이중성 지문시약으로서 Ruhemann’s Purple 화합물과 그 금속이온착 화합물의 생성 반응성 및 DNA분자 보호 가능성
Formation Reactivity of Ruhemann’s Purple Compound and Their Metal Ion Complexes as Dual Latent Fingerprint Reagent, and DNA Molecule Protection Potential
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초록
이중성 지문시약으로서 ninhydrin 유도체(N1-N6)와 아미노산 분자들(A1-A5)과의 반응생성물(Ruhemann’s Purple) 및 그 금속(M)이온 착 화합물의 반응성에 관련한 전산 화학적인 접근으로부터 유전자(DNA) 보호 가능성을 정량적으로 검토하였다. Ninhydrin 유도체와 아미노산 분자사이의 FMO에너지 도표로부터 리간드(L) 화합물(Schiff-base; Ruhemann’s Purple)로서 1,8-diazofluoren-9-one (L4) 분자의 생성이 우세하였으나 공명(resonance)현상으로 dipyridoimidazol-6-one (L6) 분자가 ZnCl2와 가장양호한 금속 착 화합물화 반응성을 나타내었다. Schiff-base (L) 생성반응 중 탈수된 물 분자들은수화된 금속 이온([M(H2O)n]z+)으로 전환되어 DNA 분자를 분해한다. 그러므로 DNA분자를 보호할수 있는 진정한 의미의 이중성 지문시약은 수화된 금속이온이나 또는 그의 aqua Schiff-base 착([M(L) (H2O)2Cl]+2) 화합물(M: L =1:1)이 아니라, 수화된 금속이온이 존재하지 않는 M: L =1:2 비율의 Schiff-base 착([M(L2) ]+2) 화합물이었다. 결론적으로 이들 수화되지 않은 착 화합물(M: L =1:2)들이 장 파장대(500-600 nm)의 차별화된 최대흡수 파장(λmax.)을 나타냄으로서 DNA 분자가 보호될 수 있는 신규 이중성 지문시약으로서 역할을 기대할 수 있었다.
Abstract
The reactivity on protection potential of the DNA molecule by formated Schif-base (Ruhemann’s Purple pigment) as ligand compound (L) through nucleophilic addition reaction between ninhydrin derivatives (N1-N6) and L-amino acids (A1-A5), and their metal complexes as dual fingerprint reagents were discussed quantitatively from the computational chemistry approach. The 1,8-diazo fluoren-9-one (L4) as Schiff-bases (L) from the frontier molecular orbital (FMO) energy diagram between ninhydrin derivatives and 20 L-amino acid molecules response the highest formation. But the L6-Zn complex formation from the reaction between dipyridoimidazol-6-one (L6) and metal salt (ZnCl2) showed the best complexation caused by resonance phenomenon. The water molecules dehydrated from the way formation of Schiff-base (L) converted into hydrated metal cation ([M(H2O)n]z+) complex that it would decompose to the DNA molecules. And the dual latent fingerprint reagent that can protect the molecule DNA in the true sense of the word was not the aqua Schiff-base metal complex ([M(L)(H2O)2 Cl]+2) of the ratio (M:L=1:1) but the Schiff-base metal complex ([M(L2)]+2) of the ratio (M:L=1:2) in the conditions under does not exist hydrated metal ions. In conclusion, these non-hydrated complexes (M:L=1:2) that are able to provide differentiated maximum (λmax.) absorbtion of long wave length (500-600 nm). Therefore, the complexes can be expected new potential role of the dual fingerprint reagent that can protect a DNA molecule.
참고문헌 (45)
- JB Friesen, "Forensic chemistry: The revelation of latent fingerprints", J Chem Educ, 92(7), pp.497~504 (2014)
- S Clark, "Chemical detection of latent fingerprints", J Chem Educ, 70, pp.593~595 (1993)
- 최미정, "땀의 성분 분석과 잠재지문 현출에 관한 연구", 분석과학, 20(2), pp.147~154 (2007), 한국분석과학회
- RA Wickenheiser, "Trace DNA: A review, disscussion of theory, and application of the transfer of trace quantities of DNA through skin contact", J Forensic Sci, 38(2), pp.442~450 (2003)
- RAH van Oorschot, "Forensic trace DNA : A review", Investig Genet, 1, pp.14~ (2010)
- W Grzybkpwski, "Nature and properties of metal cations in aqueous solutions", Polish J of Environ Stud, 15(4), pp.655~663 (2006)
- J Anastassopoul, "Metal–DNA interactions", J Molecular Structure, 651–653, pp.19~26 (2003)
- G Palermo, "Catalytic Metal Ions and Enzymatic Processing of DNA and RNA", Acc. Chem. Res, 48(2), pp.220~228 (2015)
- 최미정, "총설: DNA 감식에 미치는 잠재지문 현출시약들에 의한 금속이온과유기용매의 영향", 과학수사학회지, 11(1), pp.1~17 (2017), 한국과학수사학회[DOI]
- R Sinha, "The binding of DNA intercalating and nonintercalating compound to A-form and protonated form of poly (rC) . poly (rG): Spectroscopic and viscometric study", Bioorg Med Chem, 14(3), pp.800~814 (2006)
- 김병로, "운동과 사우나시간의 땀 성분 비교분석", 한국운동생리학회, 9(1), pp.181~189 (2000)
- SJ Montain, "Sweat mineral-element reponses during 7h of exercise-heat stress", Int J Sport Nutr Exert Metab, 17(6), pp.574~582 (2007)
- A Khedr, "The profile of free amino acids in latent fingerprint of healthy and beta-thalassemic volunteers", J Chromatography B, 878, pp.1576~1582 (2010)
- A Becue, "Fingermarks and other impressions left by the human body; A review (August 2007–July 2010)", 16th Interpol Forensic Science Symposium (2010)
- M Sibrian-Vazquez, "Principles of Fluorogenic Reagent Design for Forensics. Recent Progress Towards New Reagents to Develop Fingerprints in Blood and on Variable Surfaces", pp.127~145 (2015), Springer International Publishing Switzerland
- 엄창용, "습윤지수에 관한 QSPR 모델로 예측된 불소치환 비활성 용매 중에서 Dansyl 방법의 잠재지문 현출 효율성", 과학수사학회지, 10(1), pp.28~37 (2016), 한국과학수사학회[DOI]
- 김해중, "Crystal Violet 염료 분자의 가수분해 및 자유 라디칼 반응성에 관한 분자 궤도론적 이해", 과학수사학회지, 5(3), pp.220~227 (2011), 한국과학수사학회[DOI]
- 김세곤, "새로운 잠재지문 현출제로서 1,10-phenanthroline Europium (III) 아민류 리간드 착 화합물", 과학수사학, 3(2), pp.117~123 (2009)
- 김세곤, "잠재지문 검출제로서 Ninhydrin 유도체들과 Glycine 분자 사이의 반응성에 관한 비교분자 유사성지수분석", 과학수사학, 2(1), pp.43~49 (2008)
- 성낙도, "잠재지문 검출제로서 4,5-diazafluorene-9-one (IDFO) 분자의 활용 가능성에 관한 비교분자장분석(CoMFA)과 분자 궤도론적 이해", 과학수사학, 1(1), pp.19~27 (2007)
- 정영동, "식용색소 분말을 이용한 4-Chloro-7-nitro-1,2,3-benzoxadiazole에 의하여 현출된 잠재지문의 이미지 개선효과", 과학수사학회지, 11(4), pp.245~254 (2017), 한국과학수사학회[DOI]
- 서경숙, "몇 가지 식용색소를 이용한 Cyanoacrylate 훈증 현출지문의 개선에 미치는 색 대비효과", 과학수사학회지, 10(2), pp.97~106 (2016), 한국과학수사학회[DOI]
- 조재현, "식용색소를 이용한 비다공성 재질 상 현출지문의 색 대비효과 및 이미지 개선", 과학수사학회지, 10(3), pp.202~210 (2016), 한국과학수사학회[DOI]
- 장민호, "새로운 잠재지문 현출제로써 몇 가지 식용색소 분말의 효율성", 과학수사학회지, 9(1), pp.1~8 (2015), 한국과학수사학회[DOI]
- I Fleming, "Frontier Orbitals and Organic Chemical Reactions", pp.29~109 (1978), Wiley
- LG Zhuo, "A frontier molecular orbital theory approach to understanding the Mayr equation and to quantifying nucleophilicity and electrophilicity by using HOMO and LUMO energies", Asian J Org Chem, 1, pp.336~345 (2012)
- R Jellya, "The detection of latent fingermarks on porous surfaces using amino acid sensitive reagents: A review", Anal Chim Acta, 652(1-2), pp.128~142 (2009)
- S Wiesner, "Chemical development of latent fingerprints:IND has come of age", J For Sci, 46(5), pp.1082~1084 (2001)
- DB Hansen, "The development of novel ninhydrin analogues", Chem Soc Rev, 34, pp.408~417 (2005)
- J Almog, "Dual fingerprint reagents with enhanced sensitivity : 5-methoxy-and 5-methylthionin hydrin", J For Sci, 53(2), pp.364~368 (2008)
- O Petrovskaia, "Investigations of the reaction mechanisms of 1,2-indanediones with amino acids", J Org Chem, 66(23), pp.7666~7675 (2001)
- SJ Gardner, "Optimization and initial evaluation of 1,2-indandione as a reagent for fingerprint detection", J For Sci, 48(6), pp.1288~1292 (2003)
- MM Joullié, "Ninhydrin and ninhydrin analogs. Syntheses and applications", Teterahedron, 47(42), pp.8791~8830 (1991)
- M Friedman, "Stoichiometry of formation of Ruhemann's purple in the ninhydrin reaction", Bioorg Chem, 3(3), pp.267~280 (1974)
- C Roux, "Evaluation of 1,2-indanedione and 5,6-dimethoxy-1,2-indanedione for the detection of latent fingerprints on porous surfaces", J Forensic Sci, 45, pp.761~769 (2000)
- M Stoilovic, "Evaluation of a 1, 2-indanedione formulation containing Zinc chloride for improved fingermark detection on paper", J Forensic Identification, 57(1), pp.4~18 (2007)
- 서장원, "다양한 환경조건에 노출된 혈흔의 탐색과 유전자의 감식에 관한 평가", 과학수사학회지, 11(3), pp.194~200 (2017), 한국과학수사학회[DOI]
- DF Shriver, "Inorganic Chemistry", pp.227~236 (2001), Oxford University Press
- NK Rao, "Studies on the synthesis, characterisation and antimicrobial activity of new Co(II), Ni(II) and Zn(II) complexes of Schiff base derived from ninhydrin and glycine", Biol Metals, 3, pp.19~23 (1990)
- JH kim, "Dimethyl phosphate hydrolysis at neutral pH", J Am Chem Soc, 114(25), pp.9792~9795 (1992)
- P Imhof, "Density functional theory analysis of dimethylphosphate hydrolysis : effect of solvation and nucleophile variation", J Molecular Structure: THEOCHEM, 713(1-3), pp.1~5 (2005)
- MB Smith, "March’s Advanced Organic Chemistry;Reactions, Mechanisms and Structure", pp.229~230 (2013), John Wiely & Sons Inc
- N Williams, "Structure and nuclease activity of simple dinuclear metal complexes: Quantitative dissection of the role of metal ions", Acc Chem Res, 32, pp.485~493 (1999)
- A Sreedhara, "Catalytic hydrolysis of DNA by metal ions and complexes", J Biol Inorg Chem, 6(4), pp.337~347 (2001)