Synthesis of a deuterated probe for the confocal Raman microscopy imaging of squalenoyl nanomedicines

• Eric Buchy,
• Branko Vukosavljevic,
• Maike Windbergs,
• Dunja Sobot,
• Camille Dejean,
• Simona Mura,
• Patrick Couvreur and
• Didier Desmaële

Beilstein J. Org. Chem. 2016, 12, 1127–1135, doi:10.3762/bjoc.12.109

• fluorochrome in LDC nanoparticles can be used as far as the colloidal stability of the nanocarrier is preserved, but cannot address the intracellular tracking of the loaded drug after carrier disassembling. Thus, specific tools such as fluorescence resonance energy transfer (FRET) and fluorescence quenching

Muraymycin nucleoside-peptide antibiotics: uridine-derived natural products as lead structures for the development of novel antibacterial agents

• Daniel Wiegmann,
• Stefan Koppermann,
• Marius Wirth,
• Giuliana Niro,
• Kristin Leyerer and
• Christian Ducho

Beilstein J. Org. Chem. 2016, 12, 769–795, doi:10.3762/bjoc.12.77

• are three different assays available that provide such inhibition data: i) a fluorescence-based and ii) a radioactivity-based assay as well as iii) a relatively new Förster resonance energy transfer (FRET)-based method. The fluorescence-based assay was developed by Bugg et al. [79][80] and uses a

• . [81] uses a radioactively labelled UDP-MurNAc-pentapeptide and thin layer chromatography (TLC) separation of undecaprenyl-linked MurNAc-pentapeptide from unreacted substrate (e.g., [77][82]). The third assay was introduced in 2012 by Shapiro et al. and uses a FRET system with the FRET donor attached

• to the UDP-MurNAc-pentapeptide and the FRET acceptor in a detergent or detergent/lipid micelle that also hosts the MraY protein [83]. The overexpression and purification of the transmembrane protein MraY is challenging. MraY from different bacterial strains was heterologous overexpressed in E. coli

Orthogonal dual-modification of proteins for the engineering of multivalent protein scaffolds

• Michaela Mühlberg,
• Michael G. Hoesl,
• Christian Kuehne,
• Jens Dernedde,
• Nediljko Budisa and
• Christian P. R. Hackenberger

Beilstein J. Org. Chem. 2015, 11, 784–791, doi:10.3762/bjoc.11.88

• bond formation, respectively, to introduce two distinct modifications. In addition also amber suppression for the installation of a ketone-containing NCAA (Ac-Phe) was combined with Cys-labeling for a site-specific FRET-labeling of proteins [32]. Despite these advances, the chemical modification of

Articulated rods – a novel class of molecular rods based on oligospiroketals (OSK)

• Pablo Wessig,
• Roswitha Merkel and
• Peter Müller

Beilstein J. Org. Chem. 2015, 11, 74–84, doi:10.3762/bjoc.11.11

• biological and artificial membranes [11][12][13], the utilization as spacer in FRET systems [14], and as building blocks in porous materials [15]. Although stiffness of the whole rod is desirable in many cases, a partial flexibility is often necessary. Especially for biological and biochemical applications

A comparative study of the interactions of cationic hetarenes with quadruplex-DNA forming oligonucleotide sequences of the insulin-linked polymorphic region (ILPR)

• Darinka Dzubiel,
• Heiko Ihmels,
• Mohamed M. A. Mahmoud and
• Laura Thomas

Beilstein J. Org. Chem. 2014, 10, 2963–2974, doi:10.3762/bjoc.10.314

• fluorimetric monitoring of the temperature-dependent Förster resonance energy transfer (FRET) between the dyes [29]. In sodium cacodylate buffer (10 mM Na+, 10 mM K+, 90 mM Li+) the melting curve of the DNA has a weak transition at 50 °C and a more pronounced one at Tm = 71.0 °C (Figure 4). The results of the

Come-back of phenanthridine and phenanthridinium derivatives in the 21st century

• Lidija-Marija Tumir,
• Marijana Radić Stojković and
• Ivo Piantanida

Beilstein J. Org. Chem. 2014, 10, 2930–2954, doi:10.3762/bjoc.10.312

• bromide was introduced as a part of a heterogenic two-chromophore system, to take advantage of very efficient FRET energy transfer process (77%) from fluorescein to the RNA-intercalated phenanthridinium fluorophore (Figure 8, left) [83]. The resulting fluorescent dye exhibited improved ds-RNA-marker

• FRET systems, high resistance to photobleaching and mostly very high chemical stability. Biomedical use in human medicine was deterred

Synthesis and optical properties of pyrrolidinyl peptide nucleic acid carrying a clicked Nile red label

• Nattawut Yotapan,
• Chayan Charoenpakdee,
• Pawinee Wathanathavorn,
• Boonsong Ditmangklo,
• Hans-Achim Wagenknecht and
• Tirayut Vilaivan

Beilstein J. Org. Chem. 2014, 10, 2166–2174, doi:10.3762/bjoc.10.224

• biomolecular interactions [1][2][3]. Traditionally, the biological macromolecules are labeled with two or more dyes which can interact in a conformation/distant-dependent manner via Förster resonance energy transfer (FRET) [4][5][6]. Alternatively, the FRET pairs can be replaced by an environmentally sensitive

Multichromophoric sugar for fluorescence photoswitching

• Stéphane Maisonneuve,
• Rémi Métivier,
• Pei Yu,
• Keitaro Nakatani and
• Juan Xie

Beilstein J. Org. Chem. 2014, 10, 1471–1481, doi:10.3762/bjoc.10.151

• ) conversion extent of the DAE moiety. A nearly 100% Förster-type resonance energy transfer (FRET) from all three DCM moieties to a single DAE (in its CF) moiety was achieved. Upon visible irradiation, the initial fluorescence intensity was recovered. The observed photoswiching is reversible, with excellent

• compound fit well together, the fluorescence can be switched ON and OFF: quenching of the fluorescence through a Förster-type resonance energy transfer (FRET) process from the former to the latter would occur, when the photochromic moiety is in the colored form (state B, Figure 1). At the opposite, in the

• colorless form (state A), the absence of FRET would keep the fluorescence alive, showing that the combination of these two functional molecules leads to a photon-driven fluorescence switch. Previously, we have synthesized a fluorescent-photochromic dyad (1, Figure 2) combining a DCM fluorophore (4

Automated solid-phase peptide synthesis to obtain therapeutic peptides

• Veronika Mäde,
• Sylvia Els-Heindl and
• Annette G. Beck-Sickinger

Beilstein J. Org. Chem. 2014, 10, 1197–1212, doi:10.3762/bjoc.10.118

• chain of Dpr (α,β-diaminopropionic acid). These fluorescently labeled conjugates allowed FRET (fluorescence resonance energy transfer) measurements to investigate conformational features of the peptides [132]. With respect to the great potential of NPY ligands as pharmaceuticals for various indications

Synthesis and spectroscopic properties of 4-amino-1,8-naphthalimide derivatives involving the carboxylic group: a new molecular probe for ZnO nanoparticles with unusual fluorescence features

• Laura Bekere,
• David Gachet,
• Vladimir Lokshin,
• Wladimir Marine and
• Vladimir Khodorkovsky

Beilstein J. Org. Chem. 2013, 9, 1311–1318, doi:10.3762/bjoc.9.147

• concentration. A Stern–Volmer plot shows a simultaneous static and dynamic quenching, probably superimposed with FRET between pure acid 4 and the anionic complex, formed in ethanol. The full analysis of the formation of these complexes will be published elsewhere. The two-photon absorption cross section of 4 in

A new synthetic protocol for coumarin amino acid

• Xinyi Xu,
• Xiaosong Hu and
• Jiangyun Wang

Beilstein J. Org. Chem. 2013, 9, 254–259, doi:10.3762/bjoc.9.30

• coumarin amino acid 1a (Figure 1) is sensitive to both pH and solvent polarity, which makes it a good probe to investigate protein functionalities and biological processes related to them. The following examples are several applications of it. Shan and co-workers used compound 1a to form a FRET pair with

Ratiometric fluorescent probe for enantioselective detection of D-cysteine in aqueous solution

• Xiao-bo Zhou,
• Wing-Hong Chan,
• Albert W. M. Lee and
• Chi-Chung Yeung

Beilstein J. Org. Chem. 2011, 7, 1508–1515, doi:10.3762/bjoc.7.176

• ratiometric fluorescent chemosensors for the detection of thiols have been constructed [29][30][31]. Recently, on the basis of a native chemical-ligation reaction, Lin and coworkers reported a FRET-based probe suitable for ratiometric imaging of cysteine in living cells [31]. Therefore, it is a challenging

Supramolecular FRET photocyclodimerization of anthracenecarboxylate with naphthalene-capped γ-cyclodextrin

• Qian Wang,
• Cheng Yang,
• Gaku Fukuhara,
• Tadashi Mori,
• Yu Liu and
• Yoshihisa Inoue

Beilstein J. Org. Chem. 2011, 7, 290–297, doi:10.3762/bjoc.7.38

• .7.38 Abstract γ-Cyclodextrin (CD) derivatives with a naphthalene moiety anchored to one or two of the glucose units of the CD were synthesized in order to investigate the effects of flexible and rigid capping upon complexation, as well as Förster resonance energy transfer (FRET) and photochirogenic

• included in the CD cavity via the FRET mechanism. Compared to native γ-CD, the modified γ-CDs showed much higher first association constants (K1) but relatively lower second association constants (K2) for AC, leading to two-fold larger overall affinities (K1K2). Photocyclodimerization of AC with these

• modified γ-CDs produced more head-to-head (HH) dimers in much better enantiomeric excesses (ee) for anti-HH dimer compared to native γ-CD. Interestingly, FRET excitation further enhanced the chemical and optical yields of anti-HH dimer up to 36% and 35% ee, for which the highly efficient FRET sensitization