Abstract
Alkaloids occupy an important position in chemistry and pharmacology. Among the various alkaloids, berberine and coralyne of the protoberberine group, sanguinarine of the benzophenanthridine group, and aristololactam-b -d-glucoside of the aristolochia group have potential to form molecular complexes with nucleic acid structures and have attracted recent attention for their prospective clinical and pharmacological utility. Sanguinarine is an alkaloid studied in the treatment of cancer cell proliferation. Found in several plants, is used in traditional medicine from several countries with Mexico and India in the natural treatment of wounds, conjunctivitis and as hallucinogen. Is a toxic quaternary ammonium salt from the group of benzylisoquinoline alkaloids. It is extracted from some plants, including bloodroot (Sanguinaria canadensis), Mexican prickly poppy (Argemone mexicana Linn) Chelidonium majus and Macleaya cordata. It is also found in the root, stem and leaves of the opium poppy but not in the capsule. Sanguinarine is a toxin that kills animal cells through its action on the Na+-K+-ATPase transmembrane protein. Due to the diverse properties of this alkaloid, via computational methods was made using quantum chemistry to try to clarify some molecular properties that characterize its main sites of action as a drug. A study was made on a molecular structure of the sanguinarine, by Molecular Mechanics, PM3, Hartree-Fock, Density Functional Theory and Moller-Plesset. For calculations a cluster of six computers was used with Prescott-256 Celeron© D processors. The first principles calculations have been performed to study the equilibrium configuration of Sanguinarine molecule. Several physical properties have been calculated, including formation enthalpies, entropies, dipole moments, and the infrared emission/absorption spectrum. The results showed that the main site of molecular interaction was determined to be the hydrogen atoms. This has a strong antioxidant potential in its structure. It probably interacts with free radicals reducing their carcinogenic effect on cells. A study of the infrared spectrum complemented the paper. Absorption peaks in the infrared spectrum at 1000 cm-1, for calculation MP2/6-31G and, 1240 and 1450 cm-1 for B3LYP/6-311G ** were obtained. The MP2 and B3LYP methods showed good results for the infrared absorption spectrum. Although the base used in the MP2 method is less accurate, compared to the B3LYP whose base xxx has more accurate and broader functionalities, they are approximately equal for frequency peaks located in the 1060.6 cm-1 and 991.1 cm-1 range.
Highlights
Sanguinarine has been shown to inhibit proliferation of several types of human cancer cell including multidrugresistant cells, whereas it has minimal cytotoxicity against normal cells such as neutrophils and keratinocytes
A study was made on a molecular structure of the sanguinarine, by Molecular Mechanics [16,17,18,19,20,21,22,23,24,25,26,27,28,29], PM3 [28], Hartree-Fock [28, 30, 31], Density Functional Theory [28] and Møller-Plesset [28]
Molecular mechanics methods are based on the following principles: Nuclei and electrons are lumped into atom-like particles; Atom-like particles are spherical and have a net charge; Interactions are based on springs and classical potentials; Interactions must be preassigned to specific sets of atoms; Interactions determine the spatial distribution of atom-like particles and their energies; Note how these principles differ from those of quantum mechanics. [30,31,32,33,34]
Summary
Sanguinarine has been shown to inhibit proliferation of several types of human cancer cell including multidrugresistant cells, whereas it has minimal cytotoxicity against normal cells such as neutrophils and keratinocytes. Ricardo Gobato and Alireza Heidari: Infrared Spectrum and Sites of Action of Sanguinarine by Molecular Mechanics and ab initio Methods. The benzophenanthridines sanguinarine (SA) and dihydrosanguinarine (DHSA) display antimicrobiae and cytotoxic activities These alkaloids are accumulated in roots and mature seeds, whereas berberine, a protoberberine alkaloid with antiviral properties, is accrued both in aerial and underground tissues. The alkaloids Allocryptopine, Dihydrosanguinarine, Protopine and Sanguinarine have density similar negative and positive charges. Due to the diverse properties of this alkaloid, via computational methods was made using quantum chemistry to try to clarify some molecular properties that characterize its main sites of action as a drug. It presents a file in. pdb format (protein date bank), for the verification of the readers
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