatographic hydrophobicity index, 0 ) and the computationally calculated log P values (miLogP, ALOGP, ACD/Labs and ALOGPs). Conclusion It was found that a good correlation exists between the experimental and computed log P values. In the future, these results can give a deep insight about the anti-inflammatory and analgesic activity of the newly synthesized compounds. Electronic supplementary material The online version of this article (10.1186/s13065-019-0607-6) contains supplementary material, which is available to authorized users.

show abstract

Determination of the lipophilicity of quinolinesulfonamides by reversed-phase HPLC and theoretical calculations

Cited by 10 publications

References 29 publications

Triazene salts: Design, synthesis, ctDNA interaction, lipophilicity determination, DFT calculation, and antiproliferative activity against human cancer cell lines

Triazene salts: Design, synthesis, ctDNA interaction, lipophilicity determination, DFT calculation, and antiproliferative activity against human cancer cell lines

A Comparative Study of the Lipophilicity of Metformin and Phenformin

Assessment of lipophilicity of newly synthesized celecoxib analogues using reversed-phase HPLC

Contact Info

Product

Resources

About