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

• stimulus-responsive supramolecular vesicles and molecule-scale drug carriers are considered to have potential for cancer drug delivery. However, such supramolecular systems are not suitable for oral administration, which is a convenient and patient-preferred method of drug delivery, especially for patients

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

• formulation approaches for targeting the colon through oral administration. In our previous studies, oral chemotherapy for colon tumors was aimed and promising results were obtained with formulation development studies, mucin interaction, mucus penetration, cytotoxicity, and permeability in 2D cell culture

• , and furthermore in vivo antitumoral and antimetastatic efficacy in early and late-stage colon cancer models and biodistribution after single dose oral administration. This study was carried out to further elucidate oral camptothecin (CPT)-loaded amphiphilic cyclodextrin nanoparticles for the local

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

• ) encapsidates the dsRNA of 563 bp, are shown to silence the WSSV glycoprotein VP28 (dsRNAvp28). In experimental challenges in vivo, the VLPs- dsRNAvp28 protect shrimp against WSSV up to 40% by oral administration and 100% by IM. The novel research demonstrates that plant VLPs, which avoid zoonosis, can be

• applied to pathogen control in shrimp and also other organisms, widening the application window in nanomedicine. Keywords: antiviral therapy; CCMV; oral administration; P. vannamei; plant VLPs; RNAi; VP28; white spot syndrome virus; Introduction The white spot syndrome virus (WSSV) is recognized as one

• been in-vitro synthesized [32][42], being RNases resistant, and can release cargo in the cytoplasm of mammalian cells [32][33][43]. This work aims to evaluate the efficacy of CCMV VLP-VP28 dsRNA (VLP-dsRNAvp28) delivery against WSSV, by oral administration to shrimp through commercial feed pellets

Synthetic strategies of phosphonodepsipeptides

• Jiaxi Xu

Beilstein J. Org. Chem. 2021, 17, 461–484, doi:10.3762/bjoc.17.41

• are derivatives of the new antimalarial drug fosmidomycin and inhibited the 1-deoxy-ᴅ-xylulose 5-phosphate reductoisomerase. The phosphonodepsipeptides 194 were synthesized as prodrugs with an increased activity after oral administration due to a chemical modification of the phosphonate moiety. For

Synthesis, antiinflammatory activity, and molecular docking studies of bisphosphonic esters as potential MMP-8 and MMP-9 inhibitors

• Abimelek Cortes-Pacheco,
• María Adelina Jiménez-Arellanes,
• Francisco José Palacios-Can,
• José Antonio Valcarcel-Gamiño,
• Rodrigo Said Razo-Hernández,
• María del Carmen Juárez-Vázquez,
• Adolfo López-Torres and
• Oscar Abelardo Ramírez-Marroquín

Beilstein J. Org. Chem. 2020, 16, 1277–1287, doi:10.3762/bjoc.16.108

• derivatives 5 and 6 where the effect of benzyl or 4-methoxybenzyl substituents was assessed (Figure 2). Furthermore, the bisphosphonic esters 3–6 passed the Lipinski’s rules [22] as criteria for drugs for an oral administration as we wanted to test these derivatives through in vivo acute inflammation models

• oral administration [25]. When the bisphosphonates 3–6 (2 mg/ear) were assayed with a TPA model, the derivatives 5 (40.7% edema inhibition) and 6 (55.9% edema inhibition) were the most active ones, with 6 having a comparable edema inhibition to the positive control (indomethacin, 55.5% edema inhibition

• through gut mice (Table 2). Finally, the synthesized bisphosphonates 3 and 4 have proven to be more active (24.6% and 20.9% edema inhibition, respectively, at a 25 mg/kg dose) by oral administration than the parent compounds 1 and 2 (7.0% and 22.2% edema inhibition, respectively, at a 50 mg/kg dose

An improved, scalable synthesis of Notum inhibitor LP-922056 using 1-chloro-1,2-benziodoxol-3-one as a superior electrophilic chlorinating agent

• Nicky J. Willis,
• Elliott D. Bayle,
• George Papageorgiou,
• David Steadman,
• Benjamin N. Atkinson,
• William Mahy and
• Paul V. Fish

Beilstein J. Org. Chem. 2019, 15, 2790–2797, doi:10.3762/bjoc.15.271

• challenge. Chemical structure of Notum inhibitor LP-922056 (1). Concentrations of 1 in mouse following oral administration (p.o.) at 10 mg/kg. Synthesis of LP-922056 (1). Reagents and conditionsa: (a) (COCl)2 (3.3 equiv), DMF, CH2Cl2, 55 °C , 16 h, 63–78%; (b) NaOMe (5 equiv), 1,4-dioxane, 0 °C then rt, 16

Aqueous olefin metathesis: recent developments and applications

• Valerio Sabatino and
• Thomas R. Ward

Beilstein J. Org. Chem. 2019, 15, 445–468, doi:10.3762/bjoc.15.39

• ) may not exceed 100 µg/day for drugs administered per os (oral administration) and 1 µg/day by inhalation [51]. Some of the difficulties highlighted above can be overcome by the incorporation of quaternary ammonium tags, which simplify product purification as well as olefin metathesis in pure water [52

Solid-state studies and antioxidant properties of the γ-cyclodextrin·fisetin inclusion compound

• Joana M. Pais,
• Maria João Barroca,
• Maria Paula M. Marques,
• Filipe A. Almeida Paz and
• Susana S. Braga

Beilstein J. Org. Chem. 2017, 13, 2138–2145, doi:10.3762/bjoc.13.212

• reducing complications associated with type I diabetes [14] and features, upon oral administration, neuroprotective and memory-enhancing properties [15][16]. For this reason, fisetin is being proposed as a new approach to treat Alzheimer’s disease [17]. However, fisetin is practically insoluble in water

Interactions between cyclodextrins and cellular components: Towards greener medical applications?

• Loïc Leclercq

Beilstein J. Org. Chem. 2016, 12, 2644–2662, doi:10.3762/bjoc.12.261

• (i.e., by transporter proteins) [41]. In contrast, lipophilic derivatives (e.g., ME-β-CD) interact more readily with membranes than the hydrophilic derivatives, they cannot readily permeate cell membranes (see below) [42]. Moreover, oral administration of alkylated CD derivatives, such as ME-β-CD, is

Biosynthesis of α-pyrones

• Till F. Schäberle

Beilstein J. Org. Chem. 2016, 12, 571–588, doi:10.3762/bjoc.12.56

• ’-dichlorodihydrofluorescein (DCFH) to the fluorescent 2’,7’-dichlorofluorescein (DCF) [29]. This antioxidant activity was also linked to anti-inflammatory effects by testing the in vivo effects of 23 in a carrageenan-induced paw edema assay. Oral administration of 23 to mice prior to carrageenan injection resulted in a

Enabling technologies and green processes in cyclodextrin chemistry

• Giancarlo Cravotto,
• Marina Caporaso,
• Laszlo Jicsinszky and
• Katia Martina

Beilstein J. Org. Chem. 2016, 12, 278–294, doi:10.3762/bjoc.12.30

• solubility and toxicity, while they can also be used as carriers for inhalation and oral administration treatments [38]. New hybrid materials have been created from a combination of carbon nanotubes (CNTs) and β-CD [39] affording a peculiar cost-effective fibre. Functionalized β-CD was covalently linked to

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

• considered the most convenient route. Besides, it reduces reimbursement load in the health budget also, since it does not require therapy in medical centres [5]. By means of oral administration, it is possible to prevent the initial rapid increase and the subsequent decay of drug concentration in blood that

• CPT for cancer therapy. CDs can be a means of overcoming these problems for the in vivo behaviour of CPT upon intravenous or oral administration. CDs are natural polymers which are produced from enzymatic degradation of starch [23]. They are cyclic oligosaccharides and consist of at least 6 D

• known that complexation of drugs with CDs provide an improvement in its dissolution rate and consequently in oral absorption [27]. Besides, CDs serve as a permeability enhancer upon oral administration which plays an important role for drugs having low intestinal permeability [28][29]. Taking into

Recent progress in the discovery of small molecules for the treatment of amyotrophic lateral sclerosis (ALS)

• Allison S. Limpert,
• Margrith E. Mattmann and
• Nicholas D. P. Cosford

Beilstein J. Org. Chem. 2013, 9, 717–732, doi:10.3762/bjoc.9.82

• , riluzole demonstrates variable drug exposure in addition to highly differential serum concentrations among ALS patients following oral administration [9]. This variability correlates with the heterogeneous patient expression of the cytochrome P450 (CYP) isoform CYP1A2, which provides the primary mechanism

• SOD1 G93A mice can improve motor symptoms and increase lifespan. Oral administration of this compound at 60 mg/kg daily prior to symptom presentation, resulted in no delay in onset of hindlimb weakness, but decreased the progression of motor dysfunction as tested by rotarod [55]. When DL-3-n

Hydrophobic analogues of rhodamine B and rhodamine 101: potent fluorescent probes of mitochondria in living C. elegans

• Laurie F. Mottram,
• Safiyyah Forbes,
• Brian D. Ackley and
• Blake R. Peterson

Beilstein J. Org. Chem. 2012, 8, 2156–2165, doi:10.3762/bjoc.8.243

• , the cuticular exoskeleton of these animals is a highly cross-linked carbohydrate-rich outer layer that limits access of molecules to the epidermis for potential uptake. For oral administration, molecules that are ingested by these animals must pass through an intestine replete with a wide range of

Cyclodextrin-based nanosponges as drug carriers

• Francesco Trotta,
• Marco Zanetti and
• Roberta Cavalli

Beilstein J. Org. Chem. 2012, 8, 2091–2099, doi:10.3762/bjoc.8.235

• safe between 500 and 5000 mg/kg in Swiss albino mice: they did not show any sign of toxicity or adverse reactions. Nanosponges were then injected intravenously into mice and monitored for 24 h. Oral administration of nanosponges was also tested in mice [20] with no apparent side effects. The nanoporous

• proposed as a sustained drug-delivery system for oral administration. Acyclovir is a medium polarity drug with a solubility in water of 1.5 mg/mL. Special carboxylated nanosponges, containing dissociable carboxylic groups in their structure were developed for its encapsulation. They represent a further

• absorption from the gastrointestinal tract. The Biopharmaceutics Classification System (BCS) was developed by Amidon [45] in 1995 as a tool for predicting the extent of drug absorption after oral administration. This system divides drugs into four categories according to their solubility and intestinal

Triterpenoid saponins from the roots of Acanthophyllum gypsophiloides Regel

• Elena A. Khatuntseva,
• Vladimir M. Men’shov,
• Alexander S. Shashkov,
• Yury E. Tsvetkov,
• Rodion N. Stepanenko,
• Raymonda Ya. Vlasenko,
• Elvira E. Shults,
• Genrikh A. Tolstikov,
• Tatjana G. Tolstikova,
• Dimitri S. Baev,
• Vasiliy A. Kaledin,
• Nelli A. Popova,
• Valeriy P. Nikolin,
• Pavel P. Laktionov,
• Anna V. Cherepanova,
• Tatiana V. Kulakovskaya,
• Ekaterina V. Kulakovskaya and
• Nikolay E. Nifantiev

Beilstein J. Org. Chem. 2012, 8, 763–775, doi:10.3762/bjoc.8.87

• after a single dose administered through the oral or intraperitoneal route. The obtained data show that, in the case of oral administration of the studied compounds, LD50 was in the range of 304 ± 55 mg/kg for compound 1 and 252 ± 57 mg/kg for compound 2 with p < 0.05 (t). In the case of intraperitoneal

• the percentage difference between the mass of the healthy and the inflamed paw, relative to the mass of the healthy paw. In general, the anti-inflammatory effect of saponins 1 and 2 given intraperitoneally was dose-dependent, whereas that in the experiment with oral administration was not. Within the

• experiment based on oral administration, compound 1 did not show any reliable anti-inflammatory action. Data given in Table 5 evidences the more pronounced anti-inflammatory properties of compound 2 as compared to compound 1 in the experiment based on intraperitoneal administration. The influence of saponins

Advances in synthetic approach to and antifungal activity of triazoles

• Kumari Shalini,
• Nitin Kumar,
• Sushma Drabu and
• Pramod Kumar Sharma

Beilstein J. Org. Chem. 2011, 7, 668–677, doi:10.3762/bjoc.7.79

• opportunistic filamentous and dimorphic fungi [55][56][57][58][59]. Posaconazole is available only for oral administration and has a bioavailability of 8–47% on an empty stomach, which increases by 400% with the ingestion of a fatty meal [60]. The drug is primarily metabolized by the liver, approx. 77% of the

Synthesis of (S)-1-(2-chloroacetyl)pyrrolidine- 2-carbonitrile: A key intermediate for dipeptidyl peptidase IV inhibitors

• Santosh K. Singh,
• Narendra Manne and
• Manojit Pal

Beilstein J. Org. Chem. 2008, 4, No. 20, doi:10.3762/bjoc.4.20

• inhibition of DPP-IV and (ii) chemical stability adequate for oral administration [6] (Figure 2). Chemically, incorporation of a 2(S)-cyanopyrrolidine moiety into a molecule can be carried out by using (S)-1-(2-chloroacetyl)pyrrolidine-2-carbonitrile (6) as a reactant. Thus, compound 6 has become a widely