Infrared Spectrum and Sites of Action of Sanguinarine by Molecular Mechanics and <i>ab initio</i> Methods

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 Møller-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.

The Creation of C13H20BeLi2SeSi. The Proposal of a Bio- Inorganic Molecule, Using Ab Initio Methods for The Genesis of a Nano Membrane

“…Molecular mechanics calculates the energy of a molecule and then adjusts the energy through changes in bond lengths and angles to obtain the minimum energy structure [8][9][10][11][12][13][14][15][16][17][18][19][20][21][22][23][24].…”

“…Several simulations were performed, always having as initial dynamics the use of Molecular Mechanics [8][9][10][11][12][13][14][15][16][17][18][19][20][21][22][23][24] for the initial molecular structure, moving to ab initio calculations of quantum chemistry. All attempts were thwarted.…”

“…The silicon atom binds in double bond with the carbon chain and Selenium. It binds in double with beryllium and is simple with the two lithium atoms, thus making a stable molecular structure for Molecular Mechanics [8][9][10][11][12][13][14][15][16][17][18][19][20][21][22][23][24], Mm+ and Bio+ Charmm [26]. But in quantum calculations the seed molecule changed all its fundamental structure [1].…”

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“…The kurumi seed molecule has been well characterized, [1][2][3][4][5][6][7][8][9] and is in accordance with the ab initio computational methods [10][11][12][13][14]. Now the challenge is to build the basic structure of the bioinorganic membrane.…”

“…The study evolved to construct a biomembrane from the seed molecule (kurumi) [1][2][3][4][5][6][7][8]. The calculations default already performed admit a hydrophobic and hydrophilic molecule, the basis of the formation of a micelle and or biomembrane, as the default template [9].…”