Recent developments in photoredox-catalyzed remote ortho and para C–H bond functionalizations

• Rafia Siddiqui and
• Rashid Ali

Beilstein J. Org. Chem. 2020, 16, 248–280, doi:10.3762/bjoc.16.26

• bonds in the presence of photoredox catalyst 8, with a similar mechanism as shown in Figure 22, and the photocatalytic mechanism was elucidated by nanosecond laser flash photolysis (Scheme 24) [168]. Fluorine-18 is an important radioisotope used in the radiopharmaceutical industry (e.g., for drug

• delivery, medical imaging, etc.). Therefore, functionalization of arenes with this isotope is an important task. Although several reports are available in the literature for these transformations, they suffer from poor reactivity, unreactive starting material, and lower activities of the 18F-labeled

Light-controllable dithienylethene-modified cyclic peptides: photoswitching the in vivo toxicity in zebrafish embryos

• Sergii Afonin,
• Oleg Babii,
• Aline Reuter,
• Volker Middel,
• Masanari Takamiya,
• Uwe Strähle,
• Igor V. Komarov and
• Anne S. Ulrich

Beilstein J. Org. Chem. 2020, 16, 39–49, doi:10.3762/bjoc.16.6

• (converted to the ON photoform) by applying light of a specific wavelength, precisely at the desired site of action. Spatiotemporal resolution of such light-mediated drug delivery is limited mainly by the technical characteristics of the medical devices used for light application and by the light propagation

Construction of trisubstituted chromone skeletons carrying electron-withdrawing groups via PhIO-mediated dehydrogenation and its application to the synthesis of frutinone A

• Qiao Li,
• Chen Zhuang,
• Donghua Wang,
• Wei Zhang,
• Rongxuan Jia,
• Fengxia Sun,
• Yilin Zhang and
• Yunfei Du

Beilstein J. Org. Chem. 2019, 15, 2958–2965, doi:10.3762/bjoc.15.291

• Qiao Li Chen Zhuang Donghua Wang Wei Zhang Rongxuan Jia Fengxia Sun Yilin Zhang Yunfei Du Tianjin Key Laboratory for Modern Drug Delivery & High-Efficiency, School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072, China College of Chemical and Pharmaceutical Engineering

A chiral self-sorting photoresponsive coordination cage based on overcrowded alkenes

• Constantin Stuckhardt,
• Diederik Roke,
• Wojciech Danowski,
• Edwin Otten,
• Sander J. Wezenberg and
• Ben L. Feringa

Beilstein J. Org. Chem. 2019, 15, 2767–2773, doi:10.3762/bjoc.15.268

• coordination complexes (SCCs) represent a promising class of compounds which have been used in a variety of molecular systems [1][2][3][4][5][6]. Taking advantage of the vacant cavity inside these complexes, SCCs have been applied in drug delivery [6][7][8], supramolecular catalysis [9][10][11][12], X-ray

Probing of local polarity in poly(methyl methacrylate) with the charge transfer transition in Nile red

• Aydan Yadigarli,
• Qimeng Song,
• Sergey I. Druzhinin and
• Holger Schönherr

Beilstein J. Org. Chem. 2019, 15, 2552–2562, doi:10.3762/bjoc.15.248

• -controlled drug delivery systems [4][6][7][8][9][10], as well as dynamics of polymers at interfaces [11]. To be able to understand local properties of polymers, in particular in nanoenvironments of polymeric vesicles (polymersomes), comprising a hydrophilic corona and a hydrophobic wall [1][12], or in

Ultrafast processes triggered by one- and two-photon excitation of a photochromic and luminescent hydrazone

• Alessandro Iagatti,
• Baihao Shao,
• Alberto Credi,
• Barbara Ventura,
• Ivan Aprahamian and
• Mariangela Di Donato

Beilstein J. Org. Chem. 2019, 15, 2438–2446, doi:10.3762/bjoc.15.236

• ], drug delivery [8][9], design of molecular machines [10][11][12][13], super resolution microscopy [14][15], together with biological applications, among which photopharmacology is currently gaining increasing attention [16][17][18][19]. Photochromic molecules, which respond to light as an external

Targeted photoswitchable imaging of intracellular glutathione by a photochromic glycosheet sensor

• Xianzhi Chai,
• Hai-Hao Han,
• Yi Zang,
• Jia Li,
• Xiao-Peng He,
• Junji Zhang and
• He Tian

Beilstein J. Org. Chem. 2019, 15, 2380–2389, doi:10.3762/bjoc.15.230

• as biosensing/imaging, bioactivity modulation, drug delivery, etc [23][24]. In our system, the Glyco-DTE@MnO2 hybrid sensor undergoes decomposition when encountering the overexpressed intracellular GSH in HepG2 cell lines, following the recovery of the photoswitchable fluorescence signal regulated by

1,2,3-Triazolium macrocycles in supramolecular chemistry

• Mastaneh Safarnejad Shad,
• Pulikkal Veettil Santhini and
• Wim Dehaen

Beilstein J. Org. Chem. 2019, 15, 2142–2155, doi:10.3762/bjoc.15.211

• have led to applications in molecular recognition, sensing, molecular machines and devices, supramolecular polymers, stimuli-responsive materials, supramolecular catalysis and drug-delivery systems [4][5][6][7]. Inspired by the attractive role of various N-heterocyclic building blocks such as

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

• -responsive supramolecular self-assemblies have been constructed, the controlled drug delivery induced by morphology transitions of these supramolecular self-assemblies on the basis of host–guest-conjugated monomers (HGCMs) are few reported. In this paper, the self-assembly behaviors of AB2-type HGCMs, e.g

• varied morphology could inhibit cancer cell proliferation, indicating their potential application in the field of drug delivery. Keywords: β-cyclodextrin; controlled drug delivery; host–guest interaction; stimuli-responsive; supramolecular self-assemblies; Introduction Supramolecular self-assemblies

• hydrophobic core and β-CD moieties as outer hydrophilic shell. The basic cell experiments confirmed that the pH-responsive supramolecular self-assemblies based on β-CD-BM2 have a potential application in the field of drug delivery. Results and Discussion Synthesis of the host–guest-conjugated amphiphilic

Novel macrocycles – and old ones doing new tricks

• Wei Jiang and
• Christoph A. Schalley

Beilstein J. Org. Chem. 2019, 15, 1838–1839, doi:10.3762/bjoc.15.178

• diversified. They are not only tools for studying molecular recognition and molecular machines, but are also key components for sensing, supramolecular catalysis, (chiral) separation, drug delivery, or smart materials. Many new macrocycles have recently been reported, with pillararenes being one of the most

Design, synthesis and biological evaluation of immunostimulating mannosylated desmuramyl peptides

• Rosana Ribić,
• Ranko Stojković,
• Lidija Milković,
• Mariastefania Antica,
• Marko Cigler and
• Srđanka Tomić

Beilstein J. Org. Chem. 2019, 15, 1805–1814, doi:10.3762/bjoc.15.174

• contribute to the recognition of the adjuvant compound by specific mannose receptors expressed at immune cells. Mannosylated drug delivery systems enhance uptake and activation of dendritic cells and increase T cell proliferation [24][27][28]. Mannosylation of the adamantylated desmuramyl peptides amplified

• most suitable position of adamantane in this class of compounds is at the peptide N-terminus. Adamantane can act as membrane anchor for mannose structures and thus be exposed on liposome surfaces and as such used in targeted drug delivery [37]. It can be also incorporated into a β-cyclodextrine cavity

• , a powerful supramolecular nanoparticle carrier for targeted drug delivery [38]. Previous research suggested a design of mannosylated desmuramyl peptides with adamantane at the C-terminus in order to facilitate the incorporation into the hydrophobic layer of the cavity because of the minor steric

Anomeric sugar boronic acid analogues as potential agents for boron neutron capture therapy

• Daniela Imperio,
• Erika Del Grosso,
• Silvia Fallarini,
• Grazia Lombardi and
• Luigi Panza

Beilstein J. Org. Chem. 2019, 15, 1355–1359, doi:10.3762/bjoc.15.135

• . Galactose and fructose also allow tumor growth in the absence of glucose. Boronic acid derivatives have gained interest in the last years in different fields such as the development of enzyme inhibitors, drug delivery polymers, saccharide sensors and as boron carriers for BNCT, e.g., amino acid derivatives

Host–guest interactions between p-sulfonatocalix[4]arene and p-sulfonatothiacalix[4]arene and group IA, IIA and f-block metal cations: a DFT/SMD study

• Valya K. Nikolova,
• Cristina V. Kirkova,
• Silvia E. Angelova and
• Todor M. Dudev

Beilstein J. Org. Chem. 2019, 15, 1321–1330, doi:10.3762/bjoc.15.131

• ligands with novel features. They have found various applications in chemical [5], analytical [6][7][8][9], and engineering materials fields (self-assembling monolayers, surfactants, sensors [10][11]), in polymer synthesis [12][13], controlled drug-delivery systems [14], and so on, besides the biochemical

Fabrication, characterization and adsorption properties of cucurbit[7]uril-functionalized polycaprolactone electrospun nanofibrous membranes

• Changzhong Chen,
• Fengbo Liu,
• Xiongzhi Zhang,
• Zhiyong Zhao and
• Simin Liu

Beilstein J. Org. Chem. 2019, 15, 992–999, doi:10.3762/bjoc.15.97

• or some low-molecular weight organic compounds [1][2][3][4][5]. With the unique advantages of ultrafine diameter, high specific surface area, controllable morphology, and easy functionalization, electrospun nanofibers have potential applications in various areas including drug delivery and tissue

Towards the preparation of synthetic outer membrane vesicle models with micromolar affinity to wheat germ agglutinin using a dialkyl thioglycoside

• Dimitri Fayolle,
• Nathalie Berthet,
• Bastien Doumeche,
• Olivier Renaudet,
• Peter Strazewski and
• Michele Fiore

Beilstein J. Org. Chem. 2019, 15, 937–946, doi:10.3762/bjoc.15.90

• adjuvants, glycolipid–phospholipid drug delivery systems and for the formulation of GVs that can be used as tools to bind to various bacterial lectins depending on the mono- or disaccharides used. As a first and relevant conclusion, in silico and in vitro studies demonstrated that two of those compounds

Photochemical generation of the 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO) radical from caged nitroxides by near-infrared two-photon irradiation and its cytocidal effect on lung cancer cells

• Ayato Yamada,
• Manabu Abe,
• Yoshinobu Nishimura,
• Shoji Ishizaka,
• Masashi Namba,
• Taku Nakashima,
• Kiyofumi Shimoji and
• Noboru Hattori

Beilstein J. Org. Chem. 2019, 15, 863–873, doi:10.3762/bjoc.15.84

• Ayato Yamada Manabu Abe Yoshinobu Nishimura Shoji Ishizaka Masashi Namba Taku Nakashima Kiyofumi Shimoji Noboru Hattori Department of Chemistry, Graduate School of Science, Hiroshima University, 1-3-1 Kagamiyama, Higashi-Hiroshima, Hiroshima 739-8526, Japan Hiroshima Research Centre for Photo-Drug

• -Delivery Systems (HiU-P-DDS), Hiroshima University, 1-3-1 Kagamiyama, Higashi-Hiroshima, Hiroshima 739-8526, Japan JST-CREST, K’s Gobancho 6F, 7, Gobancho, Chiyoda-ku, Tokyo 102-0075, Japan Graduate School of Pure and Applied Sciences, University of Tsukuba, 1-1-1 Tennoudai, Tsukuba, Ibaraki 305-8571

Polyaminoazide mixtures for the synthesis of pH-responsive calixarene nanosponges

• Antonella Di Vincenzo,
• Antonio Palumbo Piccionello,
• Alberto Spinella,
• Delia Chillura Martino,
• Marco Russo and
• Paolo Lo Meo

Beilstein J. Org. Chem. 2019, 15, 633–641, doi:10.3762/bjoc.15.59

• external stimuli is a highly desirable property for tailored materials designed to accomplish particular functions, such as targeted drug delivery systems, as accounted for by the present burst in literature reports [1][2][3][4][5][6]. In this context, we have been recently interested in the synthesis of

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

• recognition, imaging, and drug delivery in aqueous media [4][5][6][67]. They have a low tendency to entangle and can rapidly self-assemble in selective solvents even at very low concentrations forming large-domain microstructures. The facile synthesis of norbornenyl-terminated di- and triblock poly

Olefin metathesis catalysts embedded in β-barrel proteins: creating artificial metalloproteins for olefin metathesis

• Daniel F. Sauer,
• Johannes Schiffels,
• Takashi Hayashi,
• Ulrich Schwaneberg and
• Jun Okuda

Beilstein J. Org. Chem. 2018, 14, 2861–2871, doi:10.3762/bjoc.14.265

• metathesis into natural metabolic pathways to allow synthesis of fine chemicals [14]. Also, a targeted reaction in a certain environment within a living cell with a precise release or activation of the catalyst would enable new ways of drug delivery. The challenge to overcome this regard is the deactivation

An overview on recent advances in the synthesis of sulfonated organic materials, sulfonated silica materials, and sulfonated carbon materials and their catalytic applications in chemical processes

• Hashem Sharghi,
• Pezhman Shiri and
• Mahdi Aberi

Beilstein J. Org. Chem. 2018, 14, 2745–2770, doi:10.3762/bjoc.14.253

• fields including adsorbent, optical devices, water purification, drug delivery, and catalysis. Silica nanoparticles with different structures have extensively investigated due to their simple preparation and diverse industrial applications. In addition, SiO2 nanoparticles with high surface area commonly

Novel solid-phase strategy for the synthesis of ligand-targeted fluorescent-labelled chelating peptide conjugates as a theranostic tool for cancer

• Sagnik Sengupta,
• Mena Asha Krishnan,
• Premansh Dudhe,
• Ramesh B. Reddy,
• Bishnubasu Giri,
• Sudeshna Chattopadhyay and
• Venkatesh Chelvam

Beilstein J. Org. Chem. 2018, 14, 2665–2679, doi:10.3762/bjoc.14.244

• tag; Fmoc-Lys-(Tfa)-OH; prostate cancer and ovarian cancer; solid-phase peptide synthesis; Introduction The understanding of cell processes is indispensable to devise new strategies for diagnosis and treatment of cancer and inflammatory diseases through targeted drug delivery techniques [1]. The

• malignancy [23] and inflammatory diseases. They are also utilized for targeted drug delivery [24][25] of therapeutics to avoid any off-site toxicity to normal and healthy cells. Unfortunately, strategies to construct diagnostic and therapeutic chemical tools consisting of a polypeptidic spacer, a homing

• which express neither PSMA nor folate receptors [panels (iv) and (viii)]. The absence of any rhodamine B bioconjugates 13 and 17 uptake in the cytoplasm of negative cell line, PC-3 cells, show that the bioconjugates are very specific which is an important criterion in targeted drug delivery systems for

Comparative cell biological study of in vitro antitumor and antimetastatic activity on melanoma cells of GnRH-III-containing conjugates modified with short-chain fatty acids

• Eszter Lajkó,
• Sarah Spring,
• Rózsa Hegedüs,
• Beáta Biri-Kovács,
• Sven Ingebrandt,
• Gábor Mező and
• László Kőhidai

Beilstein J. Org. Chem. 2018, 14, 2495–2509, doi:10.3762/bjoc.14.226

• approaches to diminish this kind of cytotoxic effects on healthy tissues is the employment of drug delivery systems directed specifically to cancer cells. The chemotherapeutic drug targeting is often based on the receptors for certain peptide hormones that are preferentially expressed by cancer cells. The

• utilization of these receptors for cancer cell targeting allows for minimizing the toxic side effects and producing high drug concentration selectively at the tumor site. In general, drug delivery systems consist of a targeting moiety in order to recognize a receptor on tumor cells and a cytotoxic drug

• )]-GnRH-III(Dau=Aoa) was shown to be the best-internalized conjugate and this ability proved to be independent of the tumor cells. Antiproliferative/cytotoxic effect of conjugates One of the major requirements for a drug-delivery conjugate is the ability to provide the antitumor activity of the attached

Coordination-driven self-assembly of discrete Ru₆–Pt₆ prismatic cages

• Aderonke Ajibola Adeyemo and
• Partha Sarathi Mukherjee

Beilstein J. Org. Chem. 2018, 14, 2242–2249, doi:10.3762/bjoc.14.199

• donors and transition metals as electron-deficient acceptors. Diverse functionalities embedded in these homometallic architectures have found useful applications in chemical sensing [24][25][26][27][28][29][30][31][32][33][34][35], catalysis [11][36][37][38][39][40][41][42][43][44][45][46], drug delivery

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

• as bioimaging and self-assembled drug delivery systems [33][34][35][36][37][38][39][40]. For example, our group demonstrated a direct host–guest complexation-based drug delivery system for oxaliplatin by carboxylatopillar[6]arene [36]. The encapsulation could not only improve the drug‘s stability in

• guests exhibit a significant fluorescence intensity enhancement and the intensity is strong enough to be distinguished by the naked eye. The easy accessibility, good water-solubility and nice binding properties make 2,2’-CBP4 be applicable in the biomedical field, for example, chemical sensors, drug

• delivery, supramolecular amphiphiles, etc. Experimental 2,2’-OEtBP4 was synthesized according to our previously reported method [47]. P and B were purchased from Shanghai Aladdin Bio-Chem Technology Co.,LTD. 1H NMR and 13C NMR spectra were recorded on a Bruker AV500 instrument. The fluorescence emission

A self-assembled photoresponsive gel consisting of chiral nanofibers

• Lei Zou,
• Dan Han,
• Zhiyi Yuan,
• Dongdong Chang and
• Xiang Ma

Beilstein J. Org. Chem. 2018, 14, 1994–2001, doi:10.3762/bjoc.14.174

• other interactions. Interestingly, some of them can be assembled into distinctive nanostructures through gel formation [4][5][6]. Various functional nanostructures have shown great potential for applications in many important areas, for example, nanofabrication [5][7][8][9][10], drug delivery [11][12