Characterization of 6-bromoferulic acid as a novel common-use matrix for matrix-assisted laser desorption/ionization time-of-flight mass spectrometry.
Journal
Rapid communications in mass spectrometry : RCM
ISSN: 1097-0231
Titre abrégé: Rapid Commun Mass Spectrom
Pays: England
ID NLM: 8802365
Informations de publication
Date de publication:
15 Apr 2020
15 Apr 2020
Historique:
received:
16
07
2019
revised:
08
10
2019
accepted:
13
10
2019
pubmed:
30
10
2019
medline:
2
12
2020
entrez:
30
10
2019
Statut:
ppublish
Résumé
Ferulic acid (FA) is a standard matrix used for analyzing proteins. In this study, the ability of a halogenated FA to serve as an effective MALDI matrix was investigated. Various halogenated FAs were synthesized, and the characteristics and performance of each were compared with those of the standard matrices α-cyano-4-hydroxycinnamic acid (CHCA) and 2,5-dihydrobenzoic acid (DHBA). The abilities of 6-bromoferulic acid (6-BFA), ferulic acid (FA), and eight other halogenated FA derivatives to ionize eight synthetic peptides were examined. Absorption measurements, MM2 structure optimizations, and proton affinity (PA) calculations were also performed for 6-BFA and FA. The suitabilities of these compounds as matrices for matrix-assisted laser desorption/ionization (MALDI) for lipids, sugar chains, polymers, cyanocobalamin, synthetic peptides, and tryptic peptides originating from two types of serum proteins were also tested. The 6-position of FA was found to be the best site for introducing a bromine because the generated compound allowed facile detection of cyanocobalamin and several peptides. 6-BFA exhibited good sensitivity for large peptides (3-5 kDa) and peptides containing acidic amino acids or proline. 6-BFA was also shown to be a suitable matrix for tandem mass spectrometry (MS/MS) analysis when using MALDI time-of-flight (TOF) mass spectrometry (MS) with a quadrupole ion trap (QIT) system. The properties of 6-BFA as a MALDI matrix differed from those of DHBA and CHCA. 6-BFA appears to be a useful matrix for de novo sequencing using MALDI-QIT-TOF-MS.
Substances chimiques
Blood Proteins
0
Coumaric Acids
0
Lipids
0
Peptides
0
ferulic acid
AVM951ZWST
Vitamin B 12
P6YC3EG204
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e8636Informations de copyright
© 2019 John Wiley & Sons, Ltd.
Références
Beavis RC, Chait BT, Fales HM. Cinnamic acid derivatives as matrices for ultraviolet laser desorption mass spectrometry of proteins. Rapid Commun Mass Spectrom. 1989;3(12):432-435.
Saenz JA, Petersen CE, Valentine NB, et al. Reproducibility of matrix-assisted laser desorption/ionization time-of-flight mass spectrometry for replicate bacterial culture analysis. Rapid Commun Mass Spectrom. 1999;13(15):1580-1585.
Meetani MA, Voorhees KJ. MALDI mass spectrometry analysis of high molecular weight proteins from whole bacterial cells: Pretreatment of samples with surfactants. J Am Soc Mass Spectrom. 2005;16(9):1422-1426.
Beavis RC, Chaudhary T, Chait BT. α-Cyano-4-hydroxycinnamic acid as a matrix for matrix-assisted laser desorption mass spectrometry. Organic Mass Spectrom. 1992;27(2):156-158.
Gobom J, Schuerenberg M, Mueller M, Theiss D, Lehrach H, Nordhoff E. Alpha-cyano-4-hydroxycinnamic acid affinity sample preparation. A protocol for MALDI-MS peptide analysis in proteomics. Anal Chem. 2001;73(3):434-438.
Leszyk JD. Evaluation of the new MALDI matrix 4-chloro-α-cyanocinnamic acid. J Biomol Tech. 2010;21(2):81-91.
Jaskolla WT, Lehmann W-D, Karas M. 4-Chloro-α-cyanocinnamic acid is an advanced, rationally designed MALDI matrix. Proc Natl Acad Sci U S A. 2008;105(34):12200-12205.
Allais F, Martinet S, Ducrot P-H. Straightforward total synthesis of 2-O-feruloyl-L-malate, 2-O-sinapoyl-L-malate and 2-O-5-hydroxyferuloyl-L-malate. Synthesis. 2009;21:3571-3578.
Pakhare D, Kusurkar R. Application of Horner-Wadsworth-Emmons olefination for the synthesis of granulatamide a, its E isomer and other amides of tryptamine. New J Chem. 2016;40(6):5428-5431.
Prunet J. Recent methods for the synthesis of (E)-alkene units in macrocyclic natural products. Angew Chem Int Ed. 2003;42(25):2826-2830.
Jafari AA, Ghadami M. Efficient synthesis of α,β-unsaturated ketones with trans-selective Horner-Wadsworth-Emmons reaction in water. Environ Chem Lett. 2016;14(2):223-228.
Webster VS. Preparation and oxidation of substituted cinnamic acid. Am J Pharm Sci Support Public Health. 1940;112:291-296.
Valento P, Fernandes E, Carvalho F, Andrade PB, Seabra RM, Bastos ML. Antioxidant activity of centaurium erythraea infusion evidenced by its superoxide radical scavenging and xanthine oxidase inhibitory activity. J Agric Food Chem. 2001;49(7):3476-3479.
Zhang X, Lin D, Jiang R, Li H, Wan J, Li H. Ferulic acid exerts antitumor activity and inhibits metastasis in breast cancer cells by regulating epithelial to mesenchymal transition. Oncol Rep. 2016;36(1):271-278.
Ren Z, Zhang R, Li Y, Li Y, Yang Z, Yang H. Ferulic acid exerts neuroprotective effects against cerebral ischemia/reperfusion-induced injury via antioxidant and anti-apoptotic mechanisms in vitro and in vivo. Int J Mol Med. 2017;40(5):1444-1456.
Choi JH, Park JK, Kim KM, Lee HJ, Kim S. In vitro and in vivo antithrombotic and cytotoxicity effects of ferulic acid. J Biochem Mol Toxicol. 2018;32(1):e22004.
Allwood DA, Dreyfus RW, Perera IK, Dyer PE. UV optical absorption of matrices used for matrix-assisted laser desorption/ionization. Rapid Commun Mass Spectrom. 1996;10(13):1575-1578.
Nagarajan V, Kamitori S, Okuyama K. Crystal structure analysis of collagen model peptide (pro-pro-Gly)10. J Biochem. 1998;124(6):1117-1123.
Valero ML, Giralt E, Andreu D. An investigation of residue-specific contributions to peptide desorption in MALDI-TOF mass spectrometry. Lett Peptide Sci. 1999;6(2-3):109-115.
Krause E, Wenschuh H, Jungblut PR. The dominance of arginine-containing peptides in MALDI-derived tryptic mass fingerprints of proteins. Anal Chem. 1999;71(19):4160-4165.
Baumgart S, Lindner Y, Kuehne R, Oberemn A, Wenschuh H, Krause E. The contributions of specific amino acid side chains to signal intensities of peptides in matrix-assisted laser desorption/ionization mass spectrometry. Rapid Commun Mass Spectrom. 2004;18(8):863-868.
Nishikaze T, Takayama M. Cooperative effect of factors governing molecular ion yields in desorption/ionization mass spectrometry. Rapid Commun Mass Spectrom. 2006;20(3):376-382.
Ventura G, Arnesano F, Calvano CD, Palmisano F, Cataldi TRI. Cyanocobalamin conjugates of cisplatin and diaminocyclohexane-platinum (II): Matrix-assisted laser desorption ionization mass spectrometry characterization using 4-chloro-a-cyanocinnamic acid as the matrix. RSC Adv. 2017;7(85):53658-53666.
Calvano DC, Ventura G, Palmisanoa F, Cataldia RIT. 4-Chloro-α-cyanocinnamic acid is an efficient soft matrix for cyanocobalamin detection in foodstuffs by matrix-assisted laser desorption/ionization mass spectrometry (MALDI MS). J Mass Spectrom. 2016;51(9):841-848.
Sleno L, Volmer AD. Some fundamental and technical aspects of the quantitative analysis of pharmaceutical drugs by matrix-assisted laser desorption/ionization mass spectrometry. Rapid Commun Mass Spectrom. 2005;19(14):1928-1936.
Snovida IS, Rak-Banville MJ, Perreault H. On the use of DHB/aniline and DHB/N,N-dimethylaniline matrices for improved detection of carbohydrates: Automated identification of oligosaccharides and quantitative analysis of sialylated glycans by MALDI-TOF mass spectrometry. J Am Soc Mass Spectrom. 2008;19(8):1138-1146.
Mirza PS, Raju NP, Vairamani M. Estimation of the proton affinity values of fifteen matrix-assisted laser desorption/ionization matrices under electrospray ionization conditions using the kinetic method. J Am Soc Mass Spectrom. 2004;15(3):431-435.
Tsai MT, Lee S, Lu IC, et al. Ion-to-neutral ratio of 2,5-dihydroxybenzoic acid in matrix-assisted laser desorption/ionization. Rapid Commun Mass Spectrom. 2013;27(9):955-963.
Lu IC, Chu KY, Lin CY, et al. Ion-to-neutral ratios and thermal proton transfer in matrix-assisted laser desorption/ionization. J Am Soc Mass Spectrom. 2015;26(7):1242-1251.
Lu IC, Lee C, Lee Y-T, Ni C-K. Ionization mechanism of matrix-assisted laser desorption/ionization. Annu Rev Anal Chem. 2015;8:21-39.
Duncan MW, Roder H, Hunsucker SW. Quantitative matrix-assisted laser desorption/ionization mass spectrometry. Brief Funct Genomic Proteomic. 2008;7(5):355-370.
Karas M, Bahr U, Strupat K, Hillenkamp F, Tsarbopoulos A, Pramanik NB. Matrix dependence of metastable fragmentation of glycoproteins in MALDI TOF mass spectrometry. Anal Chem. 1995;67(3):675-679.