pH-Responsive fluorescent supramolecular nanoparticles based on tetraphenylethylene-labelled chitosan and a six-fold carboxylated tribenzotriquinacene

• Nan Yang,
• Yi-Yan Zhu,
• Wei-Xiu Lin,
• Yi-Long Lu and
• Wen-Rong Xu

Beilstein J. Org. Chem. 2023, 19, 635–645, doi:10.3762/bjoc.19.45

• makes it suitable for oral drug delivery. However, the aggregation behavior of CS-TPE under alkaline conditions may influence its drug release efficiency. Thus, the development of modified systems with reduced propensity to accumulate should be of interest. Self-assembly behavior of TBTQ-C6/CS-TPE in

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

• treatment of colorectal tumors in terms of their drug release behavior and efficacy in 3-dimensional tumor models to predict the in vivo efficacy of different nanocarriers. The main objective was to build a bridge between formulation development and in vitro phase and animal studies. In this context, CPT

• with the cationic CD formulation. In our further research [8], it was also reported that the oral CPT-loaded poly-β-CD-C6 NPs showed antitumoral and antimetastatic effects in a colorectal tumor-bearing animal model. Drug release from amphiphilic CD nanoparticles In vitro release studies were performed

• one model [33][34]. Since it is the first study to evaluate the release kinetics of amphiphilic cyclodextrin nanoparticles, we have reported that a drug release profile that fits more than one model can be observed for amphiphilic cyclodextrin nanoparticles. In the Weibull model, the “β” (shape

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

• stability in artificial gastrointestinal juice and the intervention of Q[8] did not change its stability. Drug release behavior in vitro Figure 8 shows the release curve obtained for CPE and its inclusion complex in artificial gastrointestinal juice. Figure 8A shows that CPE was completely released after

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

• GelMA was carried out using carboxybetaine methacrylate (CBMA) as a comonomer. With the incorporation of CBMA, these hydrogels demonstrated better mechanical properties, a slower degradation rate, and a controlled drug release rate compared with the GelMA alone. The properties of the GelMA/CBMA

• preparation and storage make them desirable for replacing currently used DDS where appropriate [73][82]. Moreover, stimuli-responsive cryogels can also be used to control drug release under specific conditions. There are also some emerging areas where cryogels are proving to be uniquely equipped for certain

• both cryogels and ceramics into a mould, and a physical cross-linker was used to realise the drug theophylline after stimuli had been achieved. Due to the layer system, drug release could occur without diffusion of the subsequent layers, controlling the speed of the release in the ceramic cryogel. In

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

• (AAm) and the hydrophobic AN block [51][52][94]. Since the phase transition temperature of the copolymer can be adjusted over a wide temperature range via the ratio of the two monomers, it is frequently used for the development of novel drug release systems [272][273][274][275][276]. Due to the

On the application of 3d metals for C–H activation toward bioactive compounds: The key step for the synthesis of silver bullets

• Renato L. Carvalho,
• Amanda S. de Miranda,
• Mateus P. Nunes,
• Roberto S. Gomes,
• Guilherme A. M. Jardim and
• Eufrânio N. da Silva Júnior

Beilstein J. Org. Chem. 2021, 17, 1849–1938, doi:10.3762/bjoc.17.126

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

• reaction between 54 and 55 was performed in anhydrous methanol under an argon atmosphere to construct 56. The study on the in vitro drug release showed enhanced drug release at an acidic pH value in comparison to a neutral pH value. Importantly, the amount of DOX required for MCF-7 cells was decreased

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

• and 4.80 × 10−6 mol·L−1, respectively, which indicates that Q[8] did not affect the antioxidant activity of OA. Drug release in vitro Figure 8 shows the cumulative release of the OA and the OA@Q[8] inclusion complex in artificial gastric juice (pH 1.2) and artificial intestinal juice (pH 6.8). It can

A photochemical determination of luminescence efficiency of upconverting nanoparticles

• Baptiste Amouroux,
• Clément Roux,
• Jean-Claude Micheau,
• Fabienne Gauffre and
• Christophe Coudret

Beilstein J. Org. Chem. 2019, 15, 2671–2677, doi:10.3762/bjoc.15.260

• can find applications in material sciences such as photopolymerization [8], or micellization photocontrol [9], since the excitation wavelength lies in the first transparency window of most biological media, a spectacular range of use in biological sciences has been explored from drug release [10

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

• 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

• results further certified that the fast intracellular drug-release process of DOX-loaded FSSAs provided a large intracellular drug dose and high cytotoxicity. All these results suggested that DOX-loaded FSSAs presented a potential application in controlled drug delivery. Intracellular uptake of drug

• acidic conditions into spherical supramolecular self-assemblies with smaller size. The morphology transitions can be utilized to realize a two-stage drug release. The uptake of the DOX-loaded supramolecular self-assemblies performed efficiently and the cellular toxicity through inhibiting cell

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

• oxime bond through an aminooxyacetyl (Aoa) linker to form different drug-containing conjugates [15][16]. Based on the enzymatic stability and capability of different Dau–GnRH-III conjugates to providing appropriate intracellular drug release [15], the oxime bond was used for coupling Dau to GnRH-III or

An amphiphilic pseudo[1]catenane: neutral guest-induced clouding point change

• Tomoki Ogoshi,
• Tomohiro Akutsu and
• Tada-aki Yamagishi

Beilstein J. Org. Chem. 2018, 14, 1937–1943, doi:10.3762/bjoc.14.167

• ; Introduction Thermo-responsive molecules exhibiting a lower critical solution temperature (LCST) are very important for applications such as controlled drug release [1], molecular separation [2], and tissue culture substrates [3]. Poly(N-isopropylacrylamide) (pNIPAAm) is a widely used thermo-responsive polymer

An overview of recent advances in duplex DNA recognition by small molecules

• Sayantan Bhaduri,
• Nihar Ranjan and
• Dev P. Arya

Beilstein J. Org. Chem. 2018, 14, 1051–1086, doi:10.3762/bjoc.14.93

On the design principles of peptide–drug conjugates for targeted drug delivery to the malignant tumor site

• Eirinaios I. Vrettos,
• Gábor Mező and
• Andreas G. Tzakos

Beilstein J. Org. Chem. 2018, 14, 930–954, doi:10.3762/bjoc.14.80

• ). These are some noteworthy differences that underlie the discrimination between cancerous and normal cells and are often exploited in order to control the site of the drug release during targeted cancer chemotherapy. Review Strategies for targeted delivery of toxic warheads to malignant tumor sites The

• deactivation through deamination in its inactive metabolite dFdU, the acquired multidrug resistance (MDR) and its high hydrophilicity deterring its prolonged drug release from various vehicles [88], which therefore reduces the effective concentration of gemcitabine. It enters cells through nucleoside

• [120]. The two conjugates were subjected to stability tests and they showed slow drug release in human serum in contrast with nude mice that carboxylesterase enzymes are about 10 times higher [121]. Consequently, the two analogs were heavily evaluated in in vivo models in nude mice bearing various

Development of novel cyclic NGR peptide–daunomycin conjugates with dual targeting property

• Andrea Angelo Pierluigi Tripodi,
• Szilárd Tóth,
• Kata Nóra Enyedi,
• Gitta Schlosser,
• Gergely Szakács and
• Gábor Mező

Beilstein J. Org. Chem. 2018, 14, 911–918, doi:10.3762/bjoc.14.78

• spacer to the lysine side chain connected to the chatepsin B labile GFLG spacer that allows lysosomal drug release. Dau was conjugated to the GFLG spacer via oxime linkage through an incorporated aminooxyacetyl (Aoa) moiety. The preparation of the conjugate required a sophisticated synthetic route and

• selectivity to CD13+ cells. However, the cellular uptake and cytotoxic effect of Dau=Aoa-GFLGK(c[NleNGRE]-GG-)-NH2 was higher in comparison to the control especially on HT-29 cells. Therefore, this conjugate is more suitable for drug targeting with dual targeting property. Keywords: antitumor activity; drug

• release; NGR peptides; oxime-linkage; targeted drug delivery; Introduction Targeted chemotherapy is one of the most promising approaches for selective cancer treatment that may decrease the toxic side effects of anticancer drugs. This therapeutic approach is based on the fact that tumor specific

Synthesis and in vitro biochemical evaluation of oxime bond-linked daunorubicin–GnRH-III conjugates developed for targeted drug delivery

• Sabine Schuster,
• Beáta Biri-Kovács,
• Bálint Szeder,
• Viktor Farkas,
• László Buday,
• Zsuzsanna Szabó,
• Gábor Halmos and
• Gábor Mező

Beilstein J. Org. Chem. 2018, 14, 756–771, doi:10.3762/bjoc.14.64

• the release of the cytotoxic agent within the tumor cell. During clinical trials, only mild side effects were observed which are caused by premature drug release [17]. The receptor mediated uptake of zoptarelin has been investigated by blockage of GnRH receptors using an excess of the GnRH-I

• serum provide valuable information [37]. On the one hand toxic side effects caused by premature drug release should be avoided, on the other hand an intracellular drug release from the bioconjugates in the targeted cell is mandatory to assure the antitumor activity. Previously, we reported on the

Exploring mechanochemistry to turn organic bio-relevant molecules into metal-organic frameworks: a short review

• Vânia André,
• Sílvia Quaresma,
• João Luís Ferreira da Silva and
• M. Teresa Duarte

Beilstein J. Org. Chem. 2017, 13, 2416–2427, doi:10.3762/bjoc.13.239

• enhancement of MOF structural and stability properties [90][91]. Bioactive molecules like caffeine [92][93] and anticancer drugs [94][95][96][97][98] were incorporated in ZIF-8 and tests proved that these systems allowed for a controlled drug release. Further studies involving ZIF-8 with encapsulated

• , including doxorubicin [142]. The controlled drug release is due to the small pore size of ZIF-8 that prevents premature release and its pH sensitivity. At pH 5–6 there dissociation of the framework takes place with consequent drug release ideal to target cancer cells [95]. Mechanochemistry in the synthesis

β-Cyclodextrin- and adamantyl-substituted poly(acrylate) self-assembling aqueous networks designed for controlled complexation and release of small molecules

• Liang Yan,
• Duc-Truc Pham,
• Philip Clements,
• Stephen F. Lincoln,
• Jie Wang,
• Xuhong Guo and
• Christopher J. Easton

Beilstein J. Org. Chem. 2017, 13, 1879–1892, doi:10.3762/bjoc.13.183

• viscosity of the network as shown by ITC, 1H NMR and UV–vis spectroscopy, and rheological studies. Such networks potentially form a basis for the design of controlled drug release systems. Keywords: controlled release; cyclodextrin; network; poly(acrylate); self-assembly; Introduction The formation of

• ]. Generally, the retention and the release of the drug is controlled by the thermodynamics of drug complexation and in some systems the drug release is stimulated by either pH variation [28][30][34] or light irradiation [38][45]. The drug types include small molecular species, exemplified by diflunisal

• dependent upon the structure of the dye, and the structure of the network and its viscosity. Potentially, these systems form the basis for the development of controlled drug delivery systems for topical and wound applications, where the factors for drug release are likely to be similar to those controlling

Kinetic analysis of mechanoradical formation during the mechanolysis of dextran and glycogen

• Naoki Doi,
• Yasushi Sasai,
• Yukinori Yamauchi,
• Tetsuo Adachi,
• Masayuki Kuzuya and
• Shin-ichi Kondo

Beilstein J. Org. Chem. 2017, 13, 1174–1183, doi:10.3762/bjoc.13.116

• disclosed the formation of polystyrene on the cotton [18]. In a previous paper, we reported the synthesis of water-soluble graft polymeric prodrugs through the mechanochemical reaction of HEC and methacryloyl derivatives of 5-fluorouracil [19]. We also discussed the nature of drug release from the polymeric

Glyco-gold nanoparticles: synthesis and applications

• Federica Compostella,
• Olimpia Pitirollo,
• Alessandro Silvestri and
• Laura Polito

Beilstein J. Org. Chem. 2017, 13, 1008–1021, doi:10.3762/bjoc.13.100

• of the drug from degradation or inactivation in vivo, the opportunity to control the drug release and reduce the systemic toxicity and the exciting chance to selectively target the damaged tissue. Despite the most common carriers are based on nano- and microparticles (i.e., albumin, poly(lactic-co

Fluorescent carbon dots from mono- and polysaccharides: synthesis, properties and applications

• Stephen Hill and
• M. Carmen Galan

Beilstein J. Org. Chem. 2017, 13, 675–693, doi:10.3762/bjoc.13.67

• interaction between the positively charged amino group in DOX and the negatively charged groups on the CD surface can take place. Also van der Waals and π–π stacking interactions were attributed as contributing factors to the DOX loading and DOX incorporation into the hollow CD cavity. Drug release at acidic

Inclusion complexes of 2-methoxyestradiol with dimethylated and permethylated β-cyclodextrins: models for cyclodextrin–steroid interaction

• Mino R. Caira,
• Susan A. Bourne,
• Halima Samsodien and
• Vincent J. Smith

Beilstein J. Org. Chem. 2015, 11, 2616–2630, doi:10.3762/bjoc.11.281

• literature. Encapsulation of poorly soluble drug molecules by CDs with the aim of enhancing drug bioavailability has been practised for over four decades, the first demonstration of both in vivo and in vitro effects of complexation on drug release having been reported in the early 1970s [12][13]. Steroid

Self-assemblies of γ-CDs with pentablock copolymers PMA-PPO-PEO-PPO-PMA and endcapping via atom transfer radical polymerization of 2-methacryloyloxyethyl phosphorylcholine

• Jing Lin,
• Tao Kong,
• Lin Ye,
• Ai-ying Zhang and
• Zeng-guo Feng

Beilstein J. Org. Chem. 2015, 11, 2267–2277, doi:10.3762/bjoc.11.247

• compared with PPO or PMAA), respectively, these unmatched PRs possess the potential to be applied as dynamic-responsive materials, carriers for controlled drug release, biosensors and catalysts. Poly(methyl acrylate) (PMA) prepared via ATRP of methyl acrylate (MA) is a typical hydrophobic polymer with a

• PR supramolecular polymers show potential as dynamic-responsive materials, carriers for controlled drug release, biosensors and catalysts. Experimental Materials PPO-PEO-PPO with a central block of 90 PEO units and two flank blocks of 5 PPO units was supplied by Zhejiang Huangma Chemical Industry

Dicarboxylic esters: Useful tools for the biocatalyzed synthesis of hybrid compounds and polymers

• Ivan Bassanini,
• Karl Hult and
• Sergio Riva

Beilstein J. Org. Chem. 2015, 11, 1583–1595, doi:10.3762/bjoc.11.174

• water and could be used for drug delivery (Figure 18) [71]. A few years earlier the same authors used the same principle to synthesize amphiphilic mPEG-block-poly(profenamide-co-ester) copolymers that self-assembled in water and could be used for drug release [72]. As a follow up the same laboratory

Formulation development, stability and anticancer efficacy of core-shell cyclodextrin nanocapsules for oral chemotherapy with camptothecin

• Hale Ünal,
• Naile Öztürk and
• Erem Bilensoy

Beilstein J. Org. Chem. 2015, 11, 204–212, doi:10.3762/bjoc.11.22

• attributed to the smaller particle diameter and higher drug loading in these formulations. It was also previously reported that drug release rates from large nanoparticles were slower than the release profile from smaller nanoparticles [16][39]. This is quite understandable since smaller particle sizes have