Click Synthesis Research Articles

Unveiling the anti-cancer potentiality of phthalimide-based Analogues targeting tubulin polymerization in MCF-7 cancerous Cells: Rational design, chemical Synthesis, and Biological-coupled Computational investigation

The present study deals with an anti-cancer investigation of an array of phthalimide-1,2,3-triazole molecular conjugates with various sulfonamide fragments against human breast MCF-7 and prostate PC3 cancer cell lines. The targeted 1,2,3-triazole derivatives 4a-l and 6a-c were synthesized from focused phthalimide-based alkyne precursors using a facile click synthesis approach and were thoroughly characterized using several spectroscopic techniques (IR, 1H, 13C NMR, and elemental analysis). The hybrid click adducts 4b, 4 h, and 6c displayed cytotoxic potency (IC50 values of 1.49, 1.07, and 0.56 μM, respectively) against MCF-7 cells. On the contrary, none of the synthesized compounds showed apparent cytotoxic efficacy for PC3 cells (IC50 ranging from 9.87- >100 μM). As a part of the mechanism analysis, compound 6c demonstrated a potent inhibitory effect (78.3 % inhibition) of tubulin polymerization in vitro with an IC50 value of 6.53 µM. In addition, biological assays showed that compound 6c could prompt apoptotic cell death and induce G2/M cell cycle arrest in MCF-7 cells. Accordingly, compound 6c can be further developed as an anti-breast cancer agent through apoptosis-induction.

Microwave-assisted click synthesis, characterisation, and In silico studies of novel 2H-chromene-1,2,3-triazolyl glycoconjugates as potent anticancer and antibacterial agents

A series of novel 2H-chromene-1,2,3-triazolyl glycoconjugates 10a-w were synthesized, well characterized and evaluated for their in vitro antimicrobial and anticancer activities. Among the tested compounds, 10a, 10b, 10u, 10v, and 10w exhibited the most excellent potency against both gram-positive (S. aureus) and gram-negative (E. coli) bacterial strains relative to the standard drug, Gentamicin. The anticancer results showed that in MCF-7 cell line all the tested compounds exhibited better activity as compared to other two cancer cell lines (MDA-MB-231 and A549). Compounds 10t, 10u, 10v, and 10w showed significant cytotoxicity against MCF-7 cell line. The molecular docking studies suggested that all the four potent compounds exhibited a greater affinity for the selected receptors. Experimentally and computationally observed structure-activity relationships indicates, -OCH3 group at R2 position in benzopyran ring with tosyl-protected sugar containing compound 10b and benzyl-protected sugar containing compound 10t enhanced the antibacterial and anticancer activity respectively. Frontier molecular orbital analysis of compounds using the global reactivity parameters indicated that benzyl-protected sugar and acetyl-protected sugar containing compounds are stable and exhibits low reactivity. Moreover, molecular electrostatic potential analysis plots clearly showed that the compounds have strong electrophonic reaction potential. Moreover, the assessment of ADMET predictions revealed favourable pharmacokinetic properties of the investigated compounds. Collectively, it was observed that compounds 10u, 10v, and 10w could be considered as promising dual anticancer antibiotic inhibitors.

Synthesis of chiral Cu(II) complexes from pro-chiral Schiff base ligand and investigation of their catalytic activity in the asymmetric synthesis of 1,2,3-triazoles

A pro-chiral Schiff base ligand (HL) was synthesized by the reaction of 2-amino-2-ethyl-1,3-propanediol and pyridine-2-carbaldehyde in methanol. The reaction of HL with CuCl2·2H2O and CuBr2 in methanol gave neutral mononuclear Cu(II) complexes with general formula of [Cu(HL)Cl2] (1) and [Cu(HL)Br2] (2), respectively. By slow evaporation of the methanolic solutions of 1 and 2, their enantiomers were isolated in crystalline format. The formation of pure chiral crystals in the racemic mixture was amply authenticated by single crystal X-ray analysis, which indicated that S-[Cu(HL)Cl2], R-[Cu(HL)Cl2], and S-[Cu(HL)Br2] are crystallized in chiral P212121 space group of orthorhombic system. Preferential crystallization was used to isolate the R and S enantiomers as single crystals and the isolated compounds were also studied by CD analysis. Structural studies indicated that the origin of the chirality in these compounds is related to the coordination mode of the employed pro-chiral ligand (HL) because one of its carbon atoms has been converted to a chiral center in the synthesized complexes. Subsequently, these complexes were used in click synthesis of a β-hydroxy-1,2,3-triazole and the results of catalytic studies indicated that 1 and 2 can act as enantioselective catalysts for the asymmetric synthesis of β-hydroxy-1,2,3-triazole product under mild condition. This study illustrates the significant capacity of the use of pro-chiral ligands in preparing chiral catalysts based on complexes which can also be considered as an effective approach to cheap chiral catalysts from achiral reagents.

Fe3O4@Zein nanocomposites decorated with copper(II) as an efficient, durable, and biocompatible reusable catalyst for click synthesis of novel fluorescent 1,4-disubstituted-1,2,3-triazoles in water

In this paper, we have constructed Fe3O4@Zein-Cu(II) NPs as a novel reusable heterogeneous and superparamagnetic catalyst in Cu-catalysed azide-alkyne cycloaddition reactions (CuAAC). This magnetic Cu(II) nanocomposites were characterized by fourier transform infrared spectroscopy (FT-IR), X-ray diffraction (XRD), field emission scanning electron microscopy (FE-SEM), transmission electron microscopy (TEM), energy dispersive X-ray analysis (EDX), thermogravimetric analysis (TGA), vibration sample magnetometer (VSM) and X-ray photoelectron spectroscopy (XPS). This biocompatible and inexpensive magnetic nanocomposite catalyses smoothly the regioselective click preparation of new fluorescent 1,4-disubstituted-1,2,3-triazoles of 1,8-naphthilimide and 3-nitrophthalimide with quantum yields 0.153 to 0.371 in good to excellent yields under mild conditions in H2O without using any ligands and reducing agents. The catalyst could be easily recovered with the aid of an external magnet and reused up to seven consecutive runs without significant reduction in its activity.

Click functionalized naphthalene contained polycarbazole microspheres for use in electrochromic applications

New fluorescent and electropolymerizable monomer 2-((1-(naphthalene-1-yl)-1H-1,2,3-triazole-4-yl)methoxy)-9H-carbazole (NPC) was designed via efficient click synthesis of naphthalene and carbazole moiety. NPC was characterized using 1H NMR, 13C NMR, FTIR, fluorescence, and UV–vis spectroscopy. The produced monomer was electropolymerized by electrochemical oxidation of carbazole moieties on indium tin oxide in the ACN: BFEE (2:1, v/v) where LiClO4 was used as the supporting electrolyte. The resulting polymer film PNPC depicted well-defined electrochemical properties and a low monomer oxidation potential at around 0.80 V. PNPC displayed multi-electrochromic behaviors, which have color changing from transparent to dark blue reversibly when different voltages were applied. The remarkable electrochromic behavior of the PNPC was explained in detail with the help of spectroelectrochemical studies. The PNPC film exhibited high optic contrast of 77% at 701 nm and a fast-switching time of 1.0 s. When the surface morphology was examined via scanning electron microscopy (SEM), it was determined that PNPC film formed self-assembled microspheres electrochemically. Due to their high optical contrast and stable electrochemical characteristics, these microspheres might be a desirable option as electrode materials for use in electrochromic applications.

Synthesis, characterization, docking and antimicrobial studies of binol based amide linked symmetrical bistriazoles

The antimicrobial resistance and excessive use of modern drugs has hampered the treatment of infectious disease. Therefore, the development of new antibiotics with very good efficacy and lesser side effects is the focused area of medicinal chemists. In the present work, the design and copper (I) catalyzed click synthesis of some amide linked binol based 1,4-disubstituted 1,2,3-bistriazole hybrids from bisalkyne precursor is reported along with characterization of the newly synthesized bistriazoles with the support of IR, NMR and HRMS spectral techniques. The in vitro antimicrobial screening of these bistriazoles against selected bacterial (S. aureus, B. subtilis, and E. coli) and fungal (A. niger and C. albicans) strains signifies the importance of amide and triazole moiety in the final derivatives. The in silico docking studies further supports the antimicrobial results through various binding interactions with binding energies of compound 6f (1KZN: 9.7 kcal/mol) and 6h (4WMZ: 13,3 kcal/mol).

Construction and Characterization of Fe3O4-Bis[Imine-Pyridine]-Cu(OAc)2 Nanocomposite: A Novel and Ecofriendly Reusable Nanocatalyst for Click Synthesis of 1-aryl-1,2,3-Triazole Derivatives

1,2,3-triazoles exist in the structure of many natural compounds and are important because of their biological properties. Considering the high importance of these compounds in medical and biological processes, providing new, efficient and green catalytic systems for their synthesis is considered as an important challenge among synthetic chemists. Multicomponent reactions provide a shorter and more efficient method for the synthesis of natural compounds and complex molecules, especially heterocyclic compounds. During the last decade, the immobilization of metallic catalysts especially copper catalysts on the surface of magnetic nanoparticles modified with ligand has presented a nice and efficient catalytic system for the performance of chemical reactions. In this research work, we fabricated successfully Fe3O4-Bis[Imine-Pyridine]-Cu(OAc)2 nanocomposite and investigated its activity in the click synthesis of 1-aryl-1,2,3-triazole derivatives through the one-pot three-component reaction of aryl boronic acids with alkynes and sodium azide under mild conditions. The Fe3O4-Bis[Imine-Pyridine]-Cu(OAc)2 catalyst showed high activity and could be recovered and reused seven times without significant loss in catalytic activity and selectivity.

Nanomagnetic tetraaza (N4 donor) macrocyclic Schiff base complex of copper(ii): synthesis, characterizations, and its catalytic application in Click reactions.

In this research, a novel nanomagnetic tetra-azamacrocyclic Schiff base complex of copper(ii) was produced via a post-synthetic surface modification of an Fe3O4 surface by a silane-coupling agent that contains acetylacetone functionalities at the end of its chain. Moreover, the target Cu complex that involves a tetradentate Schiff base ligand was obtained from a template reaction with o-phenylenediamine and Cu(NO3)2·3H2O. Furthermore, the prepared complex was nominated as [Fe3O4@TAM-Schiff-base-Cu(II)]. The Fourier-transform infrared (FT-IR) analysis indicates the presence of a Schiff-base-Cu complex in the catalyst. X-ray spectroscopy (EDS) and TGA analysis reveal that approximately 6-7% of the target catalyst comprises hydrocarbon moieties. The scanning electron microscope (SEM) and transmission electron microscopy (TEM) images demonstrate the presence of uniformly shaped particles, nearly spherical in nature, with sizes ranging from 9 to 18 nm. [Fe3O4@TAM-Schiff-base-Cu(II)] was applied as a catalyst for the click synthesis of a diverse range of 5-substituted-1H-tetrazoles in PEG-400 as a green medium. Regarding the electrical properties of the Cu(ii) complex, the presence of a tetra-aza (N4 donor) macrocyclic Schiff base as an N-rich ligand was reasonable - leading to its excellent capacity to catalyze these organic transformations. Finally, the high magnetization value (44.92 emu g-1) of [Fe3O4@TAM-Schiff-base-Cu(II)] enables its recycling at least four times without compromising the catalytic efficiency.

Introduction of Click Synthesized Novel Organic-Inorganic Solid Acid Catalysts for Highly Promoted Synthesis of Substituted Xanthenes

Herein, two new organic-inorganic Brønsted acidic ionic solids with phosphotungstate anion (BAIS-PW) based on click synthesis strategy are introduced for the efficient synthesis of highly substituted xanthenes. The approach to achieve these BAIS-PW organic-inorganic hybrids includes three-step consecutive reactions. At the first step, mono and di-substituted-1H-1,2,3-triazoles were prepared under click preparation conditions. In the second step, the prepared 1,2,3-triazole substrates were reacted with 1,4-butanesultone to give targeted 1,2,3-triazolium-N-butyl sulfonate zwitterions. In the final step, organic zwitterions were treated with aqueous solution of phosphotungstic acid to achieve the desired BAIS-PW organic-inorganic hybrids with organic 1,2,3-triazolum cation and phosphotungstate anion. This is the first report describing the preparation of BAIS using click chemistry. The prepared BAIS-PW hybrids were well characterized and confirmed using FTIR, 1H and 13C NMR, XRD, elemental analysis (CHNS), DSC and TGA techniques. The introduced BAIS catalysts have good thermal stability. The catalytic efficiency of the introduced SO3H-functionalized organic-inorganic catalysts was examined for the one-pot synthesis of substituted xanthenes. It was found that low amount of BAIS catalysts (10 mmol%) is optimized amount to achieve desired substituted xanthenes under solvent free conditions in short times (5–10 min) with high isolated yields (90–95%) and high turnover number (TON) and turnover frequency (TOF). Some superiorities of the introduced catalysts are their novelty, simple separation and their reusability up to six repeated runs without significant catalytic deactivation.

Neodymium-based metal-organic framework as an efficient catalyst for green synthesis of benzylidene-2-phenylhydrazine analogues

Neodymium-based metal-organic framework (Nd-MOF) has been prepared as an efficient heterogeneous catalyst in the click synthesis of benzylidine-2-phenylhydrazine analogs for the first time. In the presence of Nd-MOF, the reaction proceeds with mild conditions and a comparable yield has been achieved with less reaction time. In order to synthesize the [Nd(NDC) 1.5 (DMF)(H 2 O) 0.5 .0.5DMF] n , neodymium is used as a metal node to act as a cation and naphthalene-2,6-dicarboxylic acid as a well-extended organic linker as a dicarboxylate anion for building good coordinated 3D polymer. The synthesized Nd-MOF nanocatalyst was characterized by Powder XRD, BET, TGA, FT-IR, SEM-EDX, and TEM. Finally, the obtained products were examined through 1 H NMR, 13 C NMR, 15 N NMR and FT-IR. The nanocatalyst was completely recyclable and reusable for ten cycles without any loss of catalytic efficiency. Further, the nanocatalyst shows a crucial role in reducing the reaction time under mild experimental conditions. Additionally, the target molecules were afforded simple handling, eco-friendly and excellent yields with maximum efficiency.

Enhancing the Theranostic Performance of Organic Photosensitizers with Aggregation-Induced Emission

ConspectusPhotodynamic therapy has been actively explored recently to combat various physiological disorders and diseases, including bacterial infections, inflammation, and cancer. As a noninvasive modality with high spatiotemporal selectivity, photodynamic therapy leverages photosensitizers, light, and reactive oxygen species to induce cytotoxicity and cell death. Specifically, upon light irradiation, photosensitizers harvest the incident light energy to generate highly reactive singlet oxygen species through photochemical reactions to disrupt the integrity of certain cellular components of the target cells. The extent to which the target cells can be damaged depends largely on the characteristics of photosensitizers. As such, the selection and design of photosensitizers are essential to ensuring effective and safe photodynamic therapy. Unfortunately, organic photosensitizers typically used in photodynamic therapy tend to suffer from a considerable reduction in singlet oxygen production when these molecules aggregate, significantly limiting the efficacy of photodynamic therapy. To address this issue, a different class of organic photosensitizers with aggregation-induced emission (AIE) characteristics, which exhibit bright fluorescence and enhanced photosensitizing activity only when they exist in an aggregated state, has been increasingly formulated for disease theranostic applications.In general, AIE photosensitizers can be designed on the basis of several major strategies. For example, AIE photosensitizers with efficient singlet oxygen generation can be formulated by minimizing their singlet–triplet energy gap via tuning the distribution of the highest occupied molecular orbital and the lowest unoccupied molecular orbital of the molecules. Simultaneously, through donor–acceptor engineering, AIE photosensitizers can be designed to have increased molar absorptivity, red-shifted absorption and emission wavelengths, and improved body clearance. In situ click synthesis can also be adopted to formulate AIE photosensitizers with suppressed dark toxicity. These design approaches can be optimized using artificial intelligence or machine learning, leading to higher throughput discovery of AIE photosensitizers with exceptional performance. Intriguingly, the therapeutic impact of AIE photosensitizers can be further strengthened by modulating their performance-related features, notably targeting specificity, target accumulation and retention, tissue penetration depth, stimulus responsivity, and theranostic modality. By precisely controlling these elements, multifunctional and biocompatible AIE photosensitizers with superior performance can be realized.Herein, we describe our recent efforts in designing and formulating organic AIE photosensitizers with improved theranostic efficacy and safety to treat bacterial infections and cancer. We first introduce different principles that can be adopted to guide the design of AIE photosensitizers. We then present various ways to strengthen the different performance-associated features of AIE photosensitizers. These include enhancement of the targeting specificity, target accumulation, and retention of AIE photosensitizers through metabolic engineering, enhancement of the tissue penetration depth of AIE photosensitizers through chemiexcitation and ionizing irradiation, enhancement of AIE photosensitization by suppressing intrinsic oxidative resistance, enhancement of the responsivity of AIE photosensitizers through stimulus-responsive building blocks, and enhancement of the overall theranostic performance of AIE photosensitizers through combinatorial therapy. Finally, we identify current challenges, potential opportunities, and future research directions for this emerging field. Through this Account, we seek to stimulate further interest and active collaborations in the development, theranostic applications, and clinical translation of organic AIE photosensitizers to treat different diseases.

Systematic investigation of the adsorption and inhibition properties of a new clickable 1,2,3‐triazole compound for mild steel in 1 M HCl medium

AbstractThe search for eco‐friendly and effective corrosion inhibitors for the acidizing processes is increasingly required. In the present study, a new 1,2,3‐triazole derivative, namely, 4‐(1‐naphthalen‐2‐ylmethyl‐1H‐[1,2,3]triazol‐4‐ylmethyl)‐morpholine (NTM), has been clicked under green click synthesis conditions and fully characterized. The inhibition performance on corroded mild steel (MS) was studied by electrochemical impedance spectroscopy (EIS), potentiodynamic polarization (PDP) and weight loss measurements. The electrochemical results indicate that NTM works as a mixed‐type inhibitor and its adsorption on the MS surface obeys the Langmuir adsorption isotherm. The corrosion process was found to be reduced at 10−3 M concentration with 94 % efficiency. An immersion time of 57.56 min using a concentration of NTM equal to 5.2×10−4 M at 298 K was selected as optimal inhibition process conditions through the Central Composite Design (CCD). These conditions were conducted to the desirability of 1.00 and 88.8 % as the expected inhibition. NTM species was adsorbed on the MS surface by physical and chemical interactions. Quantum chemical calculations performed at the DFT/6‐31G(d,p) and DFTB+ levels were used to examine the adsorption of neutral NTM and its protonated form on the MS surface, including the active centers of both species. The mode of orientations of neutral and protonated NTM on the MS surface and the corresponding adsorption energies in both gas and aqueous phases were explored by molecular simulation dynamics.

Thiol-ene click synthesis of adsorption functionalized poly(ionic liquid)s: influence of the mole fraction of pendant enes

Adsorption functionalized poly(ionic liquid)s could be thiol-ene click synthesized within surfactant-free ionic liquid microemulsions. However, the influence of the mole fraction of pendant enes on the as-prepared polymer is still unclear. Herein, the influence of the mole fraction of pendant enes on the molecular structure, surface morphology, thermostability and adsorption performance of poly(ionic liquid)s were investigated in detail. To characterize the as-prepared polymers, FTIR, NMR, TGA, DSC, SEM and UV–vis were used, and the adsorption isotherm/kinetics studies were carried out. The results showed that the mole fraction of pendant enes had a significant difference on the characterization of poly(ionic liquid)s. The lower mole fraction of pendant enes donated lower T10% value, slower degradation rates and lower Tg, and the value of 0.30 was the boundary of forming structure with various beading sizes and structure with various irregularly shaped apertures. In addition, poly(ionic liquid)s with different mole fraction of pendant enes all showed excellent adsorption performance to DR, which indicated remarkable potential in the application of dying wastewater treatment.

Thiol-ene click synthesis of β-cyclodextrin-functionalized covalent organic framework-based magnetic nanocomposites (Fe3O4@COF@β-CD) for solid-phase extraction and determination of estrogens and estrogen mimics

Estrogens and estrogen mimics have been proved to be possible carcinogenic risks to human health and have drawn extensive attention in the fields of food safety. In this work, a thiol-ene click strategy was proposed for synthesis of a novel β-cyclodextrin-functionalized covalent organic framework-based magnetic nanocomposites (Fe3O4@COF@β-CD) and then employed as adsorbents for magnetic solid-phase extraction (MSPE) of estrogens and estrogen mimics. The Fe3O4@COF@β-CD possess the merits of superparamagnetism, large surface area, and excellent adsorption performance to estrogens and estrogen mimics. By combining with high-performance liquid chromatography-fluorescence detector (HPLC-FLD), the developed method gave a good linearity (R2 ≥ 0.9989) and low limits of detection (0.9–3.4 μg kg−1) under the optimized conditions. The applicability of the presented MSPE-HPLC-FLD method was demonstrated by real milk and meat samples analysis, with the satisfactory recoveries ranging from 89.0 to 105.4% and the relative standard deviations (RSDs) ≤ 5.7%.

Discovery of triaromatic flexible agents bearing 1,2,3-Triazole with selective and potent anti-breast cancer activity and CDK9 inhibition supported by molecular dynamics

This study reports an efficient and convenient click synthesis of novel series of chromene scaffold linked to 1,2,3 triazole ring and terminal lipophilic fragments. Structures of all newly synthesized compounds were well characterized by IR, 1H NMR, 13C NMR and elemental analyses. In vitro MTT cytotoxic screening was performed using staurosporine as a reference drug against three different types: aggressive and invasive human breast cancer cell line (MDA-MB 231), Michigan cancer foundation-7 (MCF-7) and human colorectal carcinoma cell line (HCT116). These screening data showed considerable anticancer activity for these newly synthesized compounds compared to reference staurosporine drug with high degree of cell line selectivity and excellent activity with micromolar (µM) half maximal inhibitory concentration (IC50) values against tumor cells. In addition, Cyclin-Dependent Kinase1 and 9 (CDK1 and 9) assays were performed for the most active compounds to get more details about their mechanism of action. In order to assess and explain their binding affinities, molecular docking simulation was studied against CDK9 site. The results obtained from molecular docking study and those obtained from cytotoxic screening and enzyme inhibition were correlated. One of the most prominent analogs is 34 that showed high selective cytotoxicity profile against single breast cancer cell line MCF-7 and MDA-MB 231 with IC50 3.4 µM and 1.4 uM respectively. Molecular dynamics (MD) simulation of the CDK9 complex by Desmond revealed stability during 100 ns with RMSD of CDK9 complex converged at 2.1 Å after 20 ns. During MD, the interaction fractions confirmed multiple interactions of 34 with Cys106, a crucial residue for inhibition of CDK9 activity. A novel 34 triazole compound was introduced for drug design works as potent and selective hit for treatment of breast cancers after processing of optimization steps.

Design, Synthesis and Biological Evaluaion of Novel Indole-Isoxazole Conjugates as Potent Anticancer Agents

A series of new indole derived mono and bis isoxazole (4a-4f and 5a-5f) was synthesized using highly efficient and environmentally benign ionic liquid containing click synthesis. Anticipated structures of all titled compounds were in agreement with spectral and analytical (C, H and N) analyses. The newly synthesized compounds were screened for their in vitro anticancer activity against MCF-7 and HeLa. The anticancer activity screening results of 5f, 4f and 5a exhibited potent cytotoxic activity against two cancer cell lines with IC50 values nearer to the standard drug doxorubicin. The remaining compounds have shown moderate activity against the tested cell lines.

An efficient click synthesis of chalcones derivatized with two 1-(2-quinolon-4-yl)-1,2,3-triazoles

AbstractChalcones derivatized with 1-(2-quinolonyl)-1,2,3-triazoles were synthesized by reaction of 4-azido-2-quinolones with 1-phenyl-3-(4-propargyloxyphenyl)prop-2-en-1-one, or by aldol reaction of 4-{[1-(2-oxo-1,2-dihydroquinolin-4-yl)-1H-1,2,3-triazol-4-yl]methoxy}benzaldehydes with acetophenone. Whereas, chalcones bearing two 1-(2-quinolonyl)-1,2,3-triazoles were synthesized by reaction of 1,3-bis(4-propargyloxyphenyl)prop-2-en-1-one with 4-azido-2-quinolones, or by aldol condensation between 4-{4-[(4-acetylphenoxy)methyl]-1H-1,2,3-triazol-1-yl}quinolin-2(1H)-ones and 4-{[1-(2-oxo-1,2-dihydroquinolin-4-yl)-1H-1,2,3-triazol-4-yl]methoxy}benzaldehydes.

“Thiol–ene” click synthesis of chiral covalent organic frameworks for gas chromatography

A facile “thiol–ene” click strategy was reported to construct novel chiral COFs for gas chromatographic separation.

Chromene–triazole-pyrimidine based chemosensor therapeutics for the in vivo and in vitro detection of Fe3+ ions

MCR and click synthesis of selective and sensitive Fe3+ sensors that can interact with CDK2 proteins and cytotoxicity against the human cervical cancer cell line HeLa is developed.

Convergent click synthesis of macromolecular dendritic β-cyclodextrin derivatives as non-conventional drug carriers: Albendazole as guest model

From a materials science perspective, herein we present the design and synthesis of six macromolecular carbohydrate derivatives, obtained by combining the native cyclic oligosaccharide βCD and dendritic poly(ester) moieties, coupled by CuAAc click reactions, in a convergent fashion. We envisioned two structural variables to promote the formation of inclusion complexes (ICs) with the anti-parasitic drug Albendazole, the degree of substitution on the βCD (mono or hepta-substitution) and the dendritic generation (from first to third). In terms of synthetic effort and cost, the mono-substituted βCD derivatives were obtained in more approachable experimental conditions in comparison to the βCD dendrimers (hepta-substituted macrocycle). The six dendritic derivatives were more soluble in water and showed better complexation capacity than native βCD. For both, mono and hepta-substituted βCD, we observed that the amount of encapsulated ABZ increases when the dendron generation increases. Interestingly, different degrees of substitution (mono and hepta) lead comparable results of ABZ complexation. In conclusion, the encapsulation performance and the consequent solubility enhancement, make these molecular containers excellent materials to positively impact the therapeutic desirability of ABZ.