Catalyzed Azide Alkyne Cycloaddition Research Articles

Metallo-Glycodendrimeric Materials against Enterotoxigenic Escherichia coli

Conjugation of carbohydrates to nanomaterials has been extensively studied and recognized as an alternative in the biomedical field. Dendrimers synthesized with mannose at the end group and with entrapped zero-valent copper/silver could be a potential candidate against bacterial proliferation. This study is aimed at investigating the bactericidal activity of metal-glycodendrimers. The Cu(I)-catalyzed azide–alkyne cycloaddition (CuAAC) reaction was used to synthesize a new mannosylated dendrimer containing 12 mannopyranoside residues in the periphery. The enterotoxigenic Escherichia coli fimbriae 4 (ETEC:F4) viability, measured at 600 nm, showed the half-inhibitory concentration (IC50) of metal-free glycodendrimers (D), copper-loaded glycodendrimers (D:Cu) and silver-loaded glycodendrimers (D:Ag) closed to 4.5 × 101, 3.5 × 101 and to 1.0 × 10−2 µg/mL, respectively, and minimum inhibitory concentration (MIC) of D, D:Cu and D:Ag of 2.0, 1.5 and 1.0 × 10−4 µg/mL, respectively. The release of bacteria contents onto broth and the inhibition of ETEC:F4 biofilm formation increased with the number of metallo-glycodendrimer materials, with a special interest in silver-containing nanomaterial, which had the highest activity, suggesting that glycodendrimer-based materials interfered with bacteria-bacteria or bacteria–polystyrene interactions, with bacteria metabolism and can disrupt bacteria cell walls. Our findings identify metal–mannose-dendrimers as potent bactericidal agents and emphasize the effect of entrapped zero-valent metal against ETEC:F4.

Synthesis of modified Schiff base triazole appended silatrane: Elucidating the in vitro and in silico plant growth potential

In the current investigation, modified Schiff base triazole appended silatrane (MSBTAS) has been synthesized using a facile, copper(I) catalyzed alkyne azide cycloaddition (CuAAC) approach. The presence of three plant growth regulating moieties i.e. Schiff base, triazole and silatrane make MSBTAS a unique and an uncommon plant growth regulator (PGR). The effects of different concentrations of MSBTAS (25, 50, 100, and 200 µmol L−1) and three control set-ups on the root and shoot length of two staple crops i.e. Zea mays (corn) and Vigna radiata (mung bean) have been studied. MSBTAS did not show a dose-dependent relationship with the root and shoot length enhancement of the crops. The concentrations 50 µmol L−1 and 100 µmol L−1 were statistically different and better than the control groups for the increase in root and shoot length of Z. mays. For V. radiata, the concentrations 25 µmol L−1 for root length along with 25 µmol L−1 and 50 µmol L−1 for shoot length were statistically different and better than the relative control groups. The in-silico studies have been performed using molecular docking to understand the interaction between MSBTAS and the plant growth protein, resulting in a good binding energy of -7.07 kcal/mol. The docking results obtained with MSBTAS have been validated by comparing the docking results obtained with commercially available PGR, paclobutrazol.

Extending the Scope of the C-Functionalization of Cyclam via Copper(I)-Catalyzed Alkyne-Azide Cycloaddition to Bifunctional Chelators of Interest.

Cyclam, known for its potent chelation properties, is explored for diverse applications through selective N-functionalization, offering versatile ligands for catalysis, medical research, and materials science. The challenges arising from N-alkylation, which could decrease the coordination properties, are addressed by introducing a robust C-functionalization method. The facile two-step synthesis proposed here involves the click chemistry-based C-functionalization of a hydroxyethyl cyclam derivative using Cu(I)-catalyzed alkyne-azide cycloaddition (CuAAC). Boc-protecting groups prevent undesired copper coordination, resulting in compounds with a wide range of functionalities. The optimized synthesis conditions enable C-functional cyclams to be obtained easily and advantageously, with high application potential in the previously cited fields. The methodology has been extended to trehalose-based Siamese twin amphiphiles, enabling efficient gene delivery applications.

Sustained zero-order release of dexamethasone after incorporation into crosslinked PEG-dendrons using click reactions

Hydrogel-based localised drug delivery minimises systemic side effects and a linear release profile ensuring a sustained drug release over time, crucial for long-term therapy. The current paper describes the use of the Copper(I)-catalyzed Azide-Alkyne Cycloaddition (CuAAc) to append azidified Dexamethasone (Dex) onto dendrons of first- and second-generation PEGs. Crosslinking with thiolated PEGs using either thiol-acrylate or nucleophilic addition reactions yielded gels containing β-thio-ether ester groups that imparted enhanced hydrolytic susceptibility. In vitro gel degradation was followed gravimetrically and expressed as swelling ratios. Thiol-acrylate crosslinked hydrogels exhibited zero-order Dex release kinetics over 11, 27, and 16 days (G1, G1-star, and G2). Crosslinking the G1-gels by nucleophilic addition also resulted in linear release and the end point was reached in 5 days. Hydrolysis was accounted as the main release mechanism for covalently bound Dex, while physically incorporated Dex showed undefined rapid burst or first-order release, with most of the drug released in the initial 1–3 days. Eluates from covalently bound Dex maintained high activity, whereas Trap-Dex gels lost activity over time, as detected by the upregulation of luciferase expression from a transformed cell line. This novel chemistry combination offers precise drug release control applicable beyond Dex to drugs with suitable nucleophilic groups.

Tailored isatin-derived chemosensor immobilized on silica nanoparticles for targeted detection of Ni(II) ion

In this study, we have designed and synthesized a chemosensor, isatin-based triazole-linked silanes (ITS), employing the Cu(I)-catalyzed Azide-Alkyne cycloaddition reaction (CuAAC) and the synthesized silanes has been well characterized through various analytical techniques, including FT-IR, 1H NMR, 13C NMR, and ESI-MS. The developed sensor exhibited the capability to detect Ni2+ ion in a methanol/water solution (9:1, v/v) by manifesting different absorbance changes and fluorescence. In the fluorescence mode, the addition of Ni2+ ion triggers a “Turn-OFF” response in the sensor, demonstrating an ultratrace detection limit of 2.49 × 10−7 M. Successful grafting of organosilane onto silica nanoparticles has been achieved, and these new silane-coated nanoparticles demonstrate enhanced sensing abilities for Ni2+ ions, with a detection limit of 1.56 × 10−8 M. Stoichiometric data reveals a 1:1 coordination between the sensor and Ni2+ ion. Furthermore, both the synthesized alkyne and silane underwent examination for their drug-likeness profiles, providing valuable insights.

Abstract 4168: Pre-clinical demonstration of Raman spectroscopy-assisted photothermal therapy for prostate cancer

Abstract Prostate cancer (PCa) ranks among the most prevalent malignancies in men. The combination of ultrasound and fine-needle aspiration biopsy has greatly facilitated early diagnosis and expanded the range of treatment options. Traditional treatments primarily involve anti-androgens and androgen deprivation therapy; however, a recurrence occurs in approximately 30% of cases following these interventions. Our current focus is on the exploration of photothermal therapies using nanoparticles for precise tumor ablation. Among these nanoparticles, multiwalled carbon nanotubes (MWCNTs) exhibit unique structural, optical, and thermal properties that make them exceptionally appealing for biomedical applications, especially as a foundation for photothermal therapy. Our platform employs the copper (I)-catalyzed azide alkyne cycloaddition of prostate-specific membrane antigen (PSMA)-targeting peptidomimetic (Glu-urea-Lys) ligand to the MWCNTs. We used confocal microscopy to observe a significantly enhanced binding of the targeted Glu-urea-Lys-MWCNTs to the surfaces of PSMA-expressing LNCaP cells compared to IgG-MWCNTs and to PSMA-null PC3 cells. Raman microscopy further confirmed the increased presence of Glu-urea-Lys-MWCNTs on LNCaP spheroids compared to non-targeting MWCNTs. We also confirmed enhanced photothermal cell ablation in vitro using the targeted MWCNTs. Based on in vitro evidence, we established LNCaP and PC3 xenografts in nu/nu mice and evaluated the therapeutic efficacy. Using fluorescence-based imaging, we observed the enhanced localization of Glu-urea-Lys-MWCNTs within the tumors. Furthermore, we collected the tumors and conducted ex vivo analysis using Raman microscopy for a label-free detection of the targeted MWCNTs, which complemented the fluorescence imaging and laying the foundation for real-time Raman imaging in vivo. Subsequently, we applied photothermal ablation of the tumor xenografts based on a pre-optimized treatment protocol established from COMSOL simulations and prior experiments. This treatment led to complete tumor ablation with minimal recurrence and minimal non-specific damage. In conclusion, we have assessed the effectiveness of our targeted nano-photothermal platform in a pre-clinical model of PCa. Further studies will aid in the transition of photothermal therapy to clinical trials. Moreover, we aim to investigate the role of photothermal therapy in the PCa tumor microenvironment and whether such an approach can trigger post-therapeutic activation of immune responses against the tumor. Ultimately, we anticipate that our nanotherapeutic platform will contribute to a focused therapeutic approach where targeted MWCNT-laser treatment exploits overexpressed tumor markers in conjunction with various irradiation strategies to enhance ablation while minimizing damage to surrounding tissue. Citation Format: Seung Soo Lee, Gabriel Beaudoin, Jun Hui Yeoh, Frederic Leblond, Mark Trifiro, Miltiadis Paliouras. Pre-clinical demonstration of Raman spectroscopy-assisted photothermal therapy for prostate cancer [abstract]. In: Proceedings of the American Association for Cancer Research Annual Meeting 2024; Part 1 (Regular Abstracts); 2024 Apr 5-10; San Diego, CA. Philadelphia (PA): AACR; Cancer Res 2024;84(6_Suppl):Abstract nr 4168.

Water-Soluble Quaternary and Protonable Basic Chitotriazolans: Synthesis by Click Chemistry Conversion of Chitosan Azides and Investigation of Antibacterial Activity.

The azide transfer reaction and copper(I)-catalyzed alkyne-azide cycloaddition (CuAAC) can be used to convert the amino groups in chitosan to triazole 1,2,3-moieties. The resulting polymer has been named chitotriazolan. This synthesis was performed with six different quaternary ammonium alkynes and three amine alkynes to obtain a series of nine water-soluble chitotriazolan derivatives. The structure and complete conversion of the azide were confirmed by FT-IR and proton NMR spectroscopy. The derivatives were investigated for antibacterial activity against S. aureus, E. faecalis, E. coli, and P. aeruginosa. The activity of the quaternized chitotriazolan derivatives varied depending on the structure of the quaternary moiety and the species of bacteria. The basic protonable derivatives were less active or inactive against the bacteria.

1,3,4,5-Tetrasubstituted Poly(1,2,3-triazolium) Obtained through Metal-Free AA+BB Polyaddition of a Diazide and an Activated Internal Dialkyne.

A tetra(ethylene glycol)-based 1,3,4,5-tetrasubstituted poly(1,2,3-triazolium) is synthesized in two steps including: i) the catalyst-free polyaddition of a diazide and an activated internal dialkyne and ii) the N-alkylation of the resulting 1,2,3-triazole groups. In order to provide detailed structure/properties correlations different analogs are also synthesized. First, parent poly(1,2,3-triazole)s are obtained via AA+BB polyaddition using copper(I)-catalyzed alkyne-azide cycloaddition or metal-free thermal alkyne-azide cycloaddition (TAAC). Poly(1,2,3-triazole)s with higher molar masses are obtained in higher yields by TAAC polyaddition. A 1,3,4-trisubstituted poly(1,2,3-triazolium) structural analog obtained by TAAC polyaddition using a terminal activated dialkyne and subsequent N-alkylation of the 1,2,3-triazole groups enables discussing the influence of the methyl group in the C-4 or C-5 position on thermal and ion conducting properties. Obtained polymers are characterized by 1H, 13C, and 19F NMR spectroscopy, differential scanning calorimetry, thermogravimetric analysis, size exclusion chromatography, and broadband dielectric spectroscopy. The targeted 1,3,4,5-tetrasubstituted poly(1,2,3-triazolium) exhibits a glass transition temperature of -23 °C and a direct current ionic conductivity of 2.0 × 10-6 S cm-1 at 30 °C under anhydrous conditions. The developed strategy offers opportunities to further tune the electron delocalization of the 1,2,3-triazolium cation and the properties of poly(1,2,3-triazolium)s using this additional substituent as structural handle.

Synthesis of an Alternating Polycation with the Dense 1,2,3-Triazole Backbone

AbstractPolycations are an important class of water-soluble polymers because they form polyion complexes with DNA. Thus, the synthesis of polycations with controlled monomer sequences will be of increasing importance for the formation of well-defined polyion complexes. In this study, cationic homopolymer and alternating copolymer with the dense triazole backbone were synthesized by copper(I)-catalyzed azide–alkyne cycloaddition polymerization. The polycations obtained were characterized by potentiometric and turbidimetric titrations, and by complex formation with poly(acrylic acid).

Synthesis of Fused Isoxazoles of Iodoquinol as in vitro EGFR Aiming Anticancer Agents

AbstractWe have presented the synthesis of some new quinoline linked fused isoxazoles via copper (I) catalyzed azide alkyne cycloaddition (CuAAC) followed by intramolecular C−H arylation of isoxazole ring using PdCl2(PPh3)2 catalyst. All the synthesized compounds were investigated for anticancer activity against three human breast cancer cell lines such as MCF‐7, MDA‐MB‐468 and MDA‐MB‐231 using MTT assay and 5‐fluorouracil (5‐FU) was used as a standard drug. In this study, three compounds were exhibited greater activity than reference drug 5‐FU against three cell lines which further screened for in vitro tyrosine kinase EGFR inhibition and molecular docking studies by taking EGFR protein as the target. Finally, insilico pharmacokinetic profile of the same compounds was obtained using SWISSADME where two compounds following Lipinski, Ghose, Veber, Egan, and Muegge rules.

Unveiling the ion sensing capabailities of 'click' derived chalcone-tailored 1,2,3-triazolic isomers for Pb(ii) and Cu(ii) ions: DFT analysis.

In this study, two novel chalcone-derived 1,2,3-triazole-appended positional isomers (probe 6 and probe 9) were synthesized via the 'CuAAC' (Cu(i) - catalysed alkyne azide cycloaddition) methodology for the purpose of metal ion detection. The synthesized probes underwent characterization utilizing standard spectroscopic methodologies including FTIR, NMR (1H and 13C), and mass spectrometry. Subsequently, the sensing capabilities of these probes were explored using UV-Vis and fluorescence spectroscopy, wherein their selective recognition potential was established for Pb(ii) and Cu(ii), both of which can pose serious health hazards when prevalent in the environment above permissible limits. Both the probes exhibited fairly low limits of detection (LoD), determined as 5.69 μM and 6.55 μM in the case of probe 6 for Pb(ii) and Cu(ii) respectively; whereas the probe 9 exhibited an LoD of 5.06 μM and 7.52 μM for Pb(ii) and Cu(ii), respectively. The job's plot for the probe demonstrates the formation of a 1 : 1 complex between the metal and ligand. Furthermore, the interaction of the free probes with the metal ions in the metal-ligand complex was elucidated through 1H NMR analysis and validated theoretically using Density Functional Theory (DFT) simulations with the B3LYP/6-311G++(d,p) and B3LYP/LANL2DZ basis sets for geometry optimization of the probes and their corresponding metal complexes. These findings offer a reliable approach to Cu(ii) and Pb(ii) ion detection and can be further used for the potential applications in environmental monitoring and analytical chemistry.

Click chemistry-based synthesis of new 1,2,3-triazolo-benzoquinoline-3-carbonitriles: anticancer screening and DFT studies

This study emphasizes the synthesis of a novel series of 1,2,3-triazolo-benzoquinoline-3-carbonitriles by using Cu(i)-catalyzed azide–alkyne cycloaddition known as the click reaction.

Active-metal template clipping synthesis of novel [2]rotaxanes.

Mechanically interlocked molecules (MIMs) have been important synthetic targets in supramolecular chemistry due to their beautiful structures and intriguing properties. We present herein a new synthetic strategy to access [2]rotaxanes, namely active-metal template clipping. We discuss the design of the target [2]rotaxanes, synthesis and characterization of the axle, macrocycle precursors and macrocycles as well as preparation of the final [2]rotaxanes by active template copper(I)-catalyzed alkyne-azide cycloaddition (CuAAC) as key step of the synthesis. HRMS and NMR experiments have been performed to confirm the formation of the interlocked structures.

Synthesis of an alternating copolymer of the dense 1,2,3‐triazole backbone carrying t‐butyl ester and nitrile side chains

AbstractIn these decades, synthesis of polymers with controlled monomer sequences has been of increasing importance in polymer chemistry. When we tested synthesis of a heterodimer of 4‐azido‐5‐hexynoic acid derivatives carrying t‐butyl (tBu) ester and tBu amide side chains for preparation of an alternating copolymer, we unexpectedly obtained a heterodimer precursor carrying tBu ester and nitrile side chains, in a high yield. Since dense 1,2,3‐triazole polymers carrying nitrile side chains are expected as a new functional polymer, the heterodimer is polymerized by copper(I)‐catalyzed azide–alkyne cycloaddition polymerization to obtain an alternating copolymer carrying tBu ester and nitrile side chains in this study. Since 1,2,3‐triazole and nitrile moieties are known to be ligands for metal ions, the complex formation of the alternating copolymer with PdCl2 is also investigated by NMR. In the presence of PdCl2, 1H NMR spectra show broad and separated signals due to the free and complexed copolymers, indicative of slow exchange. Pulse‐field‐gradient spin‐echo NMR data indicated that the coordination of alternating copolymer to PdCl2 made the copolymer chains take a more compact conformation under dilute conditions. The density functional theory calculations indicated that the alternating copolymer coordinated to PdCl2 preferentially through the 1,2,3‐triazole nitrogen and nitrile nitrogen atoms.

Design, Synthesis, and Biological Activity Evaluation of Novel AZT and Adenosine-Derived 1,2,3-Triazoles

CuSO4/hydrazine hydrate was used as a catalyst system for copper(I)-catalyzed alkyne-azide cycloaddition (CuAAC) of AZT and 5′-azido adenosine with terminal alkynes to give 30 novel 1,2,3-triazole derivatives. Screening for their anticancer, anti-inflammatory, angiotensin-converting enzyme 2 (ACE2), and 3C-like protease (3CLpro) inhibitory activities showed that several triazoles of AZT containing murayafoline A and indirubin-3′-oxime inhibited the growth of HepG2 and LU-1 with the IC50 values ranging from 11.01 to 19.87 μg/mL. Besides that, some triazole derivatives of adenosine exhibited anti-inflammatory activity against RAW264.7 cells with the IC50 values within an interval of 12.00–59.48.00 μg/mL. Especially, two triazoles of adenosine with indirubin-3′-oxime at O- and N1 positions expressed the ACE2 and 3CLpro inhibitory activities in which the triazole of adenosine with indirubin-3′-oxime at N1 inhibited both ACE2 and 3CLpro inhibitory activities with IC50 values of 135.62 and 142.95 μg/mL, respectively.

Synthesis of Dense 1,2,3-Triazole Oligomers Consisting Preferentially of 1,5-Disubstituted Units via Ruthenium(II)-Catalyzed Azide-Alkyne Cycloaddition.

Ruthenium(II)-catalyzed azide-alkyne cycloaddition (RuAAC) polymerization of t-butyl 4-azido-5-hexynoate (tBuAH), i.e., a heterobifunctional monomer carrying azide and alkyne moieties, was investigated in this study. RuAAC of the monofunctional precursors of tBuAH yielded a dimer possessing a 1,5-disubstituted 1,2,3-triazole moiety. 1H NMR data showed that the dimer was a mixture of diastereomers. Polymerization of tBuAH using ruthenium(II) (Ru(II)) catalysts produced oligomers of Mw ≈ (2.7-3.6) × 103 consisting of 1,5-disubstituted 1,2,3-triazole units (1,5-units) as well as 1,4-disubstituted 1,2,3-triazole units (1,4-units). The fractions of 1,5-unit (f1,5) were roughly estimated to be ca. 0.8 by comparison of signals of the methine and triazole protons in 1H NMR spectra, indicating that RuAAC proceeded preferentially and thermal Huisgen cycloaddition (HC) somehow took place during the polymerization. The oligomer samples obtained were also characterized by solubility test, size exclusion chromatography (SEC), ultraviolet-visible (UV-Vis) absorption spectroscopy, and thermogravimetric analysis (TGA). The UV-Vis and TGA data indicated that the oligomer samples contained a substantial amount of Ru(II) catalysts. To the best of our knowledge, this is the first report on dense 1,2,3-triazole oligomers consisting of 1,5-units linked via a carbon atom.

Click Chemistry-Inspired Synthesis and Photophysical Studies of Calix[4]arene-Cored Galactosylated and Mannosylated Glycodendrimers

A prompt and modular copper(I)-catalyzed azide–alkyne cycloaddition ʼclickʼ approach has been exploited for the synthesis of galactose- and mannose-coated calixarene-cored G1 generation glycodendrimers. The developed calixarene glycodendrimers were characterized by using spectral techniques (1H NMR, 13C NMR and IR). In photophysical evaluation, UV and fluorescence spectra of the developed compounds were recorded in CH3CN/H2O.

Synthesis and Fungicide Activity onAsperisporium caricaeof Glycerol Derivatives Bearing 1,2,3-Triazole Fragments

In agriculture, the control of fungal infections is essential to improve crop quality and productivity. This study describes the preparation and fungicidal activity evaluation of 12 glycerol derivatives bearing 1,2,3-triazole fragments. The derivatives were prepared from glycerol in four steps. The key step corresponded to the Cu(I)-catalyzed alkyne-azide cycloaddition (CuAAC) click reaction between the azide 4-(azidomethyl)-2,2-dimethyl-1,3-dioxolane (3) and different terminal alkynes (57-91% yield). The compounds were characterized by infrared spectroscopy, nuclear magnetic resonance (1H and 13C), and high-resolution mass spectrometry. The in vitro assessment of the compounds on Asperisporium caricae, that is, the etiological agent of papaya black spot, at 750 mg L-1 showed that the glycerol derivatives significantly inhibited conidial germination with different degrees of efficacy. The most active compound 4-(3-chlorophenyl)-1-((2,2-dimethyl-1,3-dioxolan-4-yl) methyl)-1H-1,2,3-triazole (4c) presented a 91.92% inhibition. In vivo assays revealed that 4c reduced the final severity (70.7%) and area under the disease severity progress curve of black spots on papaya fruits 10 days after inoculation. The glycerol-bearing 1,2,3-triazole derivatives also present agrochemical-likeness properties. Our in silico study using molecular docking calculations show that all triazole derivatives bind favorably to the sterol 14α-demethylase (CYP51) active site at the same region of the substrate lanosterol (LAN) and fungicide propiconazole (PRO). Thus, the mechanism of action of the compounds 4a-4l may be the same as the fungicide PRO, blocking the entrance/approximation of the LAN into the CYP51 active site by steric effects. The reported results point to the fact that the glycerol derivatives may represent a scaffold to be explored for the development of new chemical agents to control papaya black spot.

Polylactic-Containing Hyperbranched Polymers through the CuAAC Polymerization of Aromatic AB2 Monomers.

We report on the synthesis and characterization of a novel class of hyperbranched polymers, in which a copper(I)-catalyzed alkyne azide cycloaddition (CuAAC) reaction (the prototypical "click" reaction) is used as the polymerization step. The AB2 monomers bear two azide functionalities and one alkyne functionality, which have been installed onto a 1,3,5 trisubstituted benzene aromatic skeleton. This synthesis has been optimized in terms of its purification strategies, with an eye on its scalability for the potential industrial applications of hyperbranched polymers as viscosity modifiers. By taking advantage of the modularity of the synthesis, we have been able to install short polylactic acid fragments as the spacing units between the complementary reactive azide and alkyne functionalities, aiming to introduce elements of biodegradability into the final products. The hyperbranched polymers have been obtained with good molecular weights and degrees of polymerization and branching, testifying to the effectiveness of the synthetic design. Simple experiments on glass surfaces have highlighted the possibility of conducting the polymerizations and the formation of the hyperbranched polymers directly in thin films at room temperature.

‘Click’-synthesized PET based fluorescent sensor for Hg(II), Pb(II) and Cr(III) recognition: DFT and docking studies

In this study, a novel photoinduced electron transfer (PET) based 1,2,3-triazole appended chemosensor probe (PRT) for the recognition of toxic heavy metal ions has been developed via Cu(I)-catalyzed alkyne-azide cycloaddition (CuAAC), a quintessential example of ‘click chemistry’ for which the 2022 Nobel prize in chemistry was awarded to Prof. K.B. Sharpless, Prof. M. Meldal and Prof. C. Bertozzi. The synthesized probe was successfully characterized via IR spectroscopy, NMR (1H and 13C) spectroscopy, and mass spectrometry; and additionally demonstrated to selectively sense the highly toxic Hg(II), Pb(II), and the biologically essential Cr(III) ions via absorption and fluorescence spectroscopy. The Job plot of PRT suggested the stoichiometric ratio of 1:1 with the sensed metal ions, whereas the association constant values determined through Benesi-Hildebrand (B-H) equation indicated the strongest binding of PRT with Cr(III) followed by Pb(II) and Hg(II) respectively, even though the competitive metal ion titration revealed the selectivity of PRT for Pb(II) over the other metal ions. The density functional theory (DFT) approach as implemented in the Gaussian 09 package with B3LYP/6-311G++(d,p) and B3LYP/LANL2DZ was used to perform geometry optimization and quantum chemical computations. Above and beyond, PRT was also docked with Interleukin (IL)-6 protein, thereby providing glimpses of its anti-inflammatory potential.