Synthesis and characterization of water-soluble C₆₀–peptide conjugates

• Yue Ma,
• Lorenzo Persi and
• Yoko Yamakoshi

Beilstein J. Org. Chem. 2024, 20, 777–786, doi:10.3762/bjoc.20.71

• C60–peptide conjugates in this study. In addition to the water solubility introduced by the peptides, these conjugates have a superior biocompatibility compared to those with synthetic polymers, such as PEG and PVP. We utilized the previously reported biscarboxylic acid derivative 3, which was

Chemical and biosynthetic potential of Penicillium shentong XL-F41

• Ran Zou,
• Xin Li,
• Xiaochen Chen,
• Yue-Wei Guo and
• Baofu Xu

Beilstein J. Org. Chem. 2024, 20, 597–606, doi:10.3762/bjoc.20.52

• diverse structures, electron-donating capabilities, and excellent biocompatibility, contributing to their potent antibacterial and anticancer activities [9][10]. Over 4000 species [8] producing indole alkaloids have been identified, and many of these compounds are now successfully employed in clinical

Effects of the aldehyde-derived ring substituent on the properties of two new bioinspired trimethoxybenzoylhydrazones: methyl vs nitro groups

• Dayanne Martins,
• Roberta Lamosa,
• Talis Uelisson da Silva,
• Carolina B. P. Ligiero,
• Sérgio de Paula Machado,
• Daphne S. Cukierman and
• Nicolás A. Rey

Beilstein J. Org. Chem. 2023, 19, 1713–1727, doi:10.3762/bjoc.19.125

• ]. The study also found that those coordination compounds were selective towards abnormal cells, exhibiting lower toxicity for healthy human hepatocytes. On the other hand, an important development in cancer research is the use of physiological metal ion complexes, which afford more biocompatibility and

Investigation of cationic ring-opening polymerization of 2-oxazolines in the “green” solvent dihydrolevoglucosenone

• Solomiia Borova and
• Robert Luxenhofer

Beilstein J. Org. Chem. 2023, 19, 217–230, doi:10.3762/bjoc.19.21

• biomedical applications, in particular as an alternative to the hydrophilic poly(ethylene glycol) (PEG), which is the polymer of choice for many biomedical applications due to its high solubility, low cytotoxicity and biocompatibility [3][4][5][6][7][8][9]. However, an ongoing discussion about pre-existing

Cyclodextrin-based Schiff base pro-fragrances: Synthesis and release studies

• Attila Palágyi,
• Jindřich Jindřich,
• Juraj Dian and
• Sophie Fourmentin

Beilstein J. Org. Chem. 2022, 18, 1346–1354, doi:10.3762/bjoc.18.140

• …) to attach the fragrance covalently with various functional groups. Additionally, CDs already occur in many daily products [16] and fulfill the requirements of biocompatibility and cost for designing pro-fragrances that could find applications in the flavor and fragrance industry [18]. In this article

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

• merits, such as ease of design and tailoring (based on the known structures from proteins), good biocompatibility and degradability, and low immunogenicity. For example, recent works have demonstrated the potential of peptide assemblies for a wide range of applications, including drug delivery [8][9][10

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

• . Chitosan is one of the most abundant bio-based polymers in nature [9]. It is the N-deacetylated form of chitin found in industrial waste [10]. Chitosan is a broadly used natural polymer because of properties such as biocompatibility, low cost, and nontoxicity. It has diverse applications, such as drug

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

• solvent below freezing temperature. Due to their inherent interconnected macroporosity, ease of preparation, and biocompatibility, they are increasingly being investigated for use in biomedical applications such as 3D-bioprinting, drug delivery, wound healing, and as injectable therapeutics. This review

• cryogel properties including biocompatibility, mechanical and thermal properties, and degradability are influenced by a variety of factors. Perhaps the most important factor is the chemical composition as this determines whether the cryogel is biocompatible or degradable and to some extent influences the

• mechanical and thermal properties of the cryogel. Mechanical properties are mainly influenced by porosity and degree of crosslinking, while crosslinking also influences biocompatibility and degradability. In chemically crosslinked cryogels the mechanical properties can be influenced by the degree of

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

• conditions, under laser irradiation, and the biocompatibility make it possible to conclude that the design of these compounds is promising for mass spectrometry, for catalysts for hydrogen production, and for photothermal cancer therapy. Representatives of isomeric bisoxindoles. Isoindigo-based OSCs with the

Chemical synthesis of C6-tetrazole ᴅ-mannose building blocks and access to a bioisostere of mannuronic acid 1-phosphate

• Eleni Dimitriou and
• Gavin J. Miller

Beilstein J. Org. Chem. 2021, 17, 1527–1532, doi:10.3762/bjoc.17.110

• ; Introduction Alginate is an important, industrially relevant polysaccharide chemically composed of β-1,4-linked ᴅ-mannuronic acid (M) and α-ʟ-guluronic acid (G) monosaccharide building blocks (Figure 1a). Because of its biocompatibility, alginate has several commercial industrial applications; for example, it

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

• evaluated, showing no adverse effects or evident disease (Figure 4A). The biocompatibility of CCMV in shrimp is of great commercial significance. The biocompatibility of CCMV suggests a broad potential to develop treatments for disease control in aquatic organisms and mammals. Plant virus-based VLPs, in

Water-soluble host–guest complexes between fullerenes and a sugar-functionalized tribenzotriquinacene assembling to microspheres

• Si-Yuan Liu,
• Xin-Rui Wang,
• Man-Ping Li,
• Wen-Rong Xu and
• Dietmar Kuck

Beilstein J. Org. Chem. 2020, 16, 2551–2561, doi:10.3762/bjoc.16.207

• motif. In the work presented here, we have introduced sugar motifs that possess good water solubility and biocompatibility [36][37][38] at the six outer peripheral positions of the TBTQ framework to provide, for the first time, a water-soluble TBTQ-based host bearing an extended cavity. The complexation

The B & B approach: Ball-milling conjugation of dextran with phenylboronic acid (PBA)-functionalized BODIPY

• Patrizia Andreozzi,
• Lorenza Tamberi,
• Elisamaria Tasca,
• Gina Elena Giacomazzo,
• Marta Martinez,
• Mirko Severi,
• Marco Marradi,
• Stefano Cicchi,
• Sergio Moya,
• Giacomo Biagiotti and
• Barbara Richichi

Beilstein J. Org. Chem. 2020, 16, 2272–2281, doi:10.3762/bjoc.16.188

• biocompatibility while remaining fluorescent. Keywords: ball milling; boronic ester; dextran; bodipy; nanoparticles; Introduction In the last few decades, mechanochemistry has gathered a great deal of attention and a lot of efforts have been focused on its use in organic synthesis, catalysis, biotransformation

• properties of BODIPY and the biocompatibility of dextran. The BODIPY dextran nanoparticles were characterized regarding their size, morphology, polarity, and toxicity in vitro. We demonstrate the feasibility of mechanochemistry for boronic ester formation [23] to a glycan polymer as a route of conjugation

• intracellularly through hydrolysis of the boronic esters. Indeed, the formation of assemblies or nanoparticles of the conjugate Dex-1b capable of solubilizing organic molecules and retaining water stability could be of interest for drug delivery, considering the exceptional biocompatibility of the dextran. We

pH- and concentration-dependent supramolecular self-assembly of a naturally occurring octapeptide

• Goutam Ghosh and
• Gustavo Fernández

Beilstein J. Org. Chem. 2020, 16, 2017–2025, doi:10.3762/bjoc.16.168

• implications for the development of a wide range of functional materials [2][3][4][5][6][7][8]. Peptides are arguably the most eminent candidates among all types of biological self-assembling building blocks because of a number of key properties. This includes a high biocompatibility [9][10][11][12][13][14

• , as mentioned above. The pH-responsive self-assembling behavior of peptides has a great importance in drug delivery, and since PEP-1 contains rich cationic residues, such as Arg, this system can be an interesting potential candidate for DDS and as an antibacterial agent [71]. Biocompatibility, drug

Heterogeneous photocatalysis in flow chemical reactors

• Christopher G. Thomson,
• Ai-Lan Lee and
• Filipe Vilela

Beilstein J. Org. Chem. 2020, 16, 1495–1549, doi:10.3762/bjoc.16.125

• in mind, it is perhaps not surprising that TiO2 as a material for photocatalysis is incredibly well studied and characterised. TiO2 has excellent physicochemical properties, good biocompatibility, is abundant in nature, and subsequently inexpensive. For these reasons, the application of TiO2 in

Morphology-tunable and pH-responsive supramolecular self-assemblies based on AB₂-type host–guest-conjugated amphiphilic molecules for controlled drug delivery

• Yang Bai,
• Cai-ping Liu,
• Di Chen,
• Long-hai Zhuo,
• Huai-tian Bu and
• Wei Tian

Beilstein J. Org. Chem. 2019, 15, 1925–1932, doi:10.3762/bjoc.15.188

• on the basis of the dissociation of host–guest interactions between β-CD and BM. Cellular toxicity of drug-loaded supramolecular self-assemblies The biocompatibility of drug-free supramolecular self-assemblies is of crucial importance for the further use of these materials as drug carriers. Herein

• , the biocompatibility of β-CD-BM2-based FSSAs towards PC-3 cells was investigated with different concentrations after incubation for 48 h. The result did not show any cytotoxicity against PC-3 cells (Figure 5a). The viability of PC-3 cells could reach 84% even when the concentration of FSSAs was up to

• 240 μg/mL, indicating a good biocompatibility. An MTT assay was then conducted to evaluate the potential of supramolecular self-assemblies as intelligent drug release carriers within a biological environment. The cellular toxicity of DOX-loaded FSSAs and free DOX·HCl against PC-3 cells was further

Mechanochemical synthesis of poly(trimethylene carbonate)s: an example of rate acceleration

• Sora Park and
• Jeung Gon Kim

Beilstein J. Org. Chem. 2019, 15, 963–970, doi:10.3762/bjoc.15.93

• Discussion Aliphatic polycarbonates are found in many biomedical applications since they have many desirable properties such as high biocompatibility, easy degradation, good mechanical properties, and low toxicity [21][22][23]. Many synthetic methods have been developed, and the chain-growth ring-opening

Design and synthesis of multivalent α-1,2-trimannose-linked bioerodible microparticles for applications in immune response studies of Leishmania major infection

• Chelsea L. Rintelmann,
• Tara Grinnage-Pulley,
• Kathleen Ross,
• Daniel E. K. Kabotso,
• Angela Toepp,
• Anne Cowell,
• Christine Petersen,
• Balaji Narasimhan and
• Nicola Pohl

Beilstein J. Org. Chem. 2019, 15, 623–632, doi:10.3762/bjoc.15.58

• glycoconjugate through recognition by phagocytic cells [43][44][45]. Here we discuss the design and synthesis of this new bioerodible microparticle 2 compared to our previously designed [11] trimannose-coated latex bead construct 1 (Figure 2) and evaluate the biocompatibility of the microparticle in spared dose

• amide bond coupling, facilitates synthetic manipulation and biocompatibility [48][49]. In an effort to make a direct comparison to our previous biological studies, trimannose-coated latex beads also were synthesized using 1 μm FluoSpheres© carboxylate-modified latex beads labeled with a red fluorophore

Synthesis and fluorescent properties of N(9)-alkylated 2-amino-6-triazolylpurines and 7-deazapurines

• Andrejs Šišuļins,
• Jonas Bucevičius,
• Yu-Ting Tseng,
• Irina Novosjolova,
• Kaspars Traskovskis,
• Ērika Bizdēna,
• Huan-Tsung Chang,
• Sigitas Tumkevičius and
• Māris Turks

Beilstein J. Org. Chem. 2019, 15, 474–489, doi:10.3762/bjoc.15.41

• biocompatibility could be applied for the cell staining in fluorescence microscopy. Applications in the cell studies The newly prepared compound library with purine and 7-deazapurine derivatives was submitted to the screening of their biological activity. The compounds of interest were studied on two cancer cell

Olefin metathesis in multiblock copolymer synthesis

• Maria L. Gringolts,
• Yulia I. Denisova,
• Eugene Sh. Finkelshtein and
• Yaroslav V. Kudryavtsev

Beilstein J. Org. Chem. 2019, 15, 218–235, doi:10.3762/bjoc.15.21

• electronics, fuel cells, gene and drug delivery [8][9][15][38][39][40]. Compared with diblock and triblock copolymers, not to speak about polymer blends, multiblock copolymers often demonstrate superior mechanical properties, biocompatibility, biodegradability, compatibilizing ability, and tendency to form

Copolymerization of epoxides with cyclic anhydrides catalyzed by dinuclear cobalt complexes

• Yo Hiranoi and
• Koji Nakano

Beilstein J. Org. Chem. 2018, 14, 2779–2788, doi:10.3762/bjoc.14.255

• significant attention owing to their good biocompatibility and biodegradability [1][2][3][4]. These attractive features allow them to be applied in medical and ecological materials as well as in commodity materials. The conventional way of synthesizing polyesters is the step-growth polymerization of diacids

Synthesis of a water-soluble 2,2′-biphen[4]arene and its efficient complexation and sensitive fluorescence enhancement towards palmatine and berberine

• Xiayang Huang,
• Xinghua Zhang,
• Tianxin Qian,
• Junwei Ma,
• Lei Cui and
• Chunju Li

Beilstein J. Org. Chem. 2018, 14, 2236–2241, doi:10.3762/bjoc.14.198

• specific structures and interesting host–guest properties [21][22][23][24][25][26][27][28][29][30][31][32]. Water-soluble pillar[n]arene derivatives, especially those containing carboxylato moieties, showed low cell toxicity and good biocompatibility, and have been applied in biomedical applications such

Applications of organocatalysed visible-light photoredox reactions for medicinal chemistry

• Michael K. Bogdos,
• Emmanuel Pinard and
• John A. Murphy

Beilstein J. Org. Chem. 2018, 14, 2035–2064, doi:10.3762/bjoc.14.179

• lumiflavin (3Lum Ered*(cat/cat•−) ≈ +1.5 V vs SCE) as the photocatalyst in aqueous buffer (Scheme 4) [44]. This work highlights the great biocompatibility of organophotoredox methodology and also is an excellent demonstration of the type of chemoselectivity achievable using these methods. Apart from the

Binding abilities of polyaminocyclodextrins: polarimetric investigations and biological assays

• Marco Russo,
• Daniele La Corte,
• Annalisa Pisciotta,
• Serena Riela,
• Rosa Alduina and
• Paolo Lo Meo

Beilstein J. Org. Chem. 2017, 13, 2751–2763, doi:10.3762/bjoc.13.271

• ][31][32][33][34][35]. Cyclodextrins (CDs), in particular, constitute appealing systems due to their biocompatibility, which allowed them to be approved by the FDA as human friendly products [36]. Thus, polycationic CDs might be used in principle as bimodal ligands for the simultaneous internalization

Synthesis and application of trifluoroethoxy-substituted phthalocyanines and subphthalocyanines

• Satoru Mori and
• Norio Shibata

Beilstein J. Org. Chem. 2017, 13, 2273–2296, doi:10.3762/bjoc.13.224

• trifluoroethoxy group in suppressing the aggregation of phthalocyanine is extremely remarkable. Therefore, it is expected that an effective medical dye can be developed by using this excellent aggregation suppressing effect. On the other hand, improving the biocompatibility of phthalocyanine is as important as

• suppressing its aggregation property. It is also necessary to improve the water solubility of the lipophilic phthalocyanine in order to increase its biocompatibility [88][89]. One frequent method to increase the water solubility of phthalocyanine involves the combination of a biomolecule such as a sugar [90

• laser only to the target tumor cells. The features of ideal PDT agents include, among others: i) strong absorption in the red wavelength region; ii) non-aggregation property; iii) high biocompatibility; iv) good selectivity to cancer cells; v) high quantum yield of singlet oxygen [96]. Since the PDT