Efficient Method for the Synthesis of Benzamides from Benzoic Acids and Aryl Isothiocyanates using K<sub>2</sub>
HPO<sub>4</sub>

Swamy, T.; Raviteja, Padma; Reddy, B. V. Subba; Vadde, Ramakrishna

doi:10.1002/slct.201701580

Cited by 15 publications

(6 citation statements)

References 40 publications

(18 reference statements)

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“…For these studies, RV-like NPs were labeled with Rhodamine B isothiocyanate by covalently binding to the carboxylic end groups of PEG . The uptake studies were performed on the 3D BBB in vitro model.…”

Section: Experimental Section/methodsmentioning

confidence: 99%

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Poly(β-amino ester) Nanoparticles Modified with a Rabies-Virus-Derived Peptide for the Delivery of ASCL1 across a 3D In Vitro Model of the Blood–Brain Barrier

Rodgers

Muzzio

Valero

et al. 2023

ACS Appl. Nano Mater.

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Gene editing has emerged as a therapeutic approach to manipulate the genome for killing cancer cells, protecting healthy tissues, and improving immune response to a tumor. The gene editing tool achaete-scute family bHLH transcription factor 1 CRISPR guide RNA (ASCL1-gRNA) is known to restore neuronal lineage potential, promote terminal differentiation, and attenuate tumorigenicity in glioblastoma tumors. Here, we fabricated a polymeric nonviral carrier to encapsulate ASCL1-gRNA by electrostatic interactions and deliver it into glioblastoma cells across a 3D in vitro model of the blood−brain barrier (BBB). To mimic rabies virus (RV) neurotropism, gene-loaded poly(β-amino ester) nanoparticles are surface functionalized with a peptide derivative of rabies virus glycoprotein (RVG29). The capability of the obtained NPs, hereinafter referred to as RV-like NPs, to travel across the BBB, internalize into glioblastoma cells, and deliver ASCL1-gRNA is investigated in a 3D BBB in vitro model through flow cytometry and CLSM microscopy. The formation of nicotinic acetylcholine receptors in the 3D BBB in vitro model is confirmed by immunochemistry. These receptors are known to bind to RVG29. Unlike Lipofectamine which primarily internalizes and transfects endothelial cells, RV-like NPs are capable to travel across the 3D BBB in vitro model, preferentially internalizing glioblastoma cells, and delivering ASCL1-gRNA at an efficiency of 10%, causing noncytotoxic effects.

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Section: Experimental Section/methodsmentioning

confidence: 99%

“…For these studies, RV-like NPs were labeled with Rhodamine B isothiocyanate by covalently binding to the carboxylic end groups of PEG. 48 The uptake studies were performed on the 3D BBB in vitro model. After cell confluency of 80% and 24 h prior to performing experiments, the media were changed.…”

Section: D Bbb In Vitromentioning

confidence: 99%

Poly(β-amino ester) Nanoparticles Modified with a Rabies-Virus-Derived Peptide for the Delivery of ASCL1 across a 3D In Vitro Model of the Blood–Brain Barrier

Rodgers

Muzzio

Valero

et al. 2023

ACS Appl. Nano Mater.

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“…Although this reaction has been known for a long time, [ 9 ] it is less concerned and underdeveloped, probably due to the competing decomposing pathways of the carboxylic carbamic anhydride intermediate to form ureas, carboxylic anhydrides, besides amides. [ 10 ] To improve the efficiency of this transformation, thiocarboxylic acids [ 11 ] or/and thioisocyanates [ 12 ] have been applied to facilitate amide formation, however, extra synthetic steps and manipulation of notorious sulfur‐containing compounds are necessary. G ü rtler has studied the catalytic activity of Lewis acids to promote amide formation from carboxylic acids and isocyanates, but the substrates are limited to several alkyl carboxylic acids and alkyl isocyanates.…”

Section: Background and Originality Contentmentioning

confidence: 99%

Iron‐Catalyzed Amide Bond Formation from Carboxylic Acids and Isocyanates^†

Zhang

2023

Chin. J. Chem.

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Comprehensive SummaryWe describe an iron‐catalyzed amide bond formation from readily available carboxylic acids and isocyanates. This method utilizes an abundant and biocompatible iron catalyst and easily accessible starting materials, generates CO2 as the only byproduct, and features broad substrate scopes with good functional group compatibility. Therefore, it provides a cost‐effective and practical protocol to access a diverse variety of amides.This article is protected by copyright. All rights reserved.

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“…A wide variety of oxidants have been employed for the cyclization of arylhydrazones to their respective fused triazole derivatives, including chemical oxidation with iron(III) 11 and copper(II) 12 chlorides, chloramine T trihydrate, 13 N -bromosuccinimide with 1,8-diazabicyclo[5.4.0]undec-7-ene, 14 RuCl 3 /oxone, 15 and electrochemical synthesis. 16 Today, hypervalent organoiodine(III) reagents are used as mild oxidizing agents.…”

Section: Table 1 Optimization Of the Reaction Condition...mentioning

confidence: 99%

Synthesis and Biological Investigation of 1,2,4-Triazolo[4,3-a]azines as Potential HSF1 Inductors

et al. 2022

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Derivatives of fused 1,2,4-triazines containing heterocyclic and metallocene fragments were obtained by one-pot oxidative cyclization of heterocyclic hydrazones in the presence of hypervalent iodine(III) reagents. For 1,2,4-triazolo[4,3-a]azines, the ability to activate HSF1 was investigated. The obtained compounds were shown to increase the degree of HSF1 activation. It was shown that the 1,2,4-triazines can be used to induce Hsp70 expression and decrease the extent of mutant HTT aggregate formation.

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Efficient Method for the Synthesis of Benzamides from Benzoic Acids and Aryl Isothiocyanates using K₂ HPO₄

Cited by 15 publications

References 40 publications

Poly(β-amino ester) Nanoparticles Modified with a Rabies-Virus-Derived Peptide for the Delivery of ASCL1 across a 3D In Vitro Model of the Blood–Brain Barrier

Poly(β-amino ester) Nanoparticles Modified with a Rabies-Virus-Derived Peptide for the Delivery of ASCL1 across a 3D In Vitro Model of the Blood–Brain Barrier

Iron‐Catalyzed Amide Bond Formation from Carboxylic Acids and Isocyanates^†

Synthesis and Biological Investigation of 1,2,4-Triazolo[4,3-a]azines as Potential HSF1 Inductors

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Efficient Method for the Synthesis of Benzamides from Benzoic Acids and Aryl Isothiocyanates using K2 HPO4

Cited by 15 publications

References 40 publications

Poly(β-amino ester) Nanoparticles Modified with a Rabies-Virus-Derived Peptide for the Delivery of ASCL1 across a 3D In Vitro Model of the Blood–Brain Barrier

Poly(β-amino ester) Nanoparticles Modified with a Rabies-Virus-Derived Peptide for the Delivery of ASCL1 across a 3D In Vitro Model of the Blood–Brain Barrier

Iron‐Catalyzed Amide Bond Formation from Carboxylic Acids and Isocyanates†

Synthesis and Biological Investigation of 1,2,4-Triazolo[4,3-a]azines as Potential HSF1 Inductors

Contact Info

Product

Resources

About

Efficient Method for the Synthesis of Benzamides from Benzoic Acids and Aryl Isothiocyanates using K₂ HPO₄

Iron‐Catalyzed Amide Bond Formation from Carboxylic Acids and Isocyanates^†