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 AJAC  Vol.3 No.12 , December 2012
Acylhydrazide and Isatin Schiff Bases as Alternate UV-Laser Desorption Ionization (LDI) Matrices for Low Molecular Weight (LMW) Peptides Analysis
Abstract: Matrix-assisted laser desorption/ionization (MALDI) is a preferred and widely used mass spectrometric technique for the analysis of macromolecules. Limited UV-LDI matrices are available for the analysis of biomolecules due to the restricted structural features to serve in the laser desorption/ionization mechanism with a problem of background signals appearing in the low mass region. This paper describes the application of Schiff base derivatives of acylhydrazide and isatin as alternate UV-LDI matrices for the analysis of peptides with significantly low background signals. Thirty one compounds have been successfully employed as matrices for the analysis of low molecular weight (LMW) peptides (<2000 Da) including bradykinin and renin substrate tetra-decapeptide. Bovine serum albumin (BSA)-digest was also analyzed and identified through database search against Swiss-Prot by using MASCOT. The MS measurements were recorded by using dried droplet sample preparation procedures by mixing the matrix solution with analyte at a volume ratio of 1:2. Finally, LMW organic compounds (<500 Da) were also analyzed by the synthesized matrix materials which showed better S/N ratios and minimal background signals for low mass range in comparison to the comparable results with α-Cyano-4-hydroxycinnamic acid (HCCA), a preferred choice for peptide analysis.
Cite this paper: S. Musharraf, A. Bibi, N. Shahid, M. Najam-ul-Haq, M. Khan, M. Taha, U. Mughal and K. Khan, "Acylhydrazide and Isatin Schiff Bases as Alternate UV-Laser Desorption Ionization (LDI) Matrices for Low Molecular Weight (LMW) Peptides Analysis," American Journal of Analytical Chemistry, Vol. 3 No. 12, 2012, pp. 779-789. doi: 10.4236/ajac.2012.312104.
References

[1]   J. Gross and K. Strupat, “Matrix-Assisted Laser Desorption/Ionization Mass Spectrometry Applied to Biological Macromolecules,” Trends in Analytical Chemistry, Vol. 17, No. 8-9, 1998, pp. 470-484. doi:10.1016/S0165-9936(98)00060-0

[2]   D. J. Rousell, S. M. Dutta, M. W. Little and K. K. Murray, “Matrix-Free Infrared Soft Laser Desorption/Ionization,” Journal of Mass Spectrometry, Vol. 39, No. 10, 2004, pp. 1182-1189. doi:10.1002/jms.706

[3]   A. Holle, A. Haase, M. Kayser and J. Hohndorf, “Optimizing UV Laser Focus Profiles for Improved MALDI Performance,” Journal of Mass Spectrometry, Vol. 41, No. 6, 2006, pp. 705-716.

[4]   J. Krause, M. Stoeckli and U. P. Schlunegger, “Studies on the Selection of New Matrices for Ultraviolet Matrix-Assisted Laser Desorption Ionization Time-of-Flight Mass Spectrometry,” Rapid Communication in Mass Spectrometry, Vol. 10, No. 15, 1996, pp. 1927-1933. doi:10.1002/(SICI)1097-0231(199612)10:15<1927::AID-RCM709>3.0.CO;2-V

[5]   P. Juhasz, P. Costello and K. Biemann, “Matrix-Assisted Laser Desorption Ionization Mass Spectrometry with 2- (4-Hydroxyphenylazo) Benzoic Acid Matrix,” Journal of the American Society for Mass Spectrometry, Vol. 4, No. 5, 1993, pp. 399-409. doi:10.1016/1044-0305(93)85005-I

[6]   K. J. Wu, A. Steding and C. H. Becker, “Matrix-Assisted Laser Desorption Time-of-Flight Mass Spectrometry of Oligonucleotides Using 3-Hydroxypicolinic Acid as an Ultraviolet-Sensitive Matrix,” Rapid Communication in Mass Spectrometry, Vol. 7, No. 2, 1993, pp. 142-146. doi:10.1002/rcm.1290070206

[7]   J. O. Metzger, R. Woisch, W. Tuszynski and R. Angermann, “New Type of Matrix for Matrix-Assisted Laser Desorption Mass Spectrometry of Polysaccharides and Proteins,” Fresenius Journal of Analytical Chemistry, Vol. 349, No. 6, 1994, pp. 473-474. doi:10.1007/BF00322937

[8]   U. Pieles, W Zürcher, M Sch?r and H. Moser, “Matrix-Assisted Laser Desorption Ionization Time-of-Flight Mass Spectrometry: A Powerful Tool for the Mass and Sequence Analysis of Natural and Modified Oligonucleotides,” Nucleic Acids Research, Vol. 21, No. 14, pp. 3191-3196.

[9]   Y. Dai, R. M. Whittal, C. A. Bridges, Y. Isogai, O. Hindsgaul and L. Li, “Matrix-Assisted Laser Desorption Ionization Mass Spectrometry for the Analysis of Monosulfated Oligosaccharides,” Carbohydrate Research, Vol. 304, No. 1, 1997, pp. 1-9. doi:10.1016/S0008-6215(97)00195-X

[10]   M. C. Fitzgerald, G. R. Parr and L. M. Smith, “Basic Matrices for the Matrix-Assisted Laser Desorption/Ionization Mass Spectrometry of Proteins and Oligonucleotides,” Analytical Chemistry, Vol. 65, No. 22, 1993, pp. 3204-3211. doi:10.1021/ac00070a007

[11]   Y. Fukuyama, R. Tanimura, K. Maeda, M. Watanabe, S. Kawabata, S. Iwamoto, S. Izumi and K. Tanaka, “Alkylated Dihydroxybenzoic Acid as a MALDI Matrix Additive for Hydrophobic Peptide Analysis,” Analytical Chemistry, Vol. 84, No. 9, 2012, pp. 4237-4243. doi:10.1021/ac300540r

[12]   S. Martic, J. D. Brennan, M. A. Brook, S. Ackloo and N. Nagy, “Towards the Development of a Covalently Tethered MALDI System—A Study of Allyl-Modified MALDI Matrixes,” Canadian Journal of Chemistry, Vol. 85, No. 1, 2007, pp. 66-76. doi:10.1139/v06-185

[13]   Z. Guo, Q. Zhang , H. Zou, B. Guo and J. Ni, “A Method for the Analysis of Low-Mass Molecules by MALDITOF Mass Spectrometry,” Analytical Chemistry, Vol. 74, No. 7, 2002, pp. 1637-1641. doi:10.1021/ac010979m

[14]   G. McCombie and R. Knochenmuss, “Small-Molecule MALDI using the Matrix Suppression Effect to Reduce or Eliminate Matrix Background Interferences,” Analytical Chemistry, Vol. 76, No. 17, 2004, pp. 4990-4997. doi:10.1021/ac049581r

[15]   F. O. Ayorinde, P. Hambright, T. N. Porter and Q. L. Keith, “Use of Meso-Tetrakis (Pentafluorophenyl) Porphyrin as a Matrix for Low Molecular Weight Alkyl Phenol Ethoxylates in Laser Desorption/Ionization Time-of-Flight Mass Spectrometry,” Rapid Communication in Mass Spectrometry, Vol. 13, No. 24, 1999, pp. 2474-2479. doi:10.1002/(SICI)1097-0231(19991230)13:24<2474::AID-RCM814>3.0.CO;2-0

[16]   A. Tholey and E. Heinzle, “Ionic (Liquid) Matrices for Matrix-Assisted Laser Desorption/Ionization Mass Spectrometry—Applications and Perspectives,” Analytical and Bioanalytical Chemistry, Vol. 386, No. 1, 2006, pp. 24-37. doi:10.1007/s00216-006-0600-5

[17]   D. W. Armstrong, L. Zhang, L. He and M. L. Gross, “Ionic Liquids as Matrixes for Matrix-Assisted Laser Desorption/Ionization Mass Spectrometry,” Analytical Chemistry, Vol. 73, No. 15, 2001, pp. 3679-3686. doi:10.1021/ac010259f

[18]   M. Najam-ul-Haq, M. Rainer, C. W. Huck, P. Hausberger, H. Kraushaar and G. K. Bonn, “Nanostructured Diamond-Like Carbon on Digital Versatile Disc as a Matrix-Free Target for Laser Desorption/Ionization Mass Spectrometry,” Analytical Chemistry, Vol. 80, No. 19, 2008, pp. 7467-7472.

[19]   J. Wei, J. M. Buriak and G. Siuzdak, “Desorption-Ionizationmass Spectrometry on Porous Silicon,” Letters to Nature, Vol. 399, No. 77, 1999, pp. 243-246. doi:10.1038/20400

[20]   S. Zhang, Y. Chen, J. A. Liu, S. X. Xiong, G. H. Wang, J. Chen and G. Q. Yang, “New Matrix of MALDI-TOF MS for Analysis of Small Molecules,” Chinese Chemical Letters, Vol. 20, No. 12, 2009, pp. 1495-1497. doi:10.1016/j.cclet.2009.06.031

[21]   T. Kinumi, T. Saisu, M. Takayama and H. Niwa, “Matrix-Assisted Laser Desorption/Ionization Time-of-Flight Mass Spectrometry Using an Inorganic Particle Matrix for Small Molecule Analysis,” Journal of Mass Spectrometry, Vol. 35, No. 3, 2000, pp. 417-422. doi:10.1002/(SICI)1096-9888(200003)35:3<417::AID-JMS952>3.0.CO;2-#

[22]   S. Ren, L. Zhang, Z. Cheng and Y. Guo, “Immobilized Carbon Nanotubes as Matrix for MALDI-TOF-MS Analysis: Applications to Neutral Small Carbohydrates,” Journal of the American Society for Mass Spectrometry, Vol. 16, No. 3, 2005, pp. 333-339. doi:10.1016/j.jasms.2004.11.017

[23]   X. Dong, J. Cheng, J. Li and Y. Wang, “Graphene as a Novel Matrix for the Analysis of Small Molecules by MALDI-TOF MS,” Analytical Chemistry, Vol. 82, No. 14, 2010, pp. 6208-6214. doi:10.1021/ac101022m

[24]   H. Kim, J. Lee, S. Park, H. W. Ro, D. Y. Yoo and D. Y. Yoon, “Observation of Low Molecular Weight Poly (Methylsilsesquioxane)s by Graphite Plate Laser Desorption/ Ionization Time-of-Flight Mass Spectrometry,” Analytical Chemistry, Vol. 72, No. 22, 2000, pp. 5673-5678. doi:10.1021/ac0003899

[25]   M. J. Dale, R. Knochenmuss and R. Zenobi, “Graphite/ Liquid Mixed Matrices for Laser Desorption/Ionization Mass Spectrometry,” Analytical Chemistry, Vol. 68, No. 19, 1996, pp. 3321-3329. doi:10.1021/ac960558i

[26]   C. Black, C. Poile, J. Langley and J. Herniman , “The Use of Pencil Lead as a Matrix and Calibrant for Matrix-Assisted Laser Desorption/Ionization,” Rapid Communication in Mass Spectrometry, Vol. 20, No. 7, 2006, pp. 1053-1060. doi:10.1002/rcm.2408

[27]   G. J. Langley, J. M. Herniman and M. S. Townell, “2B Or Not 2B, That is the Question: Further Investigations into the Use of Pencil as a Matrix for Matrix-Assisted Laser Desorption/Ionization,” Rapid Communication in Mass Spectrometry, Vol. 21, No. 2, 2007, pp. 180-190. doi:10.1002/rcm.2827

[28]   K. M. Khan, M. Khan, M. Ali, M. Taha, S. Rasheed, S. Perveen and M. I. Choudhary, “Synthesis of Bis-Schiff Bases of Isatins and their Antiglycation Activity,” Bioorganic & Medicinal Chemistry, Vol. 7, No. 22, 2009, pp. 7795-7801. doi:10.1016/j.bmc.2009.09.028

[29]   K. M. Khan, U. R. Mughal, Samreen, S. Perveen and M. I. Choudhary, “Schiff Bases of Isatin: Potential Anti-Leishmanial Agents,” Letters in Drug Design & Discovery, Vol. 5, No. 4, 2008, pp. 243-249. doi:10.2174/157018008784619915

[30]   M. W. F. Neilen, “MALDI Time-of-Flight Mass Spectrometry of Synthetic Polymers.” Mass Spectrometry Reviews, Vol. 18, No. 5, 1999, pp. 309-344. doi:10.1002/(SICI)1098-2787(1999)18:5<309::AID-MAS2>3.0.CO;2-L

[31]   S. F. Macha, P. A. Limbach and P. J. Savickas, “Application of Nonpolar Matrices for the Analysis of Low Molecular Weight Nonpolar Synthetic Polymers by Matrix-Assisted Laser Desorption/Ionization Time-of-Flight Mass Spectrometry,” Journal of the American Society for Mass Spectrometry, Vol. 11, No. 8, 2000, pp. 731-773. doi:10.1016/S1044-0305(00)00137-9

 
 
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