Nanotechnology and Healthcare in the Developing World Symposium

SYNTHESIS AND BIOCHEMICAL CHARACTERIZATION OF SOME NEW ANTIFUNGAL AGENTS DERIVED FROM COPPER (II) SURFACTANT WITH N-DONAR LIGANDS
POOJA SAXENA,NET-JRF,Chemistry

GOVT. COLLEGE DAUSA, RAJASTHAN (INDIA)

21-22 Sep.2009

ABSTRACT
The chemistry of complexes derived from copper surfactants with Ndonor ligand in mixed solvents are important for theoretical and applied areas of research including bacterial and fungicidal analysis. Metal complexes of the ligands containing nitrogen and sulphur donor atoms are known to possess antimicrobial, antiviral, antifungal and anticonvulsant activities. The N-donor ligands have been serving as the basis of a variety of drugs for over five decades. These ligands are recognized as pharmacophores have received great attention in drug discovery and Lead optimization. In the complexation copper is one of the heavy transition metal that is capable of being toxic when present beyond the tolerance level and thus copper complexes act as insecticides and fungicides. The pathogenic activity is enhanced on complexing and N-C-S linkage present in above compounds makes them to versatile biological interest and chemotherapeutic agents..

Thus on the basis of above applications, it becomes very clear that 2amino benzothiazole and their substituted derivatives have been found to be very active against variety of bacteria, fungi, herbs and intersect, so in the present investigation some new antifungal agents are derived from copper-palmitate and 2-amino benzothiazole, the molecular structure and geometry of the synthesized complexes have been confirmed by their elemental analysis, molecular weight, U.V., I.R, NMR and ESR spectral studies. The purity of the compounds has been checked by thin layer chromatography, all the compounds are colored and powdered in nature. The antifungal studies of the synthesized surfactant, ligands and complexes have been tested against different concentration by agar plate technique. The effect of solvent has been excluded by complete evaporation. It has been observed that the activity increases with the increase in the concentration of the solution. The complexes show higher activity, suggesting that the complexes are more powerful antifungal agents as compare to pure surfactant and ligands.

CONTENTS
Synthesis of complexes Spectral studies of complexes Biocidal studies of complexes

Substituted Benzothiazole

N NH2 R S
R=OCH3,NO2,Cl,CH3

Formation of Substituted Benzothiazole

The required benzothiazole was synthesized by THIOCYNOGENATION of pmethoxyaniline in the presence of thiocynogen gas, which was generated in situ by the reaction of cupric chloride and ammonium thiocynate. Mixture was refluxed for one hour. After cooling sodium carbonate was mixed to neutralize the mixture. The solid separated out was filtered and recrystallised with ethanol.

NH2 R
Substituted Aniline

( SCN )2 R

NH2 S CN 2

N
R= Cl,CH3,OCH3,NO2,

NH2 S

Substituted Benzathiazole

LIGAND MOIETY

2-amino-6-methyl benzothiazole
2-amino-6- cloro benzothiazole 2-amino-6- methoxy benzothiazole 2-amino-6-nitro benzothiazole

FORMATION OF COMPLEX
LIGAND
2

COPPER SOAP
1

MIXING REFLUX

The complexes will be prepared by mixing the metalsurfactant and ligand in the molar ratio of 1:2,dissolving in ethanol and mixture is refluxed for about 1-2 hours.

COMPLEXS
CP[BTA]T Complex of copper palmitate with 2-amino-6-methyl benzothiazole Complex of copper palmitate with 2-amino-6- cloro benzothiazole Complex of copper stearate with 2-amino-6- methoxy benzothiazole

CP[BTA]C-

CP[BTA]A-

CP[BTA]NA- Complex of copper stearate with 2-amino-6-nitro benzothiazole

Highlight on Application
These constitute a important and interesting class of drugs/dyes not only or significant but also for their usefulness to resist disease in human beings. Copper (II) surfactants have many applications in various fields like wood preservation, foaming, wetting, herbicidal, pesticidal activities, detergency, emulsification, paints, lubrication etc. Compounds having a wide range of pharmacological and biological activities, they have been used as tranquilizers, anti-inflammatory, sedative, antiviral, antimalarials etc. Complexes specially containing N donar ligand produce an excellent class of dyes for fibers which are stable towards sunlight, acidic and basic mediums.

Table-2

Analytical Data of Copper Soap, Ligand and Complexes

Metal Content(%) Soap/ Ligand /Complex CP (BTA)T (BTA)C CP(BTA)T CP(BTA)C

N- Content

S Content

Observed

Calculated

Observed

Calculated

Observed

Calculated

8.81 8.60

11.07 8.87 8.63

8.47 15.10 -

8.53 15.18 3.80 3.69

19.40 17.28 -

19.51 17.34 4.34 4.22

IR spectra of CS[BTA]NA

IR spectra of CS[BTA]A

IR spectra of CS[BTA]T

IR spectra of CS[BTA]T

IR spectra of CS[BTA]T

ANTIFUNGAL STUDY

C.albicans C.Krusi Aternaria alternata Aspergilus niger

Disk Diffusion Test

USA,CLSI M-44A

Department of Microbiology, J.L.N. Medical College, Ajmer

Prepration of Mueller Hinton agar Medium

Mueller-Hint on agar Plates

Inoculum Suspension on agar plates

Inhibitory Zone diameter was measured

Dispensing the Standard and Testing Disk on inoculated Agar Plates

Plates were stored in incubater

Disk Diffusion Test Procedure

(C T ) % Inhibitin X 100 C

T = Diameter of fungal colony in rest plate after 48 hours C= Diameter of fungal colony in control plate after 48 hours

INHIBITION ZONE (mm)

Antimicrobial activity of testing compounds against C. albicans

20 15 10 5 0

]T

]C TA

S[ B

TESTING COMPLEX

[B TA ]A [B TA ]N A [B TA ]T [B TA ]C

]A

]N TA

TA

S[ B

S[ B

TA

S[ B

INHIBITION ZONE (mm)

Antimicrobial activity of testing compounds against C. krusai

18 16 14 12 10 8 6 4 2 0

]T

]C

]A

[B TA ]T

S[ B

TESTING COMPLEX

[B TA ]N A

S[ B

S[ B

S[ B

[B TA ]C

[B TA ]A

]N

TA

TA

TA

TA

COMPARITIVE ANALYSIS OF COMPLEX ACTIVITIES

CS[BTA]A CS[BTA]NA CS[BTA]T CS[BTA]C [BTA]A [BTA]NA [BTA]T [BTA]C

Inhibition Zone (mm) of CS[BTA]C againest C.albicans

Inhibition Zone (mm) of CS[BTA]A and CS[BTA]T against C.Krusai

Inhibition Zone (mm) of CS[BTA]NA and CS[BTA]C against C.Krusai

CONCLUSION

The Biological effect of derivatives depends on the nature and structure of ligands and their metal complexes and also on the presence of the particular element Copper (II) soap exhibits lowest percentage inhibition where as the two ligands show higher percentage inhibition, But then complexes exhibit highest inhibition. Ligand and complex containing chloro group (derived from p-chloro aniline) shows higher percentage inhibition as compared to those containing methyl group (derived from toludiene). The activity of copper (II) soap, ligands and complexes is in the following order : complex > ligand > soap It has been observed that the activity increases with the increase in the concentration of the solution.

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 Thanks for your kind Attention....

Supervisor Dr. Neha Mathur Co-investigator Imran Ahmad