- A combinatorial approach to minimal peptide models of a metalloprotein active site
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Screening of a "one-bead-one-compound" peptide library containing biomimetic His/Cys ligands has led to the discovery of sequences that hydrolyze ester substrates in combination with Zn2+. The Royal Society of Chemistry 2006.
- Namuswe, Frances,Goldberg, David P.
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- CROSS-LINKING COMPOUNDS AND METHODS OF USE THEREOF
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Compounds comprising a cross-linking moiety and a protecting group are described herein along with their methods of use. The cross-linking moiety may comprise an indoxyl and the protecting group may comprise a sugar (e.g., a glucuronide or glucoside), phosphoester, or sulfoester group. The cross-linking moiety and protecting group may be attached to each other via an oxygen atom, sulfur atom, or linker. In some embodiments, the linker attaching the cross-linking moiety and protecting group is a self-immolative linker. A compound of the present invention may cross-link under physiological conditions and/or in vivo.
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Page/Page column 50-51
(2021/01/29)
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- CROSS-LINKING COMPOUNDS AND METHODS OF USE THEREOF
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Compounds of Formula IA, IB, II, III, IV, and/or V are described herein along with their methods of use. A compound of the present invention may cross-link under physiological conditions and/or in vivo.
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Page/Page column 62; 73; 75
(2021/05/15)
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- Enzymatically triggered chromogenic cross-linking agents under physiological conditions
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The ability to cross-link molecules upon enzymatic action under physiological conditions holds considerable promise for use in diverse life sciences applications. Here, an enzymatically triggered "click reaction" has been developed by exploiting the longstanding indigo-forming reaction from indoxyl β-glucoside. The covalent cross-linking proceeds in aqueous solution, requires the presence only of an oxidant (e.g., O2), and is readily detectable owing to the blue color of the resulting indigoid dye. To achieve facile indigoid formation in the presence of a bioconjugatable tether, diverse indoxyl β-glucosides were synthesized and studied in enzyme assays with four glucosidases including from tritosomes (derived from hepatic lysosomes) and rat liver homogenates. Altogether 36 new compounds (including 15 target indoxyl-glucosides for enzymatic studies) were prepared and fully characterized in pursuit of four essential requirements: enzyme triggering, facile subsequent indigoid dye formation, bioconjugatability, and synthetic accessibility. The 4,6-dibromo motif in a 5-alkoxy-substituted indoxyl-glucoside was a key design feature for fast and high-yielding indigoid dye formation. Two attractive molecular designs include (1) an indoxyl-glucoside linked to a bicyclo[6.1.0]nonyl (BCN) group for Cu-free click chemistry, and (2) a bis(indoxyl-glucoside). In both cases the linker between the reactive moieties is composed of two short PEG groups and a central triazine derivatized with a sulfobetaine moiety for water solubilization. Glucosidase treatment of the bis(indoxyl-glucoside) in aqueous solution gave oligomers that were characterized by absorption, dynamic light-scattering, and 1H NMR spectroscopy; optical microscopy; mass spectrometry; and HPLC. Key attractions of in situ indigoid dye formation, beyond enzymatic triggering under physiological conditions without exogenous catalysts or reagents, are the chromogenic readout and compatibility with attachment to diverse molecules.
- Fujita, Hikaru,Dou, Jinghuai,Matsumoto, Nobuyuki,Wu, Zhiyuan,Lindsey, Jonathan S.
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p. 719 - 743
(2020/01/31)
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- Synthesis of a 1,2-: Cis -indoxyl galactoside as a chromogenic glycosidase substrate
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A synthetically challenging 1,2-cis-indoxyl galactoside, X-α-galactoside, was first prepared in this study using a cyclic ketone indoxyl acceptor and a glycosyl trichloroacetimidate donor to produce an enol glycoside and a 4,6-O-di-tert-butylsilylene-protected galactosyl donor to complete the synthesis. The target compound shows enzyme activity in the presence of α-galactosidase.
- Nagata, Sakuto,Tomida, Hirotaka,Iwai-Hirose, Haruka,Tanaka, Hide-Nori,Ando, Hiromune,Imamura, Akihiro,Ishida, Hideharu
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p. 28241 - 28247
(2019/09/30)
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- Enzymatic glycosylation of indoxyglycosides catalyzed by a novel maltose phosphorylase from Emticicia oligotrophica
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Maltose phosphorylases (EC 2.4.1.8) catalyze the reversible conversion of maltose to glucose and glucose-1-phosphate in the presence of inorganic phosphate. Herein, we describe for the first time the use of a maltose phosphorylase for the synthesis of various anomerically modified diglycosides. The maltose phosphorylase used was isolated from the bacterium Emticicia oligotrophica and showed a high selectivity towards the phosphorolysis of maltose, whereas no phosphorolysis was observed using other glucose-containing disaccharides such as cellobiose, melibiose, sucrose and trehalose. The addition of glucose to various 5-bromo-4-chloro-3-indolyl-glycosides (X-sugars) was used to evaluate the promiscuity of the maltose phosphorylase, and product formation was verified by LC-ESI-MS and MALDI-TOF-MS. The simple expression and purification protocol and the use of maltose as an inexpensive starting material make this maltose phosphorylase from Emticicia oligotrophica a valuable novel biocatalyst for the synthesis of glucose-containing glycosides.
- Awad, Faisal Nureldin,Kulinich, Anna,Yao, Ming Jun,Duan, Xu Chu,Cai, Zhi Peng,Gu, Bin,Liu, Li,Voglmeir, Josef
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p. 301 - 314
(2016/12/07)
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- Formulation of drugs and vaccines in the form of percutaneous injectable needles
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The invention relates to percutaneous administration of drugs and vaccines in form of solid penetrating needles, “injectable needles”, comprising a polymeric matrix resulting from the polymerization of a polymerizable paste or mixture. The injectable needles are hard enough to penetrate the skin and can be administered percutaneously by simple pusher or injector delivery devices. The manufacturing procedure of the injectable needles allows for the incorporation of the drug as preformulated stable microparticles and incorporation of modifying agents to modulate stiffness, solubility and drug release. Drugs formulated in these injectable needles offer a safe, simple and effective alternative to conventional percutaneous drug delivery systems based on hypodermic needles and syringes that require refrigerated storage and reconstitution prior to administration.
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Page/Page column 22
(2016/03/19)
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- Enzymatic synthesis of colorimetric substrates to determine α-2,3- and α-2,6-specific neuraminidase activity
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Glycoconjugates containing either terminal α-2,3- or α-2,6-Neu5Ac-Gal disaccharides are found on cell surfaces of many animal glycans. Each linkage can be specifically recognized by lectins and enzymes such as neuraminidases. Here we describe a one-step enzymatic synthesis of two colorimetric substrates that allow for fast distinction of specific neuraminidase activity. The Royal Society of Chemistry 2013.
- Reyes Martinez, Juana Elizabeth,Sardzik, Robert,Voglmeir, Josef,Flitsch, Sabine L.
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p. 21335 - 21338
(2013/11/06)
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- Detection of alkaline phosphatase using surface-enhanced raman spectroscopy
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A new approach was developed to detect the activity of alkaline phosphatase (ALP) enzyme at ultralow concentrations using a surface-enhanced Raman scattering (SERS) technique. The approach is based on the use of gold nanoparticles as a SERS material whereas 5-bromo-4-chloro-3-indolyl phosphate (BCIP) is used as a substrate of ALP. The enzymatic hydrolysis of BCIP led to the formation of indigo dye derivatives, which were found to be highly SERS active. For the first time, we were able to detect ALP at a concentration of ～4 × 10-15 M or at single-molecule levels when ALP was incubated with BCIP for 1 h in the Tris-HCl buffer. The same technique also was successfully employed to detect surface-immobilized avidin, and a detection limit of 10 ng/mL was achieved. This new technique allows the detection of both free and labeled ALP as a Raman probe in enzyme immunoassays, immunoblotting, and DNA hybridization assays at ultralow concentrations.
- Ruan, Chuanmin,Wang, Wei,Gu, Baohua
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p. 3379 - 3384
(2007/10/03)
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