Cent. Eur. J. Chem.

• 6(2) • 2008 • 222–228

DOI: 10.2478/s11532-008-0011-x

Central European Journal of Chemistry

Spectrofluorometric determination of
nicardipine, nifedipine and isradipine in
pharmaceutical preparations and biological fluids
Research Article

Sheikha M. Al-Ghannam*, Abeer M. Al-Olyan

Girls College of Science, Department of Chemistry,
P.O.Box 838, Dammam-31113, Saudi Arabia

Received 4 September 2007; Accepted 19 December 2007

Abstract: A
 simple and highly sensitive spectrofluorometric method was developed for the determination of some 1,4-dihydropyridine com-
pounds namely, nicardipine, nifedipine and isradipine in pharmaceutical preparations and biological fluids. The method is based on the
reduction of nicardipine, nifedipine and isradipine with Zn/HCl and measuring the fluorescence intensity obtained (λem/λex) at 460/364,
450/393 and 446/360 nm, respectively. The factors affecting the development of the fluorophore and its stability were studied and op-
timized. The effect of some surfactants such as β-cyclodextrin (βCD), carboxymethylcelullose (CMC), sodium dodecyl sulphate (SDS)
and triton X-100, on the fluorescence intensity was studied. The fluorescence intensity-concentration plots of nicardipine, nifedipine
and isradipine were rectilinear over the ranges 0.4-6.0, 0.2-4.0 and 0.1-9.0 μg ml-1 with detection limits of 0.0028, 0.017 and 0.016
μg ml-1, respectively. The proposed method was successfully applied to commercial tablets containing the compounds; the percentage
recovery agreed well with those obtained using the official methods. The method was further extended to the in vitro determination of
the compounds in spiked human plasma and urine samples. A proposal of the reduction reaction pathway was postulated.
Keywords: Spectrofluorometric determination • Pharmaceutical preparations • Biological fluids

© Versita Warsaw and Springer-Verlag Berlin Heidelberg.

1. Introduction voltammetric [7-11], amperometric [12] thin-layer

chromatographic [13], capillary gas chromatographic
[14] and high-performance liquid chromatographic [15-
Calcium antagonists block the influx of calcium ions
17].
through voltage-operated calcium channels located
The compounds studied were: nicardipine (NIC)
in the cell membrane. Among the different groups,
1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)methyl-2-
dihydropyridines are the most numerous and include
[methyl(phenyl methyl)amino]-3,5-pyridinedicarboxylic
the largest number of novel compounds. They act upon
acid ethyl ester, nifedipine (NIF) 1,4-dihydro-2,6-dimethyl-
the L-type channel, which has a specific dihydropyridine
4-(2-nitrophenyl)-3,5-pyridine-dicarboxylic acid dimethyl
site in its extra cellular surface and bind more selectively
ester and isradipine (ISRA) 4-(4-benzofurazanyl)-1,4-
to vascular calcium channels than to those in the
dihydro-2,6-dimethyl-3,5-pyridinecarboxylic acid methyl
myocardium. Newer dihydropyridines exhibit greater
1-methylethyl ester. The formulas of these drugs are
selectivity, with evidence for specific vascular vessel
shown in Fig. 1.
bed binding. Each of these agents is effective in the
The aim of this work is to develop a simple and
treatment of hypertension and angina pectoris [1-3].
sensitive method for determination of NIC, NIF and ISRA
The therapeutic importance of dihydropyridines
in pure, pharmaceutical preparations and biological
initiated several reports on its determination,
fluids. The proposed method is based on the fact that the
both in formulations and in biological fluids, viz:
1,4-DHPs under study have no native fluorescence in
spectrofluorometric [4], spectrophotometric [5,6],

* E-mail: sm_ghannam@yahoo.com
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Figure 1. Structures of the studied 1,4-dihydropyridines.
spite of the presence of a dihydropyridine ring structure
which imparts strong fluorescence characteristics to the
compound containing it [18]. This is due to the strong
quenching effect of the nitro group or furazan ring.
Reduction of these groups to the corresponding amino
group enables the studied 1,4-DHPs to retain their
strong fluorescence. The addition of some surfactants
substantially enhanced the fluorescence produced. The
proposed method has been applied for the fluorimetric
determination of the studied compounds in biological
fluids. The most striking advantage of the proposed
method is that no prior extraction step is necessary when
applied to urine. The results obtained are promising.
2. Experimental Procedures
2.1. Apparatus
A FP-750 JASCO-PC Spectrofluorometer with a Xenon
arc lamp, and 1cm quartz cells, were used all over the
measurements.
2.2. Materials
Nicardipine hydrochloride was obtained from Sigma
chemical co. (St. Louis, MO, USA), nifedipine
hydrochloride was kindly supplied by Bayer (Wuppertal,
Germany), Isradipine was graciously gifted by Novartis
Pharma (Basle, Switzerland). The isradipine tablets
(Lomir tablets) contained 2.5 mg of isradipine per tablet
(Novartis Pharma, AG, Basle, Switzerland), while the
nifedipine tablets (Adalat retard tablets) contained 20 mg
of nifedipine per tablet (Pyaer, Allemagne, Germany),
and the nicardipine capsules (Pelcard capsules)
contained 50 mg of nicardipine per capsule (Global Napi
Pharmaceuticals, Egypt).
2.2.1. Stock solutions
Solutions containing 20 mg/100 ml of the studied drugs
were prepared in methanol. Diluted solutions were
obtained using the same solvent.
2.3. Reagents
Zinc powder and Hydrochloric acid solution 36.5-38%
(1M) were obtained from BDH (Poole, UK). Ammonium
chloride (1M) (BDH, Poole, UK) was prepared by
dissolving 5.35 g in doubly distilled water and made up
to 100 ml.
Formic acid 98-100% (1M) was obtained from Merck
(Germany). Plasma was kindly provided by King Fahd
Military Medical Complex (Dhahran, Saudi Arabia) and
kept frozen until the assay, when it was gently thawed.
Urine was obtained from healthy volunteers (males
between 25-30 years old).
2.4. Procedure
2.4.1. Preparation of calibration graphs
Aliquots containing drugs within the concentration
ranges cited in Table 1 were transferred into a set of
25 ml standard flasks. Complementary volumes of
methanol were introduced to adjust the volume to 5 ml,
and 1 ml of CMC (0.5% w/v) for nifedipine and isradipine
or 1 ml of SDS (1% w/v) for nicardipine were added. 0.45
g of zinc powder and 1-3 ml of 1 M HCl were added to
each flask. The volume was completed to the mark with
distilled water and the reaction mixture was left to stand
for 15 min at room temperature. This mixture was then
filtered through a dry filter paper and the fluorescence
intensity of the filtrate was measured at the suitable λem/
λex, depending on the drug. A blank reagent without the
drug was measured simultaneously. Calibration graphs
were constructed by plotting the fluorescence intensity
versus the final concentration (μg ml-1) of the drugs.
Alternatively, the regression equations were derived.
2.4.2. Procedure for pharmaceutical preparations
Ten tablets of the drugs were finely powdered and
thoroughly mixed. Accurately weighed amounts
equivalent to 20 mg of drug were transferred to a small
flask; 20 ml of methanol was added, gently mixed for 3-4
min and filtered into a 50 ml volumetric flask with few
ml of methanol; also the washings were passed to the
same flask. The volume was completed with methanol.
An aliquot of this solution was analyzed according to the
procedure cited before in 2.4.1. A blank reagent without
the drug was measured simultaneously. The content of
the tablets were determined either from the calibration
graph or the regression equation.
2.4.3. Procedure for spiked urine
1.0 ml aliquots of urine were transferred into a series of
25 ml standard flasks. Aliquots from the stock solution of
drug were added so that the final concentration is in the
range cited in Table 1. These solutions were analyzed
according to the procedure cited before in 2.4.1. A blank
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 Spectrofluorometric determination of nicardipine, nifedipine
and isradipine in pharmaceutical preparations and biological fluids

sample using urine without the drug was measured stability in the multiple conjugated double bonds of the
simultaneously. The content of the drug was calculated drug molecule. The high degree of resonance stability
either from the calibration graph or the regression enhances the fluorescence via delocalization of the
equation. π-electrons that can be placed in low lying excited
singlet states, which results in increase in the transition
2.4.4. Procedure for spiked plasma probability between the lowest excited singlet-state
1.0 ml aliquots of plasma were transferred into a set and the ground state [20]. The reduction process is
of centrifugation tubes. Aliquots from the drug stock proposed to proceed as shown above. The formed
solution were added so that the final concentration is fluorophore exhibits strong fluorescence for nicardipine,
in the range cited in Table 1. The solution was mixed nifedipine and isradipine at λem/λex of 460/364, 450/393
thoroughly using a votex mixer. 0.1 ml of ethanol, 1.0 ml and 446/360 nm, respectively, as shown in Fig. 2.
of 0.1 M borate-hydrochloric acid buffer (pH 9.0), and 4
ml of n-hexane/ethyl acetate (92.5:7.5 v/v) were added
to each tube and gently mixed for 5 min. and centrifuged
at 2800 rpm for 15 min. The organic phase was then
transferred to a set of small beakers and evaporated
under a stream of nitrogen. The residue was dissolved
in 5 ml methanol and then analyzed according to the
procedure cited before in 2.4.1. A blank sample using
plasma without the drug was measured simultaneously.
The content of the drug was calculated either from the
calibration graph or the regression equation.

3. Results and Discussion Figure 2. Fluorescence spectra of isradipine (1μg ml-1), nifedipine
(1 μg ml-1) and nicardipine (0.8 μg ml-1) after reduction
with Zn/HCl.
The reduction of NIC, NIF and ISRA with zinc in A) Excitation spectrum
B) Emission spectrum
hydrochloric acid was found to give a strongly fluorescent
product owing to the fluorescene enhancing structural
changes in the dihydropyridine ring that originally exhibits 3.1. Optimization of the Parameters
a strong yellow green fluorescence [18]. Upon reduction, The reaction conditions with respect to the amount of
the nitro group is reduced into the corresponding amino Zn powder, the volume of 1 M HCl and the reaction
group [19]. In addition, depending on the presence of time at constant temperature were optimized to achieve
the furazan ring structure in isradipine, the following maximum fluorescence. The first goal was to choose the
pathway reaction may be postulated (Scheme 1) [8]: most appropriate reduction system. The fluorescence
NH2
intensities of the solutions as a function of reducing
N reagents were compared. The reduction systems
HCl / Zn OH
O investigated were: Zn/HCl, Zn/NH4Cl and Zn/formic acid.
N
N H Of all the reducing agents, the highest fluorescence
Scheme 1. Postulated reaction pathway for isradipine. intensity was observed with 0.45 g of Zn powder. The
fluorescence of the solutions was investigated over a
The presence of the primary amino groups increases the hydrochloric acid (1 M) volume range of 1-7 ml. The
fluorescence of the drug due to their electron donating optimum fluorescence was achieved using 1-3 ml. The
effect that produces a high degree of resonance effect of time on the development of the fluorescence
Table 1. Analytical performance data of the proposed spectroflourometric method for nifedipine, nicardipine and isradipine in pure form.

Compound Concentration Slope Intercept Correlation Coefficient Detection Limit Quantification Limit Sy/x Sa Sb
( μg ml-1 ) (r) ( μg ml-1) ( μg ml-1)
Nifedipine 0.02 – 0.40 166.06 25.48 0.9903 0.017 0.050 1.0732 0.8379 3.6534
0.80 – 4.00 170.49 29.36 0.9982 2.6976 2.7552 1.1440
Nicardipine 0.40 – 4.00 129.89 8.43 0.9983 0.0028 0.0085 0.1362 0.1109 0.4865
0.80 – 6.00 78.02 68.32 0.9999 1.4403 1.2739 0.3623
Isradipine 0.1 0- 0.90 67.84 37.93 0.9997 0.016 0.049 0.4106 0.3302 0.6097
1.00 – 9.00 9.82 49.02 0.9978 2.4991 2.4789 0.4097

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Table 2. Spectrofluorimetric determination of the studied compounds in pure form.

Compound Amount taken (µg/ml-1) Amount found (µg/ml-1) % Recovery* Reference method
Nifedipine 0.02 0.021 103.5
0.08 0.079 98.5
0.20 0.199 99.3
0.40 0.402 100.4
0.80 0.815 101.8
1.60 1.597 99.8
2.00 1.986 99.3
4.00 3.992 99.8
Mean 100.3 100.4(n=5)
SD ± 1.61 ±1.1
F 2.0(5.14)
t 0.12(2.31)
Nicardipine 0.04 0.039 99.3
0.08 0.081 101.7
0.2 0.200 100.0
0.4 0.401 100.1
0.8 0.785 98.2
1.6 1.621 101.3
3.2 3.195 99.8
6.0 5.999 100.0
Mean 100.1 100.6% (n=5)
SD ± 1.11 ± 1.1
F 1.05(5.14)
t 0.94 (2.31)
Isradipine 0.1 0.103 102.9
0.2 0.197 98.5
0.4 0.393 98.2
0.5 0.493 98.7
0.7 0.705 100.7
0.9 0.903 100.3
1.0 1.009 100.9
4.0 4.005 100.1
6.0 5.917 98.6
7.0 7.064 100.9
9.0 8.572 95.3
Mean 99.6 99.9% (n=6)
SD ± 2.01 ± 2.7
F 1.87(5.79)
t 0.29(2.37)

The figures in parenthesis are the theoretical values of t and F values at 95% Confidence Limit.
* The average of three trials.

product and its stability was studied. The reaction
product was formed immediately, and was observed
to reach maximum development after 15 min at room
temperature and remained stable for more than 4 hours.
The effect of temperature was studied, wherein the
fluorescence intensities of the solutions were decreased
over a temperature range of 40-100ºC.
In order to examine the effect of macromolecules
surfactants with concentrations of 1% w/v of
β-cyclodextrine (βCD), sodium dodecyl sulphate (SDS),
Triton x-100 and 0.5% carboxymethylcelullose (CMC),
on the fluorescence intensities of the reduced drugs,

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 Spectrofluorometric determination of nicardipine, nifedipine
and isradipine in pharmaceutical preparations and biological fluids

Table 3. Application of the proposed spectrofluorimetric determination of studied compounds in their tablets.

Compound Amount taken (µg/ml-1) Amount found (µg/ml-1) % Recoverya

Nifdipine 0.08 0.079 98.2
(Adalat retard tablets) 0.20 0.205 102.5
0.40 0.397 99.2
0.80 0.796 99.5
1.60 1.618 101.1
Mean 100.1
SD ± 1.7
Nicardipine 0.08 0.081 101.0
( Pelcard capsules) 0.20 0.197 98.4
0.80 0.764 95.5
1.60 1.619 101.2
Mean 99.0
SD ±2.7
Isradipine 0.08 0.078 97.7
(Lomir tablets) 0.40 0.403 100.8
0.80 0.799 99.8
1.60 1.606 100.4
Mean 99.7
SD ± 1.4
a
The average of three trials.

their volumes were investigated over the range of 1-6
ml. From the results, it is evident that the addition of
SDS (1% w/v) for nicardipine or CMC (0.5% w/v) for
isradipine and nifedipine gave the highest readings, and
therefore, it was used throughout the study.
nucleus in the drug molecule, the degradation product
(pyridine derivative) does not interfere. The robustness
of this method is demonstrated by the versatility of
the experimental factors that affect the fluorescence
intensity.

3.2. Validation of the method 3.3. Analytical Applications

The method was tested for linearity, precision, Regression analysis of the data indicated a linear
reproducibility and specificity. By using the above relationship between fluorescence and concentration
fluorometric method, a linear regression equation was (μg ml-1).
obtained. The regression plot showed that there was a For (ISRA) concentration range (0.10-0.90 μg ml-1)
linear dependence of the relative fluorescence intensity FI= 67.84 C + 37.93 r = 0.9997
on the concentration of the drugs in the ranges shown in And concentration range (1.0 – 9.0 μg ml-1)
Table 2. Statistical evaluation of the regression lines gave FI= 9.82 C + 49.02 r = 0.9978
values such as: Standard deviation of the residuals (Sy/x),
standard deviation of the intercept (Sa), standard deviation For (NIC) concentration range (0.04 – 0.40 μg ml-1)
of the slope (Sb) and relative standard deviation, which FI= 8.43 C + 129.89 r = 0.9983
are shown in Table1. The good linearity of the calibration And concentration range (0.8 – 6.0 μg ml-1)
graph and the negligible scatter of the experimental FI = 78.02 C + 68.32 r = 0.9999
points are clearly evident by the correlation coefficient
For (NIF) concentration range (0.02 – 0.40 μg ml-1)
(close to 1). The quantification limits (10 Sa/slope) and
FI= 166.06 C + 25.48 r = 0.9903
detection limits (3 Sa/ slope) were calculated (Table 1).
And concentration range (0.8 – 4.0 μg ml-1)
The specificity of the method was investigated
FI = 170.49 C + 29.36 r = 0.9982
by observing any interference encountered from the
excipients of the tablets mass. It was shown that these
Statistical analysis [21] of the results obtained by the
compounds do not interfere with the proposed method
proposed method and officials [22] or reference [23]
(Table 3). At the same time because of the dependence
methods, using the Student’s t test and variance ratio F
of the reaction on the presence of the dihydropyridine
test, do not show any significant difference between the

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Table 4. Application of the proposed spectrofluorimetric determination of studied compounds in spiked human urine and plasma.

Compound Spiked human urine Spiked human plasma

Amount taken Amount found % Recovery* Amount taken Amount found % Recovery*
(µg ml-1) (µg ml-1) (µg ml-1) (µg ml-1)
Nifdipine 0.08 0.080 100.5 0.40 0.401 100.2
0.20 0.201 100.4 0.60 0.597 99.4
0.40 0.399 99.9 0.80 0.784 97.9
0.80 0.739 92.3 1.60 1.612 100.7
Mean 98.3 99.6
SD ± 3.9 ± 1.2
Nicardipine 0.04 0.039 98.0 0.10 0.097 97.2
0.40 0.401 100.3 0.40 0.407 101.8
0.80 0.816 101.9 0.80 0.786 98.2
1.00 0.989 98.9 1.00 1.002 100.2
Mean 99.8 99.3
SD ± 1.7 ± 2.1
Isradipine 0.08 0.078 97.8 0.08 0.082 103.9
0.20 0.203 101.4 0.40 0.397 99.1
0.40 0.399 99.7 0.80 0.812 104.1
0.80 0.865 102.9 1.60 1.606 100.4
Mean 100.5 101.9
SD ± 2.2 ± 2.5
* The average of three trials.

performance of the two methods regarding the accuracy
and precision, respectively, as shown in Table 2.
This method was further applied to the determination
of the three compounds in tablets. Table 3 shows
the recoveries of the different concentrations of the
compounds, wherein the results obtained are in good
agreement with those obtained from the officials or
reference methods. Statistical analysis of the results
obtained show no significant difference between the
performance of the two methods regarding accuracy and
precision using student’s t test and the variance ratio F test.
3.4. Analysis of Biological Fluids
The high sensitivity of the proposed method however,
allows the determination of nicardipine, nifedipine and
isradipine in spiked human plasma and urine. A dose
of 30 mg nifedipine, 50 mg nicardipine and 5 mg daily
isradipine are orally administered. The anticipated
concentration in biological fluids will be about 0.6, 1.0
and 0.12 μg ml-1 for nifedipine, nicardipine and isradipine,
respectively, which lies within the working concentration
range of the proposed method. The application of the
method for plasma was performed adopting the extraction
procedure described [24]. As for urine, the method was
successfully applied without prior extraction. The results
obtained in Table 4 are satisfactorily accurate and precise.
Since the pathway of degradation of the dihydropyridine
derivatives is the oxidation of the dihydropyridine ring to
pyridine [25] and also because the dihydropyridine ring
is essential for both the pharmacological action of the
drug, and the fluorescence of the product, the proposed
method can thus be considered as a stability indicating
assay for nicardipine, nifedipine and isradipine.
4. Conclusion
A simple and sensitive fluorimetric method based on the
presence of the dihydrpyridine ring has been developed
for the determination of nicardipine, nifedipine and
isradipine after reduction of the nitro group into the
fluorescence enhancing amino group. The fluorescence
intensity-concentration plots of nicardipine, nifedipine
and isradipine were rectilinear over the ranges 0.4-
6.0, 0.2-4.0 and 0.1-9.0 μg ml-1 with detection limits of
0.0028, 0.017 and 0.016 μg ml-1, respectively. The high
sensitivity of the method allowed the drug determination
in spiked human plasma and urine. Moreover, the
proposed method was applied to urine analysis
without prior extraction indicating no interference from
the endogenous component and thus revealing high
specificity of the proposed method. The detection limits
is comparable to those given by the chromatographic
methods.

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