Prediction of solubility parameters using partial least square regression

Tantishaiyakul, Vimon; Worakul, Nimit; Wongpoowarak, Wibul

doi:10.1016/j.ijpharm.2006.06.009

Cited by 41 publications

(31 citation statements)

References 29 publications

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“…The aromatic part of benzocaine is an aniline, which has a dipole moment of 1.5 Debye due to the lone electron pair of nitrogen delocalizing into the aromatic ring. The other side of the molecule has an aromatic ring of the ester group further increasing the dipole moment of benzocaine to 3.9 Debye29. Benzocaine is an arylamine, and for this class of compounds the partial positive charges on the hydrogen atoms of the primary amino group are ~+0.22 electronic charge, and the charge on N is about −0.4230.…”

Section: Resultsmentioning

confidence: 99%

Using Lidocaine and Benzocaine to Link Sodium Channel Molecular Conformations to State-Dependent Antiarrhythmic Drug Affinity

Hanck

Nikitina

McNulty

et al. 2009

Circulation Research

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A subset share characteristics that make them effective as antiarrhythmic drugs, ie, they exhibit high affinity, use-dependent block of Na current (I Na ) at high heart rates. Despite extensive study, there remains uncertainty regarding how observed block relates to specific drug-channel conformations. Several vocabularies have emerged to describe block, which in general, have their basis in kinetic models of Na channel gating and assume preferential binding to one or more states that produce no 1 or altered 2 gating. Recent availability of crystal structures in combination with mutagenesis data now allow for linking electrophysiological data, kinetic states, and drug block to specific channel conformations.It is generally accepted that lidocaine and lidocaine-like drugs bind in the inner pore of voltage-gated Na channels. Scanning mutagenesis studies with various Na channel isoforms and multiple lidocaine-like drugs have identified only one amino acid residue, a phenylalanine (Phe) in domain IV, S6 (DIVS6), which, when mutated, alters use-dependent drug affinity by more than ten-fold. When this Phe (1759 in Na V 1.5) is mutated to nonaromatic residues 3-8 or to unnatural amino acids with different electron withdrawing capabilities 9 the mutated channel shows a marked decrease in high-affinity LA block. Homology modeling with K channels predicts that this Phe faces the pore just below the selectivity filter. 10,11 This orientation of Phe is supported by the finding that its cysteine mutant is accessible to MTS reagents applied from inside the pore when the channel is maintained in an open state. 12 Furthermore, it has been shown by us 13 and others 14 that use-dependent block is intimately associated with altered movements of the structurally distant S4 segments in domains III and IV.Block assayed from negative holding potentials at low rates of stimulation is affected very little by channel mutations in contract to their effects on use-dependent block. This lower affinity block is usually called tonic block, although it has also been called rested-state block (or closed-state block)

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Section: Resultsmentioning

confidence: 99%

Using Lidocaine and Benzocaine to Link Sodium Channel Molecular Conformations to State-Dependent Antiarrhythmic Drug Affinity

Hanck

Nikitina

McNulty

et al. 2009

Circulation Research

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“…In chemical engineering developments, thermodynamic models such as Universal Quasichemical Activity Coefficient (UNIQUAC) or Non-Random Two Liquid (NRTL) models (Chen and Crafts, 2006) based on the concept of local composition or the Universal Functional Activity Coefficient (UNIFAC) predictive model (Gracin et al, 2002) using group contributions are more commonly used (Manifar and Rohani, 2005). Another approach consists in collecting experimental and theoretical molecular descriptors which are analyzed by using statistical techniques in order to obtain Quantitative Structure-Property Relationship (QSPR) models (Code et al, 2008;Tantishaiyakul et al, 2006;Yu et al, 2006) and/or solvent classifications (Chastrette et al, 1985;Gramatica et al, 1999;Katritzky et al, 2005;Xu and Redman-Furey, 2007).…”

Section: Introductionmentioning

confidence: 99%

Determination of poly(ɛ-caprolactone) solubility parameters: Application to solvent substitution in a microencapsulation process

Bordes¹,

Fréville²,

Ruffin³

et al. 2010

International Journal of Pharmaceutics

176

106

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“…Literature [18–20] shows the possibility in calculating the δ of polymers via MD techniques. Additionally, simulations on bulk systems of moderate size (1000–5000 atoms) using recent systematically-derived “class II” forcefields such as “COMPASS” are capable of making predictions of δ with an accuracy that compares with experiment [21–25].…”

Section: Introductionmentioning

confidence: 99%

Molecular modeling of temperature dependence of solubility parameters for amorphous polymers

et al. 2011

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A molecular modeling strategy is proposed to describe the temperature (T) dependence of solubility parameter (δ) for the amorphous polymers which exhibit glass-rubber transition behavior. The commercial forcefield “COMPASS” is used to support the atomistic simulations of the polymer. The temperature dependence behavior of δ for the polymer is modeled by running molecular dynamics (MD) simulation at temperatures ranging from 250 up to 650 K. Comparing the MD predicted δ value at 298 K and the glass transition temperature (Tg) of the polymer determined from δ–T curve with the experimental value confirm the accuracy of our method. The MD modeled relationship between δ and T agrees well with the previous theoretical works. We also observe the specific volume (v), cohesive energy (Ucoh), cohesive energy density (ECED) and δ shows a similar temperature dependence characteristics and a drastic change around the Tg. Meanwhile, the applications of δ and its temperature dependence property are addressed and discussed.

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Prediction of solubility parameters using partial least square regression

Cited by 41 publications

References 29 publications

Using Lidocaine and Benzocaine to Link Sodium Channel Molecular Conformations to State-Dependent Antiarrhythmic Drug Affinity

Using Lidocaine and Benzocaine to Link Sodium Channel Molecular Conformations to State-Dependent Antiarrhythmic Drug Affinity

Determination of poly(ɛ-caprolactone) solubility parameters: Application to solvent substitution in a microencapsulation process

Molecular modeling of temperature dependence of solubility parameters for amorphous polymers

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