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Search for "bioavailability" in Full Text gives 129 result(s) in Beilstein Journal of Organic Chemistry.
Inclusion complexes of 2-methoxyestradiol with dimethylated and permethylated β-cyclodextrins: models for cyclodextrin–steroid interaction
Beilstein J. Org. Chem. 2015, 11, 2616–2630, doi:10.3762/bjoc.11.281
- endogenous metabolite of the most common estrogen hormone, 17β-estradiol, has been intensively studied owing to its proven potent antiangiogenic, antiproliferative and antitumoral activities [2][3]. However, its poor bioavailability has retarded its development as a drug [4][5]. Although recent reports of
- bioavailability. We therefore embarked on a study of 2ME [11] with the objectives of investigating both the interactions between CD molecules and 2ME in the solid-state as well as the effects of CDs on the aqueous solubility of 2ME, neither of these aspects having been given significant attention in the
- 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
Versatile synthesis and biological evaluation of novel 3’-fluorinated purine nucleosides
Beilstein J. Org. Chem. 2015, 11, 2509–2520, doi:10.3762/bjoc.11.272
- it imparts improve the bioavailability of fluorine-containing drugs. Relative to the unfluorinated derivative, fluorinated drugs have demonstrated favorable pharmacological, physicochemical, pharmacokinetic, pharmacodynamic and safety profiles for a number of compounds [21][22][23]. Several
Co-solvation effect on the binding mode of the α-mangostin/β-cyclodextrin inclusion complex
Beilstein J. Org. Chem. 2015, 11, 2306–2317, doi:10.3762/bjoc.11.251
- 10330, Thailand 10.3762/bjoc.11.251 Abstract Cyclodextrins (CDs) have been extensively utilized as host molecules to enhance the solubility, stability and bioavailability of hydrophobic drug molecules through the formation of inclusion complexes. It was previously reported that the use of co-solvents
- improve their bioavailability is challenging, and a requirement for the design and development of effective formulations. There are several ways to favorably enhance the solubility of poorly soluble drugs which include micronization, chemical modification, pH adjustment, complexation [1], co-solvent
- , dissolution rate, bioavailability, and stability (in comparison to the free drug), with controlled release also being possible [13][14][15][16]. In addition, co-solvent addition is a well-established method for increasing the equilibrium solubility of non-polar drugs. Recent studies combining co-solvent
Cholesterol lowering effects of mono-lactose-appended β-cyclodextrin in Niemann–Pick type C disease-like HepG2 cells
Beilstein J. Org. Chem. 2015, 11, 2079–2086, doi:10.3762/bjoc.11.224
- cholesterol sequestration is found to be a crucial factor in developing NPC disease. Cyclodextrins (CyDs) are non-reducing cyclic glucose oligosaccharides obtained by enzymatic means from starch-containing raw materials and have been used for the enhancement of drugs solubility, stability and bioavailability
Synthesis, antimicrobial and cytotoxicity evaluation of new cholesterol congeners
Beilstein J. Org. Chem. 2015, 11, 1922–1932, doi:10.3762/bjoc.11.208
- bioavailability of anticancer drugs. Thus, SuberAniloHydroxamic acid–cholesterol conjugates (SAHA–cholesterol) [11], cholesterol-based charged liposomes encaging doxorubicin [12] or curcumin [13] showed higher activity compared with the native drugs. Synthetic coumarin-caged cholesterol derivatives, for instance
Antioxidant potential of curcumin-related compounds studied by chemiluminescence kinetics, chain-breaking efficiencies, scavenging activity (ORAC) and DFT calculations
Beilstein J. Org. Chem. 2015, 11, 1398–1411, doi:10.3762/bjoc.11.151
- scavenging properties of the pertinent antioxidant reactants. The clinical use of curcumin is limited because of its low bioavailability, due to the hydrophobic nature of the molecule [8]. Schneider et al. [9] discussed the degradation and metabolism of curcumin, through products and their mechanism of
Regulation of integrin and growth factor signaling in biomaterials for osteodifferentiation
Beilstein J. Org. Chem. 2015, 11, 773–783, doi:10.3762/bjoc.11.87
- stable gradients of growth factors to regulate their bioavailability [11]. This matrix-immobilization of the factors might result in long-term binding to cell surface receptors, since the binding affinity of ECM-factors is relatively weak compared to growth factor receptor interactions [8]. Moreover, the
Natural phenolic metabolites with anti-angiogenic properties – a review from the chemical point of view
Beilstein J. Org. Chem. 2015, 11, 249–264, doi:10.3762/bjoc.11.28
- , and reduction of VEGFA and MMP9 expression. Despite its promising pharmacological properties, curcumin suffers from low in vivo bioavailability as a consequence of its low aqueous solubility, poor chemical stability and low absorption. Therefore, many analogs (Figure 2) were synthesized in order to
- complex partner, β-catenin [41]. Unfortunately, resveratrol has a dual effect on cells, depending on the situation and cell type – it can either induce or suppress angiogenic effects [42]. The low oral bioavailability and metabolic stability of resveratrol also limits its application [43]. Therefore, in
- an attempt to increase its bioavailability and stability, the structure of resveratrol was modified by methylation of the phenol groups [44] and by introduction of other groups on the phenyl ring (compounds 9–15, Figure 4) [45]. trans-3,4,4’,5-Tetramethoxystilbene (DMU-212) has improved
Formulation development, stability and anticancer efficacy of core-shell cyclodextrin nanocapsules for oral chemotherapy with camptothecin
Beilstein J. Org. Chem. 2015, 11, 204–212, doi:10.3762/bjoc.11.22
- 10.3762/bjoc.11.22 Abstract Background: The aim of this study was to design and evaluate hybrid cyclodextrin (CD) nanocapsules intended for the oral delivery of the anticancer agent camptothecin (CPT) in order to maintain drug stability in the body and to improve its eventual bioavailability. For this
- higher when incorporated in hybrid CD nanocapsules compared with a DMSO solution. Conclusion: Oral CD nanocapsules indicating increased oral bioavailability might be a promising strategy to maintain the physiological stability and to improve the oral bioavailability of problematic anticancer drugs such
- occurs via the intravenous route [6][7]. However most anticancer drugs are not good candidates for oral delivery owing to their low absorption in the gastrointestinal tract (GI) and as a result exhibit low oral bioavailability [8][9]. In order to develop an effective oral chemotherapy, the
Synthesis and biological evaluation of a novel MUC1 glycopeptide conjugate vaccine candidate comprising a 4’-deoxy-4’-fluoro-Thomsen–Friedenreich epitope
Beilstein J. Org. Chem. 2015, 11, 155–161, doi:10.3762/bjoc.11.15
- ]. Based on the notion that the 4-fluoro substituent of 11 might also enhance the hapten’s bioavailability, which would be advantageous in long-term treatments, we decided to determine briefly its hydrolytic resistance by subjecting both the partially deprotected glycosyl amino acid 12 and its native
- bioavailability of synthetic antigens and vaccines without affecting the induced antibody response and selectivity. Degradation of 4’F-TF antigen derivative 12 and its natural (synthetic) congener 13 by β-galactosidase from bovine testes. The amounts of intact disaccharide and the evolving degradation product 15
Formation of nanoparticles by cooperative inclusion between (S)-camptothecin-modified dextrans and β-cyclodextrin polymers
Beilstein J. Org. Chem. 2015, 11, 147–154, doi:10.3762/bjoc.11.14
- trials simply due to limited aqueous solubility and thereby low bioavailability [2]. Hence, there is an urgent need for novel methods to overcome the solubility issue of these drugs and to ensure efficient transport to the desired site of action with limited adverse effects. In this respect nanoparticles
- potent anticancer activity by inhibition of topoisomerase II. Its major drawback is its extremely low aqueous solubility of 2.5 µg/mL leading to a low bioavailability and it is thus a considerable formulation challenge [4]. Furthermore, at physiological conditions its active lactone form is hydrolysed to
Synthesis of divalent ligands of β-thio- and β-N-galactopyranosides and related lactosides and their evaluation as substrates and inhibitors of Trypanosoma cruzi trans-sialidase
Beilstein J. Org. Chem. 2014, 10, 3073–3086, doi:10.3762/bjoc.10.324
- the bioavailability in vivo [31]. Triazole-substituted β-galactopyranosides and triazole-sialyl mimetics have been synthesized by click chemistry and their inhibitory activity on the hydrolysis of 2’-(4-methylumbelliferyl)-β-D-N-acetylneuraminic acid by TcTS and trypanocidal activity were evaluated
Synthesis of uniform cyclodextrin thioethers to transport hydrophobic drugs
Beilstein J. Org. Chem. 2014, 10, 2920–2927, doi:10.3762/bjoc.10.310
- -, β- and γ-CD, respectively [1]. CDs are well known to increase the bioavailability of active pharmaceutical ingredients (APIs) [2][3], and they are readily available in pharmaceutical purity and industrial quantities. Furthermore, they are water soluble and regarded as non-toxic in case of α- and γ
- -CD [4][5], while β-CD shows some toxic effects such as haemolysis at high concentrations [6]. CDs are generally employed to increase the bioavailability of those APIs scarcely soluble in water [7]. The observed solubilization of an API is generally based on the complexation of the hydrophobic part of
Cyclodextrin–polysaccharide-based, in situ-gelled system for ocular antifungal delivery
Beilstein J. Org. Chem. 2014, 10, 2903–2911, doi:10.3762/bjoc.10.308
- most eye fungal infections; however, there are resistant species that require higher concentrations than usual [5]. Unfortunately, antifungal eye drops have low ocular bioavailability due to their poor water solubility and known effective eye clearance mechanisms [6]. Thus, after administration of
Binding mode and free energy prediction of fisetin/β-cyclodextrin inclusion complexes
Beilstein J. Org. Chem. 2014, 10, 2789–2799, doi:10.3762/bjoc.10.296
- applications, β-CD has been mostly used as a drug carrier, stabilizer and additive by the formation of host–guest complexes with increased solubility and consequently better bioavailability of low water soluble organic compounds (i.e., drugs) [20][21][22][23]. The inclusion complex can also improve ligand
Preparation and evaluation of cyclodextrin polypseudorotaxane with PEGylated liposome as a sustained release drug carrier
Beilstein J. Org. Chem. 2014, 10, 2756–2764, doi:10.3762/bjoc.10.292
- ][15], protein drugs [16][17], and nucleic acids [18][19][20]. We have also developed a number of PPRXs with various drugs or drug carriers and utilized them as controlled release systems. For example, γ-CD formed PPRX with coenzyme Q10, improving the solubility and bioavailability of coenzyme Q10 [21
Anomalous diffusion of Ibuprofen in cyclodextrin nanosponge hydrogels: an HRMAS NMR study
Beilstein J. Org. Chem. 2014, 10, 2715–2723, doi:10.3762/bjoc.10.286
- examples of applications can be found in the recent literature, including biocatalysis [4], agriculture [5], environmental control [6] and pharmaceutical applications such as drug stabilization, enhancement of bioavailability and drug delivery [7][8][9][10][11]. A typical synthetic protocol for their
- gradual release over extended times, thus increasing the bioavailability at the target site [19]. In this scenario of growing importance of CDNS in pharmaceutical formulations as drug container and/or carrier, it is of paramount importance a clear understanding, at molecular level, of the state of the
Encapsulation of biocides by cyclodextrins: toward synergistic effects against pathogens
Beilstein J. Org. Chem. 2014, 10, 2603–2622, doi:10.3762/bjoc.10.273
- biocides (e.g., increased aqueous solubility and wettability, reduced vapor pressure, etc.), ii) the controlled release and bioavailability, iii) the shelf-life, iv) the storage conditions and the environmental toxicity, and v) the biocidal property of textiles which is one of the main fields of
- . In addition, the authors have reported that the complexation of carbendazim with HP-β-CD significantly improves its bioavailability and, therefore, resulting in about a two-fold increase of the fungicidal activity against Trichioderma viride (fungus) compared to carbendazim alone. As a consequence
- must be selected to maintain an acceptable biocidal activity. Beyond these considerations, many benefits can be obtained by the use of CDs (see below). iii) Controlled release and bioavailability improvement As mentioned above, the formation of inclusion complexes can be useful to enhance the
A versatile δ-aminolevulinic acid (ΑLA)-cyclodextrin bimodal conjugate-prodrug for PDT applications with the help of intracellular chemistry
Beilstein J. Org. Chem. 2014, 10, 2414–2420, doi:10.3762/bjoc.10.251
- hydrophobic cavity [7]. The cyclodextrins (CDs) are a notable family of semi-natural carbohydrate molecules approved as pharmaceutical excipients that improve the solubility and bioavailability of drugs through molecular encapsulation. We demonstrated [6] the conjugate’s (PpIX-CD) bimodal action of
Effect of cyclodextrin complexation on phenylpropanoids’ solubility and antioxidant activity
Beilstein J. Org. Chem. 2014, 10, 2322–2331, doi:10.3762/bjoc.10.241
- limited water solubility, stability and poor bioavailability [8][9]. Thus, their encapsulation may enhance their apparent solubility without losing their structural integrity and bioactivity. During the past years, cyclodextrins (CDs) have been widely used as encapsulating agents to enhance the solubility
- , stability, release and bioavailability of natural compounds [10][11][12][13]. CDs are a family of cyclic oligosaccharides obtained from enzymatic degradation of starch. The most common native CDs are α-cyclodextrin (α-CD), β-cyclodextrin (β-CD) and γ-cyclodextrin (γ-CD) composed of six, seven and eight (α
Synthesis of rigid p-terphenyl-linked carbohydrate mimetics
Beilstein J. Org. Chem. 2014, 10, 1749–1758, doi:10.3762/bjoc.10.182
- -glycosides which possess structural and functional aspects of the corresponding carbohydrates, these disadvantages can be overcome, resulting in an improved bioavailability, higher affinities and improved selectivities [8][9][10][11][12][13]. Recent results indicate that divalent rigid carbohydrate
The search for new amphiphiles: synthesis of a modular, high-throughput library
Beilstein J. Org. Chem. 2014, 10, 1578–1588, doi:10.3762/bjoc.10.163
- synthesise double and triple-chain amphiphiles. With tails in hand, attention was turned to the hydrophilic amphiphile head groups. Sugar head groups were selected for this library because sugars are popular drug targets; however, such compounds often suffer from poor bioavailability [39]. By loading such
Carbohydrate PEGylation, an approach to improve pharmacological potency
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
- trans-sialidase (TcTS) [48], a virulence factor of Trypanosoma cruzi [49][50][51]. It was shown that lactitol prevented apoptosis caused by TcTS although it is rapidly eliminated from the circulatory system [52]. With the aim to improve bioavailability, PEGylation of lactose analogs was performed using
Syntheses of fluorooxindole and 2-fluoro-2-arylacetic acid derivatives from diethyl 2-fluoromalonate ester
Beilstein J. Org. Chem. 2014, 10, 1213–1219, doi:10.3762/bjoc.10.119
- biological activity [1], a growing number of commercially significant life science products, which owe their activity to the presence of fluorine atoms within their structures, have developed. Fluorine incorporation can lead, for example, to enhanced bioavailability, metabolic stability and lipophilicity of
Automated solid-phase peptide synthesis to obtain therapeutic peptides
Beilstein J. Org. Chem. 2014, 10, 1197–1212, doi:10.3762/bjoc.10.118
- derivatives [12]. Besides this success story, there are limitations restricting the use of peptides as drugs (Table 1). Notably, their low bioavailability owing to proteolytic degradation by enzymes of the intestine, blood and cell plasma leads to short circulating half-lives [13]. Depending on their size
- , possible reduced water solubility restricts their drugability. In the last years, remarkable efforts have been made to modulate the bioavailability of peptides. Basically, delivery challenges of peptide drug candidates can be overcome by chemical modification or innovative formulation techniques such as
- making them valuable for diabetes treatment. In 2011, a lipidated analog of PP (pancreatic polypeptide), a gut hormone that is known to mediate satiety, was developed. It showed an improved bioavailability demonstrated in a prolonged action in decreasing food intake in mice [99]. Apart from albumin
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