Implementing Molecular Connectivity Theory, a Basic Tool in Modeling Drugs

Pogliani, Lionello

doi:10.1002/jps.20862

Cited by 9 publications

(12 citation statements)

References 41 publications

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“…Some points appear superimposed. The degeneracies are 10, 10, 4+2, 10, 4+2, 10, 4+2, 10, 4+2 and 10 for G [1][2][3][4][5] …”

Section: Results For the Correction For Sp 3 -Heteroatomcontaining Comentioning

confidence: 99%

“…Pogliani has examined from molecular connectivity indices to semi-empirical connectivity terms and recent trends in graph theoretical descriptors [1] and implemented the molecular connectivity theory as a basic tool in modeling drugs [2]. García-Domenech et al [3], Estrada et al [4], and Vilar et al [5] have also reviewed new trends in the applications of chemical graph theory to small molecules.…”

Section: Introductionmentioning

confidence: 98%

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Topological Charge-Transfer Indices: From Small Molecules to Proteins

Torrens¹,

Castellano²

2009

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Valence-topological charge-transfer indices are applied to the calculation of dipole moment-pH at the isoelectric point. Dipole moments calculated by algebraic-vector semisums of charge-transfer indices are defined. The ability of indices, for the description of molecular charge distribution, is established by comparing them with the dipole moment of the valence-isoelectronic series of cyclopentadiene-benzene-styrene. Both charge-transfer indices are proposed: vector semisums μ vec -μ vec V . The μ vec V is intermediate between μ vec and μ experiment . The steric effect is almost constant along series and the dominating effect is electronic. The indices are applied to the calculation of the dipole moments of the homologous series of percutaneous enhancers and the isoelectric point of 21 amino acids. In most fits no superimposition of the corresponding G k -J k /G k V -J k V pairs is observed, which diminishes the risk of collinearity. The inclusion of heteroatoms in the -electron systems is beneficial for the description of isoelectric point, because of either the role of additional p-orbitals provided by heteroatom or the role of steric factors in the -electron conjugation. The use of (valence) chargetransfer indices gives limited results for amino-acid isoelectric points. The inclusion of the number of acidic/basic groups improves the models, especially for amino acids with more than two functional groups. The fitting line for 21 amino acids is used to estimate the lysozyme isoelectric point by replacing (1+ n/n T ) with (M+ n)/n T . The lysozyme fragment results can estimate the isoelectric point of the whole protein within 1-13% error.

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“…Some points appear superimposed. The degeneracies are 10, 10, 4+2, 10, 4+2, 10, 4+2, 10, 4+2 and 10 for G [1][2][3][4][5] …”

Section: Results For the Correction For Sp 3 -Heteroatomcontaining Comentioning

confidence: 99%

Section: Introductionmentioning

confidence: 98%

Topological Charge-Transfer Indices: From Small Molecules to Proteins

Torrens¹,

Castellano²

2009

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“…For all other compounds a AH 5 0 is used. With the introduction of this 'ad hoc' theoretical descriptor ( Table 3, T b column, in parenthesis) and the exclusion of 0 v d of the last combination in order to avoid improvement due to the increasing number of descriptors, the quality of the model is, For T b the first, second and third subsets obtained excluding the '#' (18), '8' (28), and '# 1 8' (38) items in Table 3, it is found that the last descriptor gives rise to the following statistics:…”

Section: Model Based On Graph-theoretical MC Indicesmentioning

confidence: 99%

“…K 0 graphs may be used to encode the depleted hydrogen atoms. In fact, the depleted hydrogen atoms (or K 0 graphs) can be encoded by the aid of the following fractional perturbation term, [16][17][18] Exponent n is no optimization parameter, it just quantifies the importance of the hydrogen atoms in a model study, i.e., the higher the n values the lower the importance of the perturbation introduced by the hydrogen atoms. Different values of n give rise to different sets of indices, where in each set n is constant, i.e., the corresponding d v is constant.…”

Section: Introductionmentioning

confidence: 99%

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Model of twelve properties of a set of organic solvents with graph‐theoretical and/or experimental parameters

Pogliani

2009

J Comput Chem

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Twelve properties of a highly heterogeneous class of organic solvents have been modeled with a graph-theoretical molecular connectivity modified (MC) method, which allows to encode the core electrons and the hydrogen atoms. The graph-theoretical method uses the concepts of simple, general, and complete graphs, where these last types of graphs are used to encode the core electrons. The hydrogen atoms have been encoded by the aid of a graph-theoretical perturbation parameter, which contributes to the definition of the valence delta, delta(v), a key parameter in molecular connectivity studies. The model of the twelve properties done with a stepwise search algorithm is always satisfactory, and it allows to check the influence of the hydrogen content of the solvent molecules on the choice of the type of descriptor. A similar argument holds for the influence of the halogen atoms on the type of core electron representation. In some cases the molar mass, and in a minor way, special "ad hoc" parameters have been used to improve the model. A very good model of the surface tension could be obtained by the aid of five experimental parameters. A mixed model method based on experimental parameters plus molecular connectivity indices achieved, instead, to consistently improve the model quality of five properties. To underline is the importance of the boiling point temperatures as descriptors in these last two model methodologies.

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Applications of Chemical Graph Theory to Organic Molecules

Pogliani

2011

Carbon Bonding and Structures

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Implementing Molecular Connectivity Theory, a Basic Tool in Modeling Drugs

Cited by 9 publications

References 41 publications

Topological Charge-Transfer Indices: From Small Molecules to Proteins

Topological Charge-Transfer Indices: From Small Molecules to Proteins

Model of twelve properties of a set of organic solvents with graph‐theoretical and/or experimental parameters

Applications of Chemical Graph Theory to Organic Molecules

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