Synthesis and optical properties of the chloroquine enantiomers and their complexes with ferriprotoporphyrin IX in aqueous solution

Chirality

Volumn 10, Issue 7, 1998, Pages 556-563

  Blauer, Gideon ^a   Akkawi, Muataz ^a   Fleischhacker, Wilhelm ^b   Hiessböck, Romana ^b  

^a HEBREW UNIVERSITY OF JERUSALEM   (Israel)

^b UNIVERSITY OF VIENNA   (Austria)

Author keywords

Chloroquine; Circular dichroism; Enantiomers; Ferriprotoporphyrin IX; Pyroglutamic acid; Synthesis

Indexed keywords

CHLOROQUINE; HEMATIN; PYROGLUTAMIC ACID;

ABSORPTION SPECTROSCOPY; AQUEOUS SOLUTION; CIRCULAR DICHROISM; COMPLEX FORMATION; CONFERENCE PAPER; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; PH; PRIORITY JOURNAL;

EID: 0031710205     PISSN: 08990042     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1520-636X(1998)10:7<556::AID-CHIR2>3.0.CO;2-0     Document Type: Conference Paper

References (18)

1. Blauer, G. Optical properties of complexes of antimalarial drugs with ferriprotoporphyrin IX in aqueous medium. I. The system ferriprotoporphyrin IX-quinine. Arch. Biochem. Biophys. 251:306-314, 1986. II. The system ferriprotoporphyrin IX-quinidine. Arch. Biochem. Biophys. 251:315-322, 1986.
2. Blauer, G. Optical properties of complexes of antimalarial drugs with ferriprotoporphyrin IX in aqueous medium. I. The system ferriprotoporphyrin IX-quinine. Arch. Biochem. Biophys. 251:306-314, 1986. II. The system ferriprotoporphyrin IX-quinidine. Arch. Biochem. Biophys. 251:315-322, 1986.
3. Blaschke, G., Kraft, H.-P., Schwanghart, A.-D. Chloroquin-Enantiomere durch chromatographische Racemattrennung und Synthese. Chem. Ber. 111:2732-2734, 1978.
4. Craig, J.C., Bhargava, H.N., Everhart, E.T., LaBelle, B., Ohnsorge, U., Webster, R.V. Absolute configuration of the enantiomers of 7-chloro4-[[4-(diethylamino)-1-methylbutyl]amino]-quinoline (chloroquine). J. Org. Chem. 53:1167-1170, 1988.
5. Blauer, G., Ginsburg, H. Complexes of antimalarial drugs with ferriprotoporphyrin IX. Biochem. Int. 5:519-523, 1982.
6. Chou, A.C., Chevli R., Fitch, C.D. Ferriprotoporphyrin IX fulfills the criteria as the chloroquine receptor of malaria parasites. Biochemistry 19:1543-1549, 1980.
7. McIntosh, J.M., Acquaah, S.O. Azapropellanes 5. Synthesis of chiral (non-racemic) 2-methyl azapropellanes. Can. J. Chem. 66:1752-1756, 1988.
8. Bon, F., Bigg, D.C.H., Bertrand, G. Aluminium chloride promoted aminolysis of lactams. Synlett: 747-748, 1992.
9. Kenyon, R.L., Wiesner, J.A., Kwartler, C.E. Chloroquine manufacture. Ind. Eng. Chem. 41:654-662, 1949.
10. Drake, N.L., Creech, H.J., Draper, D., Garman, J.A., Haywood, S., Peck, R.M., Walton, E., Van Hook, J.O. Synthetic antimalarials. The preparation and properties of 7-chloro-4-(4-diethyl-amino-1-methylbutylamino)-quinoline (SN-7618). J. Am. Chem. Soc. 68:1214-1216, 1946.
11. Irvin, J.L., Irvin, E.M. Spectrophotometric and potentiometric evaluation of apparent acid dissociation exponents of various 4-aminoquinolines. J. Am. Chem. Soc. 69:1091-1099, 1947.
12. Brasted, R.C., Cooley, W.E. Physical methods in coordination chemistry. In: The Chemistry of Coordination Compounds. Bailar, J.C., Busch, D.H., eds. New York: Reinhold, 1956:563-624.
13. Sillén, L.G. Polynuclear complexes in solution. In: Coordination Chemistry, Vol. 1. Martell, A.E., ed. New York: van Nostrand Reinhold Co., 1971:491-541.
14. Blauer, G., Burla, R., Levy, S. Circular dichroism of ferriprotoporphyrin IX-morphine complexes in aqueous solution. Arch. Biochem. Biophys. 316:561-566, 1995.
15. Moscowitz, A. Theory and analysis of rotatory dispersion curves. In: Optical Rotatory Dispersion. Djerassi, C., ed. New York: McGraw-Hill, 1960:150-177.
16. Blauer, G., Sreerama, N., Woody, R.W. Optical activity of hemoproteins in the Soret region. Circular dichroism of the heme undecapeptide of cytochrome c in aqueous solution. Biochemistry 32:6674-6679, 1993.
17. Moreau, S., Perly B., Biguet, J. Interactions de la chloroquine avec la ferriprotoporphyrin IX. Biochimie 64:1015-1025, 1982.
18. Moreau, S., Perly, B., Chachaty, C., Deleuze, C. A nuclear magnetic resonance study of antimalarial drugs with porphyrins. Biochim. Biophys. Acta 840:107-116, 1985.