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Sci. Pharm. 2015, 83(4), 683-698; doi:10.3797/scipharm.1501-15

Host-Guest Inclusion Complexes between Amlodipine Enantiomers in Biphasic Recognition Chiral Extraction System using Tartaric Acid and β-Cyclodextrin Derivatives as Positive Confirmation Using of their Enantioselective Extraction

1
Pharmacy program, Batterjee Medical College for Sciences and Technology (BMC), 21442 Jeddah, Kingdom of Saudi Arabia
2
Chemistry Department, College of Education, Salahaddin University, Erbil, Iraq
3
School of Bioprocess Engineering, Universiti Malaysia Perlis (UniMAP), Kompleks Pusat Pengajian Jejawi 3, 02600 Arau, Perlis, Malaysia
*
Authors to whom correspondence should be addressed.
Received: 28 January 2015 / Accepted: 22 June 2015 / Published: 22 June 2015
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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.
Keywords: Chiral drug; Enantioselective extraction; Racemic amlodipine; Biphasic recognition chiral extraction system; Computational calculations Chiral drug; Enantioselective extraction; Racemic amlodipine; Biphasic recognition chiral extraction system; Computational calculations
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

AZZAM, K.M.A.; ABDALLAH, H.H.; HALIM, H.N.A.; AHMAD, M.A.; SHAIBAH, H. Host-Guest Inclusion Complexes between Amlodipine Enantiomers in Biphasic Recognition Chiral Extraction System using Tartaric Acid and β-Cyclodextrin Derivatives as Positive Confirmation Using of their Enantioselective Extraction. Sci. Pharm. 2015, 83, 683-698.

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