In silico DFT and ADME studies of Dehydrostenine A
- 1Institute of Medical Research and Medicinal Plants Studies (IMPM), P.O. Box 6163, Yaoundé, Cameroon and Department of Organic Chemistry, University of Yaoundé I, P.O Box 812, Yaoundé, Cameroon
- 2Institute of Medical Research and Medicinal Plants Studies (IMPM), P.O. Box 6163, Yaoundé, Cameroon, Department of Organic Chemistry, University of Yaoundé I, P.O Box 812, Yaoundé, Cameroon and Department of Pharmacy, Faculty of Medicine and Pharmaceutical Sciences, University of Douala, P.O Box 812, Douala, Cameroon
- 3Institute of Medical Research and Medicinal Plants Studies (IMPM), P.O. Box 6163, Yaoundé, Cameroon
Res.J.chem.sci., Volume 8, Issue (9), Pages 7-11, September,18 (2018)
Alkaloids are secondary metabolites with more or less complex structures. It's interest in computerized chemistry is little noticed unlike phytochemistry. This work consists in calculating vibrational frequencies and physico-chemical properties of a firstly optimized dehydrostenine A (DsA), a true alkaloid isolated from Stemona sessilifolia. The structural analysis was carried out using aRMSD, which allowed to visualize the differences with the crystalline structure and calculate the deviations. The chemical properties were obtained with Qikprop and revealed a very good absorbability for human oral distribution.
- Facchini P.J. (2001)., Alkaloid biosynthesis in plants: biochemistry, cell biology, molecular regulation, and metabolic engineering applications., Annual review of plant biology, 52(1), 29-66.
- Pilli R.A., Rosso G.B. and de Oliveira M.D.C.F. (2010)., The chemistry of Stemona alkaloids: An update., Natural product reports, 27(12), 1908-1937.
- Carlsson A., Lindqvist M. and Magnusson T.O.R. (1957)., 3, 4-Dihydroxyphenylalanine and 5-hydroxytryptophan as reserpine antagonists., Nature, 180(4596), 1200.
- Gorrod J.W. and Wahren J. (1993)., Nicotine and Related Alkaloids., London, England: Chapman and Hall, page xv. ISBN: 978-94-011-2110-1.
- Turabekova M.A., Rasulev B.F., Dzhakhangirov F.N. and Salikhov S.I. (2008)., Aconitum and Delphinium alkaloids: "Drug-likeness" descriptors related to toxic mode of action., Environmental toxicology and pharmacology, 25(3), 310-320.
- Dong J.L., Yang Z.D., Zhou S.Y., Yu H.T., Yao X.J., Xue H.Y. and Shu Z.M. (2017)., Two Stemona alkaloids from Stemona sessilifolia (Miq.) Miq., Phytochemistry Letters, 19, 259-262.
- Lai D.H., Yang Z.D., Xue W.W., Sheng J., Shi Y. and Yao X.J. (2013)., Isolation, characterization and acetylcholinesterase inhibitory activity of alkaloids from roots of Stemona sessilifolia., Fitoterapia, 89, 257-264.
- Cronin M.T. (2003)., Computer-aided prediction of drug toxicity and metabolism., In Modern Methods of Drug Discovery, Birkhäuser, Basel, 259-278.
- Mohamadi F., Richards N.G., Guida W.C., Liskamp R., Lipton M., Caufield C. and Still W.C. (1990)., Macro Model-an integrated software system for modeling organic and bioorganic molecules using molecular mechanics., Journal of Computational Chemistry, 11(4), 440-467.
- Bochevarov A.D., Harder E., Hughes T.F., Greenwood J. R., Braden D.A., Philipp D.M., Rinaldo D., Halls M.D., Zhang J. and Friesner R.A. (2013)., Jaguar: A High- Performance Quantum Chemistry Software Program with Strengths in Life and Materials Sciences., Int. J. Quantum Chem., 113(18), 2110-2142.
- Becke A.D. (1993)., Density‐functional thermochemistry. III. The role of exact exchange., The Journal of chemical physics, 98(7), 5648-5652.
- Lee C., Yang W. and Parr R.G. (1988)., Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density., Physical review B, 37(2), 785-789.
- Wagner A. and Himmel H.J. (2017)., aRMSD: A Comprehensive Tool for Structural Analysis., Journal of chemical information and modeling, 57(3), 428-438.
- Release S. (2016)., 3: LigPrep., Schrödinger, LLC, New York, NY.
- Release Q.S. (2017)., 1: Qik Prop., Schrödinger, LLC, New York, NY.
- Kabsch W. (1976)., A solution for the best rotation to relate two sets of vectors., Acta Crystallographica Section A: Crystal Physics, Diffraction, Theoretical and General Crystallography, 32(5), 922-923.
- Schroeder W.J., Lorensen B. and Martin K. (2004)., The visualization toolkit: an object-oriented approach to 3D graphics., Kitware.
- Politzer P. and Murray J.S. (1991)., Molecular electrostatic potentials and chemical reactivity., Reviews Computational Chemistry, 2, 273-312.
- Politzer P. and Murray J.S. (2002)., The fundamental nature and role of the electrostatic potential in atoms and molecules., Theoretical Chemistry Accounts: Theory, Computation, and Modeling (Theoretica Chimica Acta), 108(3), 134-142.
- Gunasekaran S., Kumaresan S., Balaji R.A., Anand G. and Seshadri S. (2008)., Vibrational spectra and normal coordinate analysis on structure of chlorambucil and thioguanine., Pramana: Journal of Physics, 71(6), 1291-1300.
- Sajan D., Lakshmi K.U., Erdogdu Y. and Joe I.H. (2011)., Molecular structure and vibrational spectra of 2, 6-bis (benzylidene) cyclohexanone: a density functional theoretical study., Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 78(1), 113-121.
- Sinha L., Prasad O., Narayan V. and Shukla S.R. (2011)., Raman, FT -IR spectroscopic analysis and first-order hyperpolarisability of 3-benzoyl-5-chlorouracil by first principles., Molecular Simulation, 37(2), 153-163.
- DiMasi J.A., Hansen R.W. and Grabowski H.G. (2003)., The price of innovation: new estimates of drug development costs., Journal of health economics, 22(2), 151-185.
- Hodgson J. (2001)., ADMET-turning chemicals into drugs., Nature Biotechnology, 19(8), 722-726.
- Lipinski C.A. (2004)., Lead-and drug-like compounds: the rule-of-five revolution., Drug Discovery Today: Technologies, 1(4), 337-341.
- Jorgensen W.L. and Duffy E.M. (2000)., Prediction of drug solubility from Monte Carlo simulations., Bioorganic and medicinal chemistry letters, 10(11), 1155-1158.