WO1990005308A1 - Fingerprint reagent - Google Patents

Fingerprint reagent Download PDF

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Publication number
WO1990005308A1
WO1990005308A1 PCT/GB1989/001329 GB8901329W WO9005308A1 WO 1990005308 A1 WO1990005308 A1 WO 1990005308A1 GB 8901329 W GB8901329 W GB 8901329W WO 9005308 A1 WO9005308 A1 WO 9005308A1
Authority
WO
WIPO (PCT)
Prior art keywords
amino acids
detection
benzene ring
nitrogen
tested
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/GB1989/001329
Other languages
French (fr)
Inventor
Ronald Ernest Grigg
Teirevat Mongkolaussavaratana
Charles Anthony POUNDS
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Queens University of Belfast
Original Assignee
Queens University of Belfast
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Queens University of Belfast filed Critical Queens University of Belfast
Priority to EP89913229A priority Critical patent/EP0442959B1/en
Priority to DE68917934T priority patent/DE68917934T2/en
Publication of WO1990005308A1 publication Critical patent/WO1990005308A1/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
    • G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
    • G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
    • G01N33/68—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving proteins, peptides or amino acids
    • G01N33/6803—General methods of protein analysis not limited to specific proteins or families of proteins
    • G01N33/6806—Determination of free amino acids
    • G01N33/6809—Determination of free amino acids involving fluorescent derivatizing reagents reacting non-specifically with all amino acids
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T436/00—Chemistry: analytical and immunological testing
    • Y10T436/17—Nitrogen containing
    • Y10T436/173845—Amine and quaternary ammonium
    • Y10T436/174614—Tertiary amine
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T436/00—Chemistry: analytical and immunological testing
    • Y10T436/17—Nitrogen containing
    • Y10T436/173845—Amine and quaternary ammonium
    • Y10T436/175383—Ammonia

Definitions

  • This invention relates to a method for the detection and or quantitation of ⁇ -amino acids in chemical and biochemical analyses and particularly but not exclusively to a method for the detection of latent fingerprints .
  • a common method of detection of amino acids comprises applying ninhydrin (1 , 2,3-triketohydrindene hydrate) to the amino acid .
  • the ninhydrin reacts with the amino acid on heating yielding a purple colouration .
  • ninhydrin is often used in the detection of latent fingerprints , in , for example , criminal investigation .
  • a method of detection of amino acids comprising the application , to the material being tested , of a reagent comprising the following basic formula;
  • X, Y and/or Z may be nitrogen C-H, C-alkyl or C-aryl and wherein A, B, C and/or D may be an alkyl or aryl
  • A, B, C and D are hydrogen
  • ⁇ and Z are C-H
  • a and B together are part of a benzene ring
  • A, B, C and D are hydrogen
  • a and B together are part of a benzene ring
  • a and B together are part of a benzene ring
  • a and B together form part of a benzene ring
  • a method of detecting amino acids comprises the addition to the material being tested of a compound comprising the following basic structure
  • X , Y and Z may be nitrogen , C-H , C-alkyl or C-aryl and A , B , C and D may be alkyl , aryl alkyl or aryl substituent either alone or in combination .
  • Each ring could be variously substituted, for example, with alkyl and aryl substituents.
  • the compounds of the method of the invention may be synthesised by a variety of methods.
  • One such method of producing such a compound is disclosed in Helv.Chim.Acta., 1950, 50, 1080, which reveals a
  • the compound (1) is dissolved in a suitable solvent system such as methanol/acetic acid/ trichlorotrifluorethane so as the concentration of the reagent (1) solution is in the range from substantially 0.05 to 2%.
  • the document or sample containing or supporting the amino acid such as a latent fingerprint is
  • the amino acid sample may subsequently be removed from the reagent (1) solution after a suitable time period has elapsed, for example approximately five seconds. The sample is then allowed to dry. Drying should be complete after approximately thirty seconds. The sample is then
  • the sample is subsequently removed from the reagent (1) solution and the amino acids may then be developed by, for example, heating the sample at 110°C for ten minutes.
  • the reagent (1) in combination with the amino acid produces coloured fluorescent species with ⁇
  • the fluorescent fingerprints can be made visible by using blue/green light for excitation and observing the light emission through a filter such as a 610 nm filter.
  • 1,8-Diazafluoren-9-one (1) (0.05g) was dissolved in a mixture of methanol (4ml) and acetic acid (2ml) and was then diluted up to 100ml with trichlorotrifluoroethane (Fluorosil) so as to form a reagent (1) solution.
  • a sheet of paper on which a latent fingerprint was situated was immersed in the reagent (1) solution for 5 seconds. The paper was removed from the reagent (1) solution and allowed to dry for 30 seconds. The paper was then immersed for a further five seconds and was subsequently removed from the reagent (1)
  • the fluorescent fingerprints were made visible by illumination with blue/green light (excitation) and were observed through a 610 nm filter.
  • Example 1 The method of Example 1 was repeated substituting reagent (1) for reagents (2) to (7).
  • Reagents (2) to (7) also produced fluorescent fingerprints which could be visualised by illumination with blue/green light (excitation) and observed through a 610 nm filter.

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  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Molecular Biology (AREA)
  • Hematology (AREA)
  • Chemical & Material Sciences (AREA)
  • Urology & Nephrology (AREA)
  • Physics & Mathematics (AREA)
  • Immunology (AREA)
  • Biomedical Technology (AREA)
  • Microbiology (AREA)
  • General Health & Medical Sciences (AREA)
  • Biotechnology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Biophysics (AREA)
  • Bioinformatics & Computational Biology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Food Science & Technology (AREA)
  • Medicinal Chemistry (AREA)
  • Analytical Chemistry (AREA)
  • Biochemistry (AREA)
  • Cell Biology (AREA)
  • General Physics & Mathematics (AREA)
  • Pathology (AREA)
  • Measurement Of The Respiration, Hearing Ability, Form, And Blood Characteristics Of Living Organisms (AREA)
  • Investigating Or Analysing Biological Materials (AREA)
  • Holo Graphy (AREA)
  • Electrochromic Elements, Electrophoresis, Or Variable Reflection Or Absorption Elements (AREA)
  • Sampling And Sample Adjustment (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)

Abstract

A method of detection of amino acids comprising the application, to the material being tested, of a reagent comprising basic formula (I), wherein X, Y and/or Z may be nitrogen C-H, C-alkyl or C-aryl and wherein A, B, C and/or D may be an alkyl or aryl substituent either alone or in combination.

Description

FI N GERPRI NT REAGENT
This invention relates to a method for the detection and or quantitation of α -amino acids in chemical and biochemical analyses and particularly but not exclusively to a method for the detection of latent fingerprints .
At present a common method of detection of amino acids comprises applying ninhydrin (1 , 2,3-triketohydrindene hydrate) to the amino acid . The ninhydrin reacts with the amino acid on heating yielding a purple colouration .
As amino acids are secreted from human finger tips , ninhydrin is often used in the detection of latent fingerprints , in , for example , criminal investigation .
We have discovered an alternative group of compounds which can be used for this purpose.
According to the present invention there is provided a method of detection of amino acids comprising the application , to the material being tested , of a reagent comprising the following basic formula;
Figure imgf000003_0001
wherein X, Y and/or Z may be nitrogen C-H, C-alkyl or C-aryl and wherein A, B, C and/or D may be an alkyl or aryl
substituent either alone or in combination.
In a preferred embodiment of the invention the
substituents X, Y. Z, A, B, C and D are one of the
following combinations
(1) X and Y are C-H
Z is nitrogen
A, B, C and D are hydrogen
(2) X is nitrogen
Υ and Z are C-H
A and B together are part of a benzene ring
C and D are hydrogen
(3) X, Y and Z are nitrogen
A, B, C and D are hydrogen
(4) X, Y and Z are nitrogen
A and B together are part of a benzene ring
C and D together are part of a benzene ring
(5) X and Y are C-H
Z is nitrogen
A and B together are part of a benzene ring
C and D together are part of a benzene ring
(6) Z is nitrogen
B and D are hydrogen
A and X together form part of a benzene ring
C and Y together form part of a benzene ring (7 ) X and Z are nitrogen
Y is C-H
A and B together form part of a benzene ring
C and D are hydrogen .
In order that the invention may be more readily understood, a specific embodiment thereof will now be described by way of example:
A method of detecting amino acids comprises the addition to the material being tested of a compound comprising the following basic structure
Figure imgf000005_0001
(I )
wherein X , Y and Z may be nitrogen , C-H , C-alkyl or C-aryl and A , B , C and D may be alkyl , aryl alkyl or aryl substituent either alone or in combination .
Some preferred examples of the compound used in the method are as follows :
Figure imgf000005_0002
Figure imgf000006_0001
Many substituents of functional groups are
possible. Each ring could be variously substituted, for example, with alkyl and aryl substituents.
The compounds of the method of the invention may be synthesised by a variety of methods. One such method of producing such a compound is disclosed in Helv.Chim.Acta., 1950, 50, 1080, which reveals a
method of synthesising 1,8-Diazafluoren-9-one (1).
Other compounds of the invention could be produced, for example, by appropriate substitution reactions of 1,8-Diazofluoren-9-one of (1).
In practice the compound (1) is dissolved in a suitable solvent system such as methanol/acetic acid/ trichlorotrifluorethane so as the concentration of the reagent (1) solution is in the range from substantially 0.05 to 2%.
The document or sample containing or supporting the amino acid such as a latent fingerprint is
immersed in the reagent (1) solution. The amino acid sample may subsequently be removed from the reagent (1) solution after a suitable time period has elapsed, for example approximately five seconds. The sample is then allowed to dry. Drying should be complete after approximately thirty seconds. The sample is then
re-immersed in the reagent (1) solution for example for thirty seconds. The sample is subsequently removed from the reagent (1) solution and the amino acids may then be developed by, for example, heating the sample at 110°C for ten minutes.
The reagent (1) in combination with the amino acid produces coloured fluorescent species with λ
(excitation) in the order of 470 nm and λ (emission) in the order of 570 nm on paper. The fluorescent fingerprints can be made visible by using blue/green light for excitation and observing the light emission through a filter such as a 610 nm filter.
The invention will now be further illustrated by the following examples.
Example 1
1,8-Diazafluoren-9-one (1) (0.05g) was dissolved in a mixture of methanol (4ml) and acetic acid (2ml) and was then diluted up to 100ml with trichlorotrifluoroethane (Fluorosil) so as to form a reagent (1) solution. A sheet of paper on which a latent fingerprint was situated, was immersed in the reagent (1) solution for 5 seconds. The paper was removed from the reagent (1) solution and allowed to dry for 30 seconds. The paper was then immersed for a further five seconds and was subsequently removed from the reagent (1)
solution and heated at 110°C for 10 minutes.
The fluorescent fingerprints were made visible by illumination with blue/green light (excitation) and were observed through a 610 nm filter.
The fluorescent fingerprints visualised by reagent (1) proved to reveal more fingerprint detail than ninhydrin.
Example 2
The method of Example 1 was repeated substituting reagent (1) for reagents (2) to (7). Reagents (2) to (7) also produced fluorescent fingerprints which could be visualised by illumination with blue/green light (excitation) and observed through a 610 nm filter.
It is to be understood that the scope of the invention should not be limited to the above described embodiments thereof as those embodiments are for illustration only.

Claims

CLA IMS
1 . A method of detection of amino acids comprising the application, to the material being tested , of a reagent comprising the following basic formula;
Figure imgf000010_0001
wherein X, Y and/or Z may be nitrogen C-H , C-alkyl or C-aryl and wherein A , B , C and/or D may be an alkyl or aryl substituent either along or in combination.
2. A method of detection of amino acids as claimed in claim 1, wherein substituents X, Y , Z , A , B , C, and D are one of the following combinations
(1 ) X and Y are C-H ; and
Z is nitrogen; and
A , B , C and D are hydrogen
OR (2) X is nitrogen; and
Y and Z are C-H ; and
A and B together are part of a benzene ring; and C and D are hydrogen
OR (3) X , Y and Z are nitrogen; and
A and B together are part of a benzene ring; and C and D together are part of a benzene ring
OR (4) Z , Y and Z are nitrogen; and
A and B together are part of a benzene ring; and C and D together are part of a benzene ring
OR (5) X and Y are C-H; and
Z is nitrogen; and
A and B together are part of a benzene ring; and
C and D together are part of a benzene ring
OR (6) Z is nitrogen; and
B and D are hydrogen; and
A and X together form part of a benzene ring; and C and Y together form part of a benzene ring
OR (7) X and Z are nitrogen;
Y is C-H;
A and B together form part of a benzene ring;
C and D are hydrogen
3. A method of detection of amino acids as claimed in claim 1 or claim 2, wherein the said compound (1) is dissolved in a solvent system comprising at least one of the following: alcohol, acid or halo alkane.
4. A method of detection of amino acids as claimed in claim 1, claim 2 or claim 3, wherein the said compound (1) is dissolved in a solvent system comprising at least one of the following: methanol, acetic acid or trichlorotrifluoroethane.
5. A method of detection of amino acids as claimed in claim 3 or claim 4 wherein the material being tested is at least partially immersed in the compound (1) solution.
6. A method of detection of amino acids as claimed in any preceding claim in which the material being tested is substantially dried after a first application of compound ( 1 ) prior to a second application of compound ( 1 ) to the material being tested.
7. A method of detection of amino acids as claimed in any preceding claims in which the material being tested is developed by heating .
8. A method of detection of amino acids as claimed in any preceding claim in which the amino acid is made visable by illumination by light within a certain wavelength range.
9. A method of detection of amino acids as claimed in claim 8 in which the excitation wavelength range comprises 470nm and/or the emission wavelength range comprises 5.70nm .
10. A method of detection of amino acids as substantially hereinbefore described with reference to Example 1 or Example 2.
PCT/GB1989/001329 1988-11-09 1989-11-09 Fingerprint reagent Ceased WO1990005308A1 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
EP89913229A EP0442959B1 (en) 1988-11-09 1989-11-09 Fingerprint reagent
DE68917934T DE68917934T2 (en) 1988-11-09 1989-11-09 FINGERPRINT REAGENT.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB888826237A GB8826237D0 (en) 1988-11-09 1988-11-09 Fingerprint reagent
GB8826237.3 1988-11-09

Publications (1)

Publication Number Publication Date
WO1990005308A1 true WO1990005308A1 (en) 1990-05-17

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US (1) US5221627A (en)
EP (1) EP0442959B1 (en)
AT (1) ATE110855T1 (en)
AU (1) AU638221B2 (en)
CA (1) CA2002620C (en)
DE (1) DE68917934T2 (en)
GB (1) GB8826237D0 (en)
WO (1) WO1990005308A1 (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19830040B4 (en) * 1998-06-26 2009-02-05 Sensient Imaging Technologies Gmbh New cyclopentadiquinoxaline derivatives
EP2520572A1 (en) * 2007-11-30 2012-11-07 Sumitomo Chemical Co., Ltd. Nitrogen-containing fused-ring compound, polymer comprising a nitrogen-containing fused-ring repeating unit, organic thin film, and organic thin film element
CN113512027A (en) * 2021-07-20 2021-10-19 华南理工大学 A kind of indanone quinoxaline derivative and its preparation method and application

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6352863B1 (en) * 1990-01-19 2002-03-05 La Mina, Inc. Assay device
TW387805B (en) 1997-05-12 2000-04-21 Taiho Ind Co A fingerprint indicator and the method of detection
US6485981B1 (en) * 1998-07-29 2002-11-26 Ciencia, Inc. Method and apparatus for imaging and documenting fingerprints
EP1296985B1 (en) * 2000-07-06 2005-06-01 QLT Inc. Heteropolycyclic inhibitors
KR20010025234A (en) * 2000-11-09 2001-04-06 김진삼 A certification method of credit of a financing card based on fingerprint and a certification system thereof
US7879623B2 (en) * 2006-03-31 2011-02-01 Guirguis Raouf A Integrated device for analyte, testing, confirmation, and donor identity verification
US7741103B2 (en) * 2006-03-31 2010-06-22 Guirguis Raouf A Integrated screening and confirmation device
US8940527B2 (en) * 2006-03-31 2015-01-27 Lamina Equities Corp. Integrated device for analyte testing, confirmation, and donor identity verification
US11906512B2 (en) 2006-03-31 2024-02-20 Zeus Diagnostics, LLC Integrated device for analyte testing, confirmation, and donor identity verification
US20080022888A1 (en) * 2006-07-27 2008-01-31 Armor Holdings Forensics, Inc. Ready to use combined skin marking stain compound and applicator requiring only the addition of water
WO2009067761A1 (en) * 2007-11-29 2009-06-04 University Of Technology, Sydney A method of developing latent fingerprints
US10564155B2 (en) 2017-01-27 2020-02-18 Raouf A Guirguis Dual swab fluid sample collection for split sample testing and fingerprint identification device
PL246269B1 (en) * 2022-12-31 2024-12-23 Univ Gdanski Method of visualizing fingerprint traces on an absorbent substrate and final solution for visualizing fingerprint traces on an absorbent substrate

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE621677A (en) *

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE621677A (en) *

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19830040B4 (en) * 1998-06-26 2009-02-05 Sensient Imaging Technologies Gmbh New cyclopentadiquinoxaline derivatives
EP2520572A1 (en) * 2007-11-30 2012-11-07 Sumitomo Chemical Co., Ltd. Nitrogen-containing fused-ring compound, polymer comprising a nitrogen-containing fused-ring repeating unit, organic thin film, and organic thin film element
US8378338B2 (en) 2007-11-30 2013-02-19 Sumitomo Chemical Company, Limited Conjugated compound, nitrogenated condensed-ring compound, nitrogenated condensed-ring polymer, organic thin film, and organic thin film element
CN113512027A (en) * 2021-07-20 2021-10-19 华南理工大学 A kind of indanone quinoxaline derivative and its preparation method and application

Also Published As

Publication number Publication date
AU638221B2 (en) 1993-06-24
EP0442959A1 (en) 1991-08-28
ATE110855T1 (en) 1994-09-15
DE68917934T2 (en) 1995-02-09
CA2002620A1 (en) 1990-05-09
CA2002620C (en) 2000-08-08
EP0442959B1 (en) 1994-08-31
US5221627A (en) 1993-06-22
AU4639789A (en) 1990-05-28
DE68917934D1 (en) 1994-10-06
GB8826237D0 (en) 1988-12-14

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