- Thermoresponsive dendronized copolymers for protein recognitions based on biotin–avidin interaction
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Thermoresponsive biotinylated dendronized copolymers carrying dendritic oligoethylene glycol (OEG) pendants were prepared via free radical polymerization, and their protein recognitions based on biotin–avidin interaction investigated. Both first (PG1) and second generation (PG2) dendronized copolymers were designed to examine possible thickness effects on the interaction between biotin and avidin. Inherited from the outstanding thermoresponsive properties from OEG dendrons, these biotinylated cylindrical copolymers show characteristic thermoresponsive behavior which provides an envelope to capture avidin through switching temperatures above or below their phase transition temperatures (Tcps). Thus, the recognition of polymer-supported biotin with avidin was investigated with UV/vis spectroscopy and dynamic laser light scattering. In contrast to the case for PG1, the increased thickness for copolymer PG2 hinders partially and inhibits the recognition of biotin moieties with avidin either below or above its Tcp. This demonstrates the significant architecture effects from dendronized polymers on the biotin moieties to shift onto periphery of the collapsed aggregates, which should be a prerequisite for protein recognition. These kinds of novel thermoresponsive copolymers may pave a way for the interesting biological applications in areas such as reversible activity control of enzyme or proteins, and for controlled delivery of drugs or genes.
- Zhou, Chunhua,Abdel-Rahman, Mona A.,Li, Wen,Liu, Kun,Zhang, Afang
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- BIOTINYLATION OF AMINES WITH THE PENTAFLUOROPHENYL ESTER OF D-BIOTIN
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The synthesis has been effected of the pentafluorphenyl ester of D-biotin by the reaction of D-biotin with bispentafluorophenyl carbonate or pentafluorophenyl trifluoroacetate.The possibility has been shown of using the ester obtained for the biotinylizat
- Rabinkov, A. G.,Pozdnev, V. F.,Amontov, S. V.,Kopelevich, V. M.,Gunar, V. I.
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- Synthesis and bioactivity of labelled germination stimulants for the isolation and identification of the strigolactone receptor.
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Strigolactones are highly potent germination stimulants for seeds of the parasitic weeds Striga and Orobanche spp. The induction of seed germination is thought to proceed via a receptor-mediated mechanism. Isolation and purification of the strigolactone receptor by affinity chromatography using immobilized avidin or streptavidin requires a biotin labelled strigolactone analogue. For this purpose biotin has been attached, directly as well as indirectly, via a hydrophilic linker to the amino function of optically active amino-GR24. Using the same amino substituted synthetic stimulant GR24, labelled stimulants have been prepared which may be suitable for the identification of the receptor by means of fluorescence correlation spectroscopy, scanning force microscopy or photoaffinity techniques. Bioassays of the labelled stimulants reveal that the germination activity on seeds of Striga hermonthica is retained. Crystal data for the diastereoisomer (+)-8 are reported.
- Reizelman, Anat,Wigchert, Suzanne C,del-Bianco, Cinzia,Zwanenburg, Binne
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- From Inhibition to Degradation: Targeting the Antiapoptotic Protein Myeloid Cell Leukemia 1 (MCL1)
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Protein-protein interactions (PPIs) have emerged as significant targets for therapeutic development, owing to their critical nature in diverse biological processes. An ideal PPI-based target is the protein myeloid cell leukemia 1 (MCL1), a critical prosurvival factor in cancers such as multiple myeloma where MCL1 levels directly correlate to disease progression. Current strategies for halting the antiapoptotic properties of MCL1 revolve around inhibiting its sequestration of proapoptotic factors. Existing inhibitors disrupt endogenous regulatory proteins; however, this strategy actually leads to an increase of MCL1 protein levels. Here, we show the development of hetero-bifunctional small molecules capable of selectively targeting MCL1 using a proteolysis targeting chimera (PROTAC) methodology leading to successful degradation. We have confirmed the involvement of the E3 ligase CUL4A-DDB1 cereblon ubiquitination pathway, making these PROTACs a first step toward a new class of antiapoptotic B-cell lymphoma 2 family protein degraders.
- Papatzimas, James W.,Gorobets, Evgueni,Maity, Ranjan,Muniyat, Mir Ishruna,Maccallum, Justin L.,Neri, Paola,Bahlis, Nizar J.,Derksen, Darren J.
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p. 5522 - 5540
(2019/06/17)
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- GENETICALLY ENCODED BIOTIN AND BIOTIN-ANALOGS AND USE THEREOF
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Embodiments of the present disclosure describe non-canonical amino acids characterized by the formula A—L—B, where A is an amino acid, L is a linker, and B is a biotin or a biotin-analog group. Embodiments describe translation systems comprising an orthog
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Paragraph 0082
(2018/12/02)
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- Phosphoramidite reagents and solid-phase supports based on hydroxyprolinol for the synthesis of modified oligonucleotides
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The synthesis of phosphoramidite reagents and solid-phase supports based on hydroxyprolinol for the introduction of the residues of biotin, lipoic acid, amino groups, and terminal acetylene groups at different positions of the oligonucleotide chain has been described. The efficiency of the reagents and supports has been confirmed by the synthesis of the corresponding modified oligonucleotides.
- Tatulchenkov, M. Yu.,Prokhorenko,Kvach,Navakouski,Stepanova,Pilchenko,Gontarev,Sharko,Korshun,Shmanai
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p. 386 - 396
(2017/08/08)
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- Labelling reagents having a pyridine nucleus bearing a diazomethyl function, process for synthesis of such reagents and processes for detection of biological molecules
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A process for synthesis of a labelling reagent, a process for the labelling of a biological molecule, a labelled biological molecule obtained by the process, a process for labelling and fragmentation of a single or double strand nucleic acid, a labelled n
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Page/Page column 21
(2016/03/13)
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- Synthesis of biotinylated episilvestrol: Highly selective targeting of the translation factors eIF4AI/II
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Silvestrol (1) and episilvestrol (2) are protein synthesis inhibitors, and the former has shown efficacy in multiple mouse models of cancer; however, the selectivity of these potent cytotoxic natural products has not been described. Herein, it is demonstr
- Chambers, Jennifer M.,Lindqvist, Lisa M.,Webb, Andrew,Huang, David C. S.,Savage, G. Paul,Rizzacasa, Mark A.
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supporting information
p. 1406 - 1409
(2013/05/08)
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- Biotinylated polyacrylamide-based metal-chelating polymers and their influence on antigen recognition following conjugation to a trastuzumab fab fragment
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We report the synthesis and characterization of metal-chelating polymers (MCPs) with a terminal biotin and a polyacrylamide backbone harboring multiple diethylenetriaminepentaacetic acid (DTPA) chelating sites. These polymers are conjugated to a streptavi
- Liu, Peng,Boyle, Amanda J.,Lu, Yijie,Reilly, Raymond M.,Winnik, Mitchell A.
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p. 2831 - 2842
(2012/11/06)
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- Efforts toward elucidating Thalidomide's molecular target: An expedient synthesis of the first Thalidomide biotin analogue
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Herein we describe the synthesis of the first Thalidomide-biotin analogue in order to initiate investigations into the unknown molecular mode of action of Thalidomide. In this manner we describe the attachment of biotin tether through the Huisgen 1,3-dipo
- Stewart, Scott G.,Braun, Carlos J.,Polomska, Marta E.,Karimi, Mahdad,Abraham, Lawrence J.,Stubbs, Keith A.
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scheme or table
p. 4059 - 4062
(2010/11/17)
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- Synthesis and noncovalent protein conjugation of linear-hyperbranched PEG-poly(glycerol) α,ωn-telechelics
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(Figure Presented) Linear-hyperbranched, heterobifunctional α,ωn telechelic block copolymers consisting of a linear poly(ethylene glycol) (PEG) chain and a hyperbranched polyglycerol (PG) blockhave been prepared in five steps, using a protected amino-functional in itiator. The polyfunctionality ωn (OH groups) can be adjusted by the degree of polymerization (DPn) of the polyglycerol block. Subsequent introduction of a single biotin unit by amidation in α-position permitted noncovalent bioconjugation with avidin.
- Wurm, Frederik,Klos, Johannes,Raeder, Hans Joachim,Frey, Holger
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supporting information; experimental part
p. 7954 - 7955
(2009/12/03)
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- Fluorinated lipid constructs permit facile passage of molecular cargo into living cells
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(Figure Presented) Fluorinated lipids get rapidly internalized into living cells and are also displayed on the cell surface. The uptake of lipids is energy dependent and is likely via the clathrin-mediated endocytic pathway. Fluorinated lipids are 3-5-fold more efficient in acting as molecular transporters of noncovalently bound proteins than their hydrocarbon counterparts. These materials could serve as efficient molecular transporters for molecules that function in the cytoplasm such as short interfering RNAs (siRNAs).
- Dafik, Laila,Kalsani, Venkateshwarlu,Leung, Anthony Kar Lun,Kumar, Krishna
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supporting information; experimental part
p. 12091 - 12093
(2009/12/28)
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- Novel bioconjugates of aminolevulinic acid with vitamins
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(Chemical Equation Presented) 5-Aminolevulinic acid (ALA) and derivatives thereof have been successfully used in photodynamic cancer therapy (PDT). The synthesis of novel bioconjugates combining ALA with two lipophilic and one hydrophilic vitamins is repo
- Vallinayagam, Ramakrishnan,Weber, Joanne,Neier, Reinhard
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supporting information; experimental part
p. 4453 - 4455
(2009/05/26)
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- ANTITHROMBOTIC DUAL INHIBITORS COMPRISING A BIOTIN LABEL
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The present invention relates compounds of the formula: oligosaccharide-spacer-(GpIIb/IIIa antagonist), wherein the oligosaccharide is a negatively charged oligosaccharide residue comprising four to twenty five monosaccharide units, the charge being compensated by positively charged counterions, and wherein the oligosaccharide residue is derived from an oligosaccharide which has (AT-III mediated) anti-Xa activity per se; the spacer is a bond or an essentially pharmacologically inactive linking residue; the GpIIb/IIIa antagonist is a residue mimicking the RGD and/or K(QA)GD fragment of fibrinogen, comprising a carboxylate moiety and a basic moiety located within the residue at a distance of 10-20 ? from each other; or a pharmaceutically acceptable salt thereof or a prodrug or a solvate thereof; wherein the compound of formula I further comprises at least one covalent bond with a biotin label or an analogue thereof. The compounds of the invention have antithrombotic activity and can be used in treating or preventing thrombotic diseases. The antithrombotic activity of the compound of this invention can be neutralized in case of emergency upon adminstration of avidin, streptavidin and analogues thereof having high biotin affinity.
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Page/Page column 20
(2008/06/13)
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- Non-natural glycosphingolipids and structurally simpler analogues bind HIV-1 recombinant gp120
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Interactions of recombinant gp120 (rgp120) with non-natural glycosphingolipids (GSLs) and structurally simpler analogues have been studied using a competitive adhesion assay. Conjugates of cellobiosyl ceramide and melibiosyl ceramide were synthetically pr
- McReynolds, Katherine D.,Bhat, Abhijit,Conboy, John C.,Saavedra,Gervay-Hague, Jacquelyn
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p. 625 - 637
(2007/10/03)
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- Reagents for multiple non-radioactive labelling of oligonucleotides
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Novel phosphoramidite reagents for nonradioactive polylabelling of oligonucleotides have been developed, including two branching reagents, 4 and 8, and a biotin-containing phosphoramidite 19 which can be used to incorporate a biotin moiety into any positi
- Korshun, Vladimir A.,Pestov, Nikolai B.,Nozhevnikova, Elena V.,Prokhorenko, Igor A.,Gontarev, Sergei V.,Berlin, Yuri A.
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p. 2531 - 2547
(2007/10/03)
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- SPECIFICALLY CLEAVABLE OLIGODEOXYRIBONUCLEOTIDES FOR REVERSIBLE IMMOBILIZATION OF DNA
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Carriers for the reversible immobilization of DNA were prepared using streptavidin-coated TSK gel with surface binding capacities of 50-70 nmoles of oligonucleotide per g of dry carrier, with oligonucleotides bearing biotin residues at the 5'- and 3'-ends
- Shchepinov, M. S.,Esipov, D. S.,Korobko, V. G.,Dobrynin, V. N.
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p. 520 - 528
(2007/10/02)
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