Ph.D. Chemistry Assignment "fingerprint patterns"
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INTRODUCTION
There are no known cases of two individuals sharing an identical set of fingerprint patterns; even identical twins that are produced as the result of the splitting of a single fertilized egg at a very early stage in embryonic development have different fingerprint patterns. The potential of fingerprints as a means of identification was first established in the late 19th century and its usefulness for the identification of individuals has continued to the present day [1]. Indeed fingerprints, together with DNA profiling, are universally recognized as the most important and reliable physical identification tools in law enforcement [2]. Many classification systems based on fingerprint patterns have been proposed; Faulds, Galton, Vucetich, and Henry all established systems that were adopted by law enforcement agencies [3]. The individual nature of a fingerprint is governed by several characteristics including not only the general shape and pattern but also factors such as ridge endings, bifurcations and enclosures. These must match in both their identity and location in order for a common origin to be established [3].
Fingerprints are still one of the most useful forms of physical evidence in identification. There are three major types of fingerprints: visible prints, impression prints and latent prints. Latent prints are normally invisible without some form of development. The techniques used for fingerprint identification Vary according to the surface to which the fingerprints are applied. The development of latent fingerprints on porous surfaces such as paper and cardboard are particularly well suited for chemical development. The choice of chemicals used for development is dependent on the composition of latent fingerprints. Fingerprints result from the bodily fluids on the skin surface that are secreted from various glands located in the skin. The eccrine glands compose the majority of the sweat glands located on the fingers. The composition of eccrine sweat is 99% water in addition to minor amounts of inorganic and organic compounds [4]. Small concentrations of amino acids in sweat are sufficient for development on paper. Amino acids are stable over a great period of time. Since amino acids have a high affinity for cellulose, the main component of paper, they do not bleed from/on the paper’s surface. It is possible to obtain sharp fingerprints even after extended periods of time but the best results are usually obtained within several weeks.
There is a variety of reagents currently available for the enhancement of fingermarks based on their reactivity to different components in sweat. This assignment will focus on reagents used in the detection of amino acids present in eccrine sweat. All these reagents form coloured or fluorescent products upon reaction with the amino acid and some can be made fluorescent by secondary treatment. The following section summarises some of the reagents that have been used as fingermark reagents by criminal investigation laboratories for the detection of amines and/ or amino acids.
Ninhydrin
Ninhydrin is recognised as the predominant reagent for the visualization of latent fingermarks on porous surfaces to aid criminal investigations [5–8]. On reaction with amino acids, ninhydrin(2,2-dihydroxy-1,3-indanedione) forms a non-fluorescent purple product. The reagent was first synthesised and discovered to react with amino acids in 1910 by Siegfried Ruhemann. A colour change was observed after the reagent contacted his skin, with the formation of a purple compound that was subsequently named “Ruhemann’s purple” [5,8]. It took until the mid-1950s before the suggestion was made, by Oden and von Hofsten, that ninhydrin could be used as a means to detect latent fingermarks on porous substrates [9].
Ninhydrin has now become the most extensively publicised and researched amino acid visualisation reagent [10]. Initial debates in relation to the types of amino acids responsible for this purple formation are well documented. Some indicated the involvement of all amino acids, whereas others reported that only amino acids were reactive in this way. Collective opinions suggested the likelihood that the purple colour was the same irrespective of the amino acid. This was after indications that only a fragment of the amino acid (the nitrogen of the amine group) is featured in the structure of Ruhemann’s purple [11,12]. The accepted general mechanism for the ninhydrin reaction was proposed by Friedman and Williams [13] and was confirmed, with slight modifications, by Grigg and co-workers with the use of X-ray studies [8,14]. The most documented proposal involves a Strekker degradation where reduction of a carbonyl on indanetrione forms 2-amino-1,3-indanedione (II in Scheme1) bymeans of a resonance stabilised azomethine ylide. The 2-amino-1,3-indanedione can then react with another indanetrione molecule to form the stable 1,3-dipole Ruhemann’s purple [11,14–16].
Scheme 1. (a) The reaction mechanism of ninhydrin with amino acids to form Ruhemann’s purple [11,8,10,13]. (b) The reaction of Ruhemann’s purple with metal salts to form a complex ion [17,18].
Ninhydrin analogues
The discovery of ninhydrin as an effective fingermark detection reagent prompted further investigations into ninhydrin analogues.This was based on the awareness that Ruhemann’s finding was serendipitous, not on the basis of chemical knowledge and the-oretical design. Along with this, the issues with contrast and visualisation could not be overcome by simple modification of the ninhydrin formulation and working conditions. This sparked fingermark chemists to investigate various molecules that possessed similar structural features that were responsible for the formation of Ruhemann’s purple [11,8]. In 1982, Almog and co-workers were the first to apply this methodology as a means to improve the visualisation properties with respect to fingermark detection.
In principle, the inclusion of electron donating and/or electron accepting substituents alters the electronic properties of the conjugated system,to produce variations in colour and/or photoluminescence. The general consensuswas to develop specifically coloured complexes that could be applied to aid visualisation on a variety of backgrounds—in particular, backgrounds notorious for being problematic with conventional ninhydrin treatment [11, 8]. Many ninhydrin analogues were synthesised and have been studied, some of which are shown in Fig. 3 [7, 8,19].
Some of the analogues in Fig. 3 showed promise, with both improvements in visualisation and variation in colour and luminescence [11]. The most prominent ninhydrin analogues, which surpassed initial expectations, were 1,8-diazafluorene-9-one (DFO) and 1,2-indanedione. These were of particular interest because they produce both colour and intense luminescence on reaction with the amino acids in latent fingermarks, without further treatment.
Fig. 3. Structures of ninhydrin analogues: benzo[f]ninhydrin (1H-cyclopenta[b]naphthalene-1,2,3-trione), 5-methoxyninhydrin (5-methoxy-1H-indene-1,2,3-trione), 5-(methylthio)ninhydrin (5-(methylthio)-1H-indene-1,2,3-trione), 5-aminoninhydrin (5-amino-1H-indene-1,2,3-trione), 5-dimethylninhydrin (5-(dimethylamino)-1Hindene- 1,2,3-trione), 5,6-dimethoxy-1,2-indanedione (5,6-dimethoxy-1H-indene-1,2(3H)-dione).
1,8-Diazafluoren-9-one (DFO)
DFO was first synthesised by Druey and Schmidt in 1950 [20] and introduced as a fingermark reagent by Grigg and Pounds in 1990 [21,22]. On reaction with amino acids, DFO forms a red product that is luminescent (_ex 430–580 nm, _em 560–620nm [23] when viewed under a laser [40] or an alternate light source [24]. Isolation and identification of the luminescent product has been carried out and, even though DFO is not a direct analogue of ninhydrin, it is thought to react with amino acids in a similar fashion (Scheme 2) [26,21,22,27].
Initially, DFO reacts with the amino acid to form an imine (I), which undergoes decarboxylation and hydrolysis to form an aromatic amine (II). This amine then reacts further with an excess of DFO to produce a red product (III) [27]. Unlike the ninhydrin reaction, for this reaction to proceed heat must be applied using either an oven (20 min at 100 ◦C [23]) or a dry heat/ironing press (10 s at 180 ◦C [25]). It is important to note that prolonged heat, high temperatures and humidity should be avoided as they have a detrimental effect on the luminescence of developed marks [28,24]. DFO treatment affords developed fingermarks that are strongly luminescent without any secondary treatment or reduction in temperature. Observation in the luminescence mode provides greater detection sensitivity than can be obtained with ninhydrin [29,21,22,25,30]. In the absorption mode, ninhydrin developed fingermarks possess greater contrast compared to the pale red/purple colour obtained using DFO [31,21,25]. It has been suggested that the weak red/purple colour is produced by the incomplete or slow reaction of DFO with the amino acids found in latent deposits [32,8]. Therefore, it is recommended that the colour of weakly developed fingermarks should be further enhanced by treatment with ninhydrin if necessary, particularly if background luminescence precludes detection in the luminescence mode [24,33].
Even though DFO was found to produce intensely luminescent fingermarks, research continued to investigate the enhancement of both sensitivity and contrast of the reagent. One approach, in a similar manner to ninhydrin, was to investigate the addition of metal salts. Conn et al. investigated the effect of zinc, cadmium, ruthenium and europium on the luminescence of DFO treated fingermarks. They found that, while metal salt treatment showed no significant increase in the luminescence, a change in the colour of the productwas observed with all but europium [26]. This suggests that, as with ninhydrin, the metal salts form a complex with the reaction product, thus changing its colour.
Since the introduction of DFO as a routine fingermark detection method, the precise formulation of the reagent has varied significantly [36,24,21,25,33–35]. The initial formulation suggested by Pounds et al. contained methanol, acetic acid and CFC 113, which was found to be unstable and the large amount of methanol caused the running of some inks on cheques [21]. While methanol is primarily used to dissolve DFO in the non-polar carrier solvent, it has been shown to be a necessary component of the DFO formulation as it causes the formation of a reactive hemiketal [27]. Stoilovic found that a formulation with a final polar solvent concentration below 10% would not cause any significant dispersion of writing inks on treated documents [25]. Improvements on the early formulation were made by Hardwick et al. that resulted in a formulation that was stable formonths and was simple to prepare [33] when compared to the petroleum ether/xylene formulation suggested by Masters et al. [24]. While CFC 113 was considered the best carrier solvent for DFO, environmental concerns prompted the search for new, safer carrier solvents. Didierjean et al. found that a formulation where CFC 113. was replaced with HFE 7100 developed fingermarks that were of equal or better quality than those developed with a CFC 113 based formulation [34]. The current formulation recommended by the Australian Federal Police contains 0.72 g L−1 DFO, 9% polar solvent (dichloromethane, methanol and acetic acid) in HFC 4310mee
(1,1,1,2,3,4,4,5,5,5-decafluoropentane) [36].
Typically, DFO is applied to a substrate by dipping in the reagent solution, air drying, and heating in either an oven or ironing press. In order to combat problems with particular carrier solvents (e.g.environmentally damaging, flammable, or causing ink to run), a new method of applying DFO to the substrate – referred to as “DFO-Dry” –was investigated by Bratton and Juhala [37]. This technique involved the application of DFO from soaked filter papers by processing with a steam iron filled with a 5% acetic acid solution before heating at 100 ◦C for 10 min. “DFO-Dry” does not use any heptane, petroleum ether, or CFC 113 in the working solution. The advantages of this method are reported to be equal luminescence in developed marks compared to conventional techniques without background induced luminescence or any ink migration, and the “working papers” can be prepared in advance and reused several times [37].
Scheme 2. Proposed reaction mechanism of DFO and an amino acid [26,22,27].
1,2-Indanedione
Joullie and co-workers first publicised, in 1997, the ability of 1,2-indanedione to react with the amino acids present in latent fingermarks [7,38]. Since that time, significant research has been undertaken into the use of 1,2-indanedione as a fingermark detection reagent. Similar to DFO, the reaction between _-amino acids and 1,2-indanedione results in a pale pink colour with intense room-temperature luminescence [39,7,38,40]. Studies into the mechanism of the reaction of 1,2-indanedione and amino acids suggest that it reacts initially with amines to form imines (I in Scheme 3) [15,40,41], which is then followed by decarboxylation and Strekker degradation to produce 2-amino-1-indanone (II). This can then react further with an excess of 1,2-indanedione to produce a coloured and luminescent species (III) [15]. Although proposed the reaction product has yet to be isolated and its structure confirmed.
As 1,2-indanedione is similar in structure to ninhydrin, treatment of the reaction product with metal salts has been investigated [42,31,7,38]. When 1,2-indanedione developed fingermarks were treated with zinc or cadmium chloride, the luminescence intensity of the reaction product was increased [42,31,7,38] and the colour of the product became a darker pink, improving contrast [31]. This also occurred when the zinc salt was added to the solution of 1,2- indanedione [44,7]; this was reported to decrease the shelf-life of the reagent [7]. Recent investigations have determined that the shelf-life of a revised 1,2-indanedione formulation is not adversely affected by the addition of a metal salt [31] and the development of fingermarks using a combined 1,2-indanedione/zinc (II) (INDZn) formulation is less reliant on ambient humidity [44]. The exact role of the metal salt in the 1,2-indanedione reaction has yet to be clarified but is the focus of current investigations. Early studies showed that fingermarks treated with 1,2- indanedione alone decomposed within a few days, to lose both their colour and luminescence [7]. Those treated with IND-Zn had increased longevity, taking weeks or months to lose their colour and luminescence [7]. In 2003, Gardner and Hewlett investigated the stability of 1,2-indanedione treated fingermarks when exposed to daylight for extended periods of time. They found that samples left in daylight for 28 days degraded to only 20% of their original luminescence, and samples excluded from light had increased longevity. They also found that post-treatment of the sample with zinc chloride did not slow down the degradation, and suggested that photolysis of the product was the cause of the degradation [45].
Since the discovery of 1,2-indanedione, there have been inconsistencies in the literature concerning the optimal working formulation for the development of latent fingermarks [32,42,44,31,35,45–49]. Early investigations used methanolic solutions, although it is now recommended to limit the amount of the alcohols in 1,2-indanedione solutions as they form hemiketals that interfere in the reaction with amino acids [32,15,50].
Scheme 3. Proposed reaction mechanism of 1,2-indanedione and _-amino acids [15].
Alternative amino acid sensitive reagents
With a greater understanding of fingermark chemistry and the introduction of lasers and other forensic light sources, research into chemical alternatives to ninhydrin and its analogues for amino acid detection have also been explored. Reagents that demonstratedthe greatest prospects were fluorescamine, o-phthalaldehyde and NBD-chloride (7-chloro-4-nitrobenzo-2-oxa-1,3-diazole) [51,52]. However, these reagents have not come into operational use due to disadvantages when compared to ninhydrin and its analogues. Fluorescamine and o-phthalaldehyde react with amino acids to form products that are luminescent under UV light and thus their application is limited due to interference from the UV elicited photoluminescence from the optical brighteners present in many paper substrates [51]. The products of the reaction of NBD-chloride with amino acids exhibit luminescence when excited in the visible region. However, NBD-chloride lacks specificity as it reacts with other unidentified components present in some paper substrates leading to background luminescence and reduced contrast [51]. In addition, NBD-chloride only gives products that are visible when viewed with a suitable light source [51].
Reagents based on natural products
Prior to 2004, research into non-specific amino acid targeting reagents primarily focussed on ninhydrin and related compounds. An alternative research path developed with the discovery of genipin (Fig. 4) [53], which, unlike other reagents, was not synthesised as a ninhydrin analogue. Thus began a new trend into researching natural products for fingermark detection applications
Genipin
In 2004, Almog and co-workers were first to recognise the significance of genipin as an amino acid targeting “dual” fingermark reagent. Genipin is colourless until reaction with primary amino acids, which results in the formation of a blue colour with luminescence characteristics (_ex 590 nm, _em 620 nm) without further treatment. Furthermore, the safety, simplicity and sensitivity involved in detecting fingermarks using genipin adds to its potential as a fingermark reagent [53,54].
Genipin is obtained from a number of different plant sources including Gardenia jasminoides Ellis and Genipa Americana. Extracts from these plants have been used for centuries as a traditional Chinese medicine, food and fabric colourants and as skin dyes [55,56]. Herbal medicines are available as an alternative to western medicines and are often considered to be non-toxic [57]. For this reason, genipin is considered chemically safe and less hazardous than other common fingermark reagents [53,54,56]. Genipin’s ability to stain the skin was first reported in the chemical literature by Djerassi et al. in 1960, who published that “genipin itself is colourless, but if brought to the skin, it rapidly produces an indelible bluish/violet colour.” They later established genipin’s ability to rapidly react with amino acids [54,58,59]. Along with this, they describe Oviedo
It is the ability of genipin to react with amine groups to form intensely coloured dyes, coupled with its low toxicity, that has given genipin the potential to provide operational advantages over current fingermark reagents. Almog and co-workers found that the resulting photoluminescence emits at longer wavelengths than currently observed for other fingermark reagents [53,54]. This can result in an improved signal-to-noise ratio due to the shift away from any potential background fluorescence, creating greater contrast between the fingermark and the substrate [54]. Due to the novel nature of genipin as a latent fingermark developer on porous surfaces, implementation for routine forensic use, at this stage, could be somewhat premature [53].With further optimisation and development, the use of genipin may become an important technique to aid in the development of latent fingermarks on porous surfaces, particularly on substrates where background luminescence is problematic.
One key area of research is focussing on determining the reaction mechanism and the resulting chromophore and/or fluorophore, which has yet to be verified. Investigations have been conducted looking at the reaction of genipin with simple compounds containing primary amines, which in turn indicate the formation of heterocyclic amines. These amines were further associated to form cross linking networks, containing short chain dimer, trimer and tetramer bridges [55,61,62,63]. Additionally, the reaction of genipin with amino acids has been reported to produce more than one coloured compound [54,64]. Touyama et al. reported the presence of one yellow and nine brownish-red pigments (A–I), which were proposed to be precursors of the blue product(s). It was presumed that the blue product(s) was formed through oxygen radical-induced polymerisation and dehydrogenation of a mixture of intermediary pigments as depicted in Fig. 5 [65,66].
Alternatively, Fujikawa proposed that a monomeric adduct, genipocyanin, was formed from genipin reacting with glycine which further cross linked to proteins (R in Fig. 6b) [62]. Although structural similarities are present between compounds in Fig. 6 and Touyama’s postulations featured in Fig. 5, significant conformational variations exist, exemplifying the difficulty in deducing the mechanism involved. These investigations by Fujikawa and Touyama were carried out in solution phase, which may not give a true representation of the mechanism involved on paper substrates. When amino acids from a finger mark bind to a substrate, the concentration or surface coverage is such that the amino acids are well separated. Hence the lack of mobility means that oligomeric products derived from multiple amino acid units are highly unlikely. In solution, however, the ability of amino acid and genipin units to mix permits the formation of products involving multiple amino acid and genipin units. The exact nature of the reaction occurring between genipin and latent finger mark deposits, the nature and the number of products formed in the reaction on paper substrate is thus still yet to be established.
Fig. 6. Proposed resonance structures of (a) genipocyanin; (b) a dimer from genipin
and a primary amine (R = protein) [62].
Lawsone (2-Hydroxy-1,4-naphthoquinone)
With the successful assessment of genipin as a potential amino acid targeting reagent, attention was directed towards other possible natural products associated with or displaying dying qualities. One of the most frequently used natural dyes is henna. Henna is sourced from the leaves of Lawsonia inermis and is commonly used to temporarily dye the skin and hair [67,68]. As with genipin, indigenous cultures used henna as part of religious, social and ritualistic traditions, the most prominently recognised being mehndi decorations. This tradition consists of intricate designs drawn in henna as a temporary form of body art and is applied to brides before their wedding ceremonies [68]. The first use of henna as a hair dye can be traced back to at least 4000 years ago as hair from Egyptian pharaohs contained evidence of henna [69].
Lawsone (2-hydroxy-1,4-naphthoquinone) is believed to be the molecule responsible for the dying quality of henna [67,68]. In 2008, Jelly et al. reported on the reaction of lawsone with primary amino acid residues on paper surfaces. The reaction was found to produce a dark purple/brown compound that also exhibited photoluminescence without further treatment [70]. In a similar manner to genipin, lawsone has a maximum intensity of luminescence occurring around 640 nm with excitation at 590 nm. This is operationally significant as photoluminescence emission at longer wavelengths has the potential to improve detectability by avoiding any native background interference. Nevertheless, due to the novel nature of this work, there is a significant amount of additional research required in order to assess the potential of lawsone as a tool for developing latent fingermarks on porous surfaces [70].
The reaction mechanism must be reviewed in order to obtain some level of understanding as to the way in which the chromophore/ fluorophore is produced. This, in turn, will allow for an accurate assessment of the effectiveness of lawsone as a fingermark reagent. Jelly et al. postulate the formation of a diametric product that is based on Spyroudis’s review on the reactivity of hydroxyquinones (Scheme 4).
This mechanism is similar to the ninhydrin reaction with amines and amino acids; unlike ninhydrin, lawsone does not require further treatment with ametal salt to form a luminescent product [70,71]. Naphthoquinones are a class of compounds that are well known for their bioactivity [72,73] and their ability to react with amino groups have been extensively reported [71,74–85]. 1,2-Naphthoquinone-4-sulfonate has been employed for the determination of amino acids through the formation of highly coloured compounds [86–90]. Rees and Pirie specifically studied the use of 1,2-naphthoquinone to form a purple/brown compound on reaction with cysteine, and also noted that the reaction was believed to target the amine group of the amino acid [91]. This provides strong evidence to suggest the importance of naphthoquinones for the detection and colorimetric analysis of primary amines or associated compounds and, in turn, their potential use for detecting latent fingermarks on porous surfaces.
In addition to the discovery of new reagents, there is still a need for further research to gain a better understanding of the reaction mechanisms associated with established reagents (e.g. DFO and 1,2-indanedione) and those still under development (e.g. genipin and lawsone). There are still unanswered questions as to the exact role of certain components within formulations, such as metal salts. These studies will need to utilise surface analysis techniques in order to examine the reaction intermediates and products in situ rather than in solution in order to obtain results that are applicable to fingermark detection on porous substrates. A better understanding of reaction mechanisms will potentially allow the design of amino acid reagents with enhanced properties. On an operational level, there is a requirement for more standardised approaches to determine the performance of latent fingermark treatments as a whole. Fundamental studies of the latent fingermark residue in situ, including aging studies, would aid this area of research. While there have been a number of reports in the literature regarding chemical analysis of the fingermark residue [92–95] Continued research in this field will require expertise in chemical synthesis, materials science and advanced spectroscopy, and thus there is ample room for analytical chemistry researchers to help improve and extend a key forensic techniques.
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