Table 1.
Derivatization reagents used for OTCD in MSI applications
| Reagent | Structure | Sample | Target | Platform | Application | Reference |
|---|---|---|---|---|---|---|
| Aliphatic alcohols, phenols, and thiols | ||||||
| Betaine aldehyde |
|
Atherosclerotic plaque (human) | Cholesterol | Reactive DESI‐ MSI | Lipidomics | Manicke et al. (2009) |
| Brain (rat) | Cholesterol | Reactive DESI‐ MSI | Lipidomics | C. Wu et al. (2009) | ||
| Adrenal gland (pig) | Cholesterol | Reactive DESI‐ MSI | Lipidomics | Wu et al. (2010) | ||
| 1,1‐thiocarbonyldiimidazole (TCDI) |
|
Liver and kidney (mouse) | 3‐methoxysalicylamine(3‐MoSA) (hydroxyl group) | MALDI‐MSI | Pharmacology | Chacon et al. (2011) |
| 2‐fluoro‐1‐methylpyridinium p‐tolunesolfonate (FMTPS) |
|
Hair (human) | Cannabinoids (hydroxyl group) | MALDI‐MSI | Illicit Drug Use Testing/Forensics | Beasley et al. (2016) |
| (E)‐2‐cyano‐N‐(2‐(2,5‐dioxo‐2,5‐dihydro‐1H‐pyrrol‐1‐yl) ethyl)‐3‐(4‐hydroxyphenyl) acrylamide (CHC‐Mal) |
|
Xenograft tumors (mouse) Liver and Pancreas (pig) |
sulfhydryl groups | MALDI‐MSI (reactive matrix) | Pharmacology | Fülöp et al. (2020) |
| Carboxylic acids | ||||||
| 2‐picolamine (PA) |
|
Brain (rat) | Fatty acids (carboxyl group) | MALDI‐ MSI | Lipidomics | Q. Wu et al. (2016) |
| Seeds and leaves (maize plant) | Carboxylic acids | MALDI‐MSI | Plant metabolomics | Dueñas et al. (2019) | ||
| N,N‐dimethylpiperazine iodide (DMPI) |
|
Thyroid carcinoma (human) | Fatty acids (carboxyl group) | MALDI‐MSI | Cancer metabolomics | S. S. Wang et al. (2019) |
| N,N,N‐trimethyl‐2‐(piperazin‐1‐yl)ethan‐1‐aminium iodide (TMPA) |
|
Kidney and brain (rat) | Carboxyl‐Containing Metabolites | MALDI‐MSI | Metabolomics | Sun et al. (2020) |
| 4‐(N‐methyl)‐pyridinium boronic acid |
|
Adrenal gland (pig) | Catecholamines |
LDI‐MSI SIMS‐MSI |
Endocrinology | Kaya et al. (2018) |
|
Ethyl esterification and dimethylamidation Two‐step reaction: Step 1: |
|
Leiomyosarcoma and colon carcinoma (human) | N‐glycans (linkage‐specific sialic acid) | MALDI‐MSI | Cancer metabolomics | Holst et al. (2016) |
| ||||||
| Step 2: | ||||||
| ||||||
| Unsaturated systems (alkenes) | ||||||
| Paternò–Büchi reaction |
|
Brain (mouse) | C═C double‐bond (db) positional isomers | MALDI‐MSI | Lipidomics | Bednařík et al. (2018) |
| ||||||
| Brain (mouse) | C═C double‐bond (db) positional isomers | MALDI‐MSI | Lipidomics | Wäldchen et al. (2019) | ||
| Ozone |
|
Brain (rat) | C═C double‐bond (db) positional isomers | MALDI‐MSI | Lipidomics | Paine et al. (2018) |
|
Brain (mouse) Colon (human) |
C═C double‐bond (db) positional isomers | MALDI‐MSI | Lipidomics | Bednařík et al. (2020) | ||
| meta‐Chloroperoxybenzoic acid (mCPBA) |
|
Kidney (mouse) Metastatic lung (mouse) |
C═C double‐bond (db) positional isomers | Reactive DESI‐MSI | Lipidomics | Kuo et al., 2019) |
| Amines | ||||||
| p‐N, N, N trimethylammonioanilyl N′‐hydroxysuccinimidyl carbamate iodide (TAHS) |
|
Metastatic liver (mouse) | Amino acids | MALDI‐MSI | Cancer metabolomics | Toue et al. (2014) |
| Brain (mouse) | Amino neurotransmitters | MALDI‐MSI | Neuroscience | Esteve et al. (2016) | ||
| Liver (mouse) | Amino acids | MALDI‐MSI | Proteomics | Arts et al. (2017) | ||
| Adrenal gland with Pheochromocytoma (human) | Catecholamine | MALDI ‐MSI | Cancer metabolomics | Takeo et al. (2019) | ||
| 4‐Hydroxy‐3‐methoxycinna‐maldehyde (CA) |
|
Lung (rabbit) | Isoniazid (antituberculosis drug) | MALDI‐MSI | Pharmacology | Manier et al. (2011) |
|
Adrenal gland (pig) Brian (rat) |
Amine metabolites and neurotransmitters | MALDI‐MSI | Proteomics/Neurosciences | Manier et al. (2014) | ||
| Brain (mouse) | Amino neurotransmitters | MALDI‐MSI | Neuroscience | Esteve et al. (2016) | ||
| Brain (rat) | Amino Acids | MALDI‐MSI | Metabolomics | Guo et al. (2019) | ||
| Roots and leaves (maize plant) | Amino acids | MALDI‐MSI | Plant metabolomics | Dueñas et al. (2019) | ||
| Root (maize plant) | Amino acids | MALDI‐MSI | Plant metabolomics | O'Neill and Lee (2020) | ||
| 2,4‐diphenyl‐pyrylium (DPP) |
|
Brain (mouse) | Amino neurotransmitters | MALDI‐MSI | Neuroscience | Sugiyama et al. (2019) |
| 2,4‐diphenyl‐pyranylium tetrafluoroborate (DPP‐TFB) |
|
Brain (rat, mouse, rhesus monkey) | Amino neurotransmitters | MALDI‐MSI (reactive matrix) | Neuroscience | Shariatgorji et al. (2014) |
| Brain (rat, mouse) | Amino neurotransmitters | MALDI‐MSI (reactive matrix) | Neuroscience | Shariatgorji et al. (2015) | ||
| Brain (rat, mouse) | Amino neurotransmitters | DESI‐MSI | Neuroscience | Shariatgorji et al. (2016) | ||
| Brain (mouse) | Amino neurotransmitters | MALDI‐MSI | Neuroscience | Esteve et al. (2016) | ||
| Brain glioma (mouse) | Amino neurotransmitters/metabolites | MALDI‐MSI | Cancer metabolomics | Dilillo et al., 2017) | ||
| Whole head (Drosophila) | γ‐ aminobutyric acid (GABA) | MALDI‐MSI | Neuroscience | Y. Enomoto, Phan, et al. (2018) | ||
| Brain (crustacean) | Amino neurotransmitters | MALDI‐MSI | Neuroscience | Cao et al. (2019) | ||
| Brain (mouse) | Amino neurotransmitters | DESI‐MSI | Neuroscience | Davison et al. (2019) | ||
| Pyrilium salts (general) |
|
Brain (rat, mouse) | Amino neurotransmitters | MALDI‐MSI (reactive matrix) | Neuroscience | Shariatgorji et al. (2015) |
| Fluoromethylpyridinium (FMP) |
|
Brain (rat, rhesus monkey, human) | Amino transmitters and their metabolites (phenolic hydroxyl groups) | MALDI–MSI (reactive matrix) | Neuroscience | Shariatgorji et al. (2019) |
| 2‐(4‐bromo‐phenyl)‐4,6‐ diphenyl‐pyranylium (Br‐TPP) |
|
Brain (rat, mouse) | Amino neurotransmitters |
MALDI–MSI (reactive matrix) DESI‐MSI |
Neuroscience | Shariatgorji et al. (2020) |
| Mass differential tags for relative and absolute quantification (mTRAQ®)Δ0 |
|
Brain (rat) | Amino acids and Neurotransmitters | (MALDI ‐MSI) | Neuroscience | Ito and Hiramoto (2019) |
| N‐succinimidyloxycarbony methyl) tris(2,4,6 trimethoxy phenyl) phosphonium bromide (TMPP) |
|
Brain (rat) | Peptides and Proteins | MALDI‐MSI | Proteomics | Franck et al. (2009) |
| 3‐Sulfobenzoic acid succinimidyl ester (3‐SBASE) |
|
|||||
| 4‐Sulfophenyl isothiocyanate (4‐SPITC) |
|
|||||
| Ketones/Aldehydes | ||||||
| Girard's reagent T (GT) |
|
Brain (rat, mouse) Adrenal gland (rat, mouse) | Corticsteroids | MALDI‐MSI | Intracrinology | Cobice et al. (2013) |
| Cartilage (human) | Triamcinolone acetonide (osteoarthritis drug) | MALDI‐MSI | Pharmacology | Barré et al. (2016) | ||
| Testes (mouse) | Androgens | MALDI‐MSI | Endocrinology | Cobice et al. (2016) | ||
| Testes (mouse) | Testosterone | MALDI‐MSI | Intracrinology | Shimma et al. (2016) | ||
| Brain (mouse) | Corticsteroids | MALDI‐MSI | Pharmacology | Cobice et al. (2018) | ||
| Bean seeds | Acids | MALDI‐MSI | Plant metabolomics | H. Enomoto, Sensu, et al. (2018) | ||
| Adrenal gland (rat, human) | Corticosteroids | MALDI‐MSI | Intracrinology | Sugiura et al. (2018) | ||
| Brain (rat) | Steroids | MALDI ‐MSI | Intracrinology | Guo et al. (2019) | ||
| Adrenal gland (rat, human) | Steroids | MALDI ‐MSI | Cancer metabolomics | Takeo et al. (2019) | ||
| Girard's reagent P (GP) |
|
Brain (mouse) | Sterols and Oxysterols | MALDI‐MSI | Metabolomics | Yutuc et al. (2020) |
| 2,4‐Dinitrophenylhydrazine (DNPH) |
|
Spinal cord (rat) | Malondialdehyde | DESI‐MSI (reactive) | Lipidomics (peroxidation) | Girod et al. (2012) |
| Lung (rat) | Fluticasone proprionate (asthma drug‐steroid) | MADLI‐MSI (Reactive matrix) | Pharmacology | Flinders et al. (2015) | ||
| 4‐dimethylamino‐6‐(4‐methoxy‐1‐naphthyl)‐1,3,5‐triazine‐2‐hydrazine (DMNTH) |
|
Lung (rat) | Fluticasone proprionate (asthma drug‐steroid) | MADLI‐MSI (Reactive matrix) | Pharmacology | Flinders et al. (2015) |
| Platinum‐containing compounds | ||||||
| Diethyldithiocarbamate (DDTC) |
|
Three‐dimensional multicellular tumor spheroids (MCTS) | Oxaliplatin (chemotherapy drug) | MALDI‐MSI | Pharmacology | Liu and Hummon (2016) |
| Vitamin‐D metabolites | ||||||
| Amplifex™ |
|
Kidney (mouse) | Vitamin‐D metabolites |
MALDI‐MSI DESI−MSI |
Metabolomics | Smith et al. (2020) |
Abbreviations: DESI, desorption electrospray ionization; LDI, laser desorption ionization; MALDI, matrix‐assisted laser desorption/ionization; MSI, mass spectrometry imaging; OTCD, on‐tissue chemical derivatization.