Matrix-assisted laser desorption/ionization mass spectrometry imaging of tissues via the formation of reproducible matrix crystals by fluorescence-assisted spraying method: a quantification approach

(1) Welling, P. Influence of Food and Diet on Gastrointestinal Drug

Absorption: A Review. J. Pharmacokinet. Biopharm. 1977, 5, 291–334.

(2) Ávila-Gálvez, M.; García-Villalba, R.; Martínez-Díaz, F.; OcañaCastillo, B.; Monedero-Saiz, T.; Torrecillas-Sánchez, A.; Abellán, B.;

González-Sarrías, A.; Espín. J. Metabolic Profiling of Dietary Polyphenols and Methylxanthines in Normal and Malignant Mammary Tissues

from Breast Cancer Patients. Mol. Nutr. Food Res. 2019, 63, 1801239.

(3) Hahm, T. H.; Tanaka, M.; Nguyen, H. N.; Tsutsumi, A.; Aizawa,

K.; Matsui, T. Matrix-Assisted Laser Desorption/Ionization Mass

Spectrometry-Guided Visualization Analysis of Intestinal Absorption

of Acylated Anthocyanins in Sprague-Dawley Rats. Food Chem. 2021,

334, 127586.

(4) Tanaka, M; Dohgu, X.; Komabayashi, G.; Kiyohara, H.; Takata, F.;

Kataoka, Y.; Nirasawa, T.; Maebuchi, M.; Matsui T. Brain-Transportable Dipeptides across the Blood-Brain Barrier in Mice. Sci. Rep. 2019,

9, 5769.

(5) Nguyen, H. N.; Tanaka, M.; Li, B.; Ueno, T.; Matsuda, H.; Matsui,

T. Novel in situ Visualisation of Rat Intestinal Absorption of Polyphenols via Matrix-Assisted Laser Desorption/Ionisation Mass Spectrometry Imaging. Sci. Rep. 2019, 9, 3166.

(6) Chumbley, C. W.; Reyzer, M. L.; Allen, J. L.; Marriner, G. A.; Via,

L. E.; Barry, C. E.; Caprioli, R. M. Absolute Quantitative MALDI Imaging Mass Spectrometry: A Case of Rifampicin in Liver Tissues. Anal.

Chem. 2016, 88, 2392–2398.

(7) Tang, W.; Chen, J.; Zhou, J.; Ge, J.; Zhang, Y.; Li, P.; Li. B. Quantitative MALDI Imaging of Spatial Distributions and Dynamic

Changes of Tetrandrine in Multiple Organs of Rats. Theranostics, 2019,

9, 932–944.

(8) Shiono, K.; Hashizaki, R.; Nakanishi, T.; Sakai, T.; Yamamoto, T.;

Ogata, K.; Harada, K.; Ohtani, H.; Katano, H.; Taira, S. Multi-Imaging

of Cytokinin and Abscisic Acid on the Roots of Rice (Oryza sativa)

Using Matrix-Assisted Laser Desorption/Ionization Mass Spectrometry. J. Agric. Food Chem. 2017, 65, 7624−7628.

(9) Yao, J.; Scott, J. R.; Young, M. K.; Wilkins, C. L. Importance of

Matrix: Analyte Ratio for Buffer Tolerance using 2,5-Dihydroxybenzoic Acid as A Matrix in Matrix-Assisted Laser Desorption/IonizationFourier Transform Mass Spectrometry and Matrix-Assisted Laser Desorption/Ionization-Time of Flight. J. Am. Soc. Mass Spectrom. 1998,

9, 805–813.

(10) Unsihuay, D.; Sanchez, D. M.; Laskin, J. Quantitative Mass Spectrometry Imaging of Biological Systems. Annu. Rev. Phys. Chem. 2021,

72, 307-329.

(11) Hanton, S.D.; Clark, P. A. C.; Owens, K. G.; Investigations of Matrix-Assisted Laser Desorption/Ionization Sample Preparation by

Time-of-Flight Secondary Ion Mass Spectrometry. J. Am. Soc. Mass

Spectrom. 1999, 10,. 104-111.

(12) Albrethsen, J. Reproducibility in Protein Profiling by MALDITOF Mass Spectrometry.Clin. Chem. 2007, 53, 852–858.

(13) Hamm, G.; Bonnel, D.; Legouffe, R.; Pamelard, F.; Delbos, J. M.;

Bouzom, F.; Stauber, J. Quantitative Mass Spectrometry Imaging of

Propranolol and Olanzapine Using Tissue Extinction Calculation as

Normalization Factor. J. Proteomics 2012, 75, 4952–4961.

(14) Lemaire, R.; Tabet, J. C.; Ducoroy, P.; Hendra, J. B.; Salzet, M.;

Fournier, I. Solid Ionic Matrixes for Direct Tissue Analysis and

MALDI Imaging. Anal. Chem. 2006, 78, 809–819.

(15) Taga, Y.; Iwasaki, Y.; Shigemura, Y.; Mizuno, K. Improved in

vivo Tracking of Orally Administered Collagen Hydrolysate Using Stable Isotope Labeling and LC–MS Techniques. J. Agric. Food Chem.

2019, 67, 4671–4678.

(16) Norris, J. L.; Caprioli, R. M. Absolute Quantification of Rifampicin by MALDI Imaging Mass Spectrometry Using Multiple

TOF/TOF Events in a Single Laser Shot. Chem. Rev. 2013, 113, 2309–

2342.

(17) Pirman, D. A.; Reich, R. F.; Kiss, A.; Heeren, R. M. A.; Yost, R.

A. Quantitative MALDI Tandem Mass Spectrometric Imaging of Cocaine from Brain Tissue with a Deuterated Internal Standard. Anal.

Chem. 2013, 85, 1081–1089.

(18) Sammour, D. A.; Marsching, C.; Geisel, A.; Erich, K.; Schulz, S.;

Guevara, C. R.; Rabe, J. H.; Marx, A.; Findeisen, P.; Hohenberger, P.;

Hopf, C. Quantitative Mass Spectrometry Imaging Reveals Mutation

Status-independent Lack of Imatinib in Liver Metastases of Gastrointestinal Stromal Tumors. Sci. Rep. 2019, 9, 10698.

(19) Barry, J. A.; Ait-Belkacem, R.; Hardesty, W. M.; Benakli, L.; Andonian, C.; Licea-Perez, H.; Stauber, J.; Castellino, S. Multicenter Validation Study of Quantitative Imaging Mass Spectrometry. Anal. Chem.

2019, 91, 6266–6274.

(20) Koeniger, S. L.; Talaty, N.; Luo, Y.; Ready, D.; Voorbach, M.;

Seifert, T.; Cepa, S.; Fagerland, J. A.; Bouska, J.; Buck, W.; Johnson,

R. W.; Spanton, S. A Quantitation Method for Mass Spectrometry Imaging. Rapid Commun. Mass Spectrom. 2011, 25, 503–510

(21) Prentice, B. M.; Chumbley, C. W.; Caprioli, R. M. Absolute Quantification of Rifampicin by MALDI Imaging Mass Spectrometry Using

Multiple TOF/TOF Events in a Single Laser Shot. J. Am. Soc.

Mass. Spectrom. 2017, 28, 136–144.

(22) Benabdellah, F; Touboul, D; Brunelle, A; Laprevote, O. In Situ

Primary Metabolites Localization on a Rat Brain Section by Chemical

Mass Spectrometry Imaging. Anal. Chem. 2009, 81, 5557–5560.

(23) Porta, T.; Lesur, A.; Varesio, E.; Hopfgartner, G. Quantification

in MALDI-MS Imaging: What Can We Learn from MALDI-Selected

Reaction Monitoring and What Can We Expect for Imaging? Anal. Bioanal. Chem. 2015, 407, 2177–2187.

(24) Gemperline, E.; Rawson, S.; Li, L. Optimization and Comparison

of Multiple MALDI Matrix Application Methods for Small Molecule

Mass Spectrometric Imaging. Anal. Chem. 2014, 86, 10030–10035.

(25) Xie, H.; Wu, R.; Hung, Y. L. W.; Chen, X.; Chan, T. W. D. Development of a Matrix Sublimation Device with Controllable Crystallization Temperature for MALDI Mass Spectrometry Imaging. Anal.

Chem. 2021, 93, 6342–6347.

(26) Hong, S.; Tanaka, M.; Yoshii, S.; Mine, Y.; Matsui, T. Enhanced

Visualization of Small Peptides Absorbed in Rat Small Intestine by

Phytic-Acid-Aided Matrix-Assisted Laser Desorption/Ionization-Imaging Mass Spectrometry. Anal. Chem. 2013, 85, 10033–10039.

(27) Terahara, N.; Matsui, T.; Fukui, K. Matsugano, K.; Sugita, K.

Matsumoto K. Caffeoylsophorose in a Red Vinegar Produced through

Fermentation with Purple Sweetpotato. J. Agric. Food Chem. 2003, 9,

2539–2543

(28) Zhang, J. L.; Zhang, G. D.; Zhou, T. H. Metabolism of Ferulic

Acid in Rats. J. Asian Nat. Prod. Res. 2005, 7, 49–58.

(29) Zhao, Z.; Moghadasian M. H. Chemistry, Natural Sources, Dietary

Intake and Pharmacokinetic Properties of Ferulic Acid: A Review Food.

Chem., 2008, 109, 691–702.

(30) Iwao, T.; Inoue, K.; Hayashi, Y.; Yuasa, H.; Watanabe, J. Metabolic Extraction of Nifedipine during Absorption from the Rat Small

Intestine. Drug Metab. Pharmacokin. 2002, 17, 546–553.

(31) Momma, K.; Takao, A. Fetal Cardiovascular Effects of Nifedipine

in Rats. Pediatr. Res. 1989, 26, 442–447.

(32) Rashid, J.; Mckinstry, C.; Renwick, A. G.; Dirnhuber, M.; Waller,

D. G.; George, C. F. Quercetin, an in vitro Inhibitor of CYP3A, Does

Not Contribute to the Interaction between Nifedipine and Grapefruit

Juice. Br. J. clin. Pharmac. 1993; 36: 460–463.

(33) Cornett, D. S.; Duncan, M. A.; Amster, I. Liquid Mixtures for Matrix-Assisted Laser Desorption. Anal. Chem. 1993, 65, 2608–2613.

(34) Sun, Z.; Findsen, E. W.; Isailovic, D. Atmospheric Pressure Visible-Wavelength MALDI-MS, Int. J. Mass Spectrom. 2012, 315, 66–73.

(35) Gary, R, P.; Michael, C. F.; Lloyd, M. S. Matrix- Assisted Laser

Desorption/Ionization Mass Spectrometry of Synthetic Ooligodeoxyribonucleotides. Rapid Commun. Mass Spectrom. 1992, 6, 369.

(36) Van de Plas, R.; Yang, J.; Spraggins, J.; Caprioli, R. M. Image

Fusion of Mass Spectrometry and Microscopy: A Multimodality Paradigm for Molecular Tissue Mapping. Nat. Methods 2015, 12, 366–372.

(37) Spraggins, J. M.; Djambazova, K. V.; Rivera, E. S.; Migas, L. G.;

Neumann, E. K.; Fuetterer, A.; Suetering, J.; Goedecke, N.; Ly, A.; Van

de Plas, R.; Caprioli, R. M. High-Performance Molecular Imaging with

MALDI Trapped Ion-Mobility Time-of-Flight (timsTOF) Mass Spectrometry. Anal. Chem. 2019, 91, 14552–14560.

(38) Wang, X.; Han, J.; Hardie, D. B.; Yang, J.; Pan. J.; Borchers, C.

H. Metabolomic Profiling of Prostate Cancer by Matrix Assisted Laser

Desorption/Ionization-Fourier Transform Ion Cyclotron Resonance

Mass Spectrometry Imaging using Matrix Coating Assisted by an Electric Field (MCAEF). Biochim. Biophys. Acta. 2017, 7, 755–767.

(39) Schiller, J. Süss, R.; Fuchs, B.; Müller, M.; Petković, M. Zschörnig,

O.; Waschipky, H. The Suitability of Different DHB Isomers as Matrices for the MALDI-TOF MS Analysis of Phospholipids: Which Isomer

for What Purpose?. Eur. Biophys. J. 2007, 36, 517–527

(40) Dueñas, M. E.; Carlucci, L.; Lee, Y. J. Matrix Recrystallization

for MALDI-MS Imaging of Maize Lipids at High-Spatial Resolution.

J. Am. Soc. Mass Spectrom. 2016, 27, 1575–1578.

(41) Hankin, J. A.; Barkley, R. M.; Murphy, R. C. Sublimation as a

Method of Matrix Application for Mass Spectrometric Imaging. J. Am.

Soc. Mass Spectrom. 2007, 18, 1646–1652.

(42) Zaleski, J.; Daszkiewicz, Z.; Kyziol, J. B. Structure of N,4-Dinitroaniline and Its Complex with Sulfolane at 85 K; on the Proton Donor-Acceptor Affinity of the Primary Nitramine (HNNO2) Group. Acta

Cryst. 2002, B58, 109–115.

(43) Bu, R.; Xiong, Y.; Wei, X.; Li, H.; Zhang, C. Hydrogen Bonding

in CHON-Containing Energetic Crystals: A Review. Cryst. Growth

Des. 2019, 19, 5981–5997.

(44) Quinn, J. R.; Zimmerman, S. C.; Del Bene, J. E.; Shavitt, I. Does

the A·T or G·C Base-Pair Possess Enhanced Stability? Quantifying the

Effects of CH···O Interactions and Secondary Interactions on BasePair Stability Using a Phenomenological Analysis and ab Initio Calculations. J. Am. Chem. Soc. 2007, 129, 934–941.

(45) Deegan, R. D.; Bakajin, O.; Dupont, T. F.; Huber, G.; Nagel, S. R.;

Witten, T. A. Capillary Flow as The Cause of Ring Stains from Dried

Liquid Drops. Nature, 1997, 389, 827.

(46) Medina, N.; Huth-Fehre, T.; Westman, A. Matrix-Assisted Laser

Desorption: Dependence of The Threshold Fluence on Analyte Concentration. J. Mass Spectrom. 1994, 29, 207–209.

(47) Dreisewerd, K.; Schürenberg, M.; Karas, M.; Hillenkamp, F. Influence of The Laser Intensity and Spot Size on The Desorption of Molecules and Ions in Matrix-Assisted Laser Desorption/Ionization with A

Uniform Beam Profile. Int. J. Mass Spectrom. Ion Processes 1995, 141,

127−148.

(48) Aichler, M.; Walch, A. MALDI Imaging Mass Spectrometry: Current Frontiers and Perspectives in Pathology Research and Practice.

Lab. Investig. 2015, 95, 422–431.

(49) Gessel, M. M.; Norris, J. L.; Caprioli, R. M. MALDI Imaging

Mass Spectrometry: Spatial Molecular Analysis to Enable a New Age

of Discovery. J. Proteom. 2014, 107, 71–82.

(50) Caprioli, R. M. Imaging Mass Spectrometry: Enabling a New Age

of Discovery in Biology and Medicine Through Molecular Microscop.

J. Am. Soc. Mass Spectrom. 2015, 26, 850–852.

(51) Rzagalinski I, Kovačević B., Hainz N., Meier C., Tschernig T.,

Volmer DA. Toward Higher Sensitivity in Quantitative MALDI Imaging Mass Spectrometry of CNS Drugs using A Nonpolar Matrix. Anal.

Chem. 2018, 90, 12592−12600.

(52) Rzagalinski, I.; Hainz, N.; Meier, C.; Tschernig, T.; Volmer, D. A.

MALDI Mass Spectral Imaging of Bile Acids Observed as Deprotonated Molecules and Proton-Bound Dimers from Mouse Liver Sections.

J. Am. Soc. Mass Spectrom. 2018, 29, 711−722.

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