new aspects into the chemistry of coenzyme q10 family members (calcium binding and transporting)
DESCRIPTION
NEW ASPECTS INTO THE CHEMISTRY OF COENZYME Q10 FAMILY MEMBERS (calcium binding and transporting). Rubin Gulaboski, Ivan Bogeski, Valentin Mirceski , Reinhard Kappl, Markus Hoth. Rubin Gulaboski , Ivan Bogeski , Reinhard Kappl , Markus Hoth , - PowerPoint PPT PresentationTRANSCRIPT
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NEW ASPECTS INTO THE CHEMISTRY OF COENZYME Q10 FAMILY MEMBERS(calcium binding and transporting)
Rubin Gulaboski, Ivan Bogeski,
Valentin Mirceski, Reinhard Kappl,
Markus Hoth
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Rubin Gulaboski, Ivan Bogeski, Reinhard Kappl, Markus Hoth, „Benzoquinones based Antioxidants”, European Patent Office,
Munich 2010, PATENT No. 09178735.8.
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Coenzyme Q10 is a redox mediator in the mitochondrial electron transfer chain (METC)
contributing to the mitochondrial ATP production
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QUINONE (oxidized form)
QUINOL (reduced form)
23 5
63HC3HC CH3
3HC3HC CH3
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Most of the members of METCare „one-electron” mediators
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Reactive Oxygen Species =
Mitochondrial electron transport chain is a major source of highly dangerous ROS!!!
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O2
O:O.. .... ... .
.O2
-H2O2
.OH H2O
O:O-....
.. .. :. H:O:O:H
.. ..
.. .. .O:H.... H:O:H
..
..
e-
e-
e-
e-
Oxygen Superoxide Hydrogen peroxide
Hydroxylradicalanion radical
Water
Superoxide dismutase
Glutathione PeroxidaseCatalase
Structures ofthe most common
ReactiveOxygenSpecies
evaluated from O2
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Effective „cure“ against ROS
are the Antioxidants
Ubiquinol-moderate antioxidant
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We started working on this project in 2006
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Effect of Ca2+ ions tothe redox process of2-palmytoilquinone- transfer of Ca2+ across lipid membrane
Structure of2-palmytoilhydroquinone
Our Aim: to see whether CoQ’s have something to dowith Ca2+ transfer across mitochondrial membranes
This compound can bind and transfer Ca2+ ions across biomimetic membranes
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Ca2+ -is one of the most important second messengers
Why Ca2+?
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Mechanisms of Ca2+ transfer in mitochondria
???
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O
O
O
OCH3
CH3
CH3
CH3
CH3
Coenzyme Q1
O
O
O
OCH3
CH3
CH3
n(2HC-(3HC)C=HC-CH2)
Coenzyme Q10
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Cyclic voltammogram of 100 µM CoQ1 in pH of 7.00
Experiments with Coenzyme Q1-CoQ1
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pH dependence of the redox process of CoQ1-the “yellow form” in the pH range from 1 to 9
pH increase
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O
O
O
OCH3
CH3
CH3
CH3
CH3
+ 2e-
+ 2H+
OH
OH
O
OCH3
CH3
CH3
CH3
CH3
Coenzyme Q1 (oxidized) Coenzyme Q1 (reduced)
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CoQ1-the yellow form=insensitive to Ca2+ ions
That is, ...END OF THE STORY, or MAY BE NOT?
+ 2e- + 2Ca2+=?
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-0 .00008
-0.00004
0
0.00004
I/A
60 m inu tes
I
II
I'
I I'
-0 .00008
-0.00004
0
0.00004
I/A
I
II180 m inutes
I 'I I'
-0 .00 0 06
-0 .00 0 02
0 .00 0 02
0 .00 0 06
I/A
3 m inutes I II
I'
II '
-0.00008
-0.00004
0
0.00004
-1-0.8-0.6-0.4-0.200.2E / V
I/A
24 hours II
II'
Cyclic voltammograms of CoQ1 recorded in 1 mol/L NaOH.
Scans recorded after 3 min (1) 1 h (2) 3 h (3) and 24 h (4).
Scan rate of 30 mV/s, c(CoQ1) = 0.075 mmol/L.
Significant changes in the voltammetric responses have been observed whenCoQ1 was dissolved in 1M NaOH!
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UV-Vis spectrum of 10 µM CoQ1 recorded in kinetic mode in 1 M NaOH
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Comparison of the cyclic voltammograms of CoQ1 directly dissolvedin pH of 7.00, and of CoQ1 initially dissolved in 1 M NaOH for 45 min
and retitrated afterwards to pH of 7.00
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pH increase
Effect of pH to the redox processes of CoQ1. In this situationCoQ1 was in contact with 0.1 M NaOH for 60 minutes
Next logical task: DETERMINE the MECHANISMand the STRUCTURE of the New Benzoquinone Product
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Electron Paramagnetic resonance-EPR-suitable technique for structureevaluation by the radical species
(many quinones form radicals when dissolvedin alkaline media)
Simulated EPR spectrum of the CH3 radical
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EPR spectrum of CoQ1 after reduction withhalf-equimolar amount of NaBH4 in pH of 7.00
EPR spectrum of CoQ1 obtained in 0.1 M NaOH butwithout using any reductant!!
Nine-line EPR spectrum od parent CoQ1 corresponds to presence of one CH3 and one CH2 group in the structure
CH2
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I
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NEXT STEP to determine the structure-NMR EXPERIMENTSNMR spectrum of CoQ1 in D2O
Protons of O-CH3
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CoQ1-5 minutes in NaODretitrated afterwards topD of 7.00
Signal from the protonsof METHANOL
Protons of O-CH3
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CoQ1-10 minutes in NaODRetitrated afterwards topD of 7.00
Signal from the protonsof METHANOL
Protons of O-CH3
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CoQ1-25 minutes in NaODRetitrated afterwards topD of 7.00
Signal from the protonsof METHANOL
Protons of O-CH3
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CoQ1-60 minutes in NaODRetitrated afterwards topD of 7.00
Signal from the protonsof METHANOL
Protons of O-CH3
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2-methyl-benzoquinoneTetramethyl benzoquinone
(duroquinone)
Where METHANOL doescome from, when CoQ is
dissolved in alkaline media?-from the methyl group?
or -from the METHOXY
O-CH3 group?
By using methyl benzoquinonederivatives we found that the
methyl group CAN NOT BE
CLEAVED from the aromatic
ring!!!
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O
O
O
CH3
CH3
OCH3
CH3
CH3
+ 2OH-
O
O
O-
CH3
O-
CH3
CH3
+ 2CH3OH
Coenzyme Q1 O-demethylated Coenzyme Q1
(2,3-dihydroxo-5-methyl-6-isoprenyl-benzoquinone)
????
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Ratio of the signal of Methanol vs Methoxy groups fromNMR experiments of CoQ1 in NaOD
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Color of solutions ofBenzoquinones with
2 OH groups in its structure
Color of solutions ofBenzoquinones with
1 OH group in its structure
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Benzoquinones with 2-OH groups are able to bind earth-alkaline cations
in ratio 1:2
Benzoquinones with 1-OH group are NOT able to bind (at least not strongly)
earth-alkaline cations
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New form of CoQ-1, sensitivity to Ca2+ ions
concentration of Ca2+ increase
New product is able to bind Ca2+ ions in stochiometric ratio 1:2 (L:M2+)
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Dependence of the mid-peak potential of the cyclic voltammograms of new form of CoQ1
on the logarithm of Ca2+ concentration
The slope of 59mV indicates a complexof a type 1:2 (L to M)
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O
O
O
CH3
CH3
OCH3
CH3
CH3
+ 2OH-
O
O
O-
CH3
O-
CH3
CH3
+ 2CH3OH
Coenzyme Q1 O-demethylated Coenzyme Q1
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EXPERIMENTS with Coenzyme Q10-CoQ10
Native CoQ10 is absolutelyinsoluble in water, but... it can be dissolved in
NaOH...and
it can be transformedinto a new form in
presence ofOH- anions presentin the organic phase
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The membrane-bound enzymeCytochrome P450 does the same
task as NaOH to CoQ10!!!
Coenyzme Q10 in presence of 1 M NaOH
5 µM Coenyzme Q10 in presence of 1 M NaOH and retitrated to pH of 7.0
after 3 weeks
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Effect of Ca2+ to the voltammetricresponse of CoQ10 in presence of CYP450
in pH of 7.40
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O
O
O CH3
RO
CH3
CH3
+
O
O
CH3
R-O
-O
+ 2CH3OH2OH
-
O
O
CH3
R-O
-O
O
H
H
O H
H
O
O
CH3
R-O
-O
+ OH2
O
O
CH3
R-O
-O
+ 2e-
-O
-O-O CH3
R-O
+ 2Ca2+
-O
-O-O CH3
R-O
Ca2+
Ca2+
2. Stabilization of the CH3-cleaved CoQ10 products in water
3. Reduction of the CH3-cleaved CoQ10 product and binding of Ca2+
CYP450
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Experiments with CoQ10 embedded in organic membrane in presence of organic Hydroxide to show whether the new form of CoQ10
can transfer Ca2+ ions across biological membranes
electrode
CoQ10 embedded+ OH-
Lipid membraneCa2+ out
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0
0.6
1.2
1.8
0 30 60 90 120 150 180
Ra
tio
(3
40
/38
0)
Time (min)
WT+Ca+Cyt WT+Ca
75%
80%
85%
90%
95%
100%
105%
Mito WT Mito CoQ10 KO
Mit
oc
ho
nd
ria
l C
a2+ i
nfl
ux
(s
lop
e i
n %
) ***
Experiments with wild types of mitochondria and knockout mitochondria depleted of CoQ10 in absence and in presence of CYTP450. Effect of Ca2+ ions.
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SUMMARY
Plenty of CoQ family members are present in the living systems
The chemistry and most of the functions of the native forms of Coenzyme Q family members are mainly portrayed in the
features of the 2e-/2H+ redox reaction (electron and proton transfer) that leads to reversible transformation of the quinone to
quinol forms.
If the Coezyme Q structures are in contact with high concentration of OH - ions or CYP450 enzymes, quite different
quinonic forms can be obtained.
CYP450 and NaOH can both induce scission of the both O-CH3 (methoxy) groups in the structure of the Coenzyme Q
family members, thus creating so called „O-demethylated“ quinones that bear charge of „2-“.
These new Coenzyme Q structures formed in alkaline media (or in presence of CYP450) are more polar than their parent
compounds, while also having much stronger antioxidative features.
The inherent properties of the new Coenzyme Q structures to bind the earth-alkaline cations upon their reduction classify
these compounds as potential facilitators for transferring of metal ions across biological membranes.
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Main people involved in this projectA. in Homburg
Prof. Mirceski
Bernd MorgensternBarbara Kutzky
B. Saarbrücken
C. UNi K‘Lautern Prof. Hermann
D: MKD
R. Kappl
M. HothI. Bogeski
Richi Kohler
ACKNOWLEDGMENT also toAlexander von HumboldtFoundation
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Experiments with Coenzyme Q10-CoQ10
droplet of org. solution of an electroactive compound
Electron conductor, graphite electrode
Organic water
immiscible solvent
Cat2+ 2An-
Liquid-Liquid interface
H+ OH-
Solubility of CoQ10 in water is bellow 10 pM!!!Impossible to perform experiments in water media!
CoQ10 studied voltammetrically in Thin-film voltammetry set-up
Cat2+ H+ H+
H+ OH-
CoQ10 + 2e- CoQ102-
CoQ10
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The processes in the mitochondrial electron transfer chain are driven by the differences in the standard redox potentials of the contributors
-E/V
0.0
-0.2
0.2
NADH
CoQ
Complex III
Complex IV
_
_
_