National Journal of Chemistry,2010, Volume 40, 720-735
‫ المجلد األربعين‬0202-‫المجلة القطرية للكيمياء‬
E f f e c t o f S o me H e t e r o c y c l i c Co mp o u n d s o n H u ma n
Serum AChE
Mahamood S. Abdul-Husain
Foundation of Technical Education, Baghdad, Iraq
Redha I. Al-Bayati, and Raad K. Muslih
Department of Chemistry, College of Science, Al-Mustanseririyah
University, Iraq
Acknowledgements : These compounds were gifts from Dr. Ameer Atoo.
(NJC)
(Recevied on 28/6/2010)
(Accepted for publication 29/11/2010)
Abstract
This study is designed to show the effect of fifteen heterocyclic compounds
on the activity of AChE in sera, all compounds showed strong inhibition
ranging between (80.3 %-93.7%) at concentration up to 1x 10 -2 M.it was
found that the percentage of inhibition is increased with the increase of
concentration of inhibitors and 3-phenyl-6-[5'nito-2'-furyl)ethyl]-1,2,4triazole[3,4,6], [1,3,4] thiodiazole (9) was the most effective inhibitors.
Kinetic properties of these inhibitors are studied and Lineweaver -Burk plots
were nused to determine the type of inhibition, all studied compounds
behaved as non-competitive inhibitors. The mechanism of action of
heterocyclic compounds as inhibitor to serum AChE activity was suggested.
‫الخالصة‬
‫د را ةثة سم ةثة مثر مثن المرا بثاق الحلق يثة ت يثر المتجاف ةثة لثن فعال يثة ا فث يم‬
‫ا هثثرق المرا بثثاق المدر ةثثة تثثاطير تط ي طثثي ث‬
‫تر ا حثثق الف ةثثبة الم يثثة‬
‫اال فث يم مثن‬
‫ ) ا لثن ا ل يثة لتط ثي‬7
‫ا هثرق المرا بثاق المدر ةثة‬
‫لع مثثك هثثذر‬
‫اال ةثثيتايك اث لين ا ةثثتري فثثي م نثثك دم االف ةثثان ح يث‬
‫تث داد مثثا يثثاد ترا يث المطب طثثاق ح يث‬
. ‫م الر‬
0-
‫تم في هذا الب حث‬
‫ان ف ةثثبة التط ثثي‬
‫لثثن فعال يثثة اال فث يم‬
02 * 0 ‫ بأةتسدام التراي‬% 7809 - % 3208 ‫ين‬
‫[ طايادا يثا‬4,3,1] , [6,4,3]
‫للتط ي‬
‫د ل حظ ان للمراب ت را يثا‬
‫ اذلك ت مثق د را ةثة ال سث ال الحرا يثة ل هثذر المرا بثاق ح يث‬,‫بقية المراباق‬
‫ ل قثثد تثثم فثثي هثثذر الد را ةثثة اي عثثا ا ت ث را ال يثثة تط ثثي‬.‫اف هثثا ت ةثثلك ةثثل ك مطب طثثاق ت يثثر تفاف ةثثية‬
. ‫المراباق لن اف يم االةيتايك ا لين اةتري‬
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National Journal of Chemistry,2010, Volume 40
‫ المجلد األربعين‬0202-‫المجلة القطرية للكيمياء‬
inflammatory,
cardiotonic
and
herbicidal agent [14] .
Some triazole compounds have
been found to exhibit high activity
against ten selected HIV mutants
[15]
, and other triazole compounds
have been also employed as
antibacterial
and
antifungal
[16,17]
agents
Number of triazole
compounds are endowed with large
number of medical and biological
activities
such
as
tuberculostatic [18]
and
antimicrobial [19,20] .
Introduction
Heterocyclic compounds are
widely distributed in anature and
are essential to life, they play a
vital role in the metabolism of all
living
cell
as
carbohydrate,
[1]
proteins and enzyme . There are a
vast number of pharmacological
active heterocyclic compounds,
many of which are in regular
clinical use. Many heterocyclic
compounds
are
insecticides,
because of there activity as nerve
poisons inhibiting cholinesterase
enzyme [2] .
A number of heterocyclic are
endowed with a large number of
biological and pharmacological
activities, such as antimicrobia,
[1]
[2],
antifungal
,
insecticidal
[3]
[4]
virucidal
, acaricidal
antiinflammatory and central nervous
system [5,6]
Furthermore,
some
thiadiazole
compounds have been found to
exhibit antibacterial, antiviral, and
anticancer activities [7] , and some
compounds have shown to possess
analgesic properties and exhibit a
marked activity in the control of
[8]
bacterial
growth
.
Some
biological
properties
of
thiadiazoles
are
worthy
of
consideration because of their
activities
as
fungicides,
parasiticides and amebicides [9] .
Moreover,
some
thiadiazol
compounds
are
reputed
for
exhibiting
moderate
tumor
inhibitory properties as well as
their uses as anti tubercular [1] , anti
carcinogenic [20] , and muscle
relaxant agents [11] .
Investigators
have demonstrated
that some triazole compounds
exhibit fungicidal properties [12,13] ,
and some
are useful as anti
Experimental
Different heterocyclic compounds
were examined, regarding their effects
on the activity of AChE. The solubility
of these compounds in dimethyl
sulfoxide (DMSO) solvent, and the
stock solution of each compound
(0.5M) were prepared. The effect of
the solvent DMSO on the activity of
AChE was tested and did not show any
inhibitory effect [14]. The percentage of
inhibition was calculated at different
concentrations (1X10-2 – 1x10-8) M for
each
compound.
The
different
concentrations of the compounds were
prepared by dilution with DMSO using
the stock solution.
Procedure:
AChE activity was measured in human
senim using the modified Ellman
method [15] as follows:
(50 µl) of DTNB solution (0.001 M)
was added to 2.25 ml of phosphate
buffer solution (l ml of inhibitor mixed
with 1.25 ml of buffer (pH=7.3, 0.2
M), then (10µl) of serum was added,
mixed well and (2 ml) of the mixture
was transferred to a measuring cell (3
mm), then (34 µl) of ASChI (0.06M)
was added, the change in absorbency
was measured before and after'adding
the substrate at (430 nm) for (3 min).
The
inhibition
percentage
was
calculated by comparing the activity
with and without the inhibitor and
721
National Journal of Chemistry,2010, Volume 40
‫ المجلد األربعين‬0202-‫المجلة القطرية للكيمياء‬
under the same conditions, according
the equation:
The activity in the presence of inhibitor
% Inhibition = 100- ( ‫ *)ـــــــــــــــــــــــــــــــــــــــــــــــــــــــــــــــــــــــــــــ‬100
The activitv in the absence of inhibitor
Study of Inhibition Type:
A constant concentration of
inhibitor was used with different
substrate concentrations ranging from
(0.02 - 0.09 M). These different cone,
were prepared from the stock solution
of (0.l M) ASChl. Two concentrations
(1x10-4, 1x10-6) M of compounds (2, 3,
4, 8, 10, l l , 12, 13) and (1x10-5, 1x106
) M of compounds (1, 5, 6, 7, 9, 14,
15) were used.
The enzyme activity was
determined with and without the
inhibitor. Using the line weaver- Burk
method by plotting 1/v vs. 1/[S]V the
following values were calculated:
1 ) K i value.
2) Vmapp.
3) Type of inhibition
(iv) Series (IV) include compound (9)
in table (1) and compound 3- phenyl- 6(5- nitro- 2- furyl) ethenyl]- 1, 2, 4triazole [3, 4, 6] [1, 3, 4] thiodiazole.
All compounds in these series
(I- IV) showed inhibitory effect on the
enzyme activity and the relationship
between inhibitor concentration and
percentage of inhibition are shown in
figures (1-4).
The enzyme activity decreased
with increased inhibitor concentration
until reaches the minimal value. The
highest inhibition of each compound
was observed at concentration (1 *
10"2M) as shown in fig. (5).
In order to understand the
mechanism of inhibition of these
compounds, the structural properties of
each compound within series were
compared according to the results in
figs. (1-5)and the following findings
were observed. (1) Series (I)
compounds (1) and (2) exhibited
higher percentage of inhibition (89 and
87.5%) respectively than the other two
compounds (12 and 13) which
exhibited
lower
percentage
of
inhibition
(84.1%
and
80.3%)
respectively. This could be attributed
to the presence of 5- nitrofuryl moiety
in compounds (1) and (2), in addition,
of substituted phenyl group in 1, 3, 4thiodiazole ring.
These groups enhanced the
nucleopholcity of /\ C  N attack the
binding site of inhibitor subsequently,
decreased the activity while in
compounds (12) and (13), 5- nitrofuryl
moiety were absent, so the NH2 group
may attack the active site of enzyme
but not as in compounds (1) and (2).
Results and Discussion
The present work is designed
to investigate the biological activity
and effects of different series of
heterocylic compounds (table 1) on
human serum AChE activity in vitro.
According to the results
obtained the compounds could be
Classified into four series as shown
below:(i)
Series (I) included 1, 3, 4Thiadiazole derivatives which are
compounds (1, 2, 12, 13) as shown in
table (1).
(ii)
Series (II) included 1, 2, 4Traizole derivatives, which are
compounds (3, 4, 5, 6, 7, 8, 10, 11) in
table (1).
(iii)
Series (III) included the
substituted benzoic acid hydrazone
containing 5- nitro furan moiety, this
series is included compounds (14,15)
in table (1).
722
National Journal of Chemistry,2010, Volume 40
This may be caused the delecolization
of the pair of electrons in NH2 via
N
.
‫ المجلد األربعين‬0202-‫المجلة القطرية للكيمياء‬
thiadiazol ring.
N
N
O
..NH
.
2
NH
O
NH
(8) Tri [3-(5'- nitro- T - furyl) prop 2
enylidene) amino]-4H-1, 2, 4- triazole.
(2) Series
(II)
compounds
inhibition can be divided into two
groups according to their structures:Group which have no 5nitrofuryl moiety in its structure and
includes compounds (10) 4- amino- 1,
2, 4-triazole and compound (11) 3,5diphenyl- 4- amino 1, 2, 4-traizol. 3, 5diphenyl- 4- amino 1, 2, 4- triazol
shows higher percentage of inhibition
(93.5%) than 4- amino-1, 2, 4- traizole
which could be attributed to the
presence of two phenyl groups at
position 3 and 5, this conjugation of
phenyl group wmv /\ C  N made its
availability as electron rich weaker
than free NH2 group at position 4 to
attack the active site of enzyme.
Group £b) which have 5- nitrofuryl
moiety in its structure and includes
compounds:(3) 5- Amino 2- mercapto- 4- [5'nitro- 2 ' - furyl] methylene amino,
4H- 1, 2, 4- triazole.
(4) 3- Mercapto- 5- (p- N02 phenyl)4H- 1, 2, 4, traizole.
(5) 5- Amino- 3- mercapto- 4 [3'-( 5'- nitro- 2- furyl) prop- 2 - enylidene
amino]- 4H 1, 2, 4- traizole.
(6) 5- Amino- 3- hydroxy- 4 [(3'-[ 5'- nitro- 2- furyl] prop- 2 enylidene)
amino]- 4H 1 , 2 , 4- traizole.
(7) 3- mercapto- 4- phenyl- 5- [ (3'[5'- nitro- T - furyl] prop-2 enyliden)
amino] 4H 1 , 2 , 4- traizole.
Generally, The compounds of
this group show higher percentage of
inhibition ranged between (81.892.3%).
Compound
(7)
shows
relatively higher percentage of
inhibition than compounds (8) and (4),
which may be attributed to the groups
that substituted at positions 4 and 5.
This make the electron rich side in this
compound (SH or /\ C  N ) easier to
approach the binding site of inhibitor.
Furthermore, the binding site of
inhibitor is relatively less steric than
others.
Compound (3) is more potent
inhibitor than compound (5) in spite of
the similarity of the two compounds in
structure, because compound (5) has
long chain (conjugation) at position 4
than compound (3) which causes
decrease in the ability to attack the
binding site of inhibitor, while the
inhibitory effect of compound (6) is
also relatively higher than compound
(6) which may be attributed to the high
nucleophilicity of OH group at position
3 in compound ( 6 ) , though, the
presence of other nucleophilic side (e.
g. NH2) in both of them.
723
‫ المجلد األربعين‬0202-‫المجلة القطرية للكيمياء‬
National Journal of Chemistry,2010, Volume 40
Table 1-: Heterocyclic Compounds used for interaction with AChE
Comp.
No.
Structure
Name
N
1
O 2N
O
CH
N
5-(p-methyl
phenyl)-3-[5'nitro-2'-furyl]
methylamino]l,3,4-thiodiozol e
5-(o-nitro
phenyl)-3-[3(5'nilro-2'furyl)Prop-2enylidene
amino)]-1 ,2J,4thiodizole
5-Amino-2mcrcapto -4-[5'nilro-2'furyl)methylcne
amino)]-4H1,2,4-triazole
S
N
CH3
N
2
O 2N
O
CH
CH
N
3
H2N
N
S
N
CH
NO 2
N
N
SH
N
CH
O
NO 2
Mwt.
314
326
254
phNO 2-p
3-Mercapto -5(p-N0 2 phenyl)4H-1,2,4triazole
N
4
O 2N
O
CH
N
N
N
238
HS
N
5
H2N
N
SH
N
N
6
CH
CH
CH
O
NO 2
N
H2N
N
OH
N
CH
CH
CH
O
NO 2
N
N
7
O 2N
5-Amino-3mercapto -4- [3(5'-nitro-2furyl)Prop-2methylene
amino)]-4Hl,2,4-triazole
5-Amino-3hydroxy -4-[3'(5'-nitro-2furyl)Prop-2enylidene
amino)]-4H1,2,4-triazole
3-Mercapto-4phenyl -5-[3-(5nitro-2'furyl)Prop-2enylidene)
amino]-4Hl,2,4-triazole
N
O
CH
CH
CH
N
N
SH
Ph
N
8
O 2N
O
CH
CH
CH
N
N
N
N
CH
CH
N
N
CH
HC
CH
O
724
NO 2
O
NO 2
Tri[3(5-nitro-2'furyl)
Prop-2enylidene)
amino]-4Hl,2,4-triazole
219
264
341
574
‫ المجلد األربعين‬0202-‫المجلة القطرية للكيمياء‬
National Journal of Chemistry,2010, Volume 40
3-phenyl -6-[5'nitro-2'-furyl)
ethyl]-l,2,4triazolc[3,4,6],[
1,3,4]
thiodiazole
Ph
N
9
O 2N
O
CH
N
NH
CH
S
N
10
N
339
N
N
4-Amino-1,2,4Triazole
84
3,5-diphenyl-4amino-l,2,4triazolc
236
NH2
N
11
Ph
N
N
Ph
NH2
N
12
H3C
N
O
S
O
13
N
NH2
N
C
Ph
S
S
NH2
O
14
O 2N
O
CH
N
NH
C
NO 2
O
15
O 2N
O
CH
N
NH
C
OCH 3
2-(amino-5-(pmcthoxy
phenyl)1,3,4thiadiazole
2-(amino-5-thio
benzoyloxy1,3,4-thiadiazole
5Nitrofurylidene
-N-p-N0 2 benzoic acid
hydrizde
5NilrofurylidcneN-p-methoxybenzoic
acid
hydrizde
206
237
304
289
Type of Inhibition
Type of inhibition, K mapp ,
V mapp and K j were estimated by
measuring the enzyme activity in
the absence and presence of
inhibitor at different concentrations
of substrate under the same
conditions using Lineweaver- Burk
equation and plot, as shown in
table (2) and fig (6-20).
Series (III), compounds (14) and
(15) are very similar in their
structures with the exception of the
difference in substituent group at
position 4 of phenyl ring, N0 2 and
OCH 3 respectively. However, N0 2
group withdraws electrons from
amino group and causes increase of
the electrophilic characters of the
\
/ C  N toward the binding site of
inhibitor.
Series (IV) compound (9) have
various /\ C  N group in different
position, therefore its ability to
attack the active site of enzyme is
high.
725
National Journal of Chemistry,2010, Volume 40
The
results
suggested
that
compounds
1-15
are
noncompetitive inhibitors.
In non competitive type of
inhibition which does not effect the
combination of substrate with the
enzyme, Km remained constant
while V max change dramatically.
Mechanism of Inhibition
In
the
mechanism
of
hydrolysis ACh by AChE, the
hydroxyl group of the amino acid
serine is connected with the
imidazole of the histidene residue
via hydrogen bonding which causes
increase
of
the
nucleophilic
characters of hydroxyl group to
‫ المجلد األربعين‬0202-‫المجلة القطرية للكيمياء‬
form
a covalent bond with the
carbonyl carbon of acetylcholine as
in scheme (1) to form enzymesubstrate complex, after that the
choline molecule is released and
latter the hydrolysis takes place to
produce acetic acid and regenerate
free enzyme [24,24,26] .
The proposed mechanism of action
of heterocyclic compounds as
AChE
inhibitors
studied
as
indicated are shown in schemes (25) with the consideration that the
inhibitor binding site is in close
resemblance with the active site
functional groups.
726
National Journal of Chemistry,2010, Volume 40
‫ المجلد األربعين‬0202-‫المجلة القطرية للكيمياء‬
C
C
H
H
-
O
O
R1
R1
C
N
R2
C
H
O
N
R2
HA
HA
O
O
A1
-
O
-
A1
N
HN
+
A2
A2
Scheme(2) Suggested mechanism for inhibition AChE by compounds
(1,2,3,4,5,6,7,8,14, and 15)
A1= Ser, Glu, Asp, and Tyr
A2= His, Lys, Arg, Gln, and Asn
R1
R2
N
1
O
N
S
NO 2
CH3
N
2
HC
C
O
N
3
N
O 2N
S
NO 2
N
H2N
N
SH
O
NO 2
Ph p-NO 2
4
N
O
NH
NO 2
N
HS
N
5
N
H2N
N
N
6
7
HC
SH
C
O
NO 2
C
O
NO 2
N
N
N
H2N
N
HC
OH
HC
N
C
O
SH
NO 2
Ph
N
N
8
N
N
N
CH
CH
N
N
O
N
HC
C
O
CH
NO 2
N
N
HC
CH
O
NO 2
O
14
HN
O
C
NO 2
NO 2
O
15
HN
O
NO 2
727
C
NO 2
NO 2
National Journal of Chemistry,2010, Volume 40
‫ المجلد األربعين‬0202-‫المجلة القطرية للكيمياء‬
C
C
..NH2
R
O
-
O
R
HA
H
+
N H
H
O
-
O
A
OH
O
H
A1
N
A1
N
A2
A2
Scheme(3) Suggested mechanism for inhibition AChE by compounds
(3,5,6,10,11,12, and 13)
A1= Ser, Glu, Asp, and Tyr
A2= His, Lys, Arg, Gln, and Asn
R
N
N
3
N
SH
N
CH
O
N
5
N
SH
N
N
6
10
CH
CH
O
NO 2
OH
N
CH
CH
CH
O
NO 2
N
N
N
11
CH
N
N
N
NO 2
N
Ph
N
N
N
Ph
N
12
O
CH3
S
N
N
O
13
C
S
S
Ph
728
‫ المجلد األربعين‬0202-‫المجلة القطرية للكيمياء‬
National Journal of Chemistry,2010, Volume 40
C
O
O
-
O
C
R2
C
H
O
R2
HA
HA
O
O
A1
-
O
O
R1
R1
C
-
A1
N
HN
+
A2
A2
Scheme(4) Suggested mechanism for inhibition AChE by compounds (13,14, and
15)
A1= Ser, Glu, Asp, and Tyr
A2= His, Lys, Arg, Gln, and Asn
R1
R2
N
N
Ph
13
S
14
S
NH2
NO 2
N
HN
15
O
NO 2
O
NO 2
OCH 3
N
HN
C
Ph
C
Ph
N
O 2N
O
CH
N
..
..
N
O
H
-
O
O 2N
O
CH
N
..
O
-
S
N
+
O
HA
A1
N
H
H
N
A2
A2
Scheme(5) Suggested mechanism for inhibition AChE by compound (9)
A1= Ser, Glu, Asp, and Tyr
A2= His, Lys, Arg, Gln, and Asn
729
O
NH
CH
NH
CH
S
A1
O
N
A
National Journal of Chemistry,2010, Volume 40
‫ المجلد األربعين‬0202-‫المجلة القطرية للكيمياء‬
Inhibition [%]
100
90
1
80
2
70
12
13
60
50
40
30
20
1E-09
1E-08
1E-07
1E-06 0.00001 0.0001
0.001
0.01
0.1
Inhibitor Conc. [M]
Fig. 1-: Effect of different concentration of series (I) ( compounds 1, 2, 12,
and 13) on human serum AChE activity
100
3
90
4
Inhibition [%]
5
80
6
70
7
60
8
10
50
11
40
1E-09
1E-08
1E-07
0.000001 0.00001
0.0001
0.001
0.01
0.1
Inhibitor Conc. [M]
Fig. 2-: Effect of different concentration of series (II) ( compounds 3, 4, 5, 6,
7, 8, 10, and 11) on human serum AChE activity
100
14
Inhibition [%]
95
15
90
85
80
75
70
1E-09
1E-08
1E-07
0.000001 0.00001
0.0001
0.001
0.01
0.1
Inhibitor Conc. [M]
Fig. 3-: Effect of different concentration of series (III) ( compounds 14 and
15) on human serum AChE activity
730
‫ المجلد األربعين‬0202-‫المجلة القطرية للكيمياء‬
National Journal of Chemistry,2010, Volume 40
100
9
Inhibition [%]
95
90
85
80
75
70
1E-09
1E-08
1E-07
0.000001 0.00001
0.0001
0.001
0.01
0.1
Inhibitor Conc. [M]
Fig. 4-: Effect of different concentration of series (IV) ( compound 9 on
human serum AChE activity
100
Inhibition [%]
90
80
70
60
50
40
30
20
10
0
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
Compound number
Fig. 5-: Diagram shows the effect of 10-2 M of compound (1-15) on human
serum AChE activity.
731
National Journal of Chemistry,2010, Volume 40
‫ المجلد األربعين‬0202-‫المجلة القطرية للكيمياء‬
Table (2) Kinetic Parameter of AChE with different heterocyclic
compounds
Comp. No
l x l O -4M
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
Vmapp ( j i m o i e / ml/
min)
2.169
2.33
2.345
2.55
2.62
3.02
2.234
2.63
3.16
2.48
2.817
2.38
2.91
2.75
3.209
732
Ki(M)
2.29
2.69
2.36
2.69
2.43
2.17
2.97
2.46
2.78
2.85
2.96
1.88
2.46
2.57
2.22
x
x
x
x
x
x
x
x
x
x
x
x
x
x
x
10-5
10-5
10-5
10-5
10-5
10-5
10-5
10-5
10-5
10-5
10-5
10-5
10-5
10-5
10-5
‫ المجلد األربعين‬0202-‫المجلة القطرية للكيمياء‬
1.2
1.2
1
1
0.8
0.8
1/V
1/V
National Journal of Chemistry,2010, Volume 40
Comp. 2
0.6
+ without [I]
-6
● with 10 M [I] 0.4
▲ with 10-4 M [I]
Comp. 1
0.6
+ without [I]
● with 10-6 M [I] 0.4
▲ with 10-4 M [I]
0.2
0.2
0
0
-40
-20
-40
0
20
40
-20
0
60
20
40
60
1/[S]
1/[S]
1.2
1.2
1
1
Comp. 4
+ without [I]
● with 10-6 M [I]
▲ with 10-4 M [I]
0.8
0.6
0.8
1/V
1/V
Comp. 3
+ without [I]
● with 10-6 M [I]
▲ with 10-4 M [I]
0.6
0.4
0.4
0.2
0.2
0
0
-40
-20
0
20
40
-40
60
-20
0
20
40
60
1/[S]
1/[S]
1.6
1.2
1.4
1
Comp. 5
+ without [I]
● with 10-6 M [I]
▲ with 10-4 M [I]
1/V
1/V
1.2
1
0.8
Comp. 6
+ without [I]
● with 10-6 M [I]
▲ with 10-4 M [I]
0.8
0.6
0.4
0.6
0.4
0.2
0.2
0
-40
-20
0
0
20
40
60
-40
-20
0
1/[S]
20
40
60
1/[S]
1.6
1.2
1.4
1
1
Comp. 7
+ without [I]
● with 10-6 M [I]
▲ with 10-4 M [I]
0.8
1/V
1/V
1.2
Comp. 8
+ without [I]
● with 10-6 M [I]
▲ with 10-4 M [I]
0.6
0.4
0.4
0
0
-20
0.6
0.2
0.2
-40
0.8
0
1/[S]
20
40
60
-40
-20
0
1/[S]
20
40
60
Fig. -6: Line Weaver-Burk plot of AChE in the presence and absence of compounds 1-8
733
‫ المجلد األربعين‬0202-‫المجلة القطرية للكيمياء‬
Comp. 9
+ without [I]
● with 10-6 M [I]
▲ with 10-4 M [I]
1.2
1.2
1
1
0.8
1/V
1/V
National Journal of Chemistry,2010, Volume 40
Comp. 10
+ without [I]
● with 10-6 M [I]
▲ with 10-4 M [I]
0.6
0.4
0.2
-40
20
40
60
-40
1
0.9
0.8
0.7
0.6
0.5
0.4
0.3
0.2
0.1
0
Comp. 12
+ without [I]
● with 10-6 M [I]
▲ with 10-4 M [I]
60
0 1/[S]
20
40
60
1/[S]
20
0.8
0.6
0.4
0.2
0
20
40
60
-40
-20
1.4
1.4
1.2
1.2
1
1/V
1/V
-20
40
1
Comp. 14
+ without [I]
● with 10-6 M [I]
▲ with 10-4 M [I]
0.8
0.6
0.8
0.6
0.4
0.4
0.2
0.2
0
0
-40
20
1.2
1
Comp. 13
+ without [I]
● with 10-6 M [I]
▲ with 10-4 M [I]
0 1/[S]
1.4
0 1/[S]
-20
-20
1/V
1/V
Comp. 11
+ without [I]
● with 10-6 M [I]
▲ with 10-4 M [I]
0.4
0
0 1/[S]
-20
0.6
0.2
0
-40
0.8
0 1/[S]
20
40
60
-40
-20
0
40
1/V
1.8
1.6
Comp. 15
+ without [I]
● with 10-6 M [I]
▲ with 10-4 M [I]
1.4
1.2
1
0.8
0.6
0.4
0.2
0
-40
-20
0
1/[S]
20
40
60
Fig.-7:Line Weaver-Burk plot of AChE in the presence and absence of compounds 9-15
734
60
National Journal of Chemistry,2010, Volume 40
‫ المجلد األربعين‬0202-‫المجلة القطرية للكيمياء‬
15. Zdzislaw B., C. A., 1999, 131
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18. Rist L. N. and Grambach F., C.
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19. Schoog
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20. Verma N.,
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21. Jaffer H. J.. Mahond M. J. and
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