Valence Topological Charge-Transfer Indices for Dipole Moments: Percutaneous Enhancers

Torrens, Francisco

doi:10.3390/91201222

Cited by 10 publications

(7 citation statements)

References 39 publications

(36 reference statements)

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“…Fig. (6) shows how the dipole moments of the aliphatic amine series varied with the number of C atoms n [40]. Some points result superimposed.…”

Section: Results For Percutaneous Enhancersmentioning

confidence: 99%

“…The molecular dipole moments μ (experimental and calculated as vector semisums of CT-VCT indices) were obtained for both homologous series of phenyl alcohols and 4-alkylanilines [40]. For either series the μ experiment and calculated μ vec V vary together in an alternate fashion: for odd n, μ is greater than for even n; however μ vec presents the opposite tendency.…”

Section: Results For Percutaneous Enhancersmentioning

confidence: 99%

“…Generalized valence charge-transfer (VCT) indices were applied to the calculation of the molecular dipole moment of valence-isoelectronic series of benzene, styrene [36,37] and cyclopentadiene [38]. These indices were also applied to find transdermal-delivery drug models: percutaneous enhancers phenyl alcohols [39] and 4-alkylanilines [40]. Torrens has also examined the fractal dimension of phenyl alcohols [41] and 4-alkylanilines [42] and besides Torrens introduced a new chemical index inspired by biological plastic evolution and analyzed with it the valence-isoelectronic series of aromatics [43,44].…”

Section: Introductionmentioning

confidence: 99%

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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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“…Fig. (6) shows how the dipole moments of the aliphatic amine series varied with the number of C atoms n [40]. Some points result superimposed.…”

Section: Results For Percutaneous Enhancersmentioning

confidence: 99%

Section: Results For Percutaneous Enhancersmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Topological Charge-Transfer Indices: From Small Molecules to Proteins

Torrens¹,

Castellano²

2009

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“…In earlier publications, topological Charge-Transfer (CT) indices [12] were applied to the calculation of the molecular dipole moment of hydrocarbons [13], valence-isoelectronic series of benzene, styrene [14,15] and cyclopentadiene [16], as well as phenyl alcohols [17], 4-alkylanilines [18] and amino acids [19]. In the present article, the valence CT indices have been applied to the calculation of pH at the pI isoelectric point of 21 amino acids.…”

Section: Introductionmentioning

confidence: 99%

Improvement of charge-transfer indices for multifunctional amino acids: Application to lysozyme

Torrens

Castellano

2008

SAR and QSAR in Environmental Research

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Valence topological Charge-Transfer (CT) indices are applied to the calculation of pH at the isoelectric point (pI). The model is generalized for molecules with heteroatoms. The ability of the indices for the description of molecular charge distribution is established by comparing them with the pI of 21 amino acids. Linear correlation models are obtained. The CT indices improve multivariable regression equations for pI. The variance decreases by 95%. No superimposition of the corresponding G(k)-J(k) and G(k)(V)-J(k)(V) pairs is observed in most fits, which diminishes the risk of collinearity. The inclusion of heteroatoms in pi-electron system is beneficial for the description of pI, the because of either the role of the additional p orbitals provided by heteroatom or the role of steric factors in pi-electron conjugation. The use of CT/valence CT indices {G(k), J(k), G(k)(V), J(k)(V)} gives limited results for modelling amino acid pI. The inclusion of the number of acidic/basic groups improves the models. The effect is specially noticeable for amino acids with more than two functional groups. The fitting line for 21 amino acids is used to estimate lysozyme pI replacing (1 + Delta n/n(T)) with (M + Delta n)/n(T). The results for lysozyme fragments can estimate the pI of the whole protein with 1-13% error.

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“…In earlier publications, program TOPO was applied to the valence topological charge-transfer indices for the molecular dipole moment [41,42], as well as fractal dimension of percutaneous absorption enhancer phenyl alcohols [43] and 4-alkylanilines [44]. Lysozyme showed hydrolytic activity vs. peptidoglycans [45][46][47][48].…”

Section: ) Consisting Of Repeating Units Of Disaccharide D-glucuronicmentioning

confidence: 99%

Mucoadhesive Polymer Hyaluronan as Biodegradable Cationic/Zwitterionic-Drug Delivery Vehicle

Torrens

Castellano

2015

ADMET DMPK

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Valence Topological Charge-Transfer Indices for Dipole Moments: Percutaneous Enhancers

Cited by 10 publications

References 39 publications

Topological Charge-Transfer Indices: From Small Molecules to Proteins

Topological Charge-Transfer Indices: From Small Molecules to Proteins

Improvement of charge-transfer indices for multifunctional amino acids: Application to lysozyme

Mucoadhesive Polymer Hyaluronan as Biodegradable Cationic/Zwitterionic-Drug Delivery Vehicle

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