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Pregled bibliografske jedinice broj: 641755

Does tautomerism influence the outcome of QSAR modeling?


Masand, Vijay H.; Mahajan, Devidas T.; Hadda, Taibi Ben; Jawarkar, Rahul D.; Alafeefy, Ahmed M.; Rastija, Vesna; Ali, Mohamed Ashraf
Does tautomerism influence the outcome of QSAR modeling? // Medicinal chemistry research, 23 (2014), 4; 1742-1757 doi:10.1007/s00044-013-0776-0 (međunarodna recenzija, članak, znanstveni)


CROSBI ID: 641755 Za ispravke kontaktirajte CROSBI podršku putem web obrasca

Naslov
Does tautomerism influence the outcome of QSAR modeling?

Autori
Masand, Vijay H. ; Mahajan, Devidas T. ; Hadda, Taibi Ben ; Jawarkar, Rahul D. ; Alafeefy, Ahmed M. ; Rastija, Vesna ; Ali, Mohamed Ashraf

Izvornik
Medicinal chemistry research (1054-2523) 23 (2014), 4; 1742-1757

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
tautomerism ; QSAR ; statistical robustness ; stepwise regression ; genetic algorithm

Sažetak
Tautomerism is an important aspect associated with a variety of pharmacologically and biologically active compounds. It is a challenge to account for tautomerism in computer-aided drug designing (CADD). The estimations and calculations of many physico- chemical properties and theoretical descriptors of the molecules are sensitive to tautomerism. In this study, we have attempted to analyze the effect of tautomerism on feature selection and statistical performance/characteristics of conventional quantitative structure–activity relationship (QSAR) equations. These equations are developed using 2D and 3D-descriptors employing two different statistical methods, i.e., genetic algorithm (GA) and stepwise regression (SR). Five datasets of moderate sizes viz. (1) anti-malarial activity of synthetic prodiginines against multi-drug resistant strain (N = 43), (2) anti-malarial activity of bisaryl quinolones (N = 37), (3) anti-malarial activity of phosphoramidate and phosphorothioamidate analogs of amiprophos methyl (N = 36), (4) anti-proliferative activity of substituted N-phenyl ureidobenzenesulfonate derivatives (N = 44), and (5) anti-HIV activity of indolylarylsulfones as HIV-1 non-nucleoside reverse transcriptase inhibitors (N = 36) showing different types of tautomerism were used in the study. In each case, the developed model and the selected descriptors derived using one tautomer were applied on other tautomeric forms to understand the influence of tautomerism on QSAR equations. Different parameters like R, R2, Radj 2 , Rcv 2 , F, S and Y-randomization were used for thorough validation of all the models. The results revealed that tautomerism has significant influence on feature selection. In addition, it was found that tautomerism has a great influence on the performance of QSAR models of the second and the third datasets. However, no significant influence was observed on the statistical characteristics of QSAR models for datasets 1, 4, and 5. Therefore, it is suggested that separate models need to be developed for different tautomeric forms of a dataset.

Izvorni jezik
Engleski

Znanstvena područja
Kemija, Farmacija



POVEZANOST RADA


Projekt / tema
4663 - Odnos strukture i aktivnosti flavonoida (Dragan Amić, MZOS)

Ustanove
Fakultet agrobiotehničkih znanosti Osijek

Profili:

Avatar Url Vesna Rastija (autor)

Citiraj ovu publikaciju

Masand, Vijay H.; Mahajan, Devidas T.; Hadda, Taibi Ben; Jawarkar, Rahul D.; Alafeefy, Ahmed M.; Rastija, Vesna; Ali, Mohamed Ashraf
Does tautomerism influence the outcome of QSAR modeling? // Medicinal chemistry research, 23 (2014), 4; 1742-1757 doi:10.1007/s00044-013-0776-0 (međunarodna recenzija, članak, znanstveni)
Masand, V., Mahajan, D., Hadda, T., Jawarkar, R., Alafeefy, A., Rastija, V. & Ali, M. (2014) Does tautomerism influence the outcome of QSAR modeling?. Medicinal chemistry research, 23 (4), 1742-1757 doi:10.1007/s00044-013-0776-0.
@article{article, year = {2014}, pages = {1742-1757}, DOI = {10.1007/s00044-013-0776-0}, keywords = {tautomerism, QSAR, statistical robustness, stepwise regression, genetic algorithm}, journal = {Medicinal chemistry research}, doi = {10.1007/s00044-013-0776-0}, volume = {23}, number = {4}, issn = {1054-2523}, title = {Does tautomerism influence the outcome of QSAR modeling?}, keyword = {tautomerism, QSAR, statistical robustness, stepwise regression, genetic algorithm} }

Časopis indeksira:


  • Current Contents Connect (CCC)
  • Web of Science Core Collection (WoSCC)
    • Science Citation Index Expanded (SCI-EXP)
    • SCI-EXP, SSCI i/ili A&HCI
  • Scopus


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