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Search for "bioconjugates" in Full Text gives 18 result(s) in Beilstein Journal of Organic Chemistry.
Photocatalyzed elaboration of antibody-based bioconjugates
Beilstein J. Org. Chem. 2025, 21, 616–629, doi:10.3762/bjoc.21.49
- proteins. By harnessing light to drive chemical transformations, photoredox techniques can facilitate the synthesis of antibody bioconjugates. This perspective will discuss the drive to develop and empower photoredox methods applied to antibody functionalization. Keywords: antibodies; bioconjugation
- different molecules, such as a drug and a targeting moiety. This technique has been shown to be useful in applications such as cell labeling, protein–protein interactions, and photoradiosynthesis of bioconjugates, but the most important challenge remains the lack of specificity to target one amino acid, and
The Groebke–Blackburn–Bienaymé reaction in its maturity: innovation and improvements since its 21st birthday (2019–2023)
Beilstein J. Org. Chem. 2024, 20, 1839–1879, doi:10.3762/bjoc.20.162
- yields up to 87%. The use of sugar-derived building blocks has been reported by various authors. Prasad et al. studied the synthesis of 2-(β-ᴅ-glucopyranosyl)-3-N-alkylamino-1-azaindolizines 28 to get novel bioconjugates [38] and of 5-(3”-alkyl/arylamino-1”-azaindolizin-2”-yl)-2’-deoxyuridines 31 to
Synthesis of ether lipids: natural compounds and analogues
Beilstein J. Org. Chem. 2023, 19, 1299–1369, doi:10.3762/bjoc.19.96
pH-Responsive fluorescent supramolecular nanoparticles based on tetraphenylethylene-labelled chitosan and a six-fold carboxylated tribenzotriquinacene
Beilstein J. Org. Chem. 2023, 19, 635–645, doi:10.3762/bjoc.19.45
- bioconjugates with different degrees of fluorescence labelling were synthesized as guests by controlling the feed ratios (Rf) of 4-(1,2,2-triphenylvinyl)benzaldehyde (TPE-CHO) [23] to 2 mol %, 10 mol %, and 20 mol %, respectively. They were obtained with chitosan and TPE-CHO through an aldimine condensation
- 20 mol % was calculated to be 1.6, 3.2 and 6.6 mol %, respectively, increasing as Rf increased. Fluorescent properties of CS-TPE in the solid state. CS-TPE bioconjugates were found to be AIE active, like other TPE-modified derivatives in previous works [25][26]. As shown in Figure 2a, the solid
- illumination in the solid state due to powerful self-quenching effects in the aggregates [25]. Strong emission is observed at approximately 485 nm for all CS-TPE bioconjugates in the solid state (Figure 2b). A major reason for the emission behavior is the restriction in intramolecular rotation (RIR) of
Fluorinated maleimide-substituted porphyrins and chlorins: synthesis and characterization
Beilstein J. Org. Chem. 2019, 15, 2704–2709, doi:10.3762/bjoc.15.263
- covalently conjugates thiol groups of cysteine residues in proteins or peptides by the thio-Michael addition to the double bond of the maleimide to form a corresponding succinimidyl thioether. Conjugation of the cysteine sulfhydryl group with maleimide moieties allows us to prepare the bioconjugates
Copper(I)-catalyzed tandem reaction: synthesis of 1,4-disubstituted 1,2,3-triazoles from alkyl diacyl peroxides, azidotrimethylsilane, and alkynes
Beilstein J. Org. Chem. 2018, 14, 2916–2922, doi:10.3762/bjoc.14.270
- research and synthesis of functionalized compounds that have applications in medicinal chemistry, drug discovery, materials chemistry, and as well as in bioconjugates [2][3][4][5][6][7][8][9][10][11][12]. The copper-catalyzed azide–alkyne cycloaddition (CuAAC) reaction [13][14][15][16][17][18][19][20][21
Novel solid-phase strategy for the synthesis of ligand-targeted fluorescent-labelled chelating peptide conjugates as a theranostic tool for cancer
Beilstein J. Org. Chem. 2018, 14, 2665–2679, doi:10.3762/bjoc.14.244
- groups such as Trt (chlorotrityl), Mtt (4-methyltrityl), Mmt (4-methoxytrityl) are employed to synthesise the ligand targeted fluorescent tagged bioconjugates. Using this methodology, DUPA rhodamine B conjugate (DUPA = 2-[3-(1,3-dicarboxypropyl)ureido]pentanedioic acid), targeting prostate specific
- chain protecting moieties to introduce fluorescent tags. In addition to the above drawbacks, conventional methods for the synthesis of targeted fluorescent tagged bioconjugates [31] are a mixed approach of both solid and solution phase synthesis [32]. These involve several intermediary purification
- affinity of the PSMA-targeting conjugate 13; it minimizes the repulsive interaction between the bulky dye molecule and the targeted folate protein active site in the case of folate receptor targeting bioconstruct 17, (iii) a fluorescent tag to track the cellular destination of bioconjugates and
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
Beilstein J. Org. Chem. 2018, 14, 2495–2509, doi:10.3762/bjoc.14.226
- any further experiments. Based on these findings next generation of Dau–GnRH-III bioconjugates was developed in which Ser in position 4 was replaced with Lys acylated with short-chain fatty acids with 2–6 and 13 carbon atoms by Hegedüs et al. [19]. The replacement of 4Ser by Lys with a chain of 2–6
Artificial bioconjugates with naturally occurring linkages: the use of phosphodiester
Beilstein J. Org. Chem. 2018, 14, 1946–1955, doi:10.3762/bjoc.14.169
- elaborate bioconjugates. Herein, we describe the use of a phosphodiester bond as a versatile option to access various bioconjugates. An opposite activation strategy, involving 5’-phosphitylation of the supported oligonucleotides, has allowed several biomolecules that possess an unactivated alcohol to be
- directly conjugated. It should be noted that there is no need to pre-install artificial functional groups and undesired and unpredictable perturbations possibly caused by bioconjugation can be minimized. Keywords: alkyl chain soluble supports; artificial bioconjugates; naturally occurring linkages; 5
- –Alder reaction [41][42][43][44], and hydrazone/oxime formation [45][46][47][48], have developed selective conjugation reactions under mild conditions. Although these bond-forming reactions have proven to be truly powerful approaches and will remain as first options to create novel bioconjugates
Drug targeting to decrease cardiotoxicity – determination of the cytotoxic effect of GnRH-based conjugates containing doxorubicin, daunorubicin and methotrexate on human cardiomyocytes and endothelial cells
Beilstein J. Org. Chem. 2018, 14, 1583–1594, doi:10.3762/bjoc.14.136
- bromide (MTT) assay as it was described in the published articles [14][15][20][21][22][23][24][25]. All investigated bioconjugates exerted in vitro cytostatic effect with IC50 values in low µM range except the one (2) with amide bond between the drug and carrier molecule. The data are summarised below in
On the design principles of peptide–drug conjugates for targeted drug delivery to the malignant tumor site
Beilstein J. Org. Chem. 2018, 14, 930–954, doi:10.3762/bjoc.14.80
- , including important PDCs that have progressed to phase III clinical trials. Last, we address possible difficulties that may emerge during the synthesis of PDCs, as also report ways to overcome them. Keywords: bioconjugates; cancer; drug delivery; PDC; peptide; peptide–drug conjugate; side-products in PDCs
- synthesizing a new cytotoxic agent, as it is based on an already applied drug with the addition of a small peptide. Nevertheless, the last years more complex bioconjugates have been synthesized to allow the simultaneous diagnosis and therapy (theranostics) of diseases. The therapeutic efficacy of a PDC is
Development of novel cyclic NGR peptide–daunomycin conjugates with dual targeting property
Beilstein J. Org. Chem. 2018, 14, 911–918, doi:10.3762/bjoc.14.78
- cyclic NGR peptide–Dau bioconjugates including chemostability, lysosomal degradation, cellular uptake studies and in vitro cytostatic/cytotoxic effect. Results and Discussion Synthesis of cyclic NGR–Dau conjugates The NGR cyclic peptides were prepared as shown in Figure 1. All derivatives were
- positive [17]. The effect of the new drug conjugates was compared with the toxicity of free Dau and our lead compound Dau=Aoa-GFLGK(c[KNGRE]-GG)-NH2 (K). The bioconjugates enter cancer cells most likely by receptor-mediated endocytosis (at least at lower micromolar concentration) followed by the release of
Synthesis and in vitro biochemical evaluation of oxime bond-linked daunorubicin–GnRH-III conjugates developed for targeted drug delivery
Beilstein J. Org. Chem. 2018, 14, 756–771, doi:10.3762/bjoc.14.64
- after 10 min). Additional flow cytometry studies demonstrated that the cellular uptake of the bioconjugate was inhibited in the presence of the competitive ligand triptorelin indicating a receptor-mediated pathway. For comparative purpose, six novel daunorubicin–GnRH-III bioconjugates have been
- cellular uptake of the bioconjugates were strongly affected by the amino acid exchange which in turn had an impact on the antitumor activity of the bioconjugates. Keywords: cytostatic effect; daunorubicin; drug-targeting; GnRH derivatives; oxime linkage; Introduction Cancer is one of the most serious
- cellular uptake and the subcellular localization of the drug or the drug bioconjugates [13][14]. It is well known from the literature that anthracyclines accumulate in the nucleus, in that manner they also act as DNA stains [14][15]. The first cytotoxic GnRH-I derivative, which was investigated in
Synthesis and evaluation of anti-oxidant and cytotoxic activities of novel 10-undecenoic acid methyl ester based lipoconjugates of phenolic acids
Beilstein J. Org. Chem. 2017, 13, 26–32, doi:10.3762/bjoc.13.4
- acids have been derivatized with other functionalities apart from esters. The reported compounds other than esters were amides where bioconjugates of fatty acids and amino acids were prepared and evaluated for their anti-oxidant activity by a DPPH radical assay [9]. In view of developing new conjugates
Orthogonal dual thiol–chloroacetyl and thiol–ene couplings for the sequential one-pot assembly of heteroglycoclusters
Beilstein J. Org. Chem. 2014, 10, 1557–1563, doi:10.3762/bjoc.10.160
- (Scheme 1). Such derivatives have proved to be useful in bioconjugates chemistry [25] and for the preparation of thioether-linked tetravalent glycocyclopeptides which have shown highest inhibition against a model lectin in comparison with analogues bearing oxime and triazole linkage [26]. Glycosyl thiols
Peptoids and polyamines going sweet: Modular synthesis of glycosylated peptoids and polyamines using click chemistry
Beilstein J. Org. Chem. 2013, 9, 56–63, doi:10.3762/bjoc.9.7
- conjugation methods such as the Staudinger ligation [1] or the copper-catalyzed alkyne azide cycloaddition (CuAAC) [2][3], a large number of versatile and functional bioconjugates are accessible for various applications in chemical biology [4]. To date, many therapeutically active molecules are synthetic
Dimerization of a cell-penetrating peptide leads to enhanced cellular uptake and drug delivery
Beilstein J. Org. Chem. 2012, 8, 1788–1797, doi:10.3762/bjoc.8.204
- ]. Synthesis and characterization of (sC18)2 bioconjugates In order to evaluate the potential of the sC18 dimer to effectively deliver cytotoxic drugs into cells and even enhance the cytotoxicity of functionalized cymantrenes, the synthesis of which has previously been reported [11], we synthesized a single (1
- ) and a double conjugate (2) of (sC18)2 and Cym2 (Table 1, Scheme 1). For comparison, we also synthesized bioconjugates with known cytostatic agents: the common DNA alkylating anticancer therapeutic chlorambucil (Cbl, 3), which may induce apoptosis, and the cell impermeable proapoptotic peptide (KLAKLAK
- [8]. Thus, in this case, no significant influence of the cargo on the uptake of (sC18)2 is expected, since this is largely determined by the structure of the CPP. The bioconjugates were tested for cytotoxicity in MCF-7 and HT-29 in the presence of serum by using a resazurin-based cell viability assay
Synthesis of coumarin or ferrocene labeled nucleosides via Staudinger ligation
Beilstein J. Org. Chem. 2006, 2, No. 23, doi:10.1186/1860-5397-2-23
- to be dependent on the structure of the azidonucleoside and the carboxylic acids. A detailed study of the kinetics of the Staudinger ligation with nucleoside substrates, and the possible application to the construction of labeled oligomers and novel bioconjugates for enzyme assays is in progress. A
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