Capillary electrophoretic separation and computational modeling of inclusion complexes of β-cyclodextrin and 18-crown-6 ether with primaquine and quinocide

Biomedical Chromatography

Volumn 24, Issue 4, 2010, Pages 393-398

  Elbashir, Abdalla A ^a,b   Suliman, Fakhr Eldin Osman ^c   Saad, Bahruddin ^b   Aboul Enein, Hassan Y ^d  

^a UNIVERSITY OF KHARTOUM   (Sudan)

^b SCHOOL OF PHYSICS   (Malaysia)

^c SULTAN QABOOS UNIVERSITY   (Oman)

^d NATIONAL RESEARCH CENTRE   (Egypt)

Author keywords

18 crown 6; Capillary electrophoresis; Inclusion complexes; PM3; cyclodextrin

Indexed keywords

CAPILLARY ELECTROPHORESIS; COMPLEXATION; CROWN ETHERS; ETHERS; HYDROGEN BONDS;

18-CROWN-6; 18-CROWN-6 ETHERS; CAPILLARY ELECTROPHORETIC SEPARATIONS; CHIRAL MOBILE PHASE ADDITIVE; COMPUTATIONAL MODELLING; INCLUSION COMPLEX; PM3; SEPARATION MODEL; THEORETICAL CALCULATIONS; Β-CYCLODEXTRIN;

CYCLODEXTRINS;

18 CROWN 6 ETHER; ALPHA CYCLODEXTRIN; BETA CYCLODEXTRIN; CROWN ETHER DERIVATIVE; PRIMAQUINE; QUINOCIDE; UNCLASSIFIED DRUG; 18-CROWN-6; AMINOQUINOLINE DERIVATIVE; BETA CYCLODEXTRIN DERIVATIVE; CROWN ETHER;

ARTICLE; CAPILLARY ELECTROPHORESIS; CHEMICAL STRUCTURE; HYDROGEN BOND; MOLECULAR MODEL; CHEMISTRY; DRUG STABILITY; ISOLATION AND PURIFICATION; PROCEDURES;

AMINOQUINOLINES; BETA-CYCLODEXTRINS; CROWN ETHERS; DRUG STABILITY; ELECTROPHORESIS, CAPILLARY; MODELS, MOLECULAR; PRIMAQUINE;

EID: 77950255751     PISSN: 02693879     EISSN: 10990801     Source Type: Journal    
DOI: 10.1002/bmc.1304     Document Type: Article

References (31)

1. Aree T and Chaichit N. Crystal structure of β- cyclodextrindimethylsulfoxide inclusion complex. Carbohydrate Research 2002; 337, 2487-2494.
2. Aree T and Chaichit N. Crystal structure of β-cyclodextrin-benzoic acid inclusion complex. Carbohydrate Research 2003; 338, 439-446.
3. Aree T, Jacob J, Saenger W and Hoier H. Crystal structure of αcyclodextrin-acetonitrile-hexahydrate. Carbohydrate Research 1998; 307, 191-197.
4. Brondz I, Mantzilas D, Klein U, Ekeberg D, Hvattum E, Lebedeva MN, Mikhailitsyn FS and Røe J. Nature of the main contaminant in the anti malaria drug primaquine diphosphate: a qualitative isomer analysis. Journal of Chromatography B 2004; 800, 211-223.
5. Brondz I, Klein U, Mantzilas D, Ekeberz D, Hvattum E, Schultz H and Mikhailitsyn F. Nature of the main contaminant in the drug primaquine diphosphate: GC-MS analysis. Asian Journal of Chemistry 2005a; 17, 1678-1688.
6. Brondz I and Klein U. Separation of the positional isomer quinocide from the antimalarial drug primaquine using a Discovery HS HPLC column. Supleco Reporter 2005b; 23(4).
7. Brondz I, Karaliova DE, Jennings I and Hustad JA. Separation of the positional isomer quinocide from the anti-malarial drug primaquine using a Discovery HS-F5 HPLC column. Trends in Chromatography 2005c; 1: 77-81.
8. Brondz I, Ekeberg D, Bell DS, Annino AR, Hustad JA, Svendsen R, Vlachos V and Mikhalitsyn F. Nature of the main contaminant in the drug primaquine diphosphate: SFC and SFC-MS methods of analysis. Journal of Pharmaceutical and Biomedical Analysis 2007; 43: 937-944.
9. Carson PE, Peters W and Richards WHG. Antimalarial Drugs II: Current Antimalarial and New Drug Developments. Springer: Berlin, 1984.
10. Chen Z, Uchiyama K and Hobo T. Interaction between 18-crown-6- tetracarboxylic acid and positional substituents of enantiomers and simultaneous separation of positional enantiomers of methyl-DLtryptophans by capillary electrophoresis, Electrophoresis 2001; 22: 2136-2142.
11. Chiou C-S and Shih J-S. Application of crown ethers as modifiers for the separation of amines by capillary electrophoresis. Analytica Chimica Acta 1998; 360: 69-76.
12. Deng Y and Huang M-JU. Capillary electrophoretic separation and theoretical study of inclusion complexes of sulfobutyl ether β-cyclodextrin with estrogens. International Journal of Quantum Chemistry 2004; 100: 746-752.
13. Desiraju GR. The C-H&sbond;O hydrogen bond: structural implications and supramolecular design. Accounts in Chemical Research 1996; 29: 441-449.
14. Dongre VG, Karmuse PP, Nimbalkar MM, Singh D and Kumar A. Application of GC-EI-MS for the identification and investigation of positional isomer in primaquine, an antimalarial drug. Journal of Pharmaceutical and Biomedical Analysis 2005; 39: 111-116.
15. Dongre VG, Karmuse PP, Rao PP and Kumar A. Development and validation of UPLC method for determination of primaquine phosphate and its impurities. Journal of Pharmaceutical and Biomedical Analysis 2008; 46, 236-242.
16. Dunitz JD, Dobler M, Seiler P and Phizackerley RP. Crystal structure analyses of 1,4,7,10,13,16-hexaoxacyclooctadecane and its complexes with alkali thiocyanates. Acta Crystallographica. B 1974; 30: 2733-2738.
17. Elbashir AA, Saad B, Ali AS, Saleh MI and Aboul-Enein HY. Determination of quinocide as impurity in primaquine tablets by capillary electrophoresis. Biomedical Chromatography 2009a; 23: 464-471.
18. Elbashir AA, Suliman FEO, Saad B and Aboul-Enein HY. Determination of aminoglutethimide enantiomers in pharmaceutical formulations by capillary electrophoresis using methylated-β-cyclodextrin as a chiral selector and computational calculation for their respective inclusion complexes. Talanta 2009b; 77: 1388-1393.
19. Glendening ED and Feller D. An ab initio investigation of the structure and alkaline earth divalent cation selectivity of 18-crown-6. Journal of the American Chemistry Society 1996; 118, 6052-6059.
20. Hollingdale MR. Malaria and the liver. In The Liver: Biology and Pathobiology, 2nd edn, Arias IM, Jakoby WB, Popper H and Schachter D (eds). Raven Press: New York, 1988.
21. Jeffrey GA and Saenger W. Hydrogen Bonding in Biological Structures. Springer: Berlin, 1991.
22. Luong JHT and Nguyen AL. Achiral selectivity in cyclodextrin-modified capillary electrophoresis. Journal of Chromatography A 1997; 792: 431-444.
23. Maverick E, Schweizer P and Dunitz JD. 1,4,7,10,13,16- Hexaoxacyclooctadecane: crystal structure at 100 K. Acta Crystallographica B 1980; 36: 615-620.
24. Menges RA and Armstrong DW. Chiral Separations by Liquid Chromatography. American Chemical Society: Washington, 1991.
25. Nishi H, Nakamura K, Nakai H and Sato T. Separation of enantiomers and isomers of amino compounds by capillary electrophoresis and highperformance liquid chromatography utilizing crown ethers. Journal of Chromatography A 1997; 757: 225-235.
26. Starikov EB, Saenger W and Steiner T. Quantum chemical calculations on the weak polar host-guest interactions in crystalline cyclomaltoheptaose (β-cyclodextrin)-but-2-yne-1,4-diol heptahydrate. Carbohydrate Research 1998; 307: 343-346.
27. Steiner T. Unrolling the hydrogen bond properties of C-H&sbond;O interactions. Chemical Communications 1997; 727-734.
28. Szejtli J. Cyclodextrin and Their Inclusion Complexes. Akademiai Kiado: Budapest, 1982.
29. Vale N, Moreira R and Gomes P. Primaquine revisted six decades after its discovery. European Journal of Medicinal Chemistry 2009; 44: 937-953.
30. World Health Organization. Bulletin on global malaria control. WHO Malaria Unit 1993; 71, 281-284.
31. Yan C, Xiu Z, Li X and Hao C. Molecular modeling study of β-cyclodextrin complexes with (+)-catechin and (-)-epicatechin. Journal of Molecular Graphic Modeling 2007; 26, 420-428.