123 ff4 fsf fc0 sc0 ls1 ws1">Luminescence for 30 sec 2 × 10–16 mol/l 4.7 × 10–16 mol/l 2.1 × 10–15 mol/l Not less than 20 minutes
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I. P. Ivanova et al. / Journal of Biophysical Chemistr y 3 (2012) 88-1 00 93
Table 5. The stationary concentration of hydrogen peroxide
formed in the water under the influence of background radia-
tion (calculated). The estimated time for the steady-state con-
centration is 107 seconds.
[H2O2] (mol/l) at various levels of background
radiation
[] (mol/l)
3
HCO
0.012 µSv/h 0.12 µSv/h 1.2 µSv/h
10–2 2.5 × 10–11 2.3 × 10–10 2.5 × 10–9
10–3 2.5 × 10–11 2.3 × 10–10 2.3 × 10–9
0 1.1 × 10–11 8 × 10–11 6.2 × 10–10
ide decreases.
3.6. Scheme of the Oxidation by Radicals
Generated in the Fenton Reaction with
the Formation of Luminous Products
The mechanisms of luminescence of Fenton solution
in a neutral solution (pH ~ 7) are analyzed for the fol-
lowing cases:
1) solution of Fenton (no other chemicals are intro-
duced);
2) addition of luminol;
3) ideal antioxidant M (a substance capable of oxida-
tion);
4) addition of organic substance RH, which can de-
velop a chain reaction of oxidation:
a) a substance capable of forming radicals 2
RO
(with
availability of oxygen);
b) a substance that generates only radicals R (with a
lack of oxygen). Channels reactions are conditionally
presented in Scheme 1 and numbered.
Case 1. Pure Fenton solution. Scheme 1, channel 1.
The reaction products are ferric ions and hydroxyl radi-
cals ОН. A luminescence mechanism has already been
shown (see Tables 1 and 2). The sequence of reactions of
radicals can be represented as follows: OH 2
HO
2 O2(a1g). A luminiscence of the dimer of singlet
oxygen is in the red spectrum (
= 480, 535 and 580 nm).
Luminescence duration is not determined by spending
the reagents in the Fenton reaction, but by the time re-
quired to attain a sufficiently large number of ions Fe3+
that use radicals and thus cease to glow.
O
2
Case 2. Luminescence with luminol in a neutral
medium. Scheme 1, channel 2. Luminol Lum reacts
with a hydroxyl radical, forming radical L. This radical
reacts with superoxide radicals 2, and after a chain of
reactions, conditionally presented in the scheme by two
crosses, luminescence of a quantum in the blue spectral
region appears [3,4]. This is the case as long as there is
no ferric iron. When ions Fe3+ appears, the radical 2
O
O
O
is consumed in the reaction with Fe3+. In this case the
blue glow decreases, and fully stops with high concen-
trations of Fe3+. But with low concentrations of ferric
iron the luminescence covers the blue spectral region
(luminol) and the red one (dimer of singlet oxygen),
since luminol does not intercept all the produced hy-
droxyl radicals. The luminol-dependent luminescence of
Fenton solution in a neutral solution is considered in
more detail in [5].
Case 3. An ideal antiox idant M is the substance oxi-
dized by radicals. The reaction products are low-active
radicals not capable to participate in further conversions
with a considerable rate. In this case, the hydroxyl radi-
cals are consumed in its oxidation. If the reaction rate M
+ OH is much greater than that of in channel 1, no light
emission will occur. When the rate of consumption of
ОН radicals in the processes 1 and 3 are comparable, the
luminescence will be observed in the red spectrum. With
increasing concentration of substance M luminescence
will diminish until it completely disappears. The de-
pendence of the light sum for 30 seconds on the concen-
tration of introduced material M is shown in Figure 2.
Figure 2(a) represents the results of the calculation and
(a)
(b)
Figure 2. Chemiluminescence of ideal antioxidant M
in the oxidation by the Fenton reagent, [Fe2+] = 10–3
mol/l, [H2O2] = 10–4 mol/l. Along the ordinate axis:
the ratio of the light sum for 30 seconds at a given
concentration of test substance S to the light sum for
30 seconds for a pure Fenton solution S0, S/S0. (a)
The calculation of the conditional material M. [M] -
concentration of substance, mol/l; (b) The experiment-
tal data on the chemiluminescence of alanine in Fen-
ton solution. [Al]—the alanine concentration, mg/l.
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I. P. Ivanova et al. / Journal of Biophysical Chemistr y 3 (2012) 88-1 00
94
Scheme 1. Reactions in Fenton solution, leading to light emission. Numerals indicate the following cases: 1. Only
Fenton solution; 2. Luminol is added in Fenton solution; 3. Fenton solution with ideal antioxidant M; 4. Oxidation
of organic matter RH in Fenton solution: a) in the presence of dissolved oxygen b) with a deficiency or complete
absence of oxygen.
Figure 2(b)—the experimental data for alanine, an ideal
antioxidant. The reaction constant M + ОН is taken
equal to 108 (mol·s)1.
Case 4. Oxidation of organic substances. A distinc-
tive feature of the organic substances is the ability to
continue the chain reactions. A typical scheme of oxida-
tion of organic matter RH in water solution is presented
in Table 6. The first active product of oxidation is radical
R (reaction 26). Further, in the absence of oxygen, these
radicals can be lost in interactions with each other (reac-
tion 31). No luminescence will occur if the concentration
of the substance introduced is high and it catches all the
hydroxyl radicals. In the intermediate case there can be
the situation considered for case 3 when not all hydroxyl
radicals are used by RH substance and luminescence in
channel 1 is preserved. This channel will be active in
case of the lack of oxygen if [R] >> [O2] (channel 4b,
Scheme 1). If there is enough oxygen, then radical 2
RO
(reaction 27) is formed leading to singlet oxygen emer-
gence (reaction 32). There is no interdiction implied on
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I. P. Ivanova et al. / Journal of Biophysical Chemistr y 3 (2012) 88-1 00 95
Tab le 6. Reactions of organic matter RH initiated by hydroxyl
radicals in an aqueous solution.
No Reaction k, (mol·s)–1 [11]
26. RH + OH R + H2O 108
27. R + O2
2
RO104
28. 2
RO + RH ROOH + R 106
29. ROOH + Fe2+ Fe3+ + OH + RO 100
30. RO + RO ROOR 105
31. R + R R-R 106
32. 2
RO + ROOR + O2 + O2(a1g)
2
RO107
the formation of oxygen in a particular spin state for re-
action 32. The ratio of the population probability for
triplet and singlet states is determined by the rules of
quantum mechanics and is 3:1. A dimer of singlet oxygen
irradiates in the red spectrum (channel 4a, Scheme 1).
The spectral composition of radiation has been tested
with blue and red filters. The dependence of lumines-
cence on the concentration of injected substances into
channels 4a and 4b will be different.
Case 4b. If there is no substance, [RH] = 0, the solu-
tion luminescence will be determined by channel 1 (pure
Fenton solution). With the increase of RH concentration
more radicals OH are consumed and luminescence di-
minishes until it completely disappears. The dependence
of luminescence on the concentration of introduced sub-
stances will be similar to that of shown in Figure 2.
Case 4a. The addition of RH in low concentrations in
Fenton solution has no effect on chemiluminescence. As
[RH] increases, the luminescence caused by the reaction
of the radicals 2 becomes more intense. The total
luminosity can increase tens times as large and reach
maximum intensity. With the further increase of [RH],
reaction 2 + RH (reaction 28, Table 6 ) consuming
radical 2 begins to play its role and the emission de-
creases. When [RH] >> [2
RO
RO
RO
RO
], the interaction of the
radicals 2 with each other (reaction 32, Tab l e 6 ) is
very unlikely and the emission stops.
RO
The results of calculation of S/S0 from the concentra-
tion of RH at different oxygen concentrations in solution
are shown in Figure 3(a). The flash of luminescence is
seen to decrease with the decrease of oxygen concentra-
tion and in the full absence of oxygen RH substance be-
comes almost a perfect anti-oxidant (compare Figure 2
(a)). The substantiality of calculation is confirmed by the
experimental data for albumin (Figure 3(b)), when at a
certain concentration of albumin luminescence reaches
its maximum and then decreases.
3.7. Individual Substance
There may be cases, especially for low-molecular or-
(a)
(b)
Figure 3. Chemiluminescence of organic matter RH in
the oxidation by the Fenton reagent, [Fe2+] = 10–3 mol/l,
[H2O2] = 10–4 mol/l. The ordinate axis: the ratio of the
light sum for 30 seconds at a given concentration of the
test substance to the light sum S for 30 seconds clear
solution Fenton S0, S/S0. (a) The calculation for the
conditional substance RH. [RH]—concentration of sub-
stance, mol/l. The rate constants are given in Tab le 6.
The concentration of dissolved oxygen [O2]: 1) 10–4
mol/l, 2) 10–5 mol/l, 3) [O2] = 0; (b) The experimental
data on the chemiluminescence of albumin in Fenton
solution. [A]—concentration of albumin, mg/l. The
nonmonotoneness of presented dependence is associ-
ated with experimental errors.
ganic substances, when oxidation cannot be described by
the scheme shown in Ta bl e 6 . In this case the character-
istics of the substance are to be taken into account. The
oxidation of oxalic acid by hydroxyl radicals was studied
in detail [12,13]. A simplified scheme of reactions con-
tributing to the chemiluminescence is given in Table 7.
The particularity of this case is the formation of the
radical 2
HO
(reaction 34) instead of 2 and regen-
eration of oxalic acid (reaction 35). Radicals 2
RO
HO
do
not decompose oxalic acid at an appreciable rate, so with
the increase of acid concentration the luminescence is
not reduced. The calculated dependence of the chemilu-
minescence of oxalic acid on its concentration is pre-
sented in Figure 4(a). With the increase of oxalic acid
concentration the luminescence is seen to increase. With
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I. P. Ivanova et al. / Journal of Biophysical Chemistr y 3 (2012) 88-1 00
Copyright © 2012 SciRes.
96
Table 7. The reactions of oxalic acid affecting the chemiluminescence in Fenton solution.
Reaction k (mol·s)–1 [13]
33. (COOH)2 + OH HOOC-COO + H2O 1.4 × 106
34. HOOC-COO + O2 HO2 + 2CO2 1 × 108
35. HOOC-COO + HOOC-COO (COOH)2 + 2CO2 7.7 × 106
OPEN A CCESS
(a)
(b)
Figure 4. Chemiluminescence of oxalic acid in the
course of oxidation by the Fenton reagent, [Fe2+] =
10–3 mol/l, [H2O2] = 10–4 mol/l. S/S0—see Figure 2.
(a) The calculation is according to the reaction scheme
shown in Table 7. [Oxalic]—concentration of oxalic
acid, mol/l. 1) The concentration of dissolved oxygen
[O2] = 10–4 mol/l. 2) [O2] = 10–6 mol/l. 3) [O2] = 0 (no
oxygen). 4) Chemiluminescence of Fenton solution
due to the external background radiation. (b) The ex-
perimental data for sodium oxalate, [oks]—concentra-
tion of sodium oxalate, mg/l. The nonmonotoneness of
presented data is related to experimental errors.
decreasing concentration of oxygen the intensity of che-
miluminescence decreases and in the absence of oxygen
oxalic acid behaves as an ideal antioxidant. If oxalic acid
concentration is high in the absence of oxygen not only
radicals OH generated in the Fenton reaction are con-
sumed but also those generated by external radiation
background. Figure 4(a) shows that at concentrations of
[Oxalic] = 10–2 mol/l chemiluminescence yield (curve 3)
is significantly below the level set by the background ra-
diation (line 4).
The calculated dependence is qualitatively confirmed
by the experiment with sodium oxalate (Figure 4(b)).
The main difference from the reaction schemes presented
in Tab le 6 is that with increasing concentration of oxalic
acid luminescence increases without passing through its
maximum and decreases no further as shown in Figure 3.
A higher yield of chemiluminescence compared to a pure
Fenton solution is due to the fact that in Fenton solution
most OH radicals disappear during interactions with
each other failing to transform into radicals 2
HO
. When
oxalic acid is added in a sufficiently high concentration,
so that [Oxalic] > [OH], a major part of ОН radicals
interacts with it and the radicals fully transform into
radicals 2
HO
. As the concentration of oxalic acid in-
creases, the part of radicals OH transformed into 2
HO
also grows.
3.8. The Form of Chemiluminescence Light
Impulse
Three cases are possible.
1a. Fenton solution. The maximum intensity is ob-
served at first when the reaction rate is at its maximum.
Taking into account the delay in the registration system
the front duration can be 0.1 - 0.2 seconds. The ferric
iron that is formed consumes 2 radicals and weakens
the luminescence. When 20% - 30% of the initial Fe2+ is
converted to Fe3+, the luminescence practically stops.
O
1b. Luminol in neutral medium (pH 6 - 7). The
situation is similar to a pure solution of Fenton. In Fen-
ton solution with luminol the maximum light emission
intensity is observed immediately after mixing the re-
agents. With increasing concentration of Fe2+ and H2O2
reaction rate increases and the amplitude of the light
flash grows. The characteristic forms of impulse for this
case are described [5].
2. Simple substance absorbing the hydroxyl radi-
cals (ideal antioxidant M). At first it can absorb practi-
cally all the hydroxyl radicals, so there will be no flash
of light. Noticeable luminescence appears when the part
of the substance is oxidized by radicals. The leading
front of the pulse will be longer and can take 1 - 2 sec-
onds.
3. Organic matter RH. If it absorbs not all the hy-
droxyl radicals, the luminescence of Fenton solution it-
self will be seen. As the chain reaction starts, the oxida-
tion products (radicals 2
RO
) are produced, and their in-
I. P. Ivanova et al. / Journal of Biophysical Chemistr y 3 (2012) 88-1 00 97
teraction leads to the production of an additional singlet
oxygen. It gives a new outbreak of light radiation, which
is superimposed on the luminescence of Fenton solution.
The delayed appearance of a new light impulse is deter-
mined by reaction rates 26 - 32 (Table 6) and can last 10
- 30 seconds, the flash duration being a few minutes. The
amplitude of the second light flash can exceed by far the
luminescence of Fenton solution. Calculated under the
above-stated model luminosity of the mixture of Fenton
solution with the RH substance is given in Figure 5. The
graph shows the luminescence of a pure Fenton solution
(peak 1) and luminescence formed in reactions 26 - 32
(peak 2).
The form of the light radiation impulse, as shown in
Figure 5, was really observed in the studies of chemilu-
minescence [2,3]. The emission maximum 1 and 2 can be
interpreted as follows:
Maximum 1—glow caused by reactive oxygen spe-
cies.
Maximum 2—the glow caused by free-radical proc-
esses in the sample (the formation of ).
2
Not all organic substances during oxidation pass
through a stage of formation of 2 type compounds.
In this case maximum 2 is not observed. For example, in
oxalic acid oxidation 2 is formed instead of radical
2 (see Table 7). Radical 2 plays a minor part in
the oxidation of ascorbic acid. Thus, the fact of appear-
ance or absence of maximum 2 (Figure 5) enables to
draw conclusions about the reaction mechanism. In gen-
eral case, the oxidation scheme of the test substance is
necessary to be considered for a detailed analysis of the
results of the chemiluminescence oxidation.
RO
RO
HO
RORO
3.9. Evaluation of Properties of a Certain
Antioxidant with the Fenton Reaction
Ascorbic acid can be considered as an example. Re-
searchers repeatedly note that ascorbic acid possesses
both antioxidant and prooxidant properties [14-16]. The
scheme of ascorbic acid oxidation is presented in Table 8.
The characteristics of reactions are taken from ref. [15,
17]. Ascorbic acid in an aqueous solution dissociates in
two steps (reactions 36 and 37, Ta bl e 8). At pH values
typical for biological objects (pH 6 to 7.5), ascorbic acid
remains in solution as ions AscH (more than 99%).
The primary oxidation product of AscH is radical
Asc (reaction 38, Table 8). A feature of ascorbic acid is
that neither the ion AscH nor radical Asc interacts with
oxygen [15]. Only ion Asc2 interacts with oxygen (reac-
tion 40), forming an ion-radical 2. Two radicals of
Asc transform to initial ion and DHA (dehydroascorbic
acid, reaction 39). DHA is further oxidized by oxygen to
form various compounds, including a prooxidant such as
O
Table 8. Oxidation reaction of ascorbic acid AscH2. AscH and
Asc2 are the products of the first and second stages of disso-
ciation of ascorbic acid. Asc is ascorbate ion-radical, DHA -
dehydroascorbic acid.
NoReaction The equilibrium constant, The
rate constant [15,17]
36. AscH2 AscH + H+ pKa1 = 4.1
37. AscH Asc2– + H+ pKa2 = 11.8
38.AscH + OH Asc + H2Ok3 = 1.1 × 1010 (mol·s)–1
39.2Asc + H+ AscH + DHAk4 = 1.4 × 105 (mol·s)–1
40.Asc2– + O2 Asc + 2
O
k5 = 100 (mol·s)–1
Figure 5. The intensity of chemiluminescence P of organic matter RH in Fenton solution.
[Fe2+] = 10–3 mol/l, [H2O2] = 10–4 mol/l, [RH] = 10–4 mol/l. The figures denote: 1) The flash
of chemiluminescence due to reactions in a pure Fenton solution by oxygen active forms; 2)
Chemiluminescence of singlet oxygen formed in reaction 32 (Table 6) due to free radicals.
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98
oxalic acid.
Calculated dependence of S/S0 on concentrations of
ascorbic acid without regard to the products of DHA
transformation is presented in Figure 6 for two cases: in
oxygen medium and in the one without. It is evident that
without oxygen S/S0 monotonically decreases with in-
creasing [Asc] (curve 2), and in the presence of oxygen
for [Asc] > 103 mol/l ratio S/S0 begins to increase
(curve 1). The increase is due to formation of superoxide
ion-radical 2. In the course of reactions in Fenton so-
lution, this radical can, although with a low probability,
transform into a hydroxyl radical OH. In this case,
ascorbic acid will absorb secondary radicals initiated by
its oxidation. At the concentration of [Asc] up to 1 mol/l
the antioxidant effect will occur, although the probability
of suppression of radicals with increasing concentration
of acid in solution, saturated by air, will decrease.
O
The experimentally obtained dependence S/S0 on a
wide range of concentrations of ascorbic acid [Asc] is
shown in Figure 7. Measurements were performed for
two cases: 1) the solution contains oxygen dissolved in
natural conditions, 2) solution is depleted of oxygen by
adding 0.1 ml of Na2SO3 solution at a concentration of
3.2 g/l. In a separate experiment it has been found that
the introduction of Na2SO3 has no influence on lumines-
cence of Fenton solution. With the help of color filters it
has been identified that chemiluminescence occurs in the
red spectrum.
In the presence of oxygen (curve 1) and at a low con-
centration of [Asc] value S/S0 equals to 1, which may be
primarily due to the small contribution of secondary re-
actions (initiated by the interaction AscH + OH) to the
general flow of radicals generated in the Fenton reaction.
With increasing of [Asc] ratio S/S0 exceeds 1, then it
decreases with increasing [Asc] and becomes less than 1.
When S/S0 < 1, we can see the marked antioxidant prop-
erties of the substance introduced in Fenton solution.
Value S/S0 > 1 indicates the number of secondary radi-
cals formed in reactions with introduced substance to
exceed the number of primary ones, i.e. chain reaction
takes place. In case of lack of oxygen (curve 2) the S/S0
Figure 6. The ratio dependence of the light sum during 30 sec-
onds for Fenton solution with ascorbic acid S to the light sum
for a pure Fenton solution S0 (S/S0) on the concentration of
ascorbic acid, [Asc], mol/l. 1) solution, saturated by oxygen,
[O2] = 2 × 10–4 mol/l (7 mg/l), 2) without oxygen. When [Asc]
< 103 mol/l curves 1 and 2 are the same.
Figure 7. Chemiluminescence of ascorbic acid in the oxidation by the Fenton reagent,
[Fe2+] = 10–3 mol/l, [H2O2] = 10–4 mol/l. S/S0—see Figure 6. [Asc]—concentration
of ascorbic acid, mol/l. Errors of ratio S/S0 do not exceed 5%. 1) There is oxygen dis-
solved in vivo in the solution; 2) Solution is depleted of oxygen by the addition of 0.1
ml [Na2SO3] = 3.2 g/l.
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I. P. Ivanova et al. / Journal of Biophysical Chemistr y 3 (2012) 88-1 00 99
is less than 1 for all concentrations of ascorbic acid,
which means that the ascorbic acid itself is an antioxi-
dant.
Prooxidant properties were observed in [14,15] at the
concentration of ascorbic acid of approximately 103
mol/l, which is close to the concentration at which the
maximum S/S0 is reached in Figure 7 for the solution
containing oxygen. The authors of [14,15] report ascor-
bic acid at concentrations of 103 mol/l to have different
properties compared to larger concentrations. In terms of
Scheme 1 the properties of the acid do not change with
concentration, but the ratio of individual channels of re-
actions occurring in course of Asc oxidation is changed.
According to the mechanism of its oxidation, ascorbic
acid itself cannot be prooxidant, which is confirmed by
other studies [18]. The results of the present study sug-
gest that the prooxidant properties do not appertain to the
ascorbic acid, but to products oxidized by DHA oxygen,
among which can be oxalic acid. Figure 4 shows that
oxalic acid in the presence of oxygen has prooxidant
properties. Reduction of the prooxidant activity observed
experimentally in [Asc] > 103 mol/l in the presence of
oxygen can be attributed to the expenditure of dissolved
oxygen in reaction 40, and perhaps its shortage as the
concentration of oxygen in the water is about 104 mol/l,
while [Asc] is more than 103 mol/l.
The form of the impulse also helps to draw the con-
clusion on the composition of the secondary radicals. If
the secondary radicals are of complex sedentary nature
2, which are discharged into reaction 32 (Table 6)
with the formation of singlet oxygen, a flash of light
should have the form shown in Figure 5, i.e. the delay in
appearance of light—tens of seconds, and duration of the
light pulse—a few minutes. If the secondary radicals are
highly movable (2,2), the flash of light will be
short, less than 30 seconds. Such flash is observed in
oxalic acid and at all concentrations of ascorbic acid.
Such radicals as 2 might yet form during the de-
composition of DHA. However, their formation is ex-
tended in time, is not bound by the time of introducing
the components of the Fenton reagent, and cannot be
detected by the applied technique of chemiluminescence.
Thus, the analysis of the properties of antioxidants in
Scheme 1 allows revealing the features of the tested sub-
stances.
RO
HO
RO
O
4. CONCLUSIONS
1) If 30 seconds have been selected as radiation regis-
tration time, the preferred concentration of Fenton solu-
tion reagent is [Fe2+] = 103 mol/l, [H2O2] = 104 mol/l.
2) The radiation background produced by cosmic rays
and other sources induce luminescence which is regis-
tered by luminometer and is to be taken into account.
3) The main radiant product in the solution of Fenton
is a dimer of singlet oxygen. The glow of the solution is
stopped when the ferric iron that is formed absorbs al-
most all radicals 2
O
. The same mechanism of lumi-
nescence quenching operates for luminol in a neutral
medium.
4) The luminescence of organic substances relates to
radicals 2
RO
. No luminescence appears in a non-oxy-
gen solution. In the presence of oxygen with an increas-
ing concentration of RH the reaction RH + 2
RO
R
+ ROOH begins to dominate and the emission stops.
5) Depending on the mechanism of the process, che-
miluminescence is grouped in different time intervals
after the injection of all the substances. In the period
from 0 to 30 seconds the glow is caused by reactive
oxygen species. During the time period from 30 seconds
to several miutes it is due to the emission of free-radical
reactions occurring in the sample.
6) Observed for a single substance oxidant and prooxi-
dant properties are caused by the same reaction mecha-
nism. At high concentration the intermediate radicals, the
reaction products are absorbed by the initial substance
and antioxidant properties are observed. At low concen-
trations of introduced substances intermediate radicals
are preserved and prooxidant properties are observed.
7) Prooxidant properties of ascorbic acid observed in
some cases are associated with the DHA oxidation prod-
ucts with oxygen. In the absence of oxygen the prooxi-
dant effect does not occur.
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Abbreviations
Lum—luminol
L—luminol’s radical
M—ideal antioxidant
S0—light sum of chemiluminescence for pure Fenton
solution for 30 seconds
S—light sum of chemiluminescence for 30 seconds at a
given concentration of test substance in Fenton solution
Al—alanine
A—albumin
Oxalic—oxalic acid
Oks—oksalat
Asc—ascorbic asid
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