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In vivo antimalarial activity and toxicological studies of some quinoline methanol metal complexes.


Quinolinemethanol drugs (mefloquine and quinine) are us ed in treatment of malarial due to their esquizonticide effect (Jaime and Williams, 1988). Previous work has revealed that efficacies of some therapeutic agents increased upon coordination to transition metals (Ogunniran et al, 2007). Incorporation of metallocene into chloroquine and quinine have been reported to yield compounds that were found to be active against both chloroquine sensitive and chloroquine resistant strains of plasmodium and to be safe and effective in mice as well as being non- mutagenic (Dormale et al., 1998).

Recently, we have reported the first crystal structure of polymeric zinc -quinine complex (Obaleye et al, 2007). X-ray crystallographic analysis revealed zinc coordinated to an oxygen atom from each of two sulphate bridges, a chlorine atom and quinoline atom ([N.sub.4]) of the quinine moiety. The second quinuclidine nitrogen in the quinine is protonated (Obaleye et al, 2007). In a related work, we reported the crystal structure of copperacetyl sulphadiazine complex (Obaleye et al, 2008). The Cu (II) coordinates to two molecules of acetylsulphadiazine through pyrimidine nitrogen, two chloride ions and two carbonyl oxygen atoms from adjacent acetylsulphadiazine molecule (Obaleye et al, 2008). Although few reports on synthesis and characterization of metal complexes of quinolinemethanol ligands have appeared in literatures, there is relatively little or no work reported on the toxicological and antimalarial activity studies of these compounds.

In continuation of our effort to find new antimalarial drugs effective against chloroquine resistant strain of malarial parasite. We report the biological activities (antimalarial and toxicological studies) of metal complexes of quinolinemethanol.

Materials and methods

Source of reagents

All chemical and solvent used were of analytical grades and were used without further purification. They were obtained from BDH Chemicals, England.

Source of experimental animals and parasites

A total of 42 male Albino rats of average body weight of 150g were obtained from the Animal Breeding Unit of Biochemistry Department, University of Ilorin, Ilorin, Nigeria. Plasmodium berghei and mice were collected from IMRAT, University of Ibadan, Ibadan, Nigeria.

Synthesis of Metal complexes of Quinine.

To a solution of quinine hemisulfate (2mmol) in methanol (10ml), a solution of metal chloride salt (2mmol) in methanol (10ml) was added. The mixture was stirred and heated or refluxed at 60 0C for 1 hour. The resulting solution was filtered. Precipitate formed for iron (III) quinine complex. The filtrate of cobalt, zinc, cadmium and copper (II) quinine complexes were subjected to slow evaporation at room temperature. Crystals were obtained after three weeks.

Synthesis of metal complexes of mefloquine

To a solution of mefloquine hydrochloride (20mmol) in methanol (15ml), a solution of metal chloride salt (10mmol) in methanol (10ml) was added. The resulting solution was stirred for 2 hours. The filtrate was evaporated to one-third of the initial volume and refrigerated for 2 weeks; this resulted into formation of crystals. Recrystallisation of the crystals was carried out to give suitable crystals for analysis.

Antimalarial Screening

Mice for experiment were infected as described by, Sanchez- Delgado et al (1996). Swiss mice were divided into five each, kept in metal cages and fed with mice cubes and water ad libitum.
Group  1  -  Control
Group  2  -  Chloroquine
Group  3  -  Mefloquine.
Group  4  -  Quinine
Group  5  -  Fe(QUIN)[Cl.sub.2] [H.sub.2]O] S[O.sub.4].3[H.sub.2]O
Group  6  -  [[Mef[H.sup.+]].sub.2] Cu[Cl.sub.4].4[H.sub.2]O
Group  7  -  [[Zn(QUIN)ClS[O.sub.4]].sub.[infinity]]
Group  8  -  [[Mef[H.sup.+]].sub.2] [(Fe(S[O.sub.4]).sub.2]].sup.2]

The drug solution ([1cm.sup.3]) prepared with DMSO were administered orally to the mice two times daily for five days at a dosage level of 0.64mg / 150g for mefloquine and quinine. The mice in each group were marked for easy identification. The mice were inoculated intravenously with 0.2ml of 1 x [10.sup.6] parasitized erythrocytes suspended in buffered physiological saline (pH 7.4). The mice were left for 4 days and their levels of parasitaemias were monitored daily by counting parasites in blood smear, fixed with 70% methanol and Giemsa stain. The slides were viewed under the microscope with magnification of 100. The level of parasitaemia was then determined by counting the number of infected erythrocytes / 1000 erythrocytes in tail blood smears stained with Giemsa.

1.0 ppm of solution of each of the ligands and complexes was prepared, 0.4ml each of the solution was injected daily into the mice in each group from day 0 to day 3 of infection. Level of parasitaemia was determined on day 4. Only physiological saline solution was given to the control animals. The results were expressed as the percentage of infected cells or inhibition of parasites calculated from the equation.

% inhibition = 100- Estimated number of parasite in treated mice/Estimated number of parasite in untreated mice

Toxicological Studies

Treatment of Animals.

The rats were fed for 2 weeks prior to their usage. The rats were divided into 7 groups (6 rats each). Animals in Group 1 served as control and received DMSO, while groups 2-7 were administered the ligand and complexes accordingly as stated below:
Group  1  -  Control
Group  2  -  Quinine
Group  3  -  [(Zn (QUIN) Cl S[O.sub.4]].sub.[mu]]
Group  4  -  [Fe (QUIN)[Cl.sub.2] [H.sub.2] O] S[O.sub.4]. 3[H.sub.2]O
Group  5  -  Mefloquine
Group  6  -  [[Mef[H.sup.+]].sub.2] Cu[Cl.sub.4]. 4[H.sub.2]O
Group  7  -  [[[Mef[H.sup.+]].sub.2](Fe (S[O.sub.4]).sub.2]].sub.2]

Preparation of Serum and Tissue Homogenates

The rats were sacrificed 24 hours after the last day of administration of drugs by anaesthetizing cotton wool soaked in chloroform. The blood was collected into clean labeled sample bottle and allowed to coagulate. They were then centrifuged and the serum pipetted out for analysis. The homogenates of the liver, kidney and heart were prepared in ice-cold 0.25M sucrose solution to give a final volume of five times the original tissue weight (1.5 w/v). The homogenates were kept in well labelled container and stored in the freezer before being used. The activities of alkaline phosphatase in the serum and liver, kidney and heart homogenates were estimated using the method described by Wright et al (1997).

Results and discussion

Compound 1-[[Zn (QUIN) Cl (S[O.sub.4])].sub.[infinity]]

Off white crystal; Yield: 75%; m.wt=533.3; m.p= 285[degrees]C with decomposition; soluble in methanol, DMSO, Conductivity = 90 [[OMEGA].sup.-1] [cm.sup.2] [mol.sup.-1].

IR (KBr) vmax/[cm.sup.-4] : 3373 (vOH/[H.sub.2]O), 1622 s ([delta][H.sub.2]O/C=C), 1594m, 1518s v(C=N), 2667m [([vNH.sub.2].sup.+]), 1118w, 1083m (v S[O.sub.4]), UV-vis(DMSO), X nm:263,320

Anal. Calcd. for [[C.sub.20][H.sub.25][N.sub.2] [O.sub.6] SZnCl]: C,45.90; H,5.05; N,5.15; S, 6.10 and Zn,12.34. Found: C,46.00; H,4.80;N,5.40; S,6.00 and Zn,12.48

Compound 2--[Fe(QUIN)[Cl.sub.2] ([H.sub.2]O)]S[O.sub.4].3[H.sub.2]O Brown Powder,Yield:64%;m.wt=618; 250[degrees]C soluble in methanol, DMSO; conductivity 102 [OMEGA] [-.sup.4][cm.sup.2][mol.sup.-1] IR (KBr) vmax/[cm.sup.-1] :3421-3200 (vOH/[H.sub.2]O), 1620 s ([delta][H.sub.2]O/C=C), 1620m, 1542m (vC=N), 2645m, b (vN[H.sub.2.sup.+]) 1142m, 1076m (vS[O.sub.4]). UV-vis (C[H.sub.3]OH), 353, 635. Anal. Calcd. for [[C.sub.20][H.sub.31][N.sub.2][O.sub.10] Fe[Cl.sub.3].S[O.sub.4]]: C,38.80; H,5.34; N,4.53; Fe,9.14; Found: C,39.26; H,5.06; N,4.61 and Fe,9.18

Compound 3--[[Mef[H.sup.+]].sub.2]Cu[Cl.sub.4].4[H.sub.2]O

Green Crystal, Yield: 72%; m.wt. = 1036.06, = 245[degrees]C, Soluble in methanol and DMSO, conductivity=106 [OMEGA] [sup.-1][cm.sup.2] [mol.sup.-1],

IR (KBr) vmax/[cm.sup.-1]; 3442-3000br (vOH/[H.sub.2]O), 1636s (v C=N)/ [delta] (O-H) bending / lattice water), 2600-2750vw ([vN[H.sub.2.sup.+]), 1266m (v C-N). UV-visible (methanol), [lambda], nm; 310, 335, 685.

Anal. Calcd. for [([C.sub.17][H.sub.17][N.sub.2][F.sub.6]O).sub.2] Cu[Cl.sub.4] 4[H.sub.2]O, C,39.4; H,4.10; N,5.4; Cu,6.12 : found C, 39.50; H, 4.0; N, 5.48 and Cu, 6.07.

Compound 4--[[MeF[H.sup.+]].sup.2] [[[Fe(S[O.sub.4]).sub.2]].sup.2]

Light Brown, Yield:65%, m.wt=1006, 280[degrees]C, Soluble in Methanol and DMSO, conductivity=118.6 [OMEGA] [sup.- 1][cm.sup.2] [mol.sup.-1], IR (KBr) Vmax/[cm.sup.-1]; 345 (vOH/[H.sub.2]O), 1603, 1587m (v C=N/) [delta](O-H) bending / lattice water, 2700w ([vN[H.sub.2.sup.+]), 1266m (VC-f)., UV-Visible, [lambda], nm; 310, 410, 670. Anal.Calcd. for ([C.sub.17][H.sub.17][N.sub.2][F.sub.6][O.sub.2] [[Fe[(S[O.sub.4]).sub.2]].sup.2-]. C, 40.55; H, 3.88, N,5.57; Fe,5.57. Found; C, 40.88; H, 3.61; N, 5.64; Fe, 5.75.

The complexes were characterized by elemental analysis, Infrared, UV-vis spectroscopy and conductivity. The elemental analysis results of the complexes are in good agreement with the formula [(Zn (QUIN) Cl [(S[O.sub.4])].sub.[infinity]], [Fe(QUIN)[Cl.sub.2] ([H.sub.2]O)]S[O.sub.4].3[H.sub.2]O, [[Mef[H.sup.+].sub.2]Cu[Cl.sub.4][H.sub.2]O, [[MeF[H.sup.+]].sub.2] [[Fe[(S[O.sub.4]).sub.2]].sup.2]

All the compounds synthesized were coloured ranging from their parent drug colours of white to off-white, green and brown. The compounds are also non-hygroscopic solids with different sharp melting points range from 245 to 285[degrees]C. They are soluble in methanol and dimethyl sulfoxide.

The molar conductance values measured in DMSO solutions (10-3M) for these compounds are in 90-110 [OMEGA] [sup.-1][cm.sup.2][mol.sup.-1]. According to these results, the complexes are electrolytes. Determination of stoichiometric ratio using job's method suggested the mole ratio of 1:1 and 1:2 metal to ligand for quinine and mefloquine metal complexes respectively. Spectral data showed that compound1 [[Zn(QUIN)ClS[O.sub.4]].sub.[infinity]] exhibits a tetrahedral geometry and polymeric in nature. Each Zn (II) centre is thus coordinated to an oxygen atom from each of two sulphate bridges, a chlorine atom and quinoline atom N(4) of the quinine moiety. X-ray crystallographic studies as reported previously revealed that the second quinuclidine nitrogen in the quinine is protonated (Obaleye et al, 2007). This is supported by the appearance of absorption band of 2,575[cm.sup.-1] due to [N.sup.+]H stretching in infrared spectra. Compound 2- [[Fe(QUIN)Cl.sub.2][H.sub.2]O]S[O.sub.4].3[H.sub.2]O has zwitterionic structure, this may be compared with a molecular L-histidinium trichloro zincate [L- histidine [H.sup.+]] Zn[Cl.sub.3] (Hubel et al, 1999). Tetrahedral structure with coordination of the metal at quinoline N atom was proposed for compound 2 as evidenced by shifting in bands at 1593 and 1509 [cm.sup.-1] due vc=N to higher frequency. Protonation of quinuclidine nitrogen also occurred in this compound. Compound 3--[[mef[H.sup.+]].sub.2] Cu[Cl.sub.4].4[H.sub.2]O and compound 4-[[Mef [[H.sup.+]].sub.2] [[Fe[(S[O.sub.4]).sub.2]].sup.2-] are ionic salts with no direct metal ligand bond. Tetra chlorometallate salts of the ligand were obtained. The band between 2600-2750[cm.sup.-1] due to vN[H.sub.2.sup.+] is attributed to protonation at the piperidine N atom. As expected, bands at 1455, 1436, 1267, 1216 and 1053[cm.sup.-1] showed little or no change with respect to those of the ligand. The absorption band at 1266[cm.sup.-1] due to v (C-F) in the ligand retains its position and intensity in the spectrum of the ligands.

X-ray crystallographic analysis of the compounds was carried out and the detailed data will be reported elsewhere.

The effects of oral administration of the ligands and the complexes on rat liver, kidney and serum alkaline phosphatase activities are shown in Table 1. The serum ALP activity showed no significant change (P > 0.05) on comparison with one another and the control after repeated administration of ligand and complexes. The fact that there was no significant difference in serum ALP activities of ligands and ligands- metal complexes administered rats when compared with control suggests that the integrity of the plasma membrane was not compromised (Akanji et al., 1993).

Moreover, the observed significant increase in the ALP activities of the liver and kidney of rats administered with Quinolinemethanol complexes suggests an enhancement of the activities of the enzyme by the drugs and their metabolites. The increase may also be as a result of stress imposed on the tissue by the drugs, which may lead to loss of the enzyme molecule through leakage into extra cellular fluid which has not been significantly noticed in the serum. In a bid to offset this stress, the tissue may increase the de novo synthesis of the enzymes thus accounting for the increase in ALP activities in these tissues (Umezawa and Hooper, 1982, Malomo et al, 1995)

A cursory look at Table 4 shows that the antimalarial activity of mefloquine and quinine ligands is more pronounced than chloroquine. The percentage reductions in parasiteamia are 68%, 77% and 78% for chloroquine, mefloquine and quinine respectively.

A comparism between the ligand and their complexes showed that [[Mef[H.sup.+]].sub.2] Cu[Cl.sub.4].4[H.sub.2]O, [[Mef[H.sup.+]].sub.2] [[Fe[(S[O.sub.4]).sub.2]].sup.2-], [Fe(QUIN)[CL.sub.2] [H.sub.2]O]S[O.sub.4].3[H.sub.2]0, (Zn (QUIN)Cl [(S[O.sub.4]).[infinity]] are more active than their respective free ligands and chloroquine. Thus coordination to the metal enhances the activity of the drugs. This could be due to the complexes binding first without being decomposed at the receptor site and also the deposition of free metal ions in the membrane of the parasites. It is pertinent to note that [[Mef[H.sup.+]].sub.2] [Fe [(S[O.sub.4]).sub.2]].sup.2-] and [Fe (QUIN) [Cl.sub.2] [H.sub.2]O] S[O.sub.4].3[H.sub.2]O had the best clearance with 97% and 94% reduction in parasitaemia. This finding is in agreement with results of the studies carried out by Biol et al. (2000), where they reported that incorporation of ferrocene (iron compound) into chloroquine molecule resulted into formation of ferroquine which enhances the efficacy of chloroquine. Ferrocene serves as bait while chloroquine serves as poison to the parasite. The parasites need iron for their development thereby making them to look for bait which will lead consequently to death by the poison (chloroquine). The same reason account for the high activity of iron complexes of the drugs as compared to other metal ion complexes. The release of the drug into the target site made the availability of the free metal ion (iron) which is very essential to the body system. Iron is important in the human body because of the occurrence in many heamoproteins such as haemoglobin, myoglobin and cytochromes. Also the metal ions could be reduced to its free state and could be toxic to the membrane of plasmodium thus implying man could guard its content zealously for a better living.


The characterization of the compounds using spectral analysis showed that compound 1-[[Zn(QUIN)ClS[O.sub.4]].[infinity]] is polymeric with Zinc (II) extended zigzag chains as reported in previous work of X-ray crystallographic analysis of the compound. Zwitterionic structure was found for compound 2-[Fe(QUIN) [Cl.sub.2].[H.sub.2]O]S[O.sub.4].3[H.sub.2]O. The Fe(III) is co-ordinated to quinoline N atom of the Quinine ligand. Structural determination of compound 3- [(Mef[H.sup.+]).sub.2]Cu[Cl.sub.4].4[H.sub.2]O and compound 4-[[Mef[H.sup.+]].sub.2][Fe(S[O.sub.4]).sub.2]].sub.2]-using spectral methods revealed that both are ionic salts with mefloquine being protonated at piperidine nitrogen with Cu[Cl.sub.4.sup.2-] and [[Fe(S[O.sub.4]).sub.2]].sup.2-] acting as counter ions. From the toxicological studies of quinine and mefloquine metal complexes, the metal complexes [(Mef[H.sup.+].sub.2]Cu[Cl.sub.4].4[H.sub.2]O, [[Mef[H.sup.+]].sub.2][Fe(S[O.sub.4]).sub.2]].sup.2-], Fe(QUIN) [Cl.sub.2].[H.sub.2]O]S[O.sub.4].3[H.sub.2]O and [[Zn(QUIN)ClS[O.sub.4]].sub.[infinity]] have little or no effect on rat cellular systems compared to their parent drugs. Therefore the metal complexes are much safer than their parent drugs. Generally, the four metal complexes were found to exhibit higher antimalarial activity than chloroquine and their parent ligands when screened against mice infected with plasmodium berghei.


OJA and TAC are very grateful to the University of Ilorin for the award of a research grant.


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Obaleye, J.A., M.R. Caira and A.C. Tella, 2008. Crystal structure of Dichlorobis (N-{4(2- Pyrimidinyl--kN aminosulfonylacetamide) Copper (II). Analytical Sciences, 24: 63.

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(1) Obaleye J.A, (1) Tella A.C. and (2) Arise, R.O.

(1) Department of Chemistry, University of Ilorin, P.M.B. 1515, Ilorin-Nigeria

(2) Department of Biochemistry, University of Ilorin, P.M.B. 1515, Ilorin-Nigeria

Corresponding Author: Tella A.C., Department of Chemistry, University of Ilorin, P.M.B. 1515, Ilorin-Nigeria E-mail:
Table 1: Effects of administration of some drug metal complexes on ALP
activities of rat kidney and serum.

Ligand/Complexes                                  Kidney IU/L

Control                                           64.19 [+ or -] 5.11
Quinine (QUIN)                                    72.40 [+ or -] 6.09
[[Zn (QUIN) Cl (SO4)].sub.[infinity]]             76.70 [+ or -] 6.11
[Fe(QUIN)Cl([H.sub.2]O)]S[O.sub.4].3[H.sub.2]O    80.40[+ or -] .83
Mefloquine (MFQ)                                  88.20 [+ or -] 7.98
[[[MefH.sup.[+ or -]]].sub.2]                     100.11 [+ or -] 9.80
[[[MeFH.sup.[+ or -]]].sub.2]                     93.22 [+ or -] 7.99

Ligand/Complexes                                  Liver IU/L

Control                                           20.03[+ or -] 1.90
Quinine (QUIN)                                    7.14 [+ or -] 2.15
[[Zn (QUIN) Cl (SO4)].sub.[infinity]]             28.40 [+ or -] 2.07
[Fe(QUIN)Cl([H.sub.2]O)]S[O.sub.4].3[H.sub.2]O    30.42 [+ or -] 2.73
Mefloquine (MFQ)                                  24.14-[+ or -]1.86
[[[MefH.sup.[+ or -]]].sub.2]                     37.36 [+ or -] 2.95
[[[MeFH.sup.[+ or -]]].sub.2]                     35.30 [+ or -] 2.15

Ligand/Complexes                                  Serum IU/L

Control                                           10.6 [+ or -] 0.96
Quinine (QUIN)                                    10.00 [+ or -] 0.88
[[Zn (QUIN) Cl (SO4)].sub.[infinity]]             9.24 [+ or -] 0.65
[Fe(QUIN)Cl([H.sub.2]O)]S[O.sub.4].3[H.sub.2]O    8.76 [+ or -] 0.57
Mefloquine (MFQ)                                  10.00 [+ or -] 0.99
[[[MefH.sup.[+ or -]]].sub.2]                     10.42 [+ or -] 0.98
[[[MeFH.sup.[+ or -]]].sub.2]                     9.53 [+ or -] 0.74

Table 2: Percentage reduction in parasitaemia following the
administration of ligands to infected mice.

               Number    Average %
                         parasitaemia in
                         mice before

Chloroquine    C         40
Mefloquine     M         48
Quinine        Q         50

               Average%          % reduction in
               parasitaemia      parasitaemia
               after             after
               administration    administration

Chloroquine    8                 68
Mefloquine     9                 77
Quinine        11                78

Table 3: Percentage Parasitemia of Metal Complexes

                                     Number     Average %

[[([MefH.sup.+]).sub.2]              M1         34
  Cu[Cl.sub.4]. 4[H.sub.2]O]
[[([MefH.sup.+]).sub.2]              M2         26
  Cu[Cl.sub.4]. 4[H.sub.2]O]
[([MefH.sup.+]).sub.2]               M3         38
  [Fe [(SO4).sub.2]].sup.2-]
[([MefH.sup.+]).sub.2]               M4         36
  [Fe [(SO4).sub.2]].sup.2-]
Fe(QUIN)[Cl.sub.2]([H.sub.2]OS       Q1         41
Fe(QUIN)[Cl.sub.2]([H.sub.2]OS       Q2         38
[[Zn (QUIN) Cl                       Q3         20
[[Zn (QUIN) Cl                       Q4         32

                                     Average%          % reduction
                                     parasitaemia      parasitaemia

[[([MefH.sup.+]).sub.2]              3                 91
  Cu[Cl.sub.4]. 4[H.sub.2]O]
[[([MefH.sup.+]).sub.2]              3                 89
  Cu[Cl.sub.4]. 4[H.sub.2]O]
[([MefH.sup.+]).sub.2]               1                 96
  [Fe [(SO4).sub.2]].sup.2-]
[([MefH.sup.+]).sub.2]               1                 97
  [Fe [(SO4).sub.2]].sup.2-]
Fe(QUIN)[Cl.sub.2]([H.sub.2]OS       2                 95
Fe(QUIN)[Cl.sub.2]([H.sub.2]OS       3                 92
[[Zn (QUIN) Cl                       4                 80
[[Zn (QUIN) Cl                       4                 88

Table 4: Average % reduction in parasitemia

Ligands / Complex                            Number        Percentage

Chloroquine                                  C             68
  Mefloquine                                 M             77
Quinine                                      Q             78
  [[([MefH.sup.+]).sub.2]Cu[Cl.sub.4].       M1 and M2     90
  ([MefH.sup.+]).sub.2]                      M3 and M4     97
    [[Fe [(S[O.sub.4]).sub.2]].sup.2-]
(Fe (QUIN)[Cl.sub.2][H.sub.2]O)              Q1 and Q2     94
[Zn (QUIN)Cl(S[O.sub.4])].sub.[infinity]]    Q3 and Q4     84
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Author:Obaleye, J.A.; Tella, A.C.; Arise, R.O.
Publication:Advances in Natural and Applied Sciences
Article Type:Report
Geographic Code:6NIGR
Date:Jan 1, 2009
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