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Article ; Online: Chemical labeling strategies for small molecule natural product detection and isolation.

Hughes, Chambers C

2021 Volume 38, Issue 9, Page(s) 1684–1705

Abstract: Covering: Up to 2020.It is widely accepted that small molecule natural products (NPs) evolved to carry out a particular ecological function and that these finely-tuned molecules can sometimes be appropriated for the treatment of disease in humans. ... ...

Abstract	Covering: Up to 2020.It is widely accepted that small molecule natural products (NPs) evolved to carry out a particular ecological function and that these finely-tuned molecules can sometimes be appropriated for the treatment of disease in humans. Unfortunately, for the natural products chemist, NPs did not evolve to possess favorable physicochemical properties needed for HPLC-MS analysis. The process known as derivatization, whereby an NP in a complex mixture is decorated with a nonnatural moiety using a derivatizing agent (DA), arose from this sad state of affairs. Here, NPs are freed from the limitations of natural functionality and endowed, usually with some degree of chemoselectivity, with additional structural features that make HPLC-MS analysis more informative. DAs that selectively label amines, carboxylic acids, alcohols, phenols, thiols, ketones, and aldehydes, terminal alkynes, electrophiles, conjugated alkenes, and isocyanides have been developed and will be discussed here in detail. Although usually employed for targeted metabolomics, chemical labeling strategies have been effectively applied to uncharacterized NP extracts and may play an increasing role in the detection and isolation of certain classes of NPs in the future.
MeSH term(s)	Biological Products/analysis ; Biological Products/isolation & purification ; Chromatography, High Pressure Liquid/methods ; Mass Spectrometry/methods ; Small Molecule Libraries/chemistry
Chemical Substances	Biological Products ; Small Molecule Libraries
Language	English
Publishing date	2021-09-23
Publishing country	England
Document type	Journal Article ; Research Support, Non-U.S. Gov't ; Research Support, U.S. Gov't, Non-P.H.S. ; Review
ZDB-ID	2002546-4
ISSN	1460-4752 ; 0265-0568
ISSN (online)	1460-4752
ISSN	0265-0568
DOI	10.1039/d0np00034e
Database	MEDical Literature Analysis and Retrieval System OnLINE

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Article: Chemical labeling strategies for small molecule natural product detection and isolation

Hughes, Chambers C.

Natural product reports. 2021 Sept. 23, v. 38, no. 9

2021

Abstract: It is widely accepted that small molecule natural products (NPs) evolved to carry out a particular ecological function and that these finely-tuned molecules can sometimes be appropriated for the treatment of disease in humans. Unfortunately, for the ... ...

Abstract	It is widely accepted that small molecule natural products (NPs) evolved to carry out a particular ecological function and that these finely-tuned molecules can sometimes be appropriated for the treatment of disease in humans. Unfortunately, for the natural products chemist, NPs did not evolve to possess favorable physicochemical properties needed for HPLC-MS analysis. The process known as derivatization, whereby an NP in a complex mixture is decorated with a nonnatural moiety using a derivatizing agent (DA), arose from this sad state of affairs. Here, NPs are freed from the limitations of natural functionality and endowed, usually with some degree of chemoselectivity, with additional structural features that make HPLC-MS analysis more informative. DAs that selectively label amines, carboxylic acids, alcohols, phenols, thiols, ketones, and aldehydes, terminal alkynes, electrophiles, conjugated alkenes, and isocyanides have been developed and will be discussed here in detail. Although usually employed for targeted metabolomics, chemical labeling strategies have been effectively applied to uncharacterized NP extracts and may play an increasing role in the detection and isolation of certain classes of NPs in the future.
Keywords	Lewis acids ; alkenes ; alkynes ; chemoselectivity ; cyanides ; derivatization ; ecological function ; metabolomics ; moieties ; thiols
Language	English
Dates of publication	2021-0923
Size	p. 1684-1705.
Publishing place	The Royal Society of Chemistry
Document type	Article
ZDB-ID	2002546-4
ISSN	1460-4752 ; 0265-0568
ISSN (online)	1460-4752
ISSN	0265-0568
DOI	10.1039/d0np00034e
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Article ; Online: Controls on the stable isotope composition of daily precipitation in Sydney Australia: 9 years of daily data, including Radon-222

Crawford, J. / Hughes, C.E. / Chambers, S.D.

Journal of Hydrology. 2023 Feb., v. 617 p.129123-

2023

Abstract: Daily and weekly rainfall stable isotopic data, collected over a 9-year period (for daily) and 14-year period (for weekly) at Lucas Heights, Australia, were compared. Small differences in the local meteoric water lines (LMWLs) were seen when developed ... ...

Abstract	Daily and weekly rainfall stable isotopic data, collected over a 9-year period (for daily) and 14-year period (for weekly) at Lucas Heights, Australia, were compared. Small differences in the local meteoric water lines (LMWLs) were seen when developed using daily, weekly, or monthly data (where the effect of short-term small atmospheric variability is reduced by the associated averaging). Although, if a precipitation weighted least squares method was used to derive the LMWLs, the differences between the daily and weekly derived LMWLs were lower. A systematic analysis was then conducted of the impact on the isotopic composition of precipitation from environmental conditions at the sampling site and along the air mass trajectory, the synoptic weather systems, and finally large-scale climate drivers (e.g.,El Niño-Southern Oscillation). The best correlation of δ¹⁸O was with local temperature, rainout of the air mass, and rainfall amount at the site. The correlation between precipitation amount and δ¹⁸O values was higher when daily samples were used, than when the precipitation weighted monthly values were considered (-0.36 as opposed to −0.31). A good correlation was also seen between δ¹⁸O and duration of the precipitation event (r = -0.42). The correlation between δ¹⁸O and the fraction of convective rainfall was significant, but low (r = 0.11). On a synoptic systems basis, the lowest δ values were seen in rainfall from offshore low-pressure systems, located to the east or north-east of the site; although, the largest rainfall was seen from low pressure systems arriving from the north-east. The influence of the large-scale climate drivers on the isotopic composition of precipitation was insignificant at this coastal site. When Radon-222 was used to categorise the atmospheric mixing state, rainfall amount was clearly negatively correlated with nocturnal stability, with the lowest amount of rainfall occurring on days with the most stable nocturnal periods. Most of the convective rainfall occurred on these same days, occurring after the warmer period of the day, although the total rainfall amount was low. Analysing the data within the separate radon-derived stability categories improved the correlations with rainfall amount for some of the stability categories.
Keywords	air ; climate ; hydrology ; rain ; stable isotopes ; temperature ; Australia ; Precipitation ; Radon ; LMWL
Language	English
Dates of publication	2023-02
Publishing place	Elsevier B.V.
Document type	Article ; Online
ZDB-ID	1473173-3
ISSN	1879-2707 ; 0022-1694
ISSN (online)	1879-2707
ISSN	0022-1694
DOI	10.1016/j.jhydrol.2023.129123
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Article ; Online: Correction to "The Antibacterial Synnepyrroles from Human-associated

Zhang, Lei / Esquembre, Lidia Alejo / Xia, Shu-Ning / Oesterhelt, Filipp / Hughes, Chambers C / Brötz-Oesterhelt, Heike / Teufel, Robin

ACS chemical biology

2023 Volume 18, Issue 8, Page(s) 1905

Language	English
Publishing date	2023-07-13
Publishing country	United States
Document type	Published Erratum
ISSN	1554-8937
ISSN (online)	1554-8937
DOI	10.1021/acschembio.3c00388
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Article ; Online: Progress toward the Total Synthesis of Lymphostins: Preparation of a Functionalized Tetrahydropyrrolo[4,3,2-

Seiler, Grant S / Hughes, Chambers C

The Journal of organic chemistry

2019 Volume 84, Issue 14, Page(s) 9339–9343

Abstract: The lymphostins are a family of closely related pyrrolo[4,3,2- ...

Abstract	The lymphostins are a family of closely related pyrrolo[4,3,2-
MeSH term(s)	Molecular Structure ; Oxidation-Reduction ; Quinolines/chemical synthesis
Chemical Substances	Quinolines
Language	English
Publishing date	2019-06-27
Publishing country	United States
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	123490-0
ISSN	1520-6904 ; 0022-3263
ISSN (online)	1520-6904
ISSN	0022-3263
DOI	10.1021/acs.joc.9b01041
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Article ; Online: Structure Elucidation of Antibiotics.

Moschny, Julia / Daletos, Georgios / Proksch, Peter / Hughes, Chambers C

Methods in molecular biology (Clifton, N.J.)

2022 Volume 2601, Page(s) 97–122

Abstract: To date, there are hundreds of characterized natural products with antibacterial activity against pathogenic bacteria, and several have become bonafide antibiotic drugs. The development of antibacterial natural products into antibiotic drugs, both in the ...

Abstract	To date, there are hundreds of characterized natural products with antibacterial activity against pathogenic bacteria, and several have become bonafide antibiotic drugs. The development of antibacterial natural products into antibiotic drugs, both in the past and in the future, hinges upon an accurate description of the exact chemical structure of the compound. Bolstered by some form of mass spectrometry (MS), nuclear magnetic resonance (NMR) spectroscopy is the primary technique for elucidating the chemical structure of organic molecules including natural products. By combining various one-dimensional (1D) and two-dimensional (2D) experiments, the connectivity between atoms is established and a complete "picture" of the molecule is thereby revealed.
MeSH term(s)	Anti-Bacterial Agents/pharmacology ; Biological Products ; Mass Spectrometry
Chemical Substances	Anti-Bacterial Agents ; Biological Products
Language	English
Publishing date	2022-11-14
Publishing country	United States
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ISSN	1940-6029
ISSN (online)	1940-6029
DOI	10.1007/978-1-0716-2855-3_6
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Article ; Online: The Relationship Between Insertive Oral and Anal Sex and Select Measures of the Composition of the Urethral Microbiota Among Men Who Have Sex With Men.

Chambers, Laura C / Tapia, Kenneth A / Srinivasan, Sujatha / Proll, Sean / Morgan, Jennifer L / Hoffman, Noah G / Lowens, M Sylvan / Glick, Sara N / Khosropour, Christine M / Golden, Matthew R / Hughes, James P / Manhart, Lisa E / Fredricks, David N

Sexually transmitted diseases

2024

Abstract: Background: Sexual behavior may influence the composition of the male urethral microbiota, but this hypothesis has not been tested in longitudinal studies of men who have sex with men (MSM).: Methods: From 12/2014-7/2018, we enrolled MSM with non- ... ...

Abstract	Background: Sexual behavior may influence the composition of the male urethral microbiota, but this hypothesis has not been tested in longitudinal studies of men who have sex with men (MSM). Methods: From 12/2014-7/2018, we enrolled MSM with non-gonococcal urethritis (NGU) attending a sexual health clinic. Men attended five in-clinic visits at 3-week intervals, collected weekly urine specimens at home, and reported daily antibiotics and sexual activity on weekly diaries. We applied broad-range 16S rRNA gene sequencing to urine. We used generalized estimating equations to estimate the association between urethral sexual exposures in the prior 7 days (insertive oral sex [IOS] only, condomless insertive anal intercourse [CIAI] only, IOS with CIAI [IOS + CIAI], or none) and Shannon index, number of species (observed, oral indicator, and rectal indicator), and specific taxa, adjusting for recent antibiotics, age, race/ethnicity, HIV, and pre-exposure prophylaxis. Results: Ninety-six of 108 MSM with NGU attended ≥1 follow-up visit. They contributed 1,140 person-weeks of behavioral data and 1,006 urine specimens. Compared to those with no urethral sexual exposures, those with IOS only had higher Shannon index (P = 0.03) but similar number of species and presence of specific taxa considered, adjusting for confounders; the exception was an association with Haemophilus parainfluenzae. CIAI only was not associated with measured aspects of the urethral microbiota. IOS + CIAI was only associated with presence of H. parainfluenzae and Haemophilus. Conclusions: Among MSM after NGU, IOS and CIAI did not appear to have a substantial influence on measured aspects of the composition of the urethral microbiota.
Language	English
Publishing date	2024-02-23
Publishing country	United States
Document type	Journal Article
ZDB-ID	435191-5
ISSN	1537-4521 ; 0148-5717
ISSN (online)	1537-4521
ISSN	0148-5717
DOI	10.1097/OLQ.0000000000001959
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Zs.A 1217: Show issues

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Article ; Online: Equipping for risk: Lessons learnt from the UK shale-gas experience on assessing environmental risks for the future geoenergy use of the deep subsurface.

Smedley, P L / Allen, G / Baptie, B J / Fraser-Harris, A P / Ward, R S / Chambers, R M / Gilfillan, S M V / Hall, J A / Hughes, A G / Manning, D A C / McDermott, C I / Nagheli, S / Shaw, J T / Werner, M J / Worrall, F

The Science of the total environment

2024 Volume 921, Page(s) 171036

Abstract: findings are presented from an investigation to improve understanding of the environmental risks associated with developing an unconventional-hydrocarbons industry in the UK. The EQUIPT4RISK project, funded by UK Research Councils, focused on ... ...

Abstract	findings are presented from an investigation to improve understanding of the environmental risks associated with developing an unconventional-hydrocarbons industry in the UK. The EQUIPT4RISK project, funded by UK Research Councils, focused on investigations around Preston New Road (PNR), Fylde, Lancashire, and Kirby Misperton Site A (KMA), North Yorkshire, where operator licences to explore for shale gas by hydraulic fracturing (HF) were issued in 2016, although exploration only took place at PNR. EQUIPT4RISK considered atmospheric (greenhouse gases, air quality), water (groundwater quality) and solid-earth (seismicity) compartments to characterise and model local conditions and environmental responses to HF activities. Risk assessment was based on the source-pathway-receptor approach. Baseline monitoring of air around the two sites characterised the variability with meteorological conditions, and isotopic signatures were able to discriminate biogenic methane (cattle) from thermogenic (natural-gas) sources. Monitoring of a post-HF nitrogen-lift (well-cleaning) operation at PNR detected the release of atmospheric emissions of methane (4.2 ± 1.4 t CH
Language	English
Publishing date	2024-02-17
Publishing country	Netherlands
Document type	Journal Article
ZDB-ID	121506-1
ISSN	1879-1026 ; 0048-9697
ISSN (online)	1879-1026
ISSN	0048-9697
DOI	10.1016/j.scitotenv.2024.171036
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Article ; Online: Antibacterial Marinopyrroles and Pseudilins Act as Protonophores.

Castro-Falcón, Gabriel / Straetener, Jan / Bornikoel, Jan / Reimer, Daniela / Purdy, Trevor N / Berscheid, Anne / Schempp, Florence M / Liu, Dennis Y / Linington, Roger G / Brötz-Oesterhelt, Heike / Hughes, Chambers C

ACS chemical biology

2024 Volume 19, Issue 3, Page(s) 743–752

Abstract: Elucidating the mechanism of action (MoA) of antibacterial natural products is crucial to evaluating their potential as novel antibiotics. Marinopyrroles, pentachloropseudilin, and pentabromopseudilin are densely halogenated, hybrid pyrrole-phenol ... ...

Abstract	Elucidating the mechanism of action (MoA) of antibacterial natural products is crucial to evaluating their potential as novel antibiotics. Marinopyrroles, pentachloropseudilin, and pentabromopseudilin are densely halogenated, hybrid pyrrole-phenol natural products with potent activity against Gram-positive bacterial pathogens like
MeSH term(s)	Animals ; Anti-Bacterial Agents/pharmacology ; Pyrroles/pharmacology ; Hydrocarbons, Chlorinated ; Biological Products ; Microbial Sensitivity Tests ; Mammals
Chemical Substances	pentachloropseudilin ; Anti-Bacterial Agents ; Pyrroles ; Hydrocarbons, Chlorinated ; Biological Products
Language	English
Publishing date	2024-02-20
Publishing country	United States
Document type	Journal Article
ISSN	1554-8937
ISSN (online)	1554-8937
DOI	10.1021/acschembio.3c00773
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Article ; Online: Specialized Metabolite-Mediated Predation Defense in the Marine Actinobacterium

Tuttle, Robert N / Rouse, Greg W / Castro-Falcón, Gabriel / Hughes, Chambers C / Jensen, Paul R

Applied and environmental microbiology

2021 Volume 88, Issue 1, Page(s) e0117621

Abstract: The obligate marine actinobacterial ... ...

Abstract	The obligate marine actinobacterial genus
MeSH term(s)	Actinobacteria ; Animals ; Caenorhabditis elegans ; Ecosystem ; Micromonosporaceae ; Predatory Behavior
Language	English
Publishing date	2021-10-20
Publishing country	United States
Document type	Journal Article ; Research Support, U.S. Gov't, Non-P.H.S.
ZDB-ID	223011-2
ISSN	1098-5336 ; 0099-2240
ISSN (online)	1098-5336
ISSN	0099-2240
DOI	10.1128/AEM.01176-21
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