IN SILICO STUDY OF LUPEOL DERIVATIVES AS A POTENTIAL ANTICANCER
Lupeol is a pentacyclic triterpenoid with hydrogen at the 3? position substituted by a hydroxy group. This compound is reported to show various pharmacological activities, one of which is as an anticancer. Several in vitro studies related to the anticancer activity of lupeol derivatives have been...
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id-itb.:629682022-01-24T09:44:04ZIN SILICO STUDY OF LUPEOL DERIVATIVES AS A POTENTIAL ANTICANCER Muslimawati, Khoirunnisa Indonesia Theses upeol, anticancer, molecular docking, molecular dynamics. INSTITUT TEKNOLOGI BANDUNG https://digilib.itb.ac.id/gdl/view/62968 Lupeol is a pentacyclic triterpenoid with hydrogen at the 3? position substituted by a hydroxy group. This compound is reported to show various pharmacological activities, one of which is as an anticancer. Several in vitro studies related to the anticancer activity of lupeol derivatives have been carried out before but only specific to certain types of cancer and certain derivative, also there have been no molecular studies related to these activities. The purpose of this study was to determine the pharmacophore and study the potential of lupeol derivative compounds as anticancer. The 3D structure of the receptor was obtained from the Protein Data Bank (PDB) page with the code 3ert (breast cancer), 1xkk (breast cancer), 3ruk (prostate cancer), 2xp2 (lung cancer), 1uwh (skin cancer), and 5i96 (blood cancer). Thirty-five lupeol derivatives were modeled using Avogadro 1.2.0 and optimized using Gaussian 09 with the DFT method (B3LYP/6-31G). Interaction studies were carried out by docking simulations and molecular dynamics using AutoDock 4.2 and Gromacs 5.1. Based on the docking simulation, three compounds of each receptor were selected to be studied further with molecular dynamics simulations. Molecular dynamics simulation results showed that all compounds bind in the same binding pocket as the comparison compound and were stable during the simulation time (50ns). Based on the analysis of the molecular dynamics simulation results, it was found that the test compound L17; L9; L4 (3ruk) and the test compound L29; L7 (2xp2) has a bond free energy value that is more negative than the respective standard compounds. These test compounds interact by utilizing the substituens at the C3 (formed the hydrogen bond) and the hydrophobic structure of the triterpene scaffold (formed the hydrophobic interaction). Based on these results, the test compounds of L17; L9; L4 targeting prostate cancer and L29; L7 targeting lung cancer, have the potential to further investigate its activity against each cancer target. text |
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Lupeol is a pentacyclic triterpenoid with hydrogen at the 3? position substituted by
a hydroxy group. This compound is reported to show various pharmacological
activities, one of which is as an anticancer. Several in vitro studies related to the
anticancer activity of lupeol derivatives have been carried out before but only
specific to certain types of cancer and certain derivative, also there have been no
molecular studies related to these activities. The purpose of this study was to
determine the pharmacophore and study the potential of lupeol derivative
compounds as anticancer. The 3D structure of the receptor was obtained from the
Protein Data Bank (PDB) page with the code 3ert (breast cancer), 1xkk (breast
cancer), 3ruk (prostate cancer), 2xp2 (lung cancer), 1uwh (skin cancer), and 5i96
(blood cancer). Thirty-five lupeol derivatives were modeled using Avogadro 1.2.0
and optimized using Gaussian 09 with the DFT method (B3LYP/6-31G). Interaction
studies were carried out by docking simulations and molecular dynamics using
AutoDock 4.2 and Gromacs 5.1. Based on the docking simulation, three compounds
of each receptor were selected to be studied further with molecular dynamics
simulations. Molecular dynamics simulation results showed that all compounds
bind in the same binding pocket as the comparison compound and were stable
during the simulation time (50ns). Based on the analysis of the molecular dynamics
simulation results, it was found that the test compound L17; L9; L4 (3ruk) and the
test compound L29; L7 (2xp2) has a bond free energy value that is more negative
than the respective standard compounds. These test compounds interact by utilizing
the substituens at the C3 (formed the hydrogen bond) and the hydrophobic structure
of the triterpene scaffold (formed the hydrophobic interaction). Based on these
results, the test compounds of L17; L9; L4 targeting prostate cancer and L29; L7
targeting lung cancer, have the potential to further investigate its activity against
each cancer target.
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format |
Theses |
author |
Muslimawati, Khoirunnisa |
spellingShingle |
Muslimawati, Khoirunnisa IN SILICO STUDY OF LUPEOL DERIVATIVES AS A POTENTIAL ANTICANCER |
author_facet |
Muslimawati, Khoirunnisa |
author_sort |
Muslimawati, Khoirunnisa |
title |
IN SILICO STUDY OF LUPEOL DERIVATIVES AS A POTENTIAL ANTICANCER |
title_short |
IN SILICO STUDY OF LUPEOL DERIVATIVES AS A POTENTIAL ANTICANCER |
title_full |
IN SILICO STUDY OF LUPEOL DERIVATIVES AS A POTENTIAL ANTICANCER |
title_fullStr |
IN SILICO STUDY OF LUPEOL DERIVATIVES AS A POTENTIAL ANTICANCER |
title_full_unstemmed |
IN SILICO STUDY OF LUPEOL DERIVATIVES AS A POTENTIAL ANTICANCER |
title_sort |
in silico study of lupeol derivatives as a potential anticancer |
url |
https://digilib.itb.ac.id/gdl/view/62968 |
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1822932059727855616 |