Monofunctional curcumin analogues: evaluation of green and safe developers of latent fingerprints

Article abstract of DOI:10.1007/s11696-021-01556-4

Fingerprint development is one of the most useful techniques in forensic investigation. The powder method is widely used, as it consists of a non-destructive testing. However, some of the powders commonly used are toxic and dangerous to human health. In this sense, monofunctional analogues of curcumin (3a–e) are proposed as novel coloring powders for the development of latent fingerprints. Granulometric and scanning electron microscopy analysis were performed for a better understanding of the interaction between developers and substrates. The best results for the development of fingerprints were obtained with compound (1E,4E)-1,5-di-p-tolylpenta-1,4-dien-3-one (3b). Development with this compound was specific and allowed detection both from male and female donors. Also, in an in vitro experiment, compound 3b presented low cytotoxicity in a mammalian cell line. Based on that, a novel alternative for latent fingerprint developers was proposed.

Full text of DOI:10.1007/s11696-021-01556-4

Chemical Papers
https://doi.org/10.1007/s11696-021-01556-4
ORIGINAL PAPER
Monofunctional curcumin analogues: evaluation of green and safe
developers of latent fngerprints
Bruna S. Pacheco1 · Caroline C. Da Silva1 · Bruno N. Da Rosa1 · Kristiane C. Mariotti2 · Caroline Nicolodi1 ·
Taís Poletti1 · Natália V. Segatto3 · Tiago Collares3 · Fabiana K. Seixas3 · Oscar Paniz4 · Neftali Lenin Vilarreal Carreño4 ·
Claudio M. P. Pereira1
Received: 12 May 2020 / Accepted: 3 February 2021
© Institute of Chemistry, Slovak Academy of Sciences 2021
Abstract
Fingerprint development is one of the most useful techniques in forensic investigation. The powder method is widely used,
as it consists of a non-destructive testing. However, some of the powders commonly used are toxic and dangerous to human
health. In this sense, monofunctional analogues of curcumin (3a–e) are proposed as novel coloring powders for the develop-
ment of latent fngerprints. Granulometric and scanning electron microscopy analysis were performed for a better understand-
ing of the interaction between developers and substrates. The best results for the development of fngerprints were obtained
with compound (1E,4E)-1,5-di-p-tolylpenta-1,4-dien-3-one (3b). Development with this compound was specifc and allowed
detection both from male and female donors. Also, in an in vitro experiment, compound 3b presented low cytotoxicity in a
mammalian cell line. Based on that, a novel alternative for latent fngerprint developers was proposed.
Keywords Fingermark · Forensic · Forensic materials · Curcumin derivatives
Introduction
traditional developers, some natural products have been eval-
uated for latent fngermark’s development (Francese et al.
2013; Gaskell et al. 2013). Natural product genipin has been
used as an operationally safe and environmentally benign
fngermark reagent (Levinton-Shamuilov et al. 2005). In
this way, initial studies with curcumin, the major component
extracted from Curcuma longa L., have also been reported.
Turmeric powder was used for the visualization of latent
fngerprints on nine diferent substrates (Garg et al. 2011;
Sari et al. 2019). However, natural products have numerous
disadvantages, such as difcult reproducibility of concentra-
tion, obtainment in the form of a mixture of substances and
at high costs of purifcation. In general, extraction methods
of natural products use large amounts of organic solvents
and generate high quantities of waste, causing signifcant
ecological impact.
The detection of latent fngermarks is an important feld
of study in forensic sciences and refects benefts for the
whole society. The most common approach to detect latent
fngerprints is by dusting powders. However, conventional
powders may present toxicity to humans who are submit-
ted to continuous exposure (Azman et al. 2019). To replace
* Bruna S. Pacheco
pacheco.sbruna@gmail.com
* Claudio M. P. Pereira
lahbbioufpel@gmail.com
1
Laboratory of Lipidomics and Bioorganic, Bioforensic
Research Group, Federal University of Pelotas, Pelotas,
RS 96001-970, Brazil
In the last years, many organic compounds with coloring
properties have been synthesized and tested for their suit-
ability as reagents for the detection of latent fngermarks
(Errington et al. 2016). The green chemistry approach for the
synthesis of organic substances has been a good alternative.
In this sense, our research group has worked extensively on
the clean synthesis of organic compounds applied to several
areas: biotechnology (Dias et al. 2014; Vieira et al. 2016),
2
Biometric Group - Brazilian Federal Police, Porto Alegre,
RS 90610-093, Brazil
3
Research Group on Cellular and Molecular Oncology,
Postgraduate Program in Biotechnology, Federal University
of Pelotas, Pelotas, RS 96001-970, Brazil
4
Materials Science and Engineering, Technology
Development Center, Federal University of Pelotas, Pelotas,
RS 96010-000, Brazil
Vol.:(0123456789)
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Chemical Papers
pharmaceutical (Ritter et al. 2015; Saueressig et al. 2018)
and biomaterials (Oliveira et al. 2014). Following the devel-
opment of fngerprint developers (Rosa et al. 2020; Passos
et al. 2020; Balsan et al. 2019), in this work our focus was on
the synthesis of monocarbonylic analogues of curcumin and
their possible use as latent fngermark developers. Curcumin
analogues were obtained in powder form by green proce-
dures and were identifed by spectroscopic techniques. Due
to the particular properties of these compounds, the mor-
phology of their surfaces was also studied. Also, distribu-
tion of deposited powders on the latent prints was evaluated
according to international protocols. Moreover, the cytotoxic
properties of these compounds were evaluated.
acquired on a Bruker DPX 300 instrument (300.13 MHz for
1H, 75.48 MHz for 13C), at 300 K (Scheme 2).
Representative data for monofunctional curcumin 3a:
(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one: C17H14O. EM:
234.10; MW: 234.29; Yield: 60%; yellow solid; mp (°C):
113–115; CLog Pa: 4.278; IR νmax/cm−1 3052, 3025 (C–H),
1
1654 (C=O), 1626, 1589 (C=C), 1571 (C=C); H NMR
(300 MHz, CDCl3) δ (ppm): 7.73 (d, 2H, J = 15.9 Hz;
2x = C–H); 7.58–7.61 (m, 10 H, 2 × Ph); 7.07 (d, 2H,
J = 15.9 Hz, 2x = C–H); 13C NMR (75 MHz, CDCl3) δ
(ppm): 189.01 (C=O); 143.4 (C-β); 134.8 (C-α); 130.6;
129.0; 128.5; 125.4 (12C, 2Ph); MS (APCI) m/z: 235.11
(M+1)+1.
Materials and methods
Synthesis of monofunctional curcumin analogues
3a–e
Monocarbonyl analogues of curcumin 3a–e were obtained
as previously reported in literature (Silva et al. 2019). In a
cold solution of ethanol, the proper aldehyde 1a–e (4 mmol)
and 2-propanone 2 (2 mmol), and an aqueous solution of
sodium hydroxide (40% v/v) were kept under magnetic stir-
ring until completion (approximately 2 h; monitored by thin
layer chromatography) (Scheme 1). After the reaction time,
the product was recovered as a precipitate by neutralization
with hydrochloric acid, vacuum-fltered and recrystallized
with hexane/ethyl acetate (4:1) at 40 °C. All the reagents and
solvents used in the synthesis and purifcation were acquired
from Sigma-Aldrich.
Identifcation of compounds
Low resolution mass spectra were obtained on a Shimadzu
QP2010 spectrometer operating at 70 eV. Infrared spectra
were recorded on a Varian 3100 FT-IR spectrometer. In
order to compare experimental data with literature, melting
point of the compounds were obtained by a visual fusion
Scheme 2 General scheme of the evaluation of monofunctional cur-
cumin analogues as latent fngermark developers by powder dusting
method
1
point apparatus (Fisaton 430). H and 13C spectra were
Scheme 1 General procedure
for synthesis of monocar-
bonyl analogues of curcumin
3a–e. 3a: (1E,4E)-1,5-
(diphenylpenta)-1,4-dien-3-one;
3b: (1E,4E)-1,5-di-p-tolylpenta-
1,4-dien-3-one; 3c: (1E,4E)-
1,5-bis(4-methoxyphenyl)
penta-1,4-dien-3-one; 3d:
(1E,4E)-1,5-bis(4-chlorophenyl)
penta-1,4-dien-3-one; 3e:
(1E,4E)-1,5-bis(4-fuorophenyl)
penta-1,4-dien-3-one
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Chemical Papers
IMETRO, Rio de Janeiro, Brazil) and routinely cultured
in Dulbecco’s modifed Eagle’s medium (DMEM), supple-
mented with 10% of fetal bovine serum (FBS) purchased
from Vitrocell Embriolife (Campinas, Brazil). The experi-
ment was performed with cells in the logarithmic phase of
growth.
Collection of fngerprints
The monofunctional synthetic analogues of curcumin 3a–e
were tested as development agents for latent fngermarks on
a glass surface. Sample preparation was done under macera-
tion with liquid nitrogen to ensure the dryness and homoge-
neity of the powders. The synthesized analogues 3a–e were
evaluated and the most prominent (3b) was used in a multi-
ple depletion series of fngerprint. Volunteers, composed of
fve men and three women picked at random, pressed their
fngertips onto clean glass slides. For a natural fngerprint
deposition, volunteers washed their hands with neutral soap
and water and kept doing their usual activities for a period
of 30 min. For a sebaceous deposition, the donor rubbed
the thumb on areas of the face, such as the forehead and
nose, followed by rubbing of the fngertips to enrich the print
with oily components. When placing the fngerprints, the
pressure was subjectively frm (exerting medium pressure)
and the contact time was between 3 and 5 s. For depletion
series of fngerprint, three unspecifc donators did ten suc-
cessive depositions of the same fnger on clean glass slides
(sebaceous fngerprint deposition) (Almog et al. 2014). After
the deposition, fngerprints were kept during 24 h at room
temperature. To assess aged fngerprints, sebaceous impres-
sions from fve donors were deposited on glass plates and
left untouched for 7 days at room temperature.
The cell viability was determined by measuring the reduc-
tion in soluble MTT [3-(4,5-dimethylthiazol-2-yl)-2,5-di-
phenyltetrazolium bromide] to water-insoluble formazan.
Briefy, the cells were seeded at a density of 2×104 cell per
well in a volume of 100 µL in 96-well plates and grown at
37 °C in a humidifed atmosphere of 5% CO2/95% air for
24 h. Cells were treated with diferent concentrations (3.125,
3.25, 12.5, 25, 50, 75 and 100 µM) of curcumin analogue 3b
and tested under three diferent periods of exposure (24, 48
and 72 h). Dimethylsulfoxide (DMSO) was used as vehicle
and the fnal DMSO concentration in the culture medium did
not exceed 0.5%. Moreover, a control group exposed to an
equivalent concentration of DMSO was evaluated.
After incubation time, the media was removed and 100 µL
of 5 mg MTT/mL solution were added to each well. The
plates were incubated for an additional 3 h, and the medium
was discarded. One hundred µL of DMSO was added to
each well, and the formazan was solubilized on a shaker for
5 min at 100×g. The absorbance of each well was read on a
microplate reader (Victor X5, Perkin Elmer, USA) at a wave-
length of 492 nm. Cell inhibitory growth was determined as
follows: inhibitory rate=1−[(mean absorbance of treated
cells)−(mean of control absorbance)] * 100. The assay was
performed in triplicate.
Latent fngermark development and analysis
The latent fingermark development was carried out by
powder dusting method using a whopping feather duster
(123LBW Sirchie®) and a carbosmoove brush (CFB100
Sirchie®). After the development of latent fngermark, pho-
tographs were taken with a semiprofessional Canon camera
model EOS Rebel T6.
Statistical analysis
For the cytotoxic assay, time of exposure and concentration
were analyzed separately using One-way Anova followed
by Tukey for multiple comparisons in the Statistix software.
Developed fingermarks were analyzed by Scanning
Electron Microscopy (SEM) with a Shimadzu equipment,
model SSX-550 Superscan. Glass slides of standard sizes
(10 mm×10 mm) were prepared, in which monofunctional
curcumin analogues were analyzed. In order to compare
the results, the best (3b) and worst (3d) developers were
analyzed by SEM. Substrates with the developed latent
fngermark were mounted on the stubs with carbon tape,
metallized with gold, and analyzed using beam acceleration
between 5 and 15 kV. Particle size analysis were performed
using a laser difractometer—isopoCILAS 1064, with pow-
der dispersion by ultrasound and water as dispersing agent.
Results and discussion
The reaction was performed in ethanol as solvent at room
temperature under mild conditions, yielding the products
3a–e in satisfactory percentages (60–81%).
All compounds exhibited physical and spectrometric
properties consistent with the proposed structures and in
agreement with the literature (Pereira et al. 2017) (Table 1).
These reactions were performed in ethanol, a green solvent
(Capello et al. 2007). Ethanol is one of the least toxic of the
organic solvents, which makes it more suitable for use in
industry and consumer products, being a common solvent
in medicinal preparations, for example (Jessop 2011). After
the purifcation procedure, the compounds were isolated in
high purity (99–100%).
Cytotoxicity evaluation
The mammalian cell line CHO-K1 was used for the in vitro
cytotoxicity evaluation of developer 3b. This cell line was
obtained from the Rio de Janeiro Cell Bank (PABCAM,
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Table 1 Experimental data of compounds 3a–e
Compound
Yield* (%)
66
m. p. (°C)
113–115
m. p. (°C) (Lit.)
Exact mass
234.29
3a
3b
113–114 (Chen et al. 2004)
O
65
175–177
174–176 (Weber et al. 2005)
262.35
O
H
3C
H
C
3
O
3c
70
60
125–127
184–186
127–129 (Chen et al. 2004)
184–186 (Weber et al. 2005)
294.34
303.18
H
3CO
H
OC
3
3d
O
l
C
l
C
3e
O
81
150–154
150–152 (Weber et al. 2006)
270.27
F
F
*Recrystallized products
m. p.: melting point
It is known from the literature that the powder technique
is the most widely used process for fngerprint development
at crime scenes (Sodhi 2001). The widely utilization of the
powder technique is due to its relatively ease of applica-
tion and the variety of colors commercially available. In this
sense, over the last years many research groups around the
world have been developing alternatives to improve the pow-
der technique (Barros and Stefani 2019; Sharma et al. 2018).
The monofunctional curcumin analogues synthesized in
this work (3a–e) were evaluated as latent fngermark’s devel-
opers. In a general manner, continuity of ridges, number
of identifable minutiae and contrast with background were
analogous for all samples. The compound 3b was selected
for the remaining experiments, since it presented better
defnition of the ridges and a higher contrast between the
impression and substrate.
interacted with aqueous or lipidic residues from fngerprint,
natural and sebaceous prints were developed (Figs. 1 and
2). Hands do not have sebaceous glands, so the presence
of these compounds in a fngerprint is a result of touching
other parts of the body, such as the face and the head (De
Alcaraz-Fossoul et al. 2013). The visualization of sebaceous
fngerprints was better, since the prints showed an increased
powder difusion between ridges, resulting in a better lower
contour defnition and increased thickness. No signifcant
diferences were observed among male and female fnger-
prints developed with compound 3b.
Sensitivity of the proposed developer was done by deple-
tion series (Fig. 3). From this experiment, it was possible
to observe that sebaceous prints were developed with ana-
logue 3b even after 10 sequential depositions, which indi-
cates an elevate sensitivity of the compound to identify small
amounts of residues.
In order to evaluate the infuence of donor in the devel-
opment of latent fngermarks with analogue 3b, Figs. 1 and
3 show images of samples from eight diferent donators (5
male and 3 female) developed by monofunctional curcumin
analogue 3b after 24 h of deposition. Figure 1 displays nat-
ural depositions, whereas sebaceous depositions from the
same donors are displayed in Fig. 2.
In order to use powders developed on surfaces closer to
the ones found in real cases, natural fngerprints were depos-
ited on objects, such as a glass bottle, keys, smartphone,
knife, credit card and CD (Fig. 4), which were developed
after 72 h with curcumin analogue 3b. Fingerprints could
be developed and visualized on all objects, even with the
aging time. In addition, it is noteworthy that visualization of
fngerprints were clearer on objects made of glass or metal
materials, while on plastic objects, although it is possible
to identify the prints, but in a less intense way. Figure 5
Fingerprint residues are a complex emulsion of water-sol-
uble and lipid-soluble components that may remain on top
of a surface for a signifcant period (Champod et al. 2004).
To evaluate whether the synthetic compound described here
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Fig. 1 Natural fngerprints from eight diferent donors (m1-m5; f1-f3) developed with curcumin analogue 3b after 24 h of deposition on glass
surface; m: male donors; f: female donors
Fig. 2 Sebaceous fngerprints from eight diferent donors (m1-m5; f1-f3) developed with curcumin analogue 3b after 24 h of deposition on glass
surface; m: male donors; f: female donors
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Fig. 3 Multiple sebaceous depletion series of 10 fngerprint deposited in sequence (1–10) by three diferent donors (A, B and C) and developed
with curcumin analogue 3b on glass surface. The detail shows the frst (1) and the last (10) developed fngerprint of the depletion series
shows aged fngerprints from fve donors developed after
7 days with compound 3b, demonstrating the efciency or
visualization even after a longer period of time of these aged
fngerprints.
worst performance in development (3b and 3d, respectively).
In this context, from the histograms shown in Fig. 6, it is
possible to observe that the samples possess some degree of
heterogeneity of particle size. The mean diameter for com-
pounds 3b, 3d and commercial developer were 74.95, 63.69
and 116.66 µm, respectively. Although these data presented
diferent values, the histogram distribution showed that com-
pound 3b and the commercial developer have similar distri-
bution pattern of particle sizes. Monofunctional curcumin
analogue 3b and the commercial developer showed a small
amount of particles on the 30 and 25 µm areas, respectively,
whereas the major concentration of particles was represented
as a peak on the 95 and 125 µm ranges. On the other hand,
for compound 3d, a higher heterogeneity was observed, with
two evident peaks in 19 and 125 µm.
In relation to the physical properties, the granulometric
distribution and SEM analysis are presented in Fig. 6. The
top panel (A) shows SEM images in diferent magnifcations
of the developed latent fngermarks to show which parame-
ters could infuence on the performance of fngerprint devel-
opment. Panel (B) presents the granulometric profle and
the data obtained in granulometric analysis, which shows
distribution frequency values of D10, D50 and D90, report-
ing the particle diameters in the ranges below 10%, 50% and
90%, respectively, as well as the mean particle diameter. The
analysis revealed that the mean diameter of the particles was
74.95 µm for 3b, 63.69 µm for 3d and 116.66 µm for the
commercial developer.
The great diference in particle sizes implies a low speci-
fcity of the developer 3d, that is, it adheres not only to the
fngerprint lines but also to the substrate. The heterogeneity
of compound 3d was confrmed by SEM images in high
magnifcation of 2000 × (Fig. 7). Compounds 3b and 3d
have irregular crystalline shapes, while the commercial
developer has irregular laminar structures. These laminar
particles will pile up to a limit amount, avoiding pile col-
lapses or merges with another pile (Bleay et al. 2018), which
can happen if over-powdering when the powder has a leaf
shape as is the case with the standard powder.
The study of latent fngermarks deposited in sequence
(1–10) showed that the proposed developer presented high
sensitivity, even to the weakest deposits, in which it was still
possible to see ridge detailing (detail of Fig. 3). This proves
that the monofunctional curcumin analogue 3b is efective
even at lower concentrations of latent fngermarks residues,
with good intensity and resolution on the depletion series.
Based on the preliminary data, granulometry and SEM
analysis were performed for the compounds with better and
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Fig. 4 Development of latent fngermarks using curcumin analogue 3b on diferent objects, such as a glass bottle, b knife c key, d smartphone, e
credit card and f CD after 72 h
Fig. 5 Aged fngerprints from fve donors developed after 7 days with compound 3b
In order to evaluate whether the curcumin analogue 3b
would be toxic to cells, the MTT assay was performed.
The MTT colorimetric assay is widely used to evaluate
cytotoxicity of compounds. The metabolic activity of the
cells is analyzed with the reagent 3-[4,5-dimethyl-thiazol-
2-yl]-2,5-diphenyltetrazolium bromide based on the fact that
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Fig. 6 Physical analysis of monofunctional curcumin analogues (3b
and 3d), and commercial developer Gold powder from Sirchie®. (A)
SEM analysis of latent fngerprints developed with proposed com-
pounds and the commercial in magnifcations of 20, 50, 100, 1000
and 5000x, respectively; panel (B) particle size distribution histogram
by laser difraction
viable cells metabolically reduce the yellowish and insolu-
ble MTT salt to form the blue-purple, soluble crystals of
formazan that are accumulated in the cytoplasm of the cell.
Thus, the intensity of the blue-purple coloration of the well
is directly proportional to the number of viable cells in it.
Figure 8 shows the percentage of growth inhibition of com-
pound 3b in CHO-K1 cell line.
The results obtained showed that the compound 3b was
not toxic for cells at 24 h of exposure in the range of concen-
trations tested, since none of these treatments inhibited 50%
of the cellular viability/growth. In relation to longer times
of exposure, only the two highest concentrations tested (75
e 100 µM) manifested a slight cytotoxicity toward the nor-
mal cell line. The 100 µM concentration resulted in around
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Fig. 7 Crystalline structure of compounds 3b, 3d and commercial developer, magnifed 2000 ×
Fig. 8 Cytotoxicity results against normal cell line (CHO-K1) at dif-
ferent times of exposure to compound 3b (24, 48 and 72 h). Concen-
trations ranging from 3.125 to 100 μM are presented in the x axis.
Growth/cellular inhibition (%) is indicated in the y axis, in which the
line at the y axis represents 50% of growth inhibition. Diferent letters
represent statistical diference among tested concentrations. Difer-
ences were considered signifcant when p≤0.05
Table 2 Vehicle (DMSO) cytotoxicity results (in percentage of
The synthetic compounds evaluated on this study are
promising candidates for the development of latent fnger-
prints. These compounds follow the desirable trends taken
into consideration on the research for new developers: stabil-
ity, relatively easy obtainment, manageable chemical prop-
erties and non-toxicity (Errington et al. 2016; Barros and
Stefani 2019; Yuan et al. 2018).
growth/cellular inhibition) against mammalian CHO-K1 cell
Concentration (µM)
% of growth inhibition
24 h 48 h
0.864 1.884
72 h
3.078
6.860
8.265
3.125
6.25
12.5
2.927
6.581
3.682
9.085
25
50
75
100
10.816
17.564
33.122
37.230
18.09
17.903
33.377
51.469
60.776
18.24
13.581
16.874
60.409
69.807
26.37
Conclusions
DMSO (vehicle)
In summary, curcumin analogues described in this work
were easy synthesize and their physical and chemical prop-
erties allowed the development of latent fngerprints, indi-
cating a promising class of compounds for this application.
One analogue, namely 1,5-di-p-tolylpenta-1,4-dien-3-one
(3b), was selected for further studies, in which in all assess-
ments performed with the compound allowed for the visu-
alization of the ridges. In addition, cytotoxicity data showed
that the synthetic curcumin analogue only displays some
cytotoxicity after 48 h, at concentrations higher than 70 µM.
This sets an open stage for new perspectives in the develop-
ment of emerging latent fngerprint’s developers.
60% and 70% of cellular inhibition after 48 h and 72 h of
exposure, respectively (Fig. 8). However, no statistical sig-
nifcance was observed among the diferent three periods of
time analyzed. The vehicle alone, DMSO, presented some
toxicity at all periods of time tested (Table 2), which could
indicate that the slight cytotoxicity of 3b evidenced in the
highest concentrations tested could be related to the elevated
fnal volume of DMSO in the well, and not only due to the
curcumin analogue.
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Chemical Papers
Garg RK, Kumari H, Kaur R (2011) A new technique for visuali-
zation of latent fngerprints on various surfaces using powder
from turmeric: a rhizomatous herbaceous plant (Curcuma
longa). Egypt J Forensic Sci 1:53–57. https://doi.org/10.1016/j.
ejfs.2011.04.011
Acknowledgements The authors are grateful to the National Institute
of Science and Technology (INCT Forensics – CNPq 465450/2014-
8) for the technical assistance and resources. This work is part of the
project “Revealers and Forensic Markers: Obtainment and Chemical
Properties—8634”. The authors would also like to thank FAPERGS
and the Coordenação de Aperfeiçoamento de Pessoal de Nível Supe-
rior–Brasil (CAPES)–Finance Code 001.
Gaskell C, Bleay SM, Ramadani J (2013) Natural Yellow 3: a novel
fuorescent reagent for use on grease-contaminated fngermarks
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Jessop PG (2011) Searching for green solvents. Green Chem
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Compliance with ethical standards
Levinton-Shamuilov G, Cohen Y, Azoury M, Chaikovsky A, Almog
J (2005) Genipin, a novel fngerprint reagent with colorimetric
and fuorogenic activity, part II: optimization, scope and limita-
tions. J Forensic Sci 50:1367–1371
Conflict of interest The authors declare that there is no confict of in-
terest.
Oliveira S, Pizzuti L, Quina F, Flores A, Lund R, Lencina C, Pacheco
B, Pereira CMP, Piva E (2014) Anti-Candida, anti-enzyme
activity and cytotoxicity of 3,5-diaryl-4,5- dihydro-1H-pyra-
zole-1-carboximidamides. Molecules 19:5806–5820. https://doi.
org/10.3390/molecules19055806
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