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Article ; Online: Chemical reactivity of the tryptophan/acetone/DMSO triad system and its potential applications in nanomaterial synthesis.

Huang, Chun-Yi / Liao, Hsiao-Wei / Hu, Teh-Min

RSC advances

2023 Volume 13, Issue 43, Page(s) 29802–29808

Abstract: Previously, we reported a novel browning reaction of amino acids and proteins in an organic solvent mixture composed of dimethyl sulfoxide (DMSO) and acetone. The reaction proceeds under surprisingly mild conditions, requiring no heating or additional ... ...

Abstract	Previously, we reported a novel browning reaction of amino acids and proteins in an organic solvent mixture composed of dimethyl sulfoxide (DMSO) and acetone. The reaction proceeds under surprisingly mild conditions, requiring no heating or additional reactants or catalysts. This present study aimed to investigate the chemical reactivity of the triad reaction system of l-tryptophan/aectone/DMSO. We demonstrated that, in DMSO, l-tryptophan initially catalyzed the self-aldol condensation of acetone, resulting in the formation of mesityl oxide (MO). Furthermore, we showed that the three-component system evolved into a diverse chemical space, producing various indole derivatives with aldehyde or ketone functional groups that exhibited self-assembling and nanoparticle-forming capabilities. We highlight the potential applications in nanomaterial synthesis.
Language	English
Publishing date	2023-10-11
Publishing country	England
Document type	Journal Article
ISSN	2046-2069
ISSN (online)	2046-2069
DOI	10.1039/d3ra06596k
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Article: Discovery of Natural Veterinary Herbal Medicine Products in Commercial Cow Milk by Using Nontargeted Profiling on LC–ESI–TOF Platform

Wang, San-Yuan / Liao, Hsiao-Wei

Food analytical methods. 2022 Apr., v. 15, no. 4

2022

Abstract: For centuries, herbal medicines have been used to treat humans and animals. Veterinary medicines are well-regulated; inspectors monitor milk and associated dairy products to screen for unacceptable contaminants. However, few scholars have discussed how ... ...

Abstract	For centuries, herbal medicines have been used to treat humans and animals. Veterinary medicines are well-regulated; inspectors monitor milk and associated dairy products to screen for unacceptable contaminants. However, few scholars have discussed how the by-products of veterinary herbal medicine can be found in food products. In this paper, we applied nontargeted profiling of the UHPLC–ESI–TOF platform to screen possible by-products originating from veterinary herbal medicine in commercial milk samples. These tentatively identified alkaloids showed high consistency with the plant extract of Holarrhena antidysenterica (L.) Wall. ex A. DC., which indicated the possibility that dairy farmers had used plants from genus Holarrhena as veterinary herbal medicine. This is the first report showing the presence of by-products originating from veterinary herbal medicine in commercial milk. This finding could help authorities to evaluate the use of veterinary herbal medicine in farm animals.
Keywords	Holarrhena pubescens ; farms ; herbal medicines ; milk ; plant extracts
Language	English
Dates of publication	2022-04
Size	p. 868-876.
Publishing place	Springer US
Document type	Article
ZDB-ID	2429656-9
ISSN	1936-976X ; 1936-9751
ISSN (online)	1936-976X
ISSN	1936-9751
DOI	10.1007/s12161-021-02171-5
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Article ; Online: Bias caused by incomplete metabolite extraction and matrix effect: Evaluation of critical factors for plasma sample preparation prior to metabolomics.

Liao, Hsiao-Wei / Cheng, Yu-Wen / Tang, Sung-Chun / Kuo, Ching-Hua

Journal of pharmaceutical and biomedical analysis

2022 Volume 219, Page(s) 114930

Abstract: Metabolomics is an omics strategy to study the metabolite alteration in the biological system. Unbiased observation of the metabolite level is essential for targeted metabolite quantification and untargeted metabolic profiling. State-of-the-art ... ...

Abstract	Metabolomics is an omics strategy to study the metabolite alteration in the biological system. Unbiased observation of the metabolite level is essential for targeted metabolite quantification and untargeted metabolic profiling. State-of-the-art instruments and versatile tools have been developed for accurate observation of metabolic alterations in various studies. Several analytical pitfalls, such as sample overloading and signal-saturation-induced bias, have been revealed and addressed. In this study, we proposed incomplete-metabolite-extraction-caused bias is also an important issue that results in biased observation when performing metabolomics. In the demonstration example, numerous metabolites exhibited no significant difference between extracted plasma samples with different plasma contents, which is attributed to incomplete-metabolite-extraction-caused bias and matrix effect. Matrix effect is a well-known factor that result in biased observation, it can be reduced by sample dilution and compensated by using stable isotope labelled internal standards. The detection of metabolite signals in the following consecutive extractions provided further evidence of incomplete metabolite extraction. The completeness of metabolite extraction is crucial for unbiased observation of metabolic profile changes. To address this issue, we optimized the extraction time and methanol volume to reduce the incomplete-metabolite-extraction-caused bias and evaluated the metabolite signals in consecutive extractions. Methanol extraction performed with a plasma-to-methanol ratio of 1:14 resulted in metabolite responses of less than 18.1 % in the second extractions observed by metabolomic profiling. Finally, the optimized sample preparation procedure and untargeted profiling platform were applied to detect metabolite alterations associated with patients with cerebrovascular diseases and several features with significant difference were successfully identified. This study revealed and evaluated the bias caused by incomplete metabolite extraction and matrix effect in the commonly used methanol extraction method for human plasma sample preparation for metabolomics. We anticipate the proposed metabolite extraction evaluation method could benefit more clinical and biological metabolomics studies.
MeSH term(s)	Humans ; Metabolome ; Metabolomics/methods ; Methanol ; Plasma ; Specimen Handling
Chemical Substances	Methanol (Y4S76JWI15)
Language	English
Publishing date	2022-07-06
Publishing country	England
Document type	Journal Article
ZDB-ID	604917-5
ISSN	1873-264X ; 0731-7085
ISSN (online)	1873-264X
ISSN	0731-7085
DOI	10.1016/j.jpba.2022.114930
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Article: Untargeted Microbial Exometabolomics and Metabolomics Analysis of

Kao, Cheng-Yen / Kuo, Pei-Yun / Liao, Hsiao-Wei

Metabolites

2021 Volume 11, Issue 12

Abstract: Untargeted metabolomic profiling provides the opportunity to comprehensively explore metabolites of interest. Herein, we investigated the metabolic pathways associated with Jhp0106, a glycosyltransferase enzyme ... ...

Abstract	Untargeted metabolomic profiling provides the opportunity to comprehensively explore metabolites of interest. Herein, we investigated the metabolic pathways associated with Jhp0106, a glycosyltransferase enzyme in
Language	English
Publishing date	2021-11-28
Publishing country	Switzerland
Document type	Journal Article
ZDB-ID	2662251-8
ISSN	2218-1989
ISSN	2218-1989
DOI	10.3390/metabo11120808
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Article ; Online: Quantifying payloads of antibody‒drug conjugates using a postcolumn infused-internal standard strategy with LC‒MS.

Cheng, Chih-Ning / Liao, Hsiao-Wei / Lin, Ching-Hung / Chang, Wen-Chi / Chen, I-Chun / Lu, Yen-Shen / Kuo, Ching-Hua

Analytica chimica acta

2024 Volume 1303, Page(s) 342537

Abstract: Background: Antibody‒drug conjugates (ADCs) are innovative biopharmaceutics consisting of a monoclonal antibody, linkers, and cytotoxic payloads. Monitoring circulating payload concentrations has the potential to identify ADC toxicity; however, accurate ...

Abstract	Background: Antibody‒drug conjugates (ADCs) are innovative biopharmaceutics consisting of a monoclonal antibody, linkers, and cytotoxic payloads. Monitoring circulating payload concentrations has the potential to identify ADC toxicity; however, accurate quantification faces challenges, including low plasma concentrations, severe matrix effects, and the absence of stable isotope-labeled internal standards (SIL-IS) for payloads and their derivatives. Previous studies used structural analogs as internal standards, but different retention times between structural analogs and target analytes may hinder effective matrix correction. Therefore, a more flexible approach is required for precise payload quantification. Results: We developed an LC‒MS/MS method incorporating a postcolumn-infused internal standard (PCI-IS) strategy for quantifying payloads and their derivatives of trastuzumab emtansine, trastuzumab deruxtecan, and sacituzumab govitecan, including DM1, MCC-DM1, DXd, SN-38, and SN-38G. Structural analogs (maytansine, Lys-MCC-DM1, and exatecan) were selected as PCI-IS candidates, and their accuracy performance was evaluated based on the percentage of samples within 80%-120% quantification accuracy. Compared to the approach without PCI-IS correction, exatecan enhanced the accuracy performance from 30-40%-100% for SN-38 and DXd, while maytansine and Lys-MCC-DM1 showed comparable accuracy for DM1 and MCC-DM1. This validated PCI-IS analytical method showed superior normalization of matrix effect in all analytes compared to the conventional internal standard approach. The clinical application of this approach showed pronounced differences in DXd and SN-38 concentrations before and after PCI-IS correction. Moreover, only DXd concentrations after PCI-IS correction were significantly higher in patients with thrombocytopenia (p = 0.037). Significance: This approach effectively addressed the issue of unavailability of SIL-IS for novel ADC payloads and provided more accurate quantification, potentially yielding more robust statistical outcomes for understanding the exposure-toxicity relationship in ADCs. It is anticipated that this PCI-IS strategy may be extrapolated to quantify payloads and derivatives in diverse ADCs, thereby providing invaluable insights into drug toxicity and fortifying patient safety in ADC usage.
MeSH term(s)	Humans ; Irinotecan ; Chromatography, Liquid ; Liquid Chromatography-Mass Spectrometry ; Percutaneous Coronary Intervention ; Tandem Mass Spectrometry ; Immunoconjugates ; Maytansine/therapeutic use
Chemical Substances	Irinotecan (7673326042) ; Immunoconjugates ; Maytansine (14083FR882)
Language	English
Publishing date	2024-03-25
Publishing country	Netherlands
Document type	Journal Article
ZDB-ID	1483436-4
ISSN	1873-4324 ; 0003-2670
ISSN (online)	1873-4324
ISSN	0003-2670
DOI	10.1016/j.aca.2024.342537
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Article ; Online: Nanoparticles for Augmenting Therapeutic Potential and Alleviating the Effect of Di(2-ethylhexyl) Phthalate on Gastric Cancer.

Huang, Hau-Lun / Chen, Kuo-Wei / Liao, Hsiao-Wei / Wang, Ling-Yu / Peng, Shin-Lei / Lai, Chih-Ho / Lin, Yu-Hsin

ACS applied materials & interfaces

2024 Volume 16, Issue 15, Page(s) 18285–18299

Abstract: Changes in diet culture and modern lifestyle contributed to a higher incidence of gastrointestinal-related diseases, including gastritis, implicated in the pathogenesis of gastric cancer. This observation raised concerns regarding exposure to di(2- ... ...

Abstract	Changes in diet culture and modern lifestyle contributed to a higher incidence of gastrointestinal-related diseases, including gastritis, implicated in the pathogenesis of gastric cancer. This observation raised concerns regarding exposure to di(2-ethylhexyl) phthalate (DEHP), which is linked to adverse health effects, including reproductive and developmental problems, inflammatory response, and invasive adenocarcinoma. Research on the direct link between DEHP and gastric cancer is ongoing, and further studies are required to establish a conclusive association. In our study, extremely low concentrations of DEHP exerted significant effects on cell migration by promoting the epithelial-mesenchymal transition in gastric cancer cells. This effect was mediated by the modulation of the PI3K/AKT/mTOR and Smad2 signaling pathways. To address the DEHP challenges, our initial design of TPGS-conjugated fucoidan, delivered via pH-responsive nanoparticles, successfully demonstrated binding to the P-selectin protein. This achievement has not only enhanced the antigastric tumor efficacy but has also led to a significant reduction in the expression of malignant proteins associated with the condition. These findings underscore the promising clinical therapeutic potential of our approach.
MeSH term(s)	Humans ; Diethylhexyl Phthalate ; Plasticizers ; Stomach Neoplasms ; Phosphatidylinositol 3-Kinases ; Phthalic Acids
Chemical Substances	phthalic acid (6O7F7IX66E) ; Diethylhexyl Phthalate (C42K0PH13C) ; Plasticizers ; Phosphatidylinositol 3-Kinases (EC 2.7.1.-) ; Phthalic Acids
Language	English
Publishing date	2024-04-04
Publishing country	United States
Document type	Journal Article
ISSN	1944-8252
ISSN (online)	1944-8252
DOI	10.1021/acsami.3c15976
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Article ; Online: Analysis of Peptide Stereochemistry in Single Cells by Capillary Electrophoresis-Trapped Ion Mobility Spectrometry Mass Spectrometry.

Mast, David H / Liao, Hsiao-Wei / Romanova, Elena V / Sweedler, Jonathan V

Analytical chemistry

2021 Volume 93, Issue 15, Page(s) 6205–6213

Abstract: Single cell analysis strives to probe molecular heterogeneity in morphologically similar cell populations through quantitative or qualitative measurements of genetic, proteomic, or metabolic products. Here, we applied mass analysis of single neurons to ... ...

Abstract	Single cell analysis strives to probe molecular heterogeneity in morphologically similar cell populations through quantitative or qualitative measurements of genetic, proteomic, or metabolic products. Here, we applied mass analysis of single neurons to investigate cell-cell signaling peptides. The multiplicity of endogenous cell-cell signaling peptides is a common source of chemical diversity among cell populations. Certain peptides can undergo post-translational isomerization of select residues, which has important physiological consequences. The limited number of single cell analysis techniques that are sensitive to peptide stereochemistry make it challenging to study isomerization at the individual cell level. We performed capillary electrophoresis (CE) with mass spectrometry (MS) detection to characterize the peptide content of single cells. Using complementary trapped ion mobility spectrometry (TIMS) separations, we measured the stereochemical configurations of three neuropeptide gene products derived from the pleurin precursor in individual neurons (
MeSH term(s)	Electrophoresis, Capillary ; Ion Mobility Spectrometry ; Mass Spectrometry ; Peptides ; Proteomics
Chemical Substances	Peptides
Language	English
Publishing date	2021-04-07
Publishing country	United States
Document type	Journal Article ; Research Support, N.I.H., Extramural
ZDB-ID	1508-8
ISSN	1520-6882 ; 0003-2700
ISSN (online)	1520-6882
ISSN	0003-2700
DOI	10.1021/acs.analchem.1c00445
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Article ; Online: Discovery of new dibenzodiazepine derivatives as antibacterials against intracellular bacteria.

Chen, Ling-Han / Lin, Man-Yi / Lin, Hsueh-Chun / Yang, Fan-Wei / Liao, Hsiao-Wei / Shiau, Chung-Wai / Chiu, Hao-Chieh / Su, Jung-Chen

RSC medicinal chemistry

2023 Volume 15, Issue 1, Page(s) 283–292

Abstract: The emergence and spread of multidrug-resistant bacteria underscore the critical need for novel antibacterial interventions. In our screening of 12 synthesized thienobenzodiazepines, pyridobenzodiazepines, and dibenzodiazepines, we successfully ... ...

Abstract	The emergence and spread of multidrug-resistant bacteria underscore the critical need for novel antibacterial interventions. In our screening of 12 synthesized thienobenzodiazepines, pyridobenzodiazepines, and dibenzodiazepines, we successfully identified a small molecule compound SW33. Notably, SW33 demonstrated potent inhibitory activity against intracellular multidrug-resistant and fluoroquinolone-resistant strains of
Language	English
Publishing date	2023-12-11
Publishing country	England
Document type	Journal Article
ISSN	2632-8682
ISSN (online)	2632-8682
DOI	10.1039/d3md00418j
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Article ; Online: Sequential isolation of metabolites and lipids from a single sample to achieve multiomics by using TRIzol reagent.

Kao, Cheng-Yen / Chang, Chung-Te / Kuo, Pei-Yun / Lin, Chia-Jen / Chiu, Huai-Hsuan / Liao, Hsiao-Wei

Talanta

2023 Volume 258, Page(s) 124416

Abstract: Simultaneous extraction of various types of biomolecule from a single sample can be beneficial for multiomics studies of unique specimens. An efficient and convenient sample preparation approach must be developed that can comprehensively isolate and ... ...

Abstract	Simultaneous extraction of various types of biomolecule from a single sample can be beneficial for multiomics studies of unique specimens. An efficient and convenient sample preparation approach must be developed that can comprehensively isolate and extract biomolecules from one sample. TRIzol reagent is widely used in biological studies for DNA, RNA, and protein isolation. This study evaluated the feasibility of using TRIzol reagent for the simultaneous isolation of not only DNA, RNA, and proteins but also metabolites and lipids from a single sample. Through the comparison of known metabolites and lipids obtained using the conventional methanol (MeOH) and methyl-tert-butyl ether (MTBE) extraction methods, we determined the presence of metabolites and lipids in the supernatant during TRIzol sequential isolation. Finally, we performed untargeted metabolomics and lipidomics to examine metabolite and lipid alterations associated with the jhp0417 mutation in Helicobacter pylori by using the TRIzol sequential isolation protocol and MeOH and MTBE extraction methods. Metabolites and lipids with significant differences isolated using the TRIzol sequential isolation protocol were consistent with those obtained using the conventional MeOH and MTBE extraction methods. These results indicated that TRIzol reagent can be used to simultaneously isolate metabolites and lipids from a single sample. Thus, TRIzol reagent can be used in biological and clinical research, especially in multiomics studies.
MeSH term(s)	Indicators and Reagents ; Multiomics ; RNA ; Proteins ; Methanol ; Lipids
Chemical Substances	methyl tert-butyl ether (29I4YB3S89) ; trizol ; Indicators and Reagents ; RNA (63231-63-0) ; Proteins ; Methanol (Y4S76JWI15) ; Lipids
Language	English
Publishing date	2023-03-04
Publishing country	Netherlands
Document type	Journal Article
ZDB-ID	1500969-5
ISSN	1873-3573 ; 0039-9140
ISSN (online)	1873-3573
ISSN	0039-9140
DOI	10.1016/j.talanta.2023.124416
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Article: Analysis of Peptide Stereochemistry in Single Cells by Capillary Electrophoresis–Trapped Ion Mobility Spectrometry Mass Spectrometry

Mast, David H / Liao, Hsiao-Wei / Romanova, Elena V / Sweedler, Jonathan V

Analytical chemistry. 2021 Apr. 07, v. 93, no. 15

2021

Abstract	Single cell analysis strives to probe molecular heterogeneity in morphologically similar cell populations through quantitative or qualitative measurements of genetic, proteomic, or metabolic products. Here, we applied mass analysis of single neurons to investigate cell–cell signaling peptides. The multiplicity of endogenous cell–cell signaling peptides is a common source of chemical diversity among cell populations. Certain peptides can undergo post-translational isomerization of select residues, which has important physiological consequences. The limited number of single cell analysis techniques that are sensitive to peptide stereochemistry make it challenging to study isomerization at the individual cell level. We performed capillary electrophoresis (CE) with mass spectrometry (MS) detection to characterize the peptide content of single cells. Using complementary trapped ion mobility spectrometry (TIMS) separations, we measured the stereochemical configurations of three neuropeptide gene products derived from the pleurin precursor in individual neurons (N = 3) isolated from the central nervous system of Aplysia californica. An analysis of the resultant mobility profiles indicated >98% of the detectable pleurin-derived peptides exist as the nonisomerized, all-l forms in individual neuron cell bodies. However, we observed 44% of the Plrn2 peptide from the pleurin precursor was present as the isomerized, d-residue-containing form in the nerve tissue. These findings demonstrate an unusual distribution of isomerized peptides in A. californica and establish CE–TIMS MS as a powerful analytical tool for investigating peptide stereochemistry at the single cell level.
Keywords	Aplysia californica ; analytical chemistry ; capillary electrophoresis ; central nervous system ; genes ; isomerization ; mass spectrometry ; nerve tissue ; neurons ; neuropeptides ; proteomics ; stereochemistry
Language	English
Dates of publication	2021-0407
Size	p. 6205-6213.
Publishing place	American Chemical Society
Document type	Article
Note	NAL-AP-2-clean
ZDB-ID	1508-8
ISSN	1520-6882 ; 0003-2700
ISSN (online)	1520-6882
ISSN	0003-2700
DOI	10.1021/acs.analchem.1c00445
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