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HOW TO REDUCE 3-DEOXYGLUCOSONE AND ACETALDEHYDE

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Peritoneal Dialysis International, Vol. 22, pp. 350–356
Printed in Canada. All rights reserved.
0896-8608/02 $3.00 + .00
Copyright В© 2002 International Society for Peritoneal Dialysis
HOW TO REDUCE 3-DEOXYGLUCOSONE AND ACETALDEHYDE
IN PERITONEAL DIALYSIS FLUIDS
Thomas Zimmeck, Andreas Tauer,1 Michael Fuenfrocken, and Monika Pischetsrieder1
Fresenius Medical Care Deutschland GmbH, St. Wendel; Institute of Pharmacy and
Food Chemistry,1 Friedrich Alexander University, Erlangen, Germany
Perit Dial Int 2002; 22:350–356
www.PDIConnect.com
KEY WORDS: Acetaldehyde; chemical analysis;
3-deoxyglucosone; glucose degradation products; lactate buffer; peritoneal dialysis fluids.
Correspondence to: M. Fuenfrocken, Fresenius Medical
Care Deutschland GmbH, Frankfurter Str. 6-8, 66606
St. Wendel, Germany.
michael.fuenfrocken@fmc-ag.com
Received 21 August 2001; accepted 18 October 2001.
350
ommercially available single-chamber bag
peritoneal dialysis fluids (PDFs) contain electrolytes and glucose as osmotic agents. They are buffered with sodium lactate in a weakly acidic pH range.
This composition is far from ideal and implies several risks (1). These PD solutions have proved cytotoxic in in vitro studies (2–7), and the irritant effect
of inflowing dialysis solution has been attributed to
glucose degradation products (GDPs) formed during
heat sterilization and storage (8,9). Several reactive
carbonyl compounds (RCC) have been identified in
PD solutions, in particular, 5-hydroxymethyl-furan2-carbaldehyde (HMF), formaldehyde, acetaldehyde,
glyoxal, and methylglyoxal (10). The quantities found
in these investigations were below 1 ppm for formaldehyde and glyoxal, approximately 1 ppm for methylglyoxal, and more than 10 ppm for acetaldehyde. For
some of these products a cytotoxic potential could be
confirmed (11,12). Recently, 3-deoxyglucosone (3-DG)
was detected in single- and double-chamber PDFs in
concentrations higher than those of any other RCC
so far determined (13,14). Moreover, 3-DG is of particular importance because of its high reactivity and
its potential to induce the formation of advanced
glycation end-products (AGEs) in vivo (15–17).
The chemical reactions leading to GDPs are summarized in Figure 1: HMF and methylglyoxal are
formed via the 3-deoxy degradation pathway; enolization and dehydration of glucose yields 3-DG, a
key intermediate in glucose degradation. Cyclization
and further dehydration lead to HMF, whereas
methylglyoxal is formed via a retroaldol reaction
(18,19). In contrast to these elucidated mechanisms,
formation of acetaldehyde from glucose is not so easy
to understand. One of the objectives of this study
was, therefore, to reveal how acetaldehyde is formed
in PDFs and which parameters influence its
formation.
In the development of a double-chamber PD system, the pH value of the compartment containing glucose can be selected from a range between 2 and 6.
Therefore, we investigated how pH value influences
C
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♦ Objective: 3-Deoxyglucosone (3-DG) and acetaldehyde
were found to be the major reactive carbonyl compounds
in conventional heat-sterilized peritoneal dialysis fluids
(PDFs). The aim of this study was to identify factors in the
production of PDFs promoting or inhibiting the formation
of acetaldehyde and 3-DG.
♦ Design: Single-chamber bag PDFs with different buffer
systems and pH values were analyzed for acetaldehyde.
3-Deoxyglucosone was determined in double-chamber
bag PDFs with different pH values, in commercially available samples, and in double-chamber products stored
under defined conditions.
♦ Results: Acetaldehyde was found in the presence of
lactate and malate, whereas in 2-hydroxybutanoate-buffered solution propionaldehyde was detected instead. Between pH 5.0 and 6.0 the acetaldehyde content in
lactate-buffered solutions increased strongly. The concentration of 3-DG in the chamber containing glucose in
double-chamber bags increased between pH 3.0 and 5.0
by a factor of 6. 3-Deoxyglucosone concentrations in commercially available products vary greatly, reflecting the
different pH values of these products. A time- and temperature-dependent reaction leads to a reduction in 3-DG
and an increase in 5-hydroxymethyl-furan-2-carbaldehyde
during storage.
♦ Conclusion: Acetaldehyde is produced by a reaction
that requires both lactate and glucose. Thus, its formation can be prevented by a separation of the reaction partners, glucose and lactate, in a double-chamber bag. In
double-chamber bags, pH greatly influences the formation of 3-DG. Minimal formation is observed in the region
of pH 3.0. This finding should be taken into account for
the development of new double-chamber bag PDFs.
PDI
MAY 2002 – VOL. 22, NO. 3
the formation of 3-DG in double-chamber bag PDFs
and in which concentration range 3-DG is present in
different commercially available new double-chamber bag PDFs. Finally, we analyzed 3-DG and HMF
in samples that were stored under defined conditions.
METHODS
SOLUTIONS
Single-Chamber Bags: All chemicals used were at
least p.a. quality; water was demineralized and
bidistilled. Solutions were based on a standard PD
formulation containing 99 mmol/L sodium chloride,
35 mmol/L sodium lactate, 1.75 mmol/L calcium chloride, 0.5 mmol/L magnesium chloride, and 15 g/L glucose. Prior to heat sterilization, the pH was adjusted
to 5.8 using hydrochloric acid. Solutions prepared
according to this specification but lacking glucose or
lactate served as controls.
Variation of the Buffer System: Peritoneal dialysis
fluids of the analogous composition were produced
where sodium lactate was replaced by sodium salts
of several organic acids (Table 1). Malic acid and succinic acid were used, at a concentration of 17.5 mmolL,
because they represent two base equivalents compared to lactate. Aliquots of these solutions (5 mL)
were filled into glass vials and placed into an oil bath
for 30 minutes at 121В°C for sterilizing.
Variation of pH Value: The pH was adjusted to values of 5.0 – 6.0 in steps of 0.1. The solutions were
filled into flexible non-PVC plastic containers and
sealed. Steam sterilization was performed to an Fo
value of approximately 15.
All samples were produced in duplicate. After sterilization, the bags/vials were opened and each was
examined twice for acetaldehyde and propionaldehyde by gas chromatography. The results are given
as mean of the four measurements. The standard
deviation was below 3% in all experiments and is
not shown.
Double-Chamber Bags with Different pH Values in
the Glucose Compartment: The glucose compartment
(1 L) contained 193 mmol/L sodium chloride,
3.50 mmol/L calcium chloride, 1.0 mmol/L magnesium
chloride, and 45 g/L glucose. The pH was adjusted to
values between 2.5 and 5.0 in steps of 0.5 using hydrochloric acid. The lactate compartment (1 L) contained 70 mmol/L sodium lactate and 5 mmol/L
sodium bicarbonate. The solutions were filled into flexible non-PVC plastic containers and sealed. Steam
sterilization was performed to an Fo value of approximately 15. Afterwards, the peel seam between the
compartments was ruptured and the mixed solutions
were analyzed for 3-DG.
Commercially Available Double-Chamber Bags:
Peritoneal dialysate bags were bought from a pharmacy or supplied directly from the manufacturer.
Table 2 gives a survey of the samples. 3-Deoxyglucosone was determined after mixing. All samples
were analyzed in October to December 2000 before
the expiry date of the respective solutions.
Influence of Storage Conditions on 3-DG and HMF
Concentrations: Commercial double-chamber bags
containing bicarbonate (Fresenius Medical Care, Bad
Homburg, Germany) with 134 mmol/L sodium,
1.75 mmol/L calcium, 0.5 mmol/L magnesium,
104.5 mmol/L chloride, 34 mmol/L bicarbonate, and
1.5% or 4.25% glucose (the glucose compartment has
pH 2.8 and contains 3.0% and 8.5% glucose respectively) were stored under different climatic conditions
[25В°C and 60% relative humidity (RH); 30В°C and 35%
RH; 40В°C and 75% RH] for 6 months. 3-Deoxyglucosone and HMF were determined at 0 and 6 months
in 3 samples of each solution.
GAS
CHROMATOGRAPHY
ANALYSIS
The gas chromatography system for quantitative
determination consisted of a Hewlett Packard (HP,
Waldbronn, Germany) gas chromatograph 5890 with
a split injector and a flame ionization detector and
an HP headspace sampler, model 19395A. The gas
chromatography system for the identification of
propionaldehyde consisted of an HP gas chromatograph, model 5890 II, with a split injector and a mass
selective detector (HP MSD), model 5971A. The conditions were as follows: injector temperature 250В°C;
oven temperature 50В°C; detector temperature 300В°C;
carrier gas, helium; pressure 1.0 bar; flow 7.0 mL/
351
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Figure 1 — Formation of certain aldehydes by degradation
of glucose via enolization (a), dehydration (b), cyclization
(c), and C–C-cleavage (d).
3-DG AND ACETALDEHYDE IN PD FLUIDS
ZIMMECK et al.
MAY 2002 – VOL. 22, NO. 3
PDI
TABLE 1
Formation of Acetaldehyde and Propionaldehyde in Buffered Glucose Solutions During Heat Sterilization
Buffering system
L-Lactate
D-Lactate
Pyruvate
Malate
Succinate
2-Hydroxybutanoate
Lactate-free control
Control (lactate without glucose)
a
Amount of buffer
(mmol/L)
Acetaldehyde
(mg/L)
Propionaldehyde
(mg/L)
35
35
35
17.5
17.5
35
7.3
6.9
<0.3a
6.5
<0.3
<0.3
<0.3
<0.3
<0.3a
<0.3
<0.3
<0.3
<0.3
8.5
<0.3
<0.3
Detection limit.
TABLE 2
Sample
Manufacturer
Bags
analyzed (n)
Expiry date
Product information (mmol/L unless other)
1
A
3
2002.01
2
A
3
2002.06
3
B
3
2000.10
4
B
3
2002.04
5
C
2
2003.07
Na+ 134, Ca2+ 3.5, Mg2+ 1.0, Cl– 101.5, lactate 35 mEq/L,
glucose 2.3%, pH 6.8–7.4
Na+ 134, Ca2+ 3.5, Mg2+ 1.0, Cl– 101.5, lactate 35 mEq/L,
glucose 2.3%, pH 6.8–7.4
Na+ 132, Ca2+ 2.5, Mg2+ 0.5, Cl– 95, bicarbonate 25,
lactate 15 mEq/L, glucose 2.27%, pH 7.0–7.4
Na+ 132, Ca2+ 2.5, Mg2+ 0.5, Cl– 95, bicarbonate 25,
lactate 15 mEq/L, glucose 2.27%, pH 7.0–7.4
Na+ 135, Ca2+ 2.5, Mg2+ 0.5, Cl– 98, lactate 40 mEq/L,
glucose 2.5%, pH 6.3–7.3
minute; split 18 mL/min; column HP-FFAP (modified
polyethylene glycol), internal diameter 0.32 mm,
length 50 m, film thickness 0.52 Ој; headspace conditions: equilibration for 30 minutes, bath temperature
60В°C, transfer line 90В°C.
described above was 17.5 minutes. All samples were
assessed in duplicate. Derivatization of synthesized
3-DG (20) yielded the standard curve for calculation
of concentrations.
DETERMINATION
HIGH PERFORMANCE LIQUID
(HPLC) ANALYSIS OF 3-DG
The HPLC analyses were carried out with a
diode-array detector system (Pump PU-1580,
Degaser 980-50, ternary gradient unit LG-980-02S,
diode array detector MD-1510 from JASCO, GrossUmstadt, Germany; quantification at 237 nm/
316 nm) using an RP-18 column (LC-18-DB 25 cm Г—
4.6 mm, Supelco, Deisenhofen, Germany). For elution, a binary gradient was used with 0% – 70% solvent A from 0 to 18 minutes and 70% solvent B from
18.1 to 25 minutes (solvent A, ammonium formate
buffer 5 mmol/L, pH 7.4; solvent B, methanol); 8 mL
PDF was mixed with 1 mL o-phenylenediamine solution (0.02 mol/L in methanol) and incubated at
room temperature overnight. Retention time of the
3-DG-quinoxaline derivative with the HPLC method
352
OF
HMF
CHROMATOGRAPHY
HMF was derivatized with o-toluidine in barbituric acid/acetic acid solution as described in Ref. (21).
The derivatization and the following photometric
measurement at 550 nm were performed with an
ELAN analyzer (Eppendorf, Hamburg, Germany).
RESULTS
ANALYSIS OF ACETALDEHYDE IN PDFs
DEPENDENT ON THE BUFFER SOLUTION
Table 1 shows the amounts of acetaldehyde and
propionaldehyde in differently buffered solutions.
Acetaldehyde was only detected in glucose solutions
containing lactate and malate, and not in solutions
containing pyruvate, succinate, and 2-hydroxybutanoate. In the latter, propionaldehyde was found
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Commercially Available Samples of Double-Chamber Bag Peritoneal Dialysis Fluids Analyzed for 3-Deoxyglucosone
PDI
MAY 2002 – VOL. 22, NO. 3
3-DG AND ACETALDEHYDE IN PD FLUIDS
instead. Identity of propionaldehyde was confirmed
by gas chromatography/mass spectrometry. Neither
of the aldehydes was detected in the solutions containing only glucose or lactate.
FORMATION OF ACETALDEHYDE IN SINGLECHAMBER PDFs DEPENDENT ON pH VALUE
Figure 2 illustrates the influence of different pH
values on the formation of acetaldehyde in lactatebuffered glucose solution. The formation of acetaldehyde is pH dependent: by increasing the pH from 5.0
to 6.0, the amount of acetaldehyde quadruples from
1.5 to 5.8 ppm.
FORMATION OF 3-DG IN DOUBLE-CHAMBER BAG
PDFs DEPENDENT ON pH VALUE
CHANGES IN 3-DG AND HMF CONCENTRATIONS
DURING STORAGE OF DOUBLE-CHAMBER
BAG PDFs
Double-chamber bag PDFs were stored after heat
sterilization under defined conditions. After 6 months,
changes in the concentrations of 3-DG and HMF were
measured. The amount of 3-DG decreased after sterilization (between 21% and 68%, Figure 4), whereas
Figure 2 — The formation of acetaldehyde in lactate-buffered glucose solutions is pH dependent. Data are mean values of
four measurements; standard deviation is below 3%.
353
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3-Deoxyglucosone concentration in solutions sterilized at pH 2.5, 3.0, and 3.5 is comparatively low
(3.1 ppm); whereas it rapidly increases when the pH
increases to 4.0 (8.9 ppm), 4.5 (14.7 ppm), and 5.0
(20.9 ppm) (Figure 3). The 3-DG concentrations measured in different samples of commercially available
double-chamber PDFs are shown in Table 3. The concentration of 3-DG ranged from 3.4 to 25.9 ppm, which
represents a difference between the lowest and the
highest concentration as high as 660%.
Figure 3 — The formation of 3-deoxyglucosone in acidic
lactate-free glucose solution is pH dependent. Data are
mean values of four measurements; standard deviation is
below 3%.
ZIMMECK et al.
MAY 2002 – VOL. 22, NO. 3
PDI
TABLE 3
3-Deoxyglucosone (3-DG) in Different Brands of Commercially Available Double-Chamber Peritoneal Dialysis
Systems. Glucose is separated from lactate in all systems, but sterilized at different pH values (3.0, 4.2, and
5.5 respectively). Three bags of every sample were
analyzed in duplicate, except for sample 5, of which only
two bags were available. Data are mean values of these
measurements, standard deviation is below 3%.
Sample
pH in glucose compartment
3-DG (mg/L)
1
2
3
4
5
3.0
3.0
4.2
4.2
5.5
3.4
4.1
21.7
25.9
14.9
DISCUSSION
Acetaldehyde has been referred to as a GDP (10,12).
According to the results obtained in this study, the
formation of acetaldehyde is not dependent only on
the presence of glucose, but also on the presence of
lactate. In control experiments, acetaldehyde (detection limit 0.3 mg/L) could not be detected in lactatefree glucose solution or in glucose-free lactate solution.
Furthermore, acetaldehyde was not found in solutions
in which lactate was replaced by pyruvate or succinate. These findings strongly indicate that the pre-
Figure 4 — 3-Deoxyglucosone decreases during storage
under defined conditions: 4.25% glucose stored at 25В°C
(open squares); 4.25% glucose at 30В°C (open triangles);
4.25% glucose at 40В°C (open circles); 1.5% glucose at 25В°C
(closed squares); 1.5% glucose at 30В°C (closed triangles);
1.5% glucose at 40В°C (closed circles). Data are mean values
of six measurements; standard deviation is below 3%.
354
cursor of acetaldehyde is lactate. Lactate could be
oxidatively decarboxylated in a reaction that is mediated by glucose. This hypothesis was confirmed by
the fact that propionaldehyde, which was identified
by gas chromatography/mass spectrometry analysis,
was detected instead of acetaldehyde when lactate
was replaced by 2-hydroxybutanoate. Oxidative decarboxylation of 2-hydroxybutanoate leads to the formation of propionaldehyde. According to the same
mechanism, malate is oxidized to malonsemialdehyde.
The latter compound is not stable and decarboxylates
to acetaldehyde. As a result, acetaldehyde was detected in samples that were buffered with malate. All
reactions are summarized in Figure 6. Acetaldehyde
has previously been identified as a degradation product of glucose (22), but the reaction was carried out in
concentrated sulfuric acid at a strongly acidic pH,
which is in contrast to the almost neutral diluted PD
solution. Therefore, this report is not in contradiction
to our findings. Thus, we conclude that acetaldehyde,
which is detected as a major RCC in single-chamber
bag PDFs, is formed from lactate, during heat sterilization, by a mechanism that is mediated by glucose.
Consequently, separation of glucose and lactate during heat sterilization by the use of double-chamber
bags should inhibit the formation of acetaldehyde.
Indeed, in all samples of double-chamber bag PDFs
that were investigated, acetaldehyde concentration
was below detection limit.
Commercially available PD solutions are usually
buffered at a pH between 5.0 and 5.8 because the formation of GDPs is highly favored at neutral pH, but is
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between 50% and 187% more HMF was found (Figure 5). The decrease in 3-DG and the increase in HMF
concentrations are stronger at higher storage temperature. The sum of 3-DG and HMF on a molar basis
remains unchanged.
Figure 5 — 5-Hydroxymethyl-furan-2-carbaldehyde (HMF)
increases during storage under defined conditions: 4.25%
glucose stored at 25В°C (open squares); 4.25% glucose at 30В°C
(open triangles); 4.25% glucose at 40В°C (open circles); 1.5%
glucose at 25В°C (closed squares); 1.5% glucose at 30В°C
(closed triangles); 1.5% glucose at 40В°C (closed circles). Data
are mean values of six measurements; standard deviation
is below 3%.
MAY 2002 – VOL. 22, NO. 3
PDI
3-DG AND ACETALDEHYDE IN PD FLUIDS
–
–
–
–
–
Figure 6 — Formation of aldehydes from α-hydroxycarbonic
acids by oxidative decarboxylation (a) and decarboxylation (b).
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pH 5; concentrations of acetaldehyde are four times as
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considerable increase in 3-DG concentration between
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favorable to reducing the formation of 3-DG.
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conclude that our results are relevant for industrially produced double-chamber bags.
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than one would expect from the data in Figure 3. The
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to glucose degradation.
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lots of PDFs of the same composition, we included
samples in our study that were stored under defined
conditions for 6 months. In 4.25% glucose solutions,
3-DG decreased at temperatures of 25В°C and 40В°C,
by 21% and 61% respectively after a storage period of
6 months. As 3-DG is known as a precursor of HMF
(19), we analyzed HMF as well. During storage, HMF
increased by 52% and 178% respectively (Figures 4
and 5). The sum of both GDPs on a molar basis is
nearly constant. We therefore conclude that, under
storage conditions, only minimal amounts of 3-DG are
formed de novo, but considerable amounts of 3-DG
are transformed to HMF. This transformation is enhanced by higher storage temperatures.
Until now, there have been no biological function
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3-DG level are superior to those with higher concentrations of this GDP. On the other hand, 3-DG reacts
rapidly with proteins and is a well-known precursor
of AGEs. So the principle of precaution might recommend a reduction of 3-DG to the lowest technically
possible level. Still, the possible clinical implications
of higher 3-DG and HMF levels should be investigated in in vivo studies.
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