Metal chelating properties of pyridine-2,6-bis(thiocarboxylic acid) produced by Pseudomonas spp. and the biological activities of the formed complexes

Cortese, Marc S.; Paszczynski, Andrzej; Lewis, Thomas A.; Sebat, Jonathan L.; Borek, Vladimir; Crawford, Ronald L.

doi:10.1023/a:1015241925322

Cited by 68Inorganic and Organometallic ChemistryChromium effects and bioremediationMetal Extraction and Bioleaching

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Metal chelating properties of pyridine-2,6-bis(thiocarboxylic acid) produced by Pseudomonas spp. and the biological activities of the formed complexes

Cortese, Marc S., Paszczynski, Andrzej, Lewis, Thomas A., Sebat, Jonathan L., Borek, Vladimir, Crawford, Ronald L.·2002·Biometals

DOI 10.1023/a:1015241925322

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Abstract

We evaluated the ability of pyridine-2,6-bis(thiocarboxylic acid) (pdtc) to form complexes with 19 metals and 3 metalloids. Pdtc formed complexes with 14 of the metals. Two of these metal:pdtc complexes, Co:(pdtc)2 and Cu:pdtc, showed the ability to cycle between redox states, bringing to 4 the number of known redox-active pdtc complexes. A precipitant formed when pdtc was added to solutions of As, Cd, Hg, Mn, Pb, and Se. Additionally, 14 of 16 microbial strains tested were protected from Hg toxicity when pdtc was present. Pdtc also mediated protection from the toxic effects of Cd and Te, but for fewer strains. Pdtc by itself does not facilitate iron uptake, but increases the overall level of iron uptake of Pseudomonas stutzeri strain KC and P. putida DSM301. Both these pseudomonads could reduce amorphous Fe(III) oxyhydroxide in culture. In vitro reactions showed that copper and pdtc were required for this activity. This reaction may derive its reducing power from the hydrolysis of the thiocarboxyl groups of pdtc.

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Pseudomonas putida produces the small Zn-binding siderophore PDTC.
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Leach, L. H., Morris, J. C., & Lewis, T. A. (2007) · BioMetals · doi:10.1007/s10534-006-9035-x · Cited by 34
“Fe(II):PDTC, although readily resolved by UVvisible spectrophotometry (Cortese et al. 2002), was not detected in this synthesis.”
BackgroundInfluentialSelf-citation
Studies of synthesis, structural features of Cu( i ) thiophene-2-thiocarboxylates and unprecedented desulfurization of Cu( ii ) thiocarboxylate complexes
Singh, S., Chaturvedi, J., & Bhattacharya, S. (2011) · Dalton Transactions · doi:10.1039/c1dt10629e · Cited by 30
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Stolworthy, J. C., Paszczynski, A. J., Korus, R. A., & Crawford, R. L. (2001) · Biodegradation · doi:10.1023/a:1015067729660 · Cited by 30
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Mossialos, D., & Amoutzias, G. D. (2007) · Future Microbiology · doi:10.2217/17460913.2.4.387 · Cited by 25
Heteroaromatic monothiocarboxylic acids from Pseudomonas spp.
Budzikiewicz, H. (2003) · Biodegradation · doi:10.1023/a:1024012015127 · Cited by 24
Application of Aureobasidium pullulans in iron‐poor soil. Can the production of siderophores improve iron bioavailability and yeast antagonistic activity?
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Arsenic-HypertolerantPseudomonadsIsolated from Ancient Gold and Copper-Bearing Black Shale Deposits
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“It was observed that PDTC forms soluble complexes with essential metals such as Co, Cu, Fe, Ni and Zn, but causes precipitation of toxic metals and metalloids (As, Cd, Hg, Pb, Se and Te) (Cortese et al. 2002).”
Background
Identification of siderophores of Pseudomonas stutzeri
Zawadzka, A. M., Vandecasteele, F. P. J., Crawford, R. L., & Paszczynski, A. J. (2006) · Canadian Journal of Microbiology · doi:10.1139/w06-077 · Cited by 20
“Pseudomonas stutzeri KC produces the secondary siderophore pyridine2,6-bis(thiocarboxylic acid) (pdtc), which chelates iron and several other metals (Sebat et al. 2001; Stolworthy et al. 2001; Cortese et al. 2002) and facilitates iron uptake into the cells (Lewis et al.”
BackgroundSelf-citation
Structural, functional, and evolutionary analysis of moeZ, a gene encoding an enzyme required for the synthesis of the Pseudomonas metabolite, pyridine-2,6-bis(thiocarboxylic acid)
Cortese, M. S., Caplan, A., & Crawford, R. L. (2002) · BMC Evolutionary Biology · doi:10.1186/1471-2148-2-8 · Cited by 19
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The determination of the stability constant for the iron(II) complex of the biochelator pyridine-2,6-bis(monothiocarboxylic acid)
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“Sodium dithionite (Na2S2O4) causes the reduction of the FeIII(pdtc)1−2 to FeII(pdtc) 2− 2 accompanied by a change in solution color from brown to blue (Ockels et al. 1978; Hildebrand et al. 1984; Cortese et al. 2002).”
BackgroundMethodInfluentialSelf-citation
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“Abstract 3.8.4S). The possibility of disease suppression due to siderophore production opens the door to further investigations on both the natural siderophores, produced by the indigenous fluorescent pseudomonad selectively increased in our system, as well as the synthetic siderophore-type chelator such us nitrapyrin…”
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“Its novelty lies in the ability to form stable complexes with a wide range of transition metals in addition to iron (3), a role in zinc nutrition (4), and unique reactivity with a toxic pollutant (carbon tetrachloride [CCl4]) (5).”
BackgroundSelf-citation
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“Literature suggests that SeO3 reduction can occur aerobically via detoxification [1,6], via Painter-type reactions (Equation (1)) [13,14] or with the aid of siderophores [15,16], as a form of self-defence.”
Background
A Cross-Metabolomic Approach Shows that Wheat Interferes with Fluorescent Pseudomonas Physiology through Its Root Metabolites
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“In this study, we did not detect PDTC, which is known to be quite unstable in solution [80].”
Background
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Bultreys, A. (2007) · Springer eBooks · doi:10.1007/978-3-540-71160-5_3 · Cited by 14
Ferrihydrite dissolution by pyridine-2,6-bis(monothiocarboxylic acid) and hydrolysis products
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“Evidence indicates that PDTC can function as a siderophore, a ferric iron reductant, and as an antimicrobial agent (Cortese et al., 2002; Criddle et al., 1990; Hersman et al., 2000; Lewis et al., 2004; Sebat et al., 2001).”
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“For example, PDTC is a metal chelator 39 that may inhibit MMP-9 activity directly because MMP-9 is a metalloprotease.”
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“( Cortese et al. 2002; Johnstone and Nolan 2015).”
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“…cobalt-binding ligand candidates that may be detected with this method include siderophores, to which cobalt(III) has very high binding af ﬁ nity (Cortese et al. 2002; Duckworth et al. 2009), and porphyrins, which are structurally very similar to corrins and include magnesium(II) or iron(II)…”
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Goupil, A. (2024) · theses.fr (ABES) · doi:10.70675/5cc37434zda6dz40baz974ezd8fded31cbed

Transformations of Toxic Metals and Metalloids by Pseudomonas stutzeri Strain KC and its Siderophore Pyridine-2,6-bis(thiocarboxylic acid)
Zawadzka, A. M., Paszczynski, A. J., & Crawford, R. L. (2009) · Soil biology · doi:10.1007/978-3-540-89621-0_12 · Cited by 12
Self-citation
Metal binding by pyridine-2,6-bis(monothiocarboxylic acid), a biochelator produced by Pseudomonas stutzeri and Pseudomonas putida
Stolworthy, J. C., Paszczynski, A. J., Korus, R. A., & Crawford, R. L. (2001) · Biodegradation · doi:10.1023/a:1015067729660 · Cited by 30
Self-citation
Pyridine-2,6-Bis(Thiocarboxylic Acid) Produced by Pseudomonas stutzeri KC Reduces and Precipitates Selenium and Tellurium Oxyanions
Zawadzka, A. M., Crawford, R. L., & Paszczynski, A. J. (2006) · Applied and Environmental Microbiology · doi:10.1128/aem.72.5.3119-3129.2006 · Cited by 54
Self-citation
The determination of the stability constant for the iron(II) complex of the biochelator pyridine-2,6-bis(monothiocarboxylic acid)
Brandon, M. S., Paszczynski, A. J., Korus, R., & Crawford, R. L. (2003) · Biodegradation · doi:10.1023/a:1024080521897 · Cited by 18
Self-citation
Identification and characterization of Pseudomonas membrane transporters necessary for utilization of the siderophore pyridine-2,6-bis(thiocarboxylic acid) (PDTC)
Leach, L. H., & Lewis, T. A. (2006) · Microbiology · doi:10.1099/mic.0.29116-0 · Cited by 14
Self-citation

Authors: Cortese, M. S., Paszczynski, A., Lewis, T. A., Sebat, J. L., Borek, V., & Crawford, R. L.
Affiliations: University of Idaho (US)
University of Vermont (US)
Corresponding author: Paszczynski, Andrzej
ORCID: Cortese, Marc S.
Sebat, Jonathan L.
Venue: Biometals
Publisher: Springer Science and Business Media LLC
Published: 2002-06
Volume: 15
Issue: 2
Pages: 103-120
ISSN: 0966-0844 (ISSN-L)
1572-8773
DOI: 10.1023/a:1015241925322
OpenAlex: W1605651663
Cited by: 68
References: 49
Citations by year: 2025: 3 · 2024: 5 · 2023: 2 · 2022: 2 · 2021: 5 · 2020: 5 · 2019: 2 · 2018: 2 · 2017: 2 · 2016: 2 · 2015: 5 · 2014: 2 · 2013: 1 · 2012: 2
FWCI: 1.72
Type: journal article
Language: en
Open access: closed
Licence: www.springernature.com/gp/researchers/text-and-data-mining (tdm)
www.springernature.com/gp/researchers/text-and-data-mining (vor)
Locations: BioMetals (publishedVersion)
PubMed (publishedVersion)
Cold Spring Harbor Laboratory Institutional Repository (Cold Spring Harbor Laboratory) (acceptedVersion)
Funders: U.S. Department of Energy
Topics: Physical Sciences › Chemistry › Inorganic Chemistry › Inorganic and Organometallic Chemistry
Physical Sciences › Environmental Science › Health, Toxicology and Mutagenesis › Chromium effects and bioremediation
Physical Sciences › Materials Science › Metals and Alloys › Metal Extraction and Bioleaching
Keywords: metal chelation, metal complexes, redox-active complexes, cadmium toxicity, tellurium toxicity, iron absorption, Pseudomonas stutzeri, Pseudomonas putida, iron oxyhydroxide reduction, metalloids
MeSH terms: Bacteria, Candida albicans, Chelating Agents, Diagnostic Imaging, Iron, Microbial Sensitivity Tests, Oxidation-Reduction, Pseudomonas, Pyridines, Mass Spectrometry, Molecular Structure, Metals, Heavy

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Metal chelating properties of pyridine-2,6-bis(thiocarboxylic acid) produced by Pseudomonas spp. and the biological activities of the formed complexes

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