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Selectivity of Amino Acid Reactive Reagents and Latent Finger Mark Development

This research study explores the selectivity of amino acid reactive reagents (such as ninhydrin, lawsone, juglone, and genipin) in the development of latent finger marks. The study also examines the major amino acids present in fingerprints and their reactions with these reagents. The findings can be used for forensic investigation purposes.

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Selectivity of Amino Acid Reactive Reagents and Latent Finger Mark Development

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  1. TÜBİTAK Marmara Research Center, ChemicalTechnologyInstitute, TURKEYSelectivity of AminoAcid Reactive Reagents and a Magic Way of DevelopmentofLatent Finger MarksDr. Melek Erol 28-30 September 2015 ForensicResearch 2015, Atlanta

  2. What is in a fingerprint? Major amino acids present in fingerprints L-Serine L-Glycine L-Alanine L-Asparticacid • Eccrinesecretion • Water (>98%) • Amino acids • Proteins • Urea • Uricacid • Lacticacid • Sugars • Inorganicions (Na+, K+, Cl-, Ca2+, etc.) • Sebaceous secretion • Fatty acids, • Glycerides, • Wax esters, • Squalene • Sterol esters

  3. Amino AcidReactiveReagents 2-hydroxy-1,4-naphthoquinone (Lawsone) Ninhydrin 5-hydroxy-1,4-naphthoquinone (Juglone) Genipin

  4. Ninhydrin • Predominant reagent for visualization of fingermarks on porous surfaces for criminal investigation. • First synthesized and discovered to react with amino acids in 1910 by Siegfried Ruhemann. • Forms a non-fluorescent purple product with amino acids. • Suggested for detection of latent fingermarks on porous surfaces in mid-1950s by Oden and von Hofsten. Strecker degradation 2-amino-1,3-indanedione R.Jelly et al., Analytica Chimica Acta, 2009, 652, 128-142.

  5. Ninhydrin – Amino Acid Spot Reactions at RT L-Serine L-Glycine L-Alanine L-Aspartic acid L-Histidine L-Cysteine Filter paper used as the substrate due to its low photoluminescent properties. Fresh 2 hours 6 hours ALA-1 ALA-1 SER-10 SER-10 GLY-1 GLY-1 GLY-10 GLY-10 1 mM Ninhydrin in1:1.2:10 Ethanol:Ethyl acetate: HFE7100 SER-1 SER-1 ALA-10 ALA-10 SER-10 SER-10 ALA-1 GLY-10 GLY-10 ALA-1 GLY-1 ALA-10 ALA-10 2 hours -UV SER-1 SER-1 GLY-1 Fresh –UV(365 nm) 2 hours –UV(365 nm) 6 hours –UV(365 nm)

  6. Ninhydrin–Amino Acid Spot Reactions at DifferentT’s 2 h reaction time at specified T’s 105°C RT 80°C 150°C ALA-1 SER-10 SER-10 ALA-1 ALA-1 SER-10 GLY-10 ALA-10 GLY-10 GLY-1 SER-1 GLY-1 GLY-10 GLY-10 SER-10 GLY-1 GLY-1 ALA-10 ALA-10 SER-1 ALA-10 SER-1 ALA-1 SER-1 SER-10 SER-10 SER-10 ALA-10 ALA-1 ALA-1 ALA-1 GLY-10 GLY-10 GLY-10 GLY-10 SER-1 GLY-1 GLY-1 GLY-1 SER-10 ALA-1 ALA-10 ALA-10 GLY1 SER-1 SER-1 SER-1 ALA-10 RT –UV(365 nm) 80°C –UV(365 nm) 105°C –UV(365 nm) 150°C –UV(365 nm) 1 mM Ninhydrin in 1:1.2:10 Ethanol:Ethyl acetate: HFE7100

  7. Fluorescent Emission of Ninhydrin–Amino Acid Products At 150C Aspartic acid > Glycine > Histidine > Serine > Alanine > Cysteine • Cysteine forms fluorescent product right after treatment even at RT! • Histidine forms light purple color right after treatment! λex. = 505 nm HORIBA JobinYvon FluoroLog - TCSPC Spectrofluorometer

  8. Lawsone • Responsible molecule for the dying of henna. • Forms a fluorescent brownish product with amino acids without further treatment. • Maximum luminescence around 600 nm with λex. of 530 nm. R.Jelly et al., Analytica Chimica Acta, 2009, 652, 128-142.

  9. Lawsone–Amino Acid Spot Reactions at DifferentT’s 2 h reaction time at specified T’s 80°C 105°C 150°C RT SER-1 GLY-1 ALA-1 SER-1 ALA-1 GLY-1 GLY-10 ALA-10 GLY-10 SER-10 ALA-10 SER-10 SER-1 GLY-1 SER-1 ALA-1 GLY1 GLY-1 ALA-10 ALA-1 GLY-10 ALA-10 GLY-10 SER-10 SER-10 80°C –UV(365 nm) 105°C –UV(365 nm) 150 °C –UV(365 nm) RT –UV(365 nm) 1 mM Lawsone in 1:20:20 DMF:Acetone:HFE7100

  10. Fluorescent Emission of Lawsone–Amino Acid Products At 150C Cysteine > Serine > Glycine > Aspartic acid  Alanine > Histidine • Slight fluorescence occurence at 80C! • Most densely color observed with Histidine! λex. = 530 nm HORIBA JobinYvon FluoroLog - TCSPC Spectrofluorometer

  11. Juglone • A dye for cloth and inks, and a coloring agent for foods and cosmetics. • Suggested for its potential fingermark detection on porous surfaces. • Maximum luminescence around 597 nm with λex. of 530 nm. 2 h reaction time at specified T’s 80°C 105°C 150°C RT SER-1 ALA-1 SER-1 ALA-1 ALA-1 GLY-1 GLY-10 SER-1 GLY-1 GLY-10 SER-10 GLY-1 ALA-10 GLY-10 ALA-10 SER-10 SER-10 ALA-10 ALA-1 SER-1 GLY-1 GLY-10 SER-1 SER-1 ALA-1 ALA-1 GLY-1 ALA-10 GLY-10 SER-10 GLY-1 ALA-10 GLY-10 SER-10 ALA-10 SER-10 RT –UV(365 nm) 80°C –UV(365 nm) 105°C –UV(365 nm) 150°C –UV(365 nm) 1 mM Juglone in 1:20:20 DMF:Acetone:HFE7100

  12. Fluorescent Emission of Juglone–Amino Acid Products At 150C Serine > Histidine > Alanine > Glysine  Aspartic acid > Cysteine • Cysteine forms highly fluorescent product at RT and it diminishes with increasing T! λex. = 530 nm HORIBA JobinYvon FluoroLog - TCSPC Spectrofluorometer

  13. Genipin • Extracted from plants of Gardenia jasminoides Ellis and Genipa Americana. • Used as a traditionalChinese medicine, food and fabric colourants and as skin dyes, natural protein cross-linker, has low cytotoxicity. • Forms a fluorescentblue product with amino acids without further treatment. • Maximum luminescence around 613 nm with λex. of 555 nm. R.Jelly et al., Analytica Chimica Acta, 2009, 652, 128-142.

  14. Genipin–Amino Acid Spot Reactions at Different T’s 2 h reaction time at specified T’s RT 105°C 150°C 80°C SER-1 SER-1 SER-10 GLY-1 ALA-1 ALA-1 GLY-10 GLY-1 ALA-1 ALA-10 ALA-10 GLY-10 GLY-10 GLY-1 ALA-10 SER-10 SER-10 SER-1 SER-1 GLY-1 SER-10 SER-1 ALA-1 GLY-10 ALA-1 GLY10 ALA-1 GLY-10 GLY-1 ALA-10 ALA-10 GLY-1 GLY-10 ALA10 SER-10 ALA-10 SER-10 SER-1 RT- UV(365 nm) 80°C –UV(365 nm) 105°C –UV(365 nm) 150°C –UV(365 nm) 1 mM Genipin in 1:1.2:10 Ethanol:Ethyl acetate: HFE7100

  15. Fluorescent Emission of Genipin–Amino Acid Products At 150C Aspartic acid > Glycine > Histidine > Alanine > Serine >> Cysteine • Strongest fluorescence observed between genipin and aspartic acid at 150°C! λex. = 555 nm HORIBA JobinYvon FluoroLog - TCSPC Spectrofluorometer

  16. Comparison of Fluorescence of Active Reagents at 150°C 2-methoxy- 1,4-naphthoquinone Lawsone Ninhydrin Genipin Juglone 365 nm, yellow filter

  17. Fluorescence of Amino Acids and Fingerprints due to Thermal Effects 365 nm 365 nm DFO heat Fluorescence sensitizer 530 nm, yellow filter 365 nm, UV filter

  18. How do fingermarks develop with thermal effect, without any chemical? Magic fluorescent product!

  19. Conclusions • Allreagentsgavefluorescencewith amino acidsandfingerprints at 150C. • Allnaphthoquinonederivativesandgenipinworked as fluorescencesensitizer. • Highestfluorescenceobservedwithgenipin. • Fluorescence of ninhidrintreatedfingermarks at 150C mostlyduetofluorescence of fingermark, ninhydrinnotfluorescencesensitizer! • Fluorescentproductformationbetweencellulosesurfaceand amino acids at hightemperature!

  20. Thanks… Serkan GÜRBÜZ Dr. Cemil DİZMAN Dr. Serdar SEZER • TÜBİTAK KAMAG 1007-110G085 • TurkishNationalPolice

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