On the Development of Selective Chelators for Cadmium: Synthesis, Structure and Chelating Properties of 3-((5-(trifluoromethyl)-1,3,4-thiadiazol-2-yl)amino)benzo[d]isothiazole 1,1-dioxide, a Novel Thiadiazolyl Saccharinate

Leal, Joana F.; Guerreiro, Bruno; Amado, Patrícia S. M.; Fernandes, A. L. T.; Barreira, Luísa; Paixão, J. A.; Cristiano, Maria Lurdes Santos

doi:10.3390/molecules26061501

Cited by 6 publications

(4 citation statements)

References 34 publications

(32 reference statements)

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“…It would be necessary to have a proper solution in the case of applying pMet-lead to wastewater Pb detections. The strategy of using metal chelators similar to tricine (Zn), such as penicillamine to Cu [51], DMPS to Hg [52], and 3-((5-(trifluoromethyl)-1,3,4-thiadiazol-2-yl)amino)benzo[d]isothiazole 1,1-dioxide (AL14) [53] to Cd could be a good solution to integrate into pMet-lead in the future.…”

Section: Discussionmentioning

confidence: 99%

Portable FRET-Based Biosensor Device for On-Site Lead Detection

Lai

Chang²,

Chou

et al. 2022

Biosensors

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Most methods for measuring environmental lead (Pb) content are time consuming, expensive, hazardous, and restricted to specific analytical systems. To provide a facile, safe tool to detect Pb, we created pMet-lead, a portable fluorescence resonance energy transfer (FRET)-based Pb-biosensor. The pMet-lead device comprises a 3D-printed frame housing a 405-nm laser diode—an excitation source for fluorescence emission images (YFP and CFP)—accompanied by optical filters, a customized sample holder with a Met-lead 1.44 M1 (the most recent version)-embedded biochip, and an optical lens aligned for smartphone compatibility. Measuring the emission ratios (Y/C) of the FRET components enabled Pb detection with a dynamic range of nearly 2 (1.96), a pMet-lead/Pb dissociation constant (Kd) 45.62 nM, and a limit of detection 24 nM (0.474 μg/dL, 4.74 ppb). To mitigate earlier problems with a lack of selectivity for Pb vs. zinc, we preincubated samples with tricine, a low-affinity zinc chelator. We validated the pMet-lead measurements of the characterized laboratory samples and unknown samples from six regions in Taiwan by inductively coupled plasma mass spectrometry (ICP-MS). Notably, two unknown samples had Y/C ratios significantly higher than that of the control (3.48 ± 0.08 and 3.74 ± 0.12 vs. 2.79 ± 0.02), along with Pb concentrations (10.6 ppb and 15.24 ppb) above the WHO-permitted level of 10 ppb in tap water, while the remaining four unknowns showed no detectable Pb upon ICP-MS. These results demonstrate that pMet-lead provides a rapid, sensitive means for on-site Pb detection in water from the environment and in living/drinking supply systems to prevent potential Pb poisoning.

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Section: Discussionmentioning

confidence: 99%

Portable FRET-Based Biosensor Device for On-Site Lead Detection

Lai

Chang²,

Chou

et al. 2022

Biosensors

View full text Add to dashboard Cite

show abstract

“…It would be necessary to have a proper solution in case of applying pMet-lead to wastewater Pb detections. The strategy of using metal chelators similar to tricine (Zn), such as penicillamine to Cu [51], DMPS to Hg [52], and 3-((5-(trifluoromethyl)-1,3,4-thiadiazol-2-yl)amino)benzo[d]isothiazole 1,1-dioxide (AL14) [53] to Cd will be a good solution combined inside pMet-lead in the future.…”

Section: Discussionmentioning

confidence: 99%

Portable FRET-Based Biosensor Device for On-Site Lead Detections

Lai¹,

Chang²,

Chou³

et al. 2022

Preprint

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Most methods for measuring environmental lead (Pb) content are time consuming, expensive, hazardous, and restricted to specific analytical systems. To provide a facile, safe tool to detect Pb, we created pMet-lead, a portable fluorescence resonance energy transfer (FRET)-based Pb biosensor. pMet-lead comprises a 3D-printed frame housing a 405-nm laser diode — an excitation source for fluorescence emission images (YFP and CFP) — accompanied by optical filters, a customized sample holder with a Met-lead 1.44 M1 (the most recent version)-embedded biochip, and an optical lens aligned for smartphone compatibility. Measuring the emission ratios (Y/C) of the FRET component enables Pb detection with a dynamic range of nearly 2 (1.96), pMet-lead/Pb dissociation constant (Kd) 45.62 nM, and limit of detection 40 nM (0.832 μg/dL, 8.32 ppb). To mitigate earlier problems with lack of selectivity for Pb vs. zinc, we preincubated samples with tricine, a low-affinity zinc chelator. We validated pMet-lead measurements of characterized laboratory samples and unknown samples from six regions in Taiwan by inductively coupled plasma mass spectrometry (ICP-MS). Notably, two unknowns had Y/C ratios significantly higher than that of the control (3.48 ± 0.08 and 3.74 ± 0.12 vs. 2.79 ± 0.02), along with Pb concentrations (10.6 ppb and 15.24 ppb) above the WHO-permitted level of 10 ppb in tap water, while the rest four unknowns showing no detectable Pb upon ICP-MS. These results demonstrate that pMet-lead provides a rapid, sensitive means for on-site Pb detection in water from the environment and in living/drinking supply systems to prevent potential Pb poisoning.

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“…Several 1,3,4-thiadiazole-based molecules were found to display a broad range of biological activities, such as antimicrobial [39], anticancer [40], antifungal [41], anti-inflammatory [42], antituberculosis [43], antioxidant [44], anticonvulsant [45], anti-depressant and anxiolytic [46], and antihypertensive [47]. The most notable thiadiazole-based drug so far is acetazolamide [N-(5-sulfamoyl-1,3,4thiadiazol-2-yl)acetamide] (Figure 1), recognized as a carbonic anhydrase inhibitor, used for the treatment of high-altitude illness [48], epileptic seizures [49], glaucoma [50], idiopathic intracranial hypertension [51], hemiplegic migraine [52], or obstructive sleep apnea [53]. Following up on recent research aimed at the discovery of biologically active heterocyclic derivatives of the azole-type, strongly inspired by the conviction of Barry Sharpless on the conception of new molecules ("If chemists choose simple reactions, where there is a strong intrinsic drive for the molecules to bond together, they avoid many of the side reactions, with a minimal loss of material."…”

Section: Introductionmentioning

confidence: 99%

Hybrid azole-based conjugates as upcoming anticancer and antimicrobial agents

Frija,

Guerreiro,

Costa

et al. 2023

Explor Drug Sci

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Aim: This study discloses the synthesis and the antimicrobial and anticancer activities of four molecules of structural basis saccharin-thiadiazolyl (4), saccharin-pyridyl (6, 8), and tetrazole-thiadiazolyl (11). Methods: Antimicrobial properties of the molecules were evaluated by the well-diffusion method, against Gram-positive bacteria [Staphylococcus aureus American Type Culture Collection (ATCC) 25923, Staphylococcus epidermidis ATCC 12228, Mycobacterium smegmatis ATCC 607], Gram-negative bacteria (Pseudomonas aeruginosa ATCC 27853) and yeast (Saccharomyces cerevisiae ATCC 2601 and Candida albicans ATCC 10231) strains. The anticancer activity of the compounds was assessed through i) proliferation assays for HCT116, MCF-7, and A375 human cell lines [cells were treated with serial dilutions of compounds and the effect on cell propagation was evaluated by sulforhodamine B (SRB) assay]; ii) antiproliferative and cytotoxic assays for glioma-type cell lines A172 (glioblastoma), U87 (brain-likely glioblastoma), and H4 (neuroglioma; cells were treated with diverse concentrations and the cell viability was assessed using a modified Alamar blue® assay). Results: Compound 11 exhibited significant inhibitory activity against S. aureus and S. epidermidis, with the further molecules demonstrating some inhibitory potential against all the tested Gram-positive, Gram-negative, and yeast strains. Similarly, derivative 11 showed an interesting antiproliferative activity against human colon adenocarcinoma (HCT116), human breast adenocarcinoma (MCF-7), and melanoma (A375) cells, with 50% growth inhibition (GI50) values varying from 3.55 µmol/L to 11.5 µmol/L, in the same order of magnitude of those shown by etoposide. Treatment of brain-like glioblastoma cells (U87) with 11, at the concentration of 100 µg/mL, induced a decrease in cell viability by 50% after 48 h and 72 h. Besides, results attained for A172 cells have shown that compound 11 only induces a significant decrease in cell viability upon treatment at 100 µg/mL for 72 h. A divergent observation was recorded for H4 cells, where the treatment with derivative 11 had promoted a significant decrease in cell viability (< 40–60%), even at concentrations as low as 0.39 µg/mL, after 24 h. Conclusions: This investigation reveals the potential of distinct azole-based conjugates, in particular the tetrazole-thiadiazolyl (11) derivative, as scaffolds worth further investigations, in the frame of antimicrobial and antineoplastic chemotherapy.

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On the Development of Selective Chelators for Cadmium: Synthesis, Structure and Chelating Properties of 3-((5-(trifluoromethyl)-1,3,4-thiadiazol-2-yl)amino)benzo[d]isothiazole 1,1-dioxide, a Novel Thiadiazolyl Saccharinate

Cited by 6 publications

References 34 publications

Portable FRET-Based Biosensor Device for On-Site Lead Detection

Portable FRET-Based Biosensor Device for On-Site Lead Detection

Portable FRET-Based Biosensor Device for On-Site Lead Detections

Hybrid azole-based conjugates as upcoming anticancer and antimicrobial agents

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