title: Host-Guest Inclusion Complexes between Amlodipine Enantiomers in the Biphasic Recognition Chiral Extraction System using Tartaric Acid and β-Cyclodextrin Derivatives as Positive Confirmation by using their Enantioselective Extraction.
abstract: The current work reports an extended theoretical study from our previous experimental work for the enantioselective extraction of amlodipine enantiomers in a biphasic recognition chiral extraction system (BRCES) consisting of hydrophobic D-diisopropyl tartrate dissolved in organic phase (n-decanol) and hydrophilic hydroxypropyl-β-cyclodextrin (HP-β-CD) in aqueous phase (acetate buffer) which preferentially recognize the R-enantiomer and S-enantiomer, respectively. The calculations were simulated using a semi-empirical PM3 method as a part of the Gaussian09 software package and were used to optimize the structures of the hosts, guests, and host-guest complexes in the gas phase without any restrictions. It was found that HP-β-CD has the strongest recognition ability among the three β-CD derivatives studied, namely HP-β-CD, hydroxyethyl-β-cyclodextrin (HE-β-CD), and methylated-β-cyclodextrin (Me-β-CD), due to the large interaction energies (Ecomp = -14.3025 kcal/ mol), while D-diisopropyl tartrate has the strongest ability among the four tartaric acid derivatives studied namely; L-diisopropyl tartrate, D-diisopropyl tartrate, L-diethyl tartrate, and D-diethyl tartrate (Ecomp = -5.9964 kcal/ mol). The computational calculations for the enantioselective partitioning of amlodipine enantiomers rationalized the reasons for the different behaviors for this extraction. The present theoretical results may be informative to scientists who are devoting themselves to developing models for their experimental parts or for enhancing the hydrophobic drug solubility in drug delivery systems.
authors.affiliation: Pharmacy program, Batterjee Medical College for Sciences and Technology (BMC), 21442 Jeddah, Kingdom of Saudi Arabia.
authors.forename: Khaldun M
authors.initials: KM
authors.lastname: Al Azzam
authors.affiliation: Chemistry Department, College of Education, Salahaddin University, Erbil, Iraq.
authors.forename: Hassan H
authors.initials: HH
authors.lastname: Abdallah
authors.affiliation: School of Bioprocess Engineering, Universiti Malaysia Perlis (UniMAP), Kompleks Pusat Pengajian Jejawi 3, 02600 Arau, Perlis, Malaysia.
authors.forename: Hairul N Abdul
authors.initials: HN
authors.lastname: Halim
authors.affiliation: School of Bioprocess Engineering, Universiti Malaysia Perlis (UniMAP), Kompleks Pusat Pengajian Jejawi 3, 02600 Arau, Perlis, Malaysia.
authors.forename: Maizatul Akmam
authors.initials: MA
authors.lastname: Ahmad
authors.affiliation: Pharmacy program, Batterjee Medical College for Sciences and Technology (BMC), 21442 Jeddah, Kingdom of Saudi Arabia.
authors.forename: Hassan
authors.initials: H
authors.lastname: Shaibah
keywords: Biphasic recognition chiral extraction system; Chiral drug; Computational calculations; Enantioselective extraction; Racemic amlodipine
references.citation: Spectrochim Acta A Mol Biomol Spectrosc. 2012 Oct;96:736-43
references.pmid: 22885088
references.citation: Acta Crystallogr B. 2002 Dec;58(Pt 6):1036-43
references.pmid: 12456984
references.citation: Anal Chim Acta. 2010 Aug 3;674(2):249-55
references.pmid: 20678638
references.citation: Anal Chem. 1997 Jun 1;69(11):1999-2007
references.pmid: 21639239
references.citation: J Cardiovasc Pharmacol. 2002 Feb;39(2):208-14
references.pmid: 11791006
references.citation: Int J Quantum Chem. 2009;109(1):81-90
references.pmid: 20046208
references.citation: J Phys Chem B. 2012 Jan 26;116(3):943-50
references.pmid: 22181971
references.citation: J Mol Model. 2007 Dec;13(12):1173-213
references.pmid: 17828561
references.citation: J Comput Chem. 2008 Feb;29(3):416-33
references.pmid: 17631650
references.citation: J Clin Forensic Med. 2003 Sep;10(3):169-72
references.pmid: 15275013
references.citation: Prim Care Companion J Clin Psychiatry. 2003 Apr;5(2):70-73
references.pmid: 15156233
references.citation: J Pharm Biomed Anal. 2004 Apr 16;35(2):379-87
references.pmid: 15063470