QSAR study of estrogens with the help of PM3‐based descriptors

Pasha, Farhan Ahmad; Srivastava, H. K.; Singh, Priyanka

doi:10.1002/qua.20569

Cited by 44 publications

(32 citation statements)

References 34 publications

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“…The hardness, initially a qualitative concept, has now been put on sound quantum mechanical basis and the concept is further sublimated by enunciation of maximum hardness principle. Hardness provides with a better picture due to the maximum hardness principle and can be used as a QSAR model for predicting biological activity of any compound [42]. But structures are no static.…”

Section: Resultsmentioning

confidence: 99%

A Quest for the Origin of Barrier to the Internal Rotation ofHydrogen Peroxide (H2O2) and Fluorine Peroxide (F2O2)

Ghosh

2006

IJMS

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Abstract:In order to understand the structure-property relationship, SPR, an energypartitioning quest for the origin of the barrier to the internal rotation of two iso-structural molecules, hydrogen peroxide, H 2 O 2 , and fluorine peroxide, F 2 O 2 is performed. The hydrogen peroxide is an important bio-oxidative compound generated in the body cells to fight infections and is an essential ingredient of our immune system. The fluorine peroxide is its analogue. We have tried to discern the interactions and energetic effects that entail the nonplanar skew conformation as the equilibrium shape of the molecules. The physical process of the dynamics of internal rotation initiates the isomerization reaction and generates infinite number of conformations. The decomposed energy components faithfully display the physical process of skewing and eclipsing as a function of torsional angles and hence are good descriptors of the process of isomerization reaction of hydrogen peroxide (H 2 O 2 ) and dioxygen difluoride (F 2 O 2 ) associated with the dynamics of internal rotation. It is observed that the one-center, two-center bonded and nonbonded interaction terms are sharply divided in two groups. One group of interactions hinders the skewing and favours planar cis/trans forms while the other group favours skewing and prefers the gauche conformation of the molecule. The principal energetic effect forcing the molecules into the nonplanar gauche form is the variation "O-O' bond energy with torsion in both the molecules. It is demonstrated that the barrier is not a regional effect rather it is made by the conjoint action of all one-and two-center bonding and nonbonding interactions comprising the entire framework of the molecule. The present study claims to reveal one amazing feature of nonbonded interactions. Computed results of nonbonding interactions demonstrate that the nature of interaction between two formally positively charged non-bonding H atoms (H δ+ ----

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Section: Resultsmentioning

confidence: 99%

A Quest for the Origin of Barrier to the Internal Rotation ofHydrogen Peroxide (H2O2) and Fluorine Peroxide (F2O2)

Ghosh

2006

IJMS

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“…A measure lower than one, in turn, assesses the steroid as androgenic. 10 Several authors had developed quantitative structure-activity relationship (QSAR) models for estrogens, 11 androgens, 12 progestagens, 13 and corticosteroid 14 steroid hormones. The dataset of steroids, studied more extensively with different methods by several research groups, is the steroid benchmark with the corresponding globulin affinity.…”

Section: Introductionmentioning

confidence: 99%

Applying pattern recognition methods plus quantum and physico‐chemical molecular descriptors to analyze the anabolic activity of structurally diverse steroids

et al. 2007

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The great cost associated with the development of new anabolic-androgenic steroid (AASs) makes necessary the development of computational methods that shorten the drug discovery pipeline. Toward this end, quantum, and physicochemical molecular descriptors, plus linear discriminant analysis (LDA) were used to analyze the anabolic/androgenic activity of structurally diverse steroids and to discover novel AASs, as well as also to give a structural interpretation of their anabolic-androgenic ratio (AAR). The obtained models are able to correctly classify 91.67% (86.27%) of the AASs in the training (test) sets, respectively. The results of predictions on the 10% full-out cross-validation test also evidence the robustness of the obtained model. Moreover, these classification functions are applied to an "in house" library of chemicals, to find novel AASs. Two new AASs are synthesized and tested for in vivo activity. Although both AASs are less active than some commercially AASs, this result leaves a door open to a virtual variational study of the structure of the two compounds, to improve their biological activity. The LDA-assisted QSAR models presented here, could significantly reduce the number of synthesized and tested AASs, as well as could increase the chance of finding new chemical entities with higher AAR.

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“…In this paper forty nine phenols [29] and are reported in This model includes the molecular weight, total energy, hardness and chemical potential. All these values are molecular property and we already have tested these values as a molecular descriptor in our previous communication [30][31][32][33][34][35] . The predicted activity (A Pred) from equation-12 is reported in table-2.…”

Section: Resultsmentioning

confidence: 99%

DFT Based Electrophilicity Index and QSAR study of Phenols as Anti Leukaemia Agent

Pasha¹,

Srivastava²,

Beg³

et al. 2006

American J. of Immunology

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Density Functional reactivity indices based QSAR study of 49 phenol derivatives is presented in this paper. Two different models to describe the anti leukaemia activity of phenols have been made. First QSAR model includes molecular properties like molecular weight (Mw), hardness (η), chemical potential (µ), total energy, and electrophilicity index (ω). Various regression models have been made and regression quality indicates that these descriptors provides valuable information and have significant role in assessment of activity of phenols. Klopman gave first quantum chemical treatment to describe the reactivity of a chemical system in terms of acidic softness E n and basic softness E m at atomic level. In this paper we have derived the partial electrophilicity by the multiplication of global electrophilicity index (given by Parr etal) and the acidic softness En (given by Klopman). This total electrophilicity index has been used as descriptors along with the other atomic properties like highest negative charge (Q min ) etc in second QSAR model. This model also provides good results. The DFT calculations have been performed by using B88-PW91 GGA energy functional with the DZVP basis set on Cache pro software and the regression models have been made on project leader software associated with CAChe. These DFT models have high predictive power and have sufficient reliability to describe the Anti leukaemia activity of phenols which is clear from its correlation coefficient r 2 and cross validation coefficient r cv 2 .

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QSAR study of estrogens with the help of PM3‐based descriptors

Cited by 44 publications

References 34 publications

A Quest for the Origin of Barrier to the Internal Rotation ofHydrogen Peroxide (H2O2) and Fluorine Peroxide (F2O2)

A Quest for the Origin of Barrier to the Internal Rotation ofHydrogen Peroxide (H2O2) and Fluorine Peroxide (F2O2)

Applying pattern recognition methods plus quantum and physico‐chemical molecular descriptors to analyze the anabolic activity of structurally diverse steroids

DFT Based Electrophilicity Index and QSAR study of Phenols as Anti Leukaemia Agent

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