Menadione: a platform and a target to valuable compounds synthesis

• Acácio S. de Souza,
• Ruan Carlos B. Ribeiro,
• Dora C. S. Costa,
• Fernanda P. Pauli,
• David R. Pinho,
• Matheus G. de Moraes,
• Fernando de C. da Silva,
• Luana da S. M. Forezi and
• Vitor F. Ferreira

Beilstein J. Org. Chem. 2022, 18, 381–419, doi:10.3762/bjoc.18.43

• a quantitative yield. Still about reduction reactions, Niemczyk and Van Arnum described a green methodology for reduction of menadione (10), during the pegylation of 14 to improving the solubility of the studied compounds [118]. The authors reduced 10 with sodium dithionite under ultrasound

• irradiation, generating the reduced adduct in 79% yield (Scheme 20). Depending on the type of solvent used, the yield may vary due to oxidation of the alcohol 14 back to 10 because of its low stability in solution. The pegylation strategy involved monomethoxypoly(ethyleneglycol)succinimide carbonate (mPEG-SC

• , 68), giving the pegylated product and N-hydroxysuccinimide (NHS) as the sole byproduct. The latter can be recycled again to the pegylation reagent. This study showed better results when compared to the methodology for a phosphorylation of 14 developed by Fieser [119], a procedure carried out in two

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

BODIPY-based fluorescent liposomes with sesquiterpene lactone trilobolide

• Ludmila Škorpilová,
• Silvie Rimpelová,
• Michal Jurášek,
• Miloš Buděšínský,
• Jana Lokajová,
• Roman Effenberg,
• Petr Slepička,
• Tomáš Ruml,
• Eva Kmoníčková,
• Pavel B. Drašar and
• Zdeněk Wimmer

Beilstein J. Org. Chem. 2017, 13, 1316–1324, doi:10.3762/bjoc.13.128

• ]amine) [37] in DMF gave a cholesterol-containing clickate 4 in 49% yield. The pegylation of 4 with amino-PEG4-alkyne in the presence of EDCI (N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride), 4-DMAP (4-dimethylaminopyridine) and HOBt (N-hydroxybenzotriazole) in DMF provided an alkyne

Carbohydrate PEGylation, an approach to improve pharmacological potency

• M. Eugenia Giorgi,
• Rosalía Agusti and
• Rosa M. de Lederkremer

Beilstein J. Org. Chem. 2014, 10, 1433–1444, doi:10.3762/bjoc.10.147

• polyethylene glycol (PEG), known as PEGylation, has been widely used to improve the bioavailability of proteins and low molecular weight drugs. The covalent conjugation of PEG to the carbohydrate moiety of a protein has been mainly used to enhance the pharmacokinetic properties of the attached protein while

• -carbohydrates, in particular multiarm PEGylation, is presented. Keywords: bioavailability; carbohydrates; conjugates; glycoPEGylation; multivalent glycosystems; multivalent PEGylation; Introduction In recent years, the modification of biotherapeutics by covalent conjugation with polyethyleneglycol (PEG) known

• as PEGylation has emerged as an effective strategy to improve the therapeutic potential of drugs through less frequent dosing [1][2][3]. PEG is a biologically inert, non-immnunogenic linear polyether diol that confers proteins greater solubility in aqueous and organic media. It is being used in

Automated solid-phase peptide synthesis to obtain therapeutic peptides

• Veronika Mäde,
• Sylvia Els-Heindl and
• Annette G. Beck-Sickinger

Beilstein J. Org. Chem. 2014, 10, 1197–1212, doi:10.3762/bjoc.10.118

• essentially improved microwave-assisted instruments is discussed. In order to improve pharmacokinetic properties of peptides, lipidation and PEGylation are described as covalent conjugation methods, which can be applied by a combination of automated and manual synthesis approaches. The synthesis and

• : automated synthesis; automation; lipidation; PEGylation; peptide drugs; solid-phase peptide synthesis; therapeutic peptides; Introduction Peptides and proteins are involved in a large variety of biochemical processes and physiological functions. Peptides can consist of up to 50 amino acids and have

• for modulating peptide stability with an emphasis on lipidation and PEGylation are characterized. Last, the syntheses of selected peptide hormones are presented exemplarily. Review Chemical synthesis of peptides and its automation Solid-phase peptide synthesis – the way from homogeneous to

Amyloid-β probes: Review of structure–activity and brain-kinetics relationships

• Todd J. Eckroat,
• Abdelrahman S. Mayhoub and
• Sylvie Garneau-Tsodikova

Beilstein J. Org. Chem. 2013, 9, 1012–1044, doi:10.3762/bjoc.9.116

• ) [14]. Dimethylation of the amino group seems to be crucial for Aβ binding, since analogues with free amino groups or monomethyl amino groups revealed lower affinity [14]. On the other hand, pegylation is not that essential for plaque binding as tertiary amine analogues with different degrees of

• pegylation (n = 0–3) all showed similar affinity. In biodistribution experiments using normal mice, the [18F]-labeled chalcone 19a showed high brain uptake rate and good clearance, whereas the [11C]-labeled chalcone 19b revealed reasonable brain uptake rate, but very fast clearance [14]. The [18F]-labeled

• primary amine analogues [16]. Also as with chalcones, the degree of pegylation had only minor effects on binding properties. Compounds 29a–c showed uptake rates indicative of high to sufficient levels for brain imaging (2.89–4.17% ID/g at 2 min) and moderate clearance rates [16]. The flavone backbone of

Theoretical study on β-cyclodextrin inclusion complexes with propiconazole and protonated propiconazole

• Adrian Fifere,
• Narcisa Marangoci,
• Stelian Maier,
• Adina Coroaba,
• Dan Maftei and
• Mariana Pinteala

Beilstein J. Org. Chem. 2012, 8, 2191–2201, doi:10.3762/bjoc.8.247

• modified (by pegylation for example) in order to avoid the shielding of the cavity during the inclusion process, and, as a consequence, to improve the systemic bioavailability and pharmacokinetics of the inclusion complexes. Results and Discussions The most stable conformations of the β-CD/PP and β-CD/PPH

Chemical modification allows phallotoxins and amatoxins to be used as tools in cell biology

• Jan Anderl,
• Hartmut Echner and
• Heinz Faulstich

Beilstein J. Org. Chem. 2012, 8, 2072–2084, doi:10.3762/bjoc.8.233

• been described as a method to improve the solubility of drugs, prolong their half-lives in plasma, or modulate their pharmacokinetics [35]. An effect not described to our knowledge so far is that pegylation can enhance, several hundred-fold, the penetration of a hydrophilic drug into cells. Linkers