Comparative Molecular Field Analysis of Heterocyclic Monoazo Dye−Fiber Affinities

Abstract

This paper presents quantitative structure-activity relationship (QSAR) models for a series of 21 heterocyclic monoazo dyes applied on cellulose fiber by comparative molecular field analysis. The electronic and structural properties of these dyes were calculated by the semiempirical PM3 method; the results indicate the predominance of electrostatic interactions in dye-cellulose binding. The dominant contribution of the LUMO orbital molecular energy, used as descriptor, can be explained by the contribution to the solvation of the dye molecules.

Continuous indicator fields: a novel universal type of molecular fields

“…Various 2D and 3D-QSPR models for Dl have been reported in literature [43,44]. Its 3D-QSPR modeling have mostly been performed in the framework of the pharmacophore concept [45][46][47][48][49][50][51] and using the hypothesis concerning the availability of specific binding sites inside cavities in the crystalline areas of cellulose. Several 3D-QSPR models for azo and anthraquinone vat dyes have been built using CoMFA [45][46][47][48][49] and CoMSA [50,51] methods.…”

“…Its 3D-QSPR modeling have mostly been performed in the framework of the pharmacophore concept [45][46][47][48][49][50][51] and using the hypothesis concerning the availability of specific binding sites inside cavities in the crystalline areas of cellulose. Several 3D-QSPR models for azo and anthraquinone vat dyes have been built using CoMFA [45][46][47][48][49] and CoMSA [50,51] methods. It has been shown that the affinity of anthraquinone vat dyes to cellulose is largely dominated by electrostatic and steric interactions, whereas the additions of molecular orbital (HOMO and LUMO) energies along with dipole moments to the set of descriptors does not vary the model performance [46].…”

Mapping dye pharmacophores by the Comparative Molecular Surface Analysis (CoMSA): application to heterocyclic monoazo dyes

“…This scheme uses a single Kohonen network (a template network) for processing data from more than one molecule. Then, we can sample points on Table 1 Experimental dye affinity (ÀÁm 0 ) [12] of heterocyclic azo dyes arid this included by the CoMSA method …”

“…Although it is not clear if we can treat it similarly to the contacts taking place during targeting a receptor by a drug molecule, several QSAR studies have been published recently [4][5][6][7][8][9][10][11] that make use of this concept in investigations of cellulose dyeing. Both 2D and 3D QSAR modeling have been applied including the Hansch, MTD and Comparative Molecular Surface Analysis (C0MFA) methods that appeared to provide quite satisfactory models for different compound series [8][9][10]12]. In particular, the results of the CoMFA method indicated that the electrostatic field dominantly contributes to the dyeing affinity.…”

“…The aim of the current study is a systematic analysis of the tinctorial properties of heterocyclic monoazo dyes using the Comparative Molecular Surface Analysis (CoMSA) as a novel method for 3D QSAR modeling [14][15][16][17]. Dyeing cellulose with these compounds has been investigated by Alberti et al [18][19][20] and CoMFA study has been reported elsewhere [12]. We endeavored to use the CoMSA method both for verifying the applicability of the pharmcophore concept in dye chemistry as well as for discussing some more general rules in modeling 3D QSAR.…”