Synthesis of new representatives of A₃B-type carboranylporphyrins based on meso-tetra(pentafluorophenyl)porphyrin transformations

• Victoria M. Alpatova,
• Evgeny G. Rys,
• Elena G. Kononova and
• Valentina A. Ol'shevskaya

Beilstein J. Org. Chem. 2024, 20, 767–776, doi:10.3762/bjoc.20.70

• compounds in drug development [34][35][36][37]. Owing to their stability, carboranes also may increase the in vivo stability and bioavailability of pharmaceuticals that might otherwise rapidly metabolize [38]. The functionalization of porphyrins with carborane clusters provides dual-action photo(radio

Research progress on the pharmacological activity, biosynthetic pathways, and biosynthesis of crocins

• Zhongwei Hua,
• Nan Liu and
• Xiaohui Yan

Beilstein J. Org. Chem. 2024, 20, 741–752, doi:10.3762/bjoc.20.68

• ) ameliorates myocardial ischemia or myocardial infarction induced by coronary ligation. Although crocin and crocetin derivatives exhibit a diverse scope of biological activity, they are characterized by poor stability and low bioavailability, which has significantly impeded clinical developments. Recently

• , novel pharmaceutical systems, such as liposomes, microcapsules, and nanoparticles, were adopted to enhance the stability and bioavailability of these compounds [13][14][15]. To find a sustainable way of supplying crocins, researchers have developed various approaches to produce them, including plant

• broad pharmacological properties. They are promising drugs for treating cardiovascular and liver diseases. Despite numerous pharmacological properties, the exact mechanisms of action of crocins remain elusive. The therapeutic potential of crocins is impeded by the limited bioavailability and rapid

New variochelins from soil-isolated Variovorax sp. H002

• Jabal Rahmat Haedar,
• Aya Yoshimura and
• Toshiyuki Wakimoto

Beilstein J. Org. Chem. 2024, 20, 692–700, doi:10.3762/bjoc.20.63

• form of insoluble ferric oxide, diminishing its bioavailability. To mitigate this problem, many microorganisms utilize specialized metabolites known as siderophores to efficiently sequester iron. Siderophores are abundantly produced under iron-deficient growth conditions and secreted through dedicated

Synthesis of 2,2-difluoro-1,3-diketone and 2,2-difluoro-1,3-ketoester derivatives using fluorine gas

• Alexander S. Hampton,
• David R. W. Hodgson,
• Graham McDougald,
• Linhua Wang and
• Graham Sandford

Beilstein J. Org. Chem. 2024, 20, 460–469, doi:10.3762/bjoc.20.41

• present in many agrochemical and pharmaceutical products owing to the beneficial properties imparted such as increased metabolic stability, lipophilicity and bioavailability of the bioactive entity [1][2][3]. In 2018, 30% of FDA approved drugs contained at least one fluorine atom, with an average of 2.7

Cyclodextrins permeabilize DPPC liposome membranes: a focus on cholesterol content, cyclodextrin type, and concentration

• Ghenwa Nasr,
• Hélène Greige-Gerges,
• Sophie Fourmentin,
• Abdelhamid Elaissari and
• Nathalie Khreich

Beilstein J. Org. Chem. 2023, 19, 1570–1579, doi:10.3762/bjoc.19.115

• fields, mainly in drug delivery where they are used as pharmaceutical excipients to increase the drug permeability through biological membranes improving drug bioavailability and efficacy [2][4][5]. Furthermore, the CDs peculiarities helped to develop a combined system in which CD–guest complexes are

Access to cyclopropanes with geminal trifluoromethyl and difluoromethylphosphonate groups

• Ita Hajdin,
• Romana Pajkert,
• Mira Keßler,
• Jianlin Han,
• Haibo Mei and
• Gerd-Volker Röschenthaler

Beilstein J. Org. Chem. 2023, 19, 541–549, doi:10.3762/bjoc.19.39

• . Phosphonates containing CF2 groups can sterically and electronically mimic oxygen, enabling the second dissociation constant, pKa2, to closer mirror those of the phosphates due to the electron-withdrawing effect of fluorine [39]. As a result, improved lipophilicity, metabolic stability or bioavailability of

Discrimination of β-cyclodextrin/hazelnut (Corylus avellana L.) oil/flavonoid glycoside and flavonolignan ternary complexes by Fourier-transform infrared spectroscopy coupled with principal component analysis

• Nicoleta G. Hădărugă,
• Gabriela Popescu,
• Dina Gligor (Pane),
• Cristina L. Mitroi,
• Sorin M. Stanciu and
• Daniel Ioan Hădărugă

Beilstein J. Org. Chem. 2023, 19, 380–398, doi:10.3762/bjoc.19.30

• compounds [5]. The resulting supramolecular inclusion complexes provide enhanced water solubility and bioavailability/bioaccessibility of the nanoencapsulated bioactive compounds, higher oxidative and thermal stability or photostability of labile compounds, and their controlled release [6][7]. Vegetable oil

• the release of indomethacin in rats. Similar α-CD-based emulsions were obtained using wheat germ, sweet almond, borage, and virgin coconut oils [9][18][19]. The stability and bioavailability of peony (Paeonia suffruticosa Andr.) seed oil were significantly enhanced by complexation with β-CD through

• improving the bioavailability of ALA. This omega-3 FA was found in significantly higher concentrations in the plasma of rats fed with this complex [21]. Some vegetable oils were also encapsulated using combined matrices or polymers containing CDs as was demonstrated for example for kenaf (Hibiscus

Insight into oral amphiphilic cyclodextrin nanoparticles for colorectal cancer: comprehensive mathematical model of drug release kinetic studies and antitumoral efficacy in 3D spheroid colon tumors

• Sedat Ünal,
• Gamze Varan,
• Juan M. Benito,
• Yeşim Aktaş and
• Erem Bilensoy

Beilstein J. Org. Chem. 2023, 19, 139–157, doi:10.3762/bjoc.19.14

• the physicochemical properties and poor bioavailability of many widely used anticancer drugs. Specifically in the treatment of CRC, since the colon is the most distant part of the gastrointestinal (GI) tract, the ability of oral delivery of anticancer drugs to reach the colon in a stable and effective

Inclusion complexes of the steroid hormones 17β-estradiol and progesterone with β- and γ-cyclodextrin hosts: syntheses, X-ray structures, thermal analyses and API solubility enhancements

• Alexios I. Vicatos,
• Zakiena Hoossen and
• Mino R. Caira

Beilstein J. Org. Chem. 2022, 18, 1749–1762, doi:10.3762/bjoc.18.184

• × 10−3 mg·cm−3 at 27 °C [6][9], and a significantly higher oral bioavailability relative to that of BES. The steroid hormone PRO is commercially available either in its natural form or as micronized natural progesterone [10]. A substantial volume of research on the topic of CD inclusion of BES and PRO

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

• various organic molecules have been described so far. It was proved that the complexation of volatile organic compounds, such as aldehydes, into the CD’s cavity reduces the volatility and increases the solubility and bioavailability of these compounds [5][6][7][8][9][10][11][12][13][14]. The release of

Synthesis of a new water-soluble hexacarboxylated tribenzotriquinacene derivative and its competitive host–guest interaction for drug delivery

• Man-Ping Li,
• Nan Yang and
• Wen-Rong Xu

Beilstein J. Org. Chem. 2022, 18, 539–548, doi:10.3762/bjoc.18.56

• targeting of cancer cells, resulting in low bioavailability and systemic side effects [6]. To address these drawbacks, various approaches have been developed to improve the bioavailability of these and other drugs and to enable their targeted delivery to cancer cells [7][8][9][10]. In recent years

Ready access to 7,8-dihydroindolo[2,3-d][1]benzazepine-6(5H)-one scaffold and analogues via early-stage Fischer ring-closure reaction

• Irina Kuznetcova,
• Felix Bacher,
• Daniel Vegh,
• Hsiang-Yu Chuang and
• Vladimir B. Arion

Beilstein J. Org. Chem. 2022, 18, 143–151, doi:10.3762/bjoc.18.15

• copper(II) complexes prepared revealed an enhanced aqueous solubility and bioavailability indeed, along with very high cytotoxicity [8][9][10][11][12][13][14][15][16][17][18][19][20][21]. Moreover, the metal-free ligands and copper(II) complexes derived from backbone D revealed cytotoxicity in the

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

• in drug delivery Polymers are commonly used in drug-delivery applications as they can improve bioavailability of hydrophobic drugs and facilitate a controlled release of the drug. This leads to numerous benefits, including the increased time spent in the therapeutic zone, which allows the drug to be

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

• notably lagged behind and is still limited by insufficient bioavailability and difficulties with tissue specific delivery. Relatively high doses are required to overcome poor cellular uptake and endosomal entrapment, which increases the risk of toxicity. These limitations remain unsolved problems waiting

Iodine-catalyzed electrophilic substitution of indoles: Synthesis of (un)symmetrical diindolylmethanes with a quaternary carbon center

• Thanigaimalai Pillaiyar,
• Masoud Sedaghati,
• Andhika B. Mahardhika,
• Lukas L. Wendt and
• Christa E. Müller

Beilstein J. Org. Chem. 2021, 17, 1464–1475, doi:10.3762/bjoc.17.102

• interest due to fluorine’s unique physical and chemical properties, such as its small size, high electronegativity, and high C–F bond dissociation energy [22][23][24]. Organofluoro compounds developed as drug molecules often display increased metabolic stability and bioavailability compared to non

Synthesis of 10-O-aryl-substituted berberine derivatives by Chan–Evans–Lam coupling and investigation of their DNA-binding properties

• Peter Jonas Wickhorst,
• Mathilda Blachnik,
• Denisa Lagumdzija and
• Heiko Ihmels

Beilstein J. Org. Chem. 2021, 17, 991–1000, doi:10.3762/bjoc.17.81

• compared to ct DNA. Since the ligands show essentially the same DNA binding properties as the parent berberine (1a), they have the potential to exhibit a similar DNA-targeted bioactivity. The latter may even be improved due to the higher lipophilicity and thus more balanced bioavailability of the ligands

Application of the Meerwein reaction of 1,4-benzoquinone to a metal-free synthesis of benzofuropyridine analogues

• Rashmi Singh,
• Tomas Horsten,
• Rashmi Prakash,
• Swapan Dey and
• Wim Dehaen

Beilstein J. Org. Chem. 2021, 17, 977–982, doi:10.3762/bjoc.17.79

• dibenzofuran have been less explored, although they may have significant bioactivity. Introducing nitrogen to the dibenzofuran system is expected to increase the water solubility and potential bioavailability due to enhanced hydrogen bonding. Figure 2 presents a few examples of azadibenzofuran molecules. One

Synthesis of trifluoromethyl ketones by nucleophilic trifluoromethylation of esters under a fluoroform/KHMDS/triglyme system

• Yamato Fujihira,
• Yumeng Liang,
• Makoto Ono,
• Kazuki Hirano,
• Takumi Kagawa and
• Norio Shibata

Beilstein J. Org. Chem. 2021, 17, 431–438, doi:10.3762/bjoc.17.39

• their biological properties, bioavailability, and ADME [7][8]. While tremendous methodologies have been developed for the synthesis of organofluorine compounds [9][10], many of the laboratory methods are not always suitable for industrial production in terms of their synthetic complexity, handling, and

¹⁹F NMR as a tool in chemical biology

• Diana Gimenez,
• Aoife Phelan,
• Cormac D. Murphy and
• Steven L. Cobb

Beilstein J. Org. Chem. 2021, 17, 293–318, doi:10.3762/bjoc.17.28

• species [1]. This reflects its low bioavailability, as it is typically found in insoluble minerals, and its physicochemical properties, in particular its high redox potential and the poor reactivity of the fluoride ion in aqueous solution. Despite its near-absence in biology, it is a particularly

The preparation and properties of 1,1-difluorocyclopropane derivatives

• Kymbat S. Adekenova,
• Peter B. Wyatt and
• Sergazy M. Adekenov

Beilstein J. Org. Chem. 2021, 17, 245–272, doi:10.3762/bjoc.17.25

Particle size effect in the mechanically assisted synthesis of β-cyclodextrin mesitylene sulfonate

• Stéphane Menuel,
• Sébastien Saitzek,
• Eric Monflier and
• Frédéric Hapiot

Beilstein J. Org. Chem. 2020, 16, 2598–2606, doi:10.3762/bjoc.16.211

• bioavailability [11][12][13]. In our previous studies, CDs acted either as reactants [14][15], or as additives [16][17], and were shown to display supramolecular interactions with the other reaction partners. We demonstrated that the formation of CD/substrate supramolecular complexes favored the dispersion of the

Synthesis of novel fluorinated building blocks via halofluorination and related reactions

• Attila Márió Remete,
• Tamás T. Novák,
• Melinda Nonn,
• Matti Haukka,
• Ferenc Fülöp and
• Loránd Kiss

Beilstein J. Org. Chem. 2020, 16, 2562–2575, doi:10.3762/bjoc.16.208

• lipophilicity, metabolism, binding, and bioavailability are often beneficial [1][2][3][4][5][6][7][8][9]. Fluorinated organic compounds are common amongst drugs [8][9], and the synthesis of fluorinated compounds has become a rapidly developing area [9][10][11][12][13][14][15][16][17][18]. In addition to

Palladium nanoparticles supported on chitin-based nanomaterials as heterogeneous catalysts for the Heck coupling reaction

• Tony Jin,
• Malickah Hicks,
• Davis Kurdyla,
• Sabahudin Hrapovic,
• Edmond Lam and
• Audrey Moores

Beilstein J. Org. Chem. 2020, 16, 2477–2483, doi:10.3762/bjoc.16.201

• coupling; heterogeneous catalysis; nanomaterial; Introduction Over the past decades, biomass-based nanomaterials have become a highly prevalent topic of research owing to their sustainability, bioavailability, unique structural and morphological characteristics [1]. Particularly dominant in this field are

Host–guest interaction of cucurbit[8]uril with oroxin A and its effect on the properties of oroxin A

• Zhishu Zeng,
• Jun Xie,
• Guangyan Luo,
• Zhu Tao and
• Qianjun Zhang

Beilstein J. Org. Chem. 2020, 16, 2332–2337, doi:10.3762/bjoc.16.194

• constants [14] have shown that Q[n]s are ideal drug carriers [15][16]. Moreover, Q[n]s can enhance the physical stability [17][18] and increase the solubility [19][20] of drug molecules. After Q[n]s forms a host–guest complex with drug molecules, it can also improve the bioavailability and delivery capacity

Photosensitized direct C–H fluorination and trifluoromethylation in organic synthesis

• Shahboz Yakubov and
• Joshua P. Barham

Beilstein J. Org. Chem. 2020, 16, 2151–2192, doi:10.3762/bjoc.16.183

• a positive impact on the biological absorption and distribution. Moreover, C–H/C–F substitution strongly decreases the basicity of neighboring amines (and lowers the pKa by a similar increment) due to the σ-inductive effect of F. This results in i) a higher oral bioavailability [19], ii) a potential