The role of chemistry in the success of oligonucleotides as therapeutics

• Pawan Kumar and
• Tom Brown

Beilstein J. Org. Chem. 2022, 18, 197–199, doi:10.3762/bjoc.18.22

• unmet medical need in the CNS space, and to treat diseases that have been elusive until now. Developing lipid nanoparticles that can selectively deliver oligonucleotides to a desired tissue is also an attractive strategy. Importantly, siRNA encapsulated into lipid nanoparticles has been shown to be

• effective in patisiran, the first RNAi drug to reach patients. Lipid nanoparticles are also being used in the new generation of RNA vaccines for tackling the COVID pandemic. Another noteworthy advancement is the ease and scale with which oligonucleotides are being produced today. Without access to larger

Synthesis and bioactivity of pyrrole-conjugated phosphopeptides

• Qiuxin Zhang,
• Weiyi Tan and
• Bing Xu

Beilstein J. Org. Chem. 2022, 18, 159–166, doi:10.3762/bjoc.18.17

• transition of nanoparticles to nanofibers, which is a transition observed in the case of 1 [43]. Incubating 2–10 with HeLa cells reveals that these phosphopeptides exhibit comparable inhibitory activity as that of 1 against the proliferation of HeLa cells at 200 μM. But 2–10 at 400 μM, differing drastically

• dephosphorylation. Previous literature has demonstrated that 1, as a precursor, is capable of forming hydrogels upon dephosphorylation catalyzed by ALP [43][62]. To be more specific, ALP enables a morphological transition from nanoparticles of 1 to networks of nanofibers of the corresponding dephosphorylated

• peptides, resulting in hydrogelation (Figure 3A) [62]. In comparison with 1, 4a, forming networks of nanoparticles at 400 μM and 200 μM, exhibits little change in the morphology of the assemblies after being incubated with 1 U/mL of ALP for 24 h (Figure 3B), although LC–MS confirms the enzymatic

Green synthesis of C5–C6-unsubstituted 1,4-DHP scaffolds using an efficient Ni–chitosan nanocatalyst under ultrasonic conditions

• Soumyadip Basu,
• Sauvik Chatterjee,
• Suman Ray,
• Suvendu Maity,
• Prasanta Ghosh,
• Asim Bhaumik and
• Chhanda Mukhopadhyay

Beilstein J. Org. Chem. 2022, 18, 133–142, doi:10.3762/bjoc.18.14

• yield, the use of an eco-friendly solvent and a recyclable nanocatalyst, as well as reaction at room temperature. Keywords: 1,4-DHPs; green synthesis; magnetically recyclable catalyst; Ni–chitosan nanoparticles; ultrasonication; Introduction Homogeneous catalysts, despite having an outstanding

• the reduction of the environmental effects of chemical synthesis [22]. The use of ultrasonic irradiation allows for optimal mixing of the reactants and the catalyst by enhancing the homogeneity of the reaction medium. It also decreases the chance of agglomeration of the heterogeneous nanoparticles

Stepwise PEG synthesis featuring deprotection and coupling in one pot

• Logan Mikesell,
• Dhananjani N. A. M. Eriyagama,
• Yipeng Yin,
• Bao-Yuan Lu and
• Shiyue Fang

Beilstein J. Org. Chem. 2021, 17, 2976–2982, doi:10.3762/bjoc.17.207

• obtained. However, for many other applications, which include as linkers in organic synthesis and bioconjugation [8], as ingredients in nanomedicines to stabilize nanoparticles and to assist nanoparticle cell entry [9][10][11], and as PEGylation agents to stabilize drugs based on biologic molecules such as

Host–guest interaction and properties of cucurbit[8]uril with chloramphenicol

• Lin Zhang,
• Jun Zheng,
• Guangyan Luo,
• Xiaoyue Li,
• Yunqian Zhang,
• Zhu Tao and
• Qianjun Zhang

Beilstein J. Org. Chem. 2021, 17, 2832–2839, doi:10.3762/bjoc.17.194

• in water and has a bitter taste. Upon forming an inclusion complex with cyclodextrin, the solubility and bitter taste of CPE can be improved [4][5]. Ramesh Gannimani et al. [6] reported that the inclusion complex of cyclodextrin and CPE loaded silver nanoparticles possessed stronger antibacterial

Cryogels: recent applications in 3D-bioprinting, injectable cryogels, drug delivery, and wound healing

• Luke O. Jones,
• Leah Williams,
• Tasmin Boam,
• Martin Kalmet,
• Chidubem Oguike and
• Fiona L. Hatton

Beilstein J. Org. Chem. 2021, 17, 2553–2569, doi:10.3762/bjoc.17.171

• . 5.2.2. Injectable nanocomposite cryogels: Nanocomposite cryogels comprise a typical cryogel with nanoparticulate fillers incorporated into the structure. Addition of nanoparticles is often conducted to impart specific properties, such as improving mechanical properties or provide therapeutic properties

• tetrazine-norbornene coupling. Laponite nanoparticles were then incorporated within the walls of the cryogel. The results showed the so-called “click alginate” was able to produce cryogels with an interconnected porous structure, and high deformability allowing it to be used through a 16-gauge needle. The

• acetalated dextran nanoparticles in an injectable cryogel to combat the negative effects of chemotherapy and even suggested this approach as a potential method of vaccination (Figure 4) [82]. The injectable alginate cryogel was loaded with several therapeutic compounds, including spermine-modified acetalated

Post-functionalization of drug-loaded nanoparticles prepared by polymerization-induced self-assembly (PISA) with mitochondria targeting ligands

• Janina-Miriam Noy,
• Fan Chen and
• Martina Stenzel

Beilstein J. Org. Chem. 2021, 17, 2302–2314, doi:10.3762/bjoc.17.148

• -phenylarsenoxide-based agents. This can also lead to deactivation of the drug as these organoarsenic drugs react readily with blood proteins, in particular transferrin [10]. In order to limit premature inactivation of the arsenic drugs, a range of nanoparticles have been developed to enhance stability, thus

• increase activity [11][12]. These nanoparticles have been decorated with targeting ligands to enhance the accumulation of the drug in cancer tissue. The activity of arsenic drugs could, however, also be enhanced by targeting mitochondria inside the cells, the target of action of arsenic drugs. To the

• mitochondrial matrix than in the cytosol [20]. TPP derivatives were attached to PEGylated poly(ε-caprolactone) (PCL), and corresponding micellar formulation enabled the delivery of coenzyme Q10 (CoQ10) to the mitochondria [21]. In addition, PEGylated TPP-conjugated poly(lactic-co-glycolic acid) nanoparticles

Constrained thermoresponsive polymers – new insights into fundamentals and applications

• Patricia Flemming,
• Alexander S. Münch,
• Andreas Fery and
• Petra Uhlmann

Beilstein J. Org. Chem. 2021, 17, 2123–2163, doi:10.3762/bjoc.17.138

• , have been intensively studied in solution. For the application of such polymers in novel sensors, drug delivery systems or as multifunctional coatings, they typically have to be transferred into specific arrangements, such as micelles, polymer films or grafted nanoparticles. However, it turns out that

• turbidimetry (determination of the cloud point) is available. For thermoresponsive interfaces in the form of polymer brushes on a flat substrate or on nanoparticles, however, there are only very limited comparable analytical characterization methods, which consequently leads to a distortion of terminologies

• will be briefly introduced concerning the relationship between their morphology and the temperature-induced phase transition. These polymer arrangements of constrained mobility include star polymers, micelles and grafted linear polymers on flat surfaces as well as on nanoparticles. In general, these

Progress and challenges in the synthesis of sequence controlled polysaccharides

• Giulio Fittolani,
• Theodore Tyrikos-Ergas,
• Denisa Vargová,
• Manishkumar A. Chaube and
• Martina Delbianco

Beilstein J. Org. Chem. 2021, 17, 1981–2025, doi:10.3762/bjoc.17.129

• industrial applications in coating materials, cosmetics and pharmaceuticals [211]. Owing to their superior biological and mechanical properties, chitin and chitosan are used in fibers, gels, sponges, films, beads, and nanoparticles [212]. Tunable stiffness, solubility, and transparency can be obtained by

Cerium-photocatalyzed aerobic oxidation of benzylic alcohols to aldehydes and ketones

• Girish Suresh Yedase,
• Sumit Kumar,
• Jessica Stahl,
• Burkhard König and
• Veera Reddy Yatham

Beilstein J. Org. Chem. 2021, 17, 1727–1732, doi:10.3762/bjoc.17.121

• acting as the terminal oxidant [13][14][15][16][17][18][19][20][21][22][23][24][25][26][27][28][29][30][31][32][33]. Most aerobic oxidation reactions utilize either metal complexes and nanoparticles or persistent radical reagents as catalysts [21]. In the past ten years, visible light-induced

Chemical approaches to discover the full potential of peptide nucleic acids in biomedical applications

• Nikita Brodyagin,
• Martins Katkevics,
• Venubabu Kotikam,
• Christopher A. Ryan and
• Eriks Rozners

Beilstein J. Org. Chem. 2021, 17, 1641–1688, doi:10.3762/bjoc.17.116

A recent overview on the synthesis of 1,4,5-trisubstituted 1,2,3-triazoles

• Pezhman Shiri,
• Ali Mohammad Amani and
• Thomas Mayer-Gall

Beilstein J. Org. Chem. 2021, 17, 1600–1628, doi:10.3762/bjoc.17.114

• bond functionalization reaction sequence with triazole-bearing aryl iodide 140, catalyzed by alloy-structured Pd/Cu bimetallic nanoparticles stabilized by a binaphthyl moiety, Pd/Cu-BNP 139. The Pd/Cu-BNP nanoparticles 139 were demonstrated to be an efficient and recyclable catalyst, and triazoles

• transformation (Scheme 40). The synthetic route for the Pd/Cu-BNP nanoparticles 139 is also shown in Scheme 40. Pd/Cu-BNP was synthesized by the following procedure as illustrated in Scheme 40. First, 1,1'-binaphthyl-2,2'-diamine (BINAM, 137) was transformed to [1,1'-binaphthalene]-2,2'-bis(diazonium

• ) tetrafluoroborate (138) in the presence of HBF4 and NaNO2 at 0 °C. Next, the nanoparticles were obtained from the reduction of Pd(OAc)2 and Cu(OAc)2 employing NaBH4 in the presence of diazonium salt [63]. A possible mechanism for the synthesis of polycyclic triazoles 142 was proposed by Sekar et al. as well [63

Recent advances in the application of isoindigo derivatives in materials chemistry

• Andrei V. Bogdanov and
• Vladimir F. Mironov

Beilstein J. Org. Chem. 2021, 17, 1533–1564, doi:10.3762/bjoc.17.111

• composite with platinum nanoparticles stabilized with poly(acrylic acid) [113]. Such a catalytic system, obtained by layer-by-layer self-assembly with the addition of poly(diallyldimethylammonium chloride) on the indium tin oxide surface, provided hydrogen formation in photoelectrolytic cycles with a

• silicon nanoparticles coated with a carbon shell (Si@C) for lithium ion batteries [115]. The specific capacity of a battery designed using polyisoindigo 67 (up to 1400 mA⋅h/g) with high stability (up to 500 cycles) indicates a high potential of such structures in the search for alternatives to the

• existing polymer conductive binder mixed with carbon additives (Scheme 31). Isoindigo derivatives have begun to find use in biomedical applications. Thus, nanoparticles of isoindigoid polymers have shown good potential as agents for photoacoustic and photothermal cancer therapy [116][117][118][119][120

Antiviral therapy in shrimp through plant virus VLP containing VP28 dsRNA against WSSV

• Santiago Ramos-Carreño,
• Ivone Giffard-Mena,
• Jose N. Zamudio-Ocadiz,
• Alfredo Nuñez-Rivera,
• Ricardo Valencia-Yañez,
• Jaime Ruiz-Garcia,
• Maria Teresa Viana and
• Ruben D. Cadena-Nava

Beilstein J. Org. Chem. 2021, 17, 1360–1373, doi:10.3762/bjoc.17.95

• , damaging the VLPs. Therefore, further studies should be on how this can be administered in the pellets at industrial levels. Other studies by IM injection of chemically modified chitosan nanoparticles loaded with anti-VP28 RNA [20] and antisense plasmid constructs for VP28 [24] have shown protection of 95

A comprehensive review of flow chemistry techniques tailored to the flavours and fragrances industries

• Guido Gambacorta,
• James S. Sharley and
• Ian R. Baxendale

Beilstein J. Org. Chem. 2021, 17, 1181–1312, doi:10.3762/bjoc.17.90

• offer the advantage of high surface-to-volume ratio and scalability. These systems consist of nanoparticles embedded into a porous polymer matrix. In heterogeneous catalysis, a higher particle stability and good distribution of the catalyst leads to a reduction in pressure drop alongside a stronger

Enhanced target cell specificity and uptake of lipid nanoparticles using RNA aptamers and peptides

• Roslyn M. Ray,
• Anders Højgaard Hansen,
• Maria Taskova,
• Bernhard Jandl,
• Jonas Hansen,
• Citra Soemardy,
• Kevin V. Morris and
• Kira Astakhova

Beilstein J. Org. Chem. 2021, 17, 891–907, doi:10.3762/bjoc.17.75

• Lipid nanoparticles (LNPs) constitute a facile and scalable approach for delivery of payloads to human cells. LNPs are relatively immunologically inert and can be produced in a cost effective and scalable manner. However, targeting and delivery of LNPs across the blood–brain barrier (BBB) has proven

• the usefulness of aptamer-loaded LNPs to increase target cell specificity and potentially deliverability of central-nervous-system-active RNAi therapeutics across the BBB. Keywords: aptamer; blood–brain barrier; gene therapy; HIV-1; lipid nanoparticle; Introduction Lipid nanoparticles (LNPs

• than one technique. Nevertheless, the small size of these nanoparticles (<100 nm) is ideal for in vivo applications as they may bypass the reticuloendothelial system and thereby increase LNP circulation time in vivo [41]. LNPs with postinsertion T7 peptide Previous studies have demonstrated the ability

Microwave-assisted multicomponent reactions in heterocyclic chemistry and mechanistic aspects

• Shivani Gulati,
• Stephy Elza John and
• Nagula Shankaraiah

Beilstein J. Org. Chem. 2021, 17, 819–865, doi:10.3762/bjoc.17.71

• the microwave-assisted synthesis of steroidal pyridines 123 utilizing steroidal ketones 122, aldehydes 5, malononitrile (51)/methyl cyanoacetate and ammonium acetate as structural units and MgO nanoparticles as a catalyst in ethanol solvent. The reaction proceeded even in absence of a catalyst but

Valorisation of plastic waste via metal-catalysed depolymerisation

• Francesca Liguori,
• Carmen Moreno-Marrodán and
• Pierluigi Barbaro

Beilstein J. Org. Chem. 2021, 17, 589–621, doi:10.3762/bjoc.17.53

• catalyst replacements for zinc acetate in the glycolysis of PET are examples of this direction [129][130]. Recent studies focused on molecular complexes as homogeneous catalysts, whereas heterogeneous systems based on solid-supported metal nanoparticles (NPs) have been scarcely investigated. 3.1

A new and efficient methodology for olefin epoxidation catalyzed by supported cobalt nanoparticles

• Lucía Rossi-Fernández,
• Viviana Dorn and
• Gabriel Radivoy

Beilstein J. Org. Chem. 2021, 17, 519–526, doi:10.3762/bjoc.17.46

• Lucia Rossi-Fernandez Viviana Dorn Gabriel Radivoy INQUISUR-CONICET, Departamento de Química, Universidad Nacional del Sur, Avenida Alem 1253, Bahía Blanca, B8000CPB, Argentina 10.3762/bjoc.17.46 Abstract A new heterogeneous catalytic system consisting of cobalt nanoparticles (CoNPs) supported on

• materials and it could be recovered and reused maintaining its unaltered high activity. Keywords: alkenes; cobalt nanoparticles; epoxides; oxidation; TBHP; Introduction Olefin oxidation reactions are key synthetic transformations in the production of oxygenated chemicals of high interest for both academic

• the other hand, the use of supported cobalt nanoparticles as efficient catalysts for the epoxidation of olefins has received increasing attention in the last years. In most cases, a crucial influence of the support (TiO2, HAP, CNTs, SBA, SiO2), the oxidant agent (molecular oxygen or TBHP) and the

Synthesis and physicochemical evaluation of fluorinated lipopeptide precursors of ligands for microbubble targeting

• Masayori Hagimori,
• Estefanía E. Mendoza-Ortega and
• Marie Pierre Krafft

Beilstein J. Org. Chem. 2021, 17, 511–518, doi:10.3762/bjoc.17.45

• -surfactants to the phospholipid molecules of the MB shell and strongly reduce its interfacial tension [35][36]. Recent studies have reported that the fluorine–fluorine interactions that develop between the FC and the MB shell component (e.g., fluorinated biomarkers [37] and fluorinated nanoparticles

• , including dendronized iron oxide nanoparticles [38] and nanodiamonds [39]) efficiently reinforce the interfacial film cohesion, thus enhancing the stability of the MBs. Various types of perfluoroalkylated amphiphiles have been reported that were designed for biomedical applications and display highly

Multiswitchable photoacid–hydroxyflavylium–polyelectrolyte nano-assemblies

• Alexander Zika and
• Franziska Gröhn

Beilstein J. Org. Chem. 2021, 17, 166–185, doi:10.3762/bjoc.17.17

• also studied by AFM. For this, assembly solutions where drop cast on mica surfaces. The results are given in Figure 6 and overall they are in agreement with the DLS results. To compare the sizes of the assemblies quantitatively, the volumes of the nanoparticles measured by AFM on the surfaces are

Insight into functionalized-macrocycles-guided supramolecular photocatalysis

• Minzan Zuo,
• Krishnasamy Velmurugan,
• Kaiya Wang,
• Xueqi Tian and
• Xiao-Yu Hu

Beilstein J. Org. Chem. 2021, 17, 139–155, doi:10.3762/bjoc.17.15

• between thiol-functionalized β-CD and oleic acid-protected CdS nanocrystals [29]. These spherical CdS–CD nanoparticles could be employed as a photocatalyst for the dehydrogenation of alcohols to aldehydes (at a low concentration of the reactant of 1 mM, ≥92% selectivity) or diols (at a high concentration

• reported a light-harvesting system for photocatalysis based on the water-soluble pillar[5]arene WP5 [56]. The large cavity volume of the formed nanoparticles enabled two guest β-carotene (β-CAR) and chlorophyll-b (Chl-b) molecules to be encapsulated within the cavity (Figure 18). The β-CAR and Chl-b

• of 4-nitrophenol after irradiation with a mercury lamp. The Pt or Ag nanoparticles could also be achieved by the photocatalyst property of the system in the presence of ascorbic acid. The mechanism can be explained in a way where Chl-b firstly absorbs light and generates the excited state, followed

Supramolecular polymerization of sulfated dendritic peptide amphiphiles into multivalent L-selectin binders

• David Straßburger,
• Svenja Herziger,
• Katharina Huth,
• Moritz Urschbach,
• Rainer Haag and
• Pol Besenius

Beilstein J. Org. Chem. 2021, 17, 97–104, doi:10.3762/bjoc.17.10

• competitive surface plasmon resonance (SPR) binding assay, whereby neutral supramolecular polymers of I were used as control experiment. L-Selectin-coated gold nanoparticles were incubated with analyte solutions of different concentrations and subsequently probed on an SPR-chip modified with immobilized

• ) measured by SPR. L-Selectin-coated nanoparticles were preincubated with solutions of the supramolecular polymers. Their affinity towards multimerized artificial ligands composed of sulfated tyrosine and sialyl-LewisX, immobilized on an SPR-chip was probed. The binding signal is plotted relative to a sample

Control over size, shape, and photonics of self-assembled organic nanocrystals

• Chen Shahar,
• Yaron Tidhar,
• Yunmin Jung,
• Haim Weissman,
• Sidney R. Cohen,
• Ronit Bitton,
• Iddo Pinkas,
• Gilad Haran and
• Boris Rybtchinski

Beilstein J. Org. Chem. 2021, 17, 42–51, doi:10.3762/bjoc.17.5

• ). Convenient control over the structure and function of organic nanocrystals can enhance their utility in new and developed technologies. Keywords: aromatic amphiphiles; exciton diffusion; organic nanocrystals; perylene diimides; self-assembly; Introduction Semiconductor and metal nanoparticles exhibit size

Molecular basis for protein–protein interactions

• Brandon Charles Seychell and
• Tobias Beck

Beilstein J. Org. Chem. 2021, 17, 1–10, doi:10.3762/bjoc.17.1

• form binary nanoparticle superlattices. a) Surface engineering of the protein container to yield either positively (right) or negatively (left) charged containers. b) Nanoparticle synthesis. The different nanoparticles are illustrated in different colours. c) Self-assembly of the different charged