Design, synthesis and photochemical properties of the first examples of iminosugar clusters based on fluorescent cores

• Mathieu L. Lepage,
• Antoine Mirloup,
• Manon Ripoll,
• Fabien Stauffert,
• Anne Bodlenner,
• Raymond Ziessel and
• Philippe Compain

Beilstein J. Org. Chem. 2015, 11, 659–667, doi:10.3762/bjoc.11.74

• ; fluorescent probes; iminosugars; 4-methylumbelliferone; multivalency; pyrene; Introduction Since the isolation in the 1970’s of 1-deoxynojirimycin (DNJ) from natural sources and the finding of its biological activity as an α-glucosidase inhibitor, thousands of sugar mimetics with a nitrogen atom replacing

• Discussion Synthetic design The fluorescent probes were designed as analogues of the best multivalent pharmacological chaperones/correctors reported so far that typically display three to four copies of a DNJ ligand linked to a central core via an alkyl chain spacer (Figure 1) [24][25][26]. The choice of the

• large Stokes shift of 6850 cm−1 and a longer excited state life time (τ = 71.7 ns) [72]. Again the excitation spectrum matches the absorption one proving that aggregation is unlikely under the used aqueous conditions. From a general point of view, fluorescent probes have been used for the detection of

Fluoride-driven ‘turn on’ ESPT in the binding with a novel benzimidazole-based sensor

• Kai Liu,
• Xiaojun Zhao,
• Qingxiang Liu,
• Jianzhong Huo,
• Bolin Zhu and
• Shihua Diao

Beilstein J. Org. Chem. 2015, 11, 563–567, doi:10.3762/bjoc.11.61

• ]. However, to OH-based anion sensors it has been paid less attention [25][26]. In fact, we have succeeded in designing and synthesizing the anion fluorescent probes, based on ESPT [15][16], containing phenolic OH as H-bond donor. In these systems, the probe displayed a narrower linear range for fluoride

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

• ligand-ILPR complexes are different from the ones observed with other native quadruplex-forming DNA sequences. Keywords: DNA ligands; fluorescent probes; ILPR; nucleic acids; quadruplex DNA; Introduction The “insulin-linked polymorphic region” (ILPR) is a physiologically relevant G-rich DNA sequence

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

Pyrene-modified PNAs: Stacking interactions and selective excimer emission in PNA₂DNA triplexes

• Alex Manicardi,
• Lucia Guidi,
• Alice Ghidini and
• Roberto Corradini

Beilstein J. Org. Chem. 2014, 10, 1495–1503, doi:10.3762/bjoc.10.154

• properties. PNA fluorescent probes bearing pyrene units as “universal base” were described [31][32], and recently, pyrrolidinyl-PNA bearing a uracil-linker pyrene unit showed good fluorescence response and mismatch recognition [33]; though terminal pyrene units were shown to stabilize triplexes formed by

Synthesis of fluorescent (benzyloxycarbonylamino)(aryl)methylphosphonates

• Michał Górny vel Górniak,
• Anna Czernicka,
• Piotr Młynarz,
• Waldemar Balcerzak and
• Paweł Kafarski

Beilstein J. Org. Chem. 2014, 10, 741–745, doi:10.3762/bjoc.10.68

• for profiling the proteolytic secretomes with the obtained profiles being useful as diagnostic tools [6][7][8]. Also conjugates of drugs with fluorescent probes have been used as so called theranostics (combination of therapeutics and diagnostics) [9][10]. Diaryl esters of α-aminoalkanephosphonic

• carrying fluorescent probes in their side chains or in the ester phosphonate moieties might find an application in constructing fluorescent probes for studying structural requirements of enzymes having serine in their active sites (proteinases and phosphatases) or to study their elevated level in various

Isocyanide-based multicomponent reactions towards cyclic constrained peptidomimetics

• Gijs Koopmanschap,
• Eelco Ruijter and
• Romano V.A. Orru

Beilstein J. Org. Chem. 2014, 10, 544–598, doi:10.3762/bjoc.10.50

Flow synthesis of a versatile fructosamine mimic and quenching studies of a fructose transport probe

• Matthew B. Plutschack,
• D. Tyler McQuade,
• Giulio Valenti and
• Peter H. Seeberger

Beilstein J. Org. Chem. 2013, 9, 2022–2027, doi:10.3762/bjoc.9.238

• overexpress Glut5 and poorly transported into cells known to express little Glut5 [2][5][18]. We demonstrated that the transport is inhibited by fructose but not by other dietary sugars (glucose, glucosamine) [17]. Furthering our understanding of fluorescent probes like NBDM will expedite the development of

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

• different sensitivities to pH and solvent polarity, and can serve as new fluorescent probes in a variety of applications. Results and Discussion Scheme 1 gives an outline of the new protocol used to synthesize compound 1. First, the coumarin ring with a 4-chloromethyl group (compound 3) was formed through

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

• expression of mitochondria-targeted fluorescent proteins. The high bioavailabilty of these novel fluorescent probes may facilitate the identification of agents and factors that affect diverse aspects of mitochondrial biology in vivo. Keywords: Caenorhabditis elegans; chemical biology; fission; fluorophores

• have led some investigators interested in imaging fusion and fission of mitochondria in C. elegans [28] to forego the use of small-molecule fluorescent probes and instead to use time-consuming molecular biology methods to generate transgenic animals that express fluorescent proteins, such as mitoGFP

• mitochondria in C. elegans. These studies revealed that the hydrophobic rosamines HRB 9 and HR101 10 represent highly potent and selective fluorescent probes of these organelles. Treatment of C. elegans with these compounds for as little as two hours at concentrations as low as 100 pM enables selective imaging

The effect of the formyl group position upon asymmetric isomeric diarylethenes bearing a naphthalene moiety

• Renjie Wang,
• Shouzhi Pu,
• Gang Liu and
• Shiqiang Cui

Beilstein J. Org. Chem. 2012, 8, 1018–1026, doi:10.3762/bjoc.8.114

• of biomolecules in organisms, exemplified by its use in fluorescent probes, fluorescence imaging, and molecular switches in logic circuits [15][16][17][18][19][20][21][22]. In general, in order to efficiently realize the artificial induction of photosensitivity in biomolecules, the photoactive

Diarylethene-modified nucleotides for switching optical properties in DNA

• Sebastian Barrois and
• Hans-Achim Wagenknecht

Beilstein J. Org. Chem. 2012, 8, 905–914, doi:10.3762/bjoc.8.103

• we have synthetically attached various chromophores, such as ethynylpyrenes [44][45], BODIPY [46], ethynyl nile red [47][48] and others, to 2’-deoxyuridines for electron transfer studies and for fluorescent probes. To gain greater insight into the counterbase selectivity, we performed PEX experiments

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

• under physiological conditions is of interest in a wide variety of disciplines including chemistry and medicine. Owing to the intrinsic sensitivity of fluorescence, the development of fluorescent probes for thiols has been extensively invesigated. The subject has been recently reviewed by Yoon and

• ]. The facile cyclization of β- or γ-aminothiols with aldehydes containing fluorescent probes forms the basis for the development of several fluorescent probes [12][13][14][15][16][17]. In addition, cleavage of disulfide-based probes by thiols [18][19][20][21] and other thiol-sensing tactics have been

An easy assembled fluorescent sensor for dicarboxylates and acidic amino acids

• Xiao-bo Zhou,
• Yuk-Wang Yip,
• Wing-Hong Chan and
• Albert W. M. Lee

Beilstein J. Org. Chem. 2011, 7, 75–81, doi:10.3762/bjoc.7.11

• Xiao-bo Zhou Yuk-Wang Yip Wing-Hong Chan Albert W. M. Lee Department of Chemistry, Hong Kong Baptist University, Kowloon Tong, Hong Kong SAR, China 10.3762/bjoc.7.11 Abstract Two mesitylene based neutral receptors 1 and 2 bearing two thiourea binding sites were constructed as fluorescent probes

• developed fluorescent probes for detecting dicarboxylates and trifunctional aminoacids [17][18]. To continue our interest in this research direction, we report here the facile synthesis and molecular recognition properties of two new sensing probes 1 and 2. Trimethyl- or triethylbenzene have been widely

Anthracene coupled adenine for the selective sensing of copper ions

• Kumaresh Ghosh and
• Tanushree Sen

Beilstein J. Org. Chem. 2010, 6, No. 44, doi:10.3762/bjoc.6.44

• ions, especially Cu2+ ion. Conclusion In conclusion, the above studies have led to the development of adenine–linked fluorescent probes 1 and 2, which selectively respond to copper ions. The chemosensors display fluorescent changes upon complexation with Cu2+ ions. The emission of 1 is greatly

Synthesis of coumarin or ferrocene labeled nucleosides via Staudinger ligation

• Ivana Kosiova,
• Andrea Janicova and
• Pavol Kois

Beilstein J. Org. Chem. 2006, 2, No. 23, doi:10.1186/1860-5397-2-23

• ), which were synthesised in our department as part of studies into new ligands. Coumarins as fluorescent probes or labels [28][29][30] have extensive and diverse applications, they exhibit extended spectral range, are photostable and have high emission quantum yields. Ferrocene derivatives are often used