A new and efficient protocol for preparation of thiol esters from carboxylic acids and thiols in the presence of 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (TBTU)

Movassagh, Barahman; Balalaie, Saeed; Shaygan, Pershang

doi:10.3998/ark.5550190.0008.d07

Cited by 12 publications

(7 citation statements)

References 7 publications

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“…In this study, APG-loaded PLGA-NPs were surface-functionalized with DMSA using an EDC/NHS coupling method to obtain the corresponding thiol ester. 50 During nanoparticle fabrication, TPGS was used as a stabilizer to improve emulsification and encapsulation efficiency. FTIR studies revealed the absence of any chemical interaction of the flavonoid and formulation ingredients during preparation.…”

Section: ■ Discussionmentioning

confidence: 99%

“…As reported, an active lung targeting strategy of magnetic NPs could be improved through conjugation of DMSA on the surfaces of NPs. In this study, APG-loaded PLGA-NPs were surface-functionalized with DMSA using an EDC/NHS coupling method to obtain the corresponding thiol ester . During nanoparticle fabrication, TPGS was used as a stabilizer to improve emulsification and encapsulation efficiency.…”

Section: Discussionmentioning

confidence: 99%

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Apigenin-Loaded PLGA-DMSA Nanoparticles: A Novel Strategy to Treat Melanoma Lung Metastasis

Sen

Ganguly

et al. 2021

Mol. Pharmaceutics

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The flavone apigenin (APG), alone as well as in combination with other chemotherapeutic agents, is known to exhibit potential anticancer effects in various tumors and inhibit growth and metastasis of melanoma. However, the potential of apigenin nanoparticles (APG-NPs) to prevent lung colonization of malignant melanoma has not been well investigated. APG-loaded PLGA-NPs were surface-functionalized with meso-2,3-dimercaptosuccinic acid (DMSA) for the treatment of melanoma lung metastasis. DMSAconjugated APG-loaded NPs (DMSA-APG-NPs) administered by an oral route exhibited sustained APG release and showed considerable enhancement of plasma half-life, C max value, and bioavailability compared to APG-NPs both in plasma and the lungs. DMSAconjugated APG-NPs showed comparably higher cellular internalization in B16F10 and A549 cell lines compared to that of plain NPs. Increased cytotoxicity was observed for DMSA-APG-NPs compared to APG-NPs in A549 cells. This difference between the two formulations was lower in B16F10 cells. Significant depolarization of mitochondrial transmembrane potential and an enhanced level of caspase activity were observed in B16F10 cells treated with DMSA-APG-NPs compared to APG-NPs as well. Western blot analysis of various proteins was performed to understand the mechanism of apoptosis as well as prevention of melanoma cell migration and invasion. DMSA conjugation substantially increased accumulation of DMSA-APG-NPs given by an intravenous route in the lungs compared to APG-NPs at 6 and 8 h. This was also corroborated by scintigraphic imaging studies with radiolabeled formulations administered by an intravenous route. Conjugation also allowed comparatively higher penetration as evident from an in vitro three-dimensional tumor spheroid model study. Finally, the potential therapeutic efficacy of the formulation was established in experimental B16F10 lung metastases, which suggested an improved bioavailability with enhanced antitumor and antimetastasis efficacy of DMSA-conjugated APG-NPs following oral administration.

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Section: ■ Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

Apigenin-Loaded PLGA-DMSA Nanoparticles: A Novel Strategy to Treat Melanoma Lung Metastasis

Sen

Ganguly

et al. 2021

Mol. Pharmaceutics

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“…The dialyzed samples were lyophilized and stored in an auto-dry desiccator for future use. PPG-cRGD NPs were synthesized by esterification reaction as reported previously [ 28 , 29 ]. Briefly, PPG (50 mg) was added with 4-dimethylaminopyridine (DMAP) (100 mmol) and cRGD (60 mmol) in 10 mL of DMF.…”

Section: Methodsmentioning

confidence: 99%

Design of an Amphiphilic Poly(aspartamide)-Mediated Self-Assembled Nanoconstruct for Long-Term Tumor Targeting and Bioimaging

2019

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Biodegradable polymers have been developed for the targeted delivery of therapeutics to tumors. However, tumor targeting and imaging are usually limited by systemic clearance and non-specific adsorption. In this study, we used poly(amino acid) derivatives, such as poly(succinimide), to synthesize a nanomicelle-forming poly(hydroxyethylaspartamide) (PHEA, P) modified sequentially with octadecylamine, polyethylene glycol (PEG, P), and glycine (G) to design PHEA-PEG-glycine (PPG) nanoparticles (NPs). These PPG NPs were further tethered to cyclic Arg-Gly-Asp (cRGD) sequences for formulating tumor-targeting PPG-cRGD NPs, and then loaded with IR-780 dye (PPG-cRGD-IR-780) for visualizing tumor homing. cRGD cloaked in PPG NPs could bind specifically to both tumor endothelium and cancer cells overexpressing αvβ3 integrins. PPG-cRGD NPs exhibited enhanced physiological stability, cellular viability, and targeted intracellular uptake in cancer cells. In addition, PPG-cRGD NPs offered enhanced systemic circulation, leading to preferential tumor targeting and prolonged fluorescence tumor imaging for nearly 30 days. Nevertheless, non-targeted formulations demonstrated premature systemic clearance with short-term tumor imaging. Histochemical analysis showed no damage to normal organs, reaffirming the biocompatibility of PHEA polymers. Overall, our results indicated that PPG-cRGD NPs, which were manipulated to obtain optimal particle size and surface charge, and were complemented with tumor targeting, could improve the targeted and theranostic potential of therapeutic delivery.

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“…92 [31] (1.0 mmol), olefin/alkyne/alkyl or acyl halide (1.0 mmol), Fe 3 O 4 MNPs (0.04 mmol, 4 mol%), neat, room temperature. b Isolated yield.…”

Section: CLmentioning

confidence: 99%

“…In a recent report, bis(triflimide)iron(III) salt was introduced as a potential catalyst for the hydrothiolation of styrene derivatives in a Markovnikov fashion [29]. The growing importance of thioethers and thiol esters in organic synthesis has stimulated recent extensive research towards improved methods for their preparations [26][27][28]30,31]. In continuation of our interest in applications of Fe 3 O 4 MNPs for organic transformations [11d-e], herein we report a simple and highly efficient protocol for the preparation of thioethers, vinyl thioethers, thiol esters and thia-Michael adducts under neat and neutral reaction conditions (Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

Magnetite (Fe3O4) Nanoparticles: An Efficient and Reusable Catalyst for the Synthesis of Thioethers, Vinyl Thioethers, Thiol Esters, and Thia-Michael Adducts under Solvent-Free Condition

Yousefi

Movassagh

2013

Proceedings of the 17th International Electronic Conference on Synthetic Organic Chemistry

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Magnetic iron(III) oxide nanoparticles (Fe 3 O 4 MNPs) were used as a readily available, highly efficient and recyclable catalyst for the anti-Markovnikov 1,2-addition of thiols to alkenes and alkynes, affording thioethers and vinyl thioethers in excellent yields in short reaction times under mild and solvent-free conditions. This catalyst was also utilized for thia-Michael addition, substitution reaction, and the synthesis of thiol esters.

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A new and efficient protocol for preparation of thiol esters from carboxylic acids and thiols in the presence of 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (TBTU)

Abstract: A novel and convenient method has been developed for the synthesis of thiol esters from the corresponding carboxylic acids and thiols at room temperature using 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (TBTU) as the coupling reagent.

Cited by 12 publications

References 7 publications

Apigenin-Loaded PLGA-DMSA Nanoparticles: A Novel Strategy to Treat Melanoma Lung Metastasis

Apigenin-Loaded PLGA-DMSA Nanoparticles: A Novel Strategy to Treat Melanoma Lung Metastasis

Design of an Amphiphilic Poly(aspartamide)-Mediated Self-Assembled Nanoconstruct for Long-Term Tumor Targeting and Bioimaging

Magnetite (Fe3O4) Nanoparticles: An Efficient and Reusable Catalyst for the Synthesis of Thioethers, Vinyl Thioethers, Thiol Esters, and Thia-Michael Adducts under Solvent-Free Condition

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