69917-80-2Relevant academic research and scientific papers
Synthesis of cystamidin A (pyrrole-3-propanamide), a reported calpain inhibitor
Bihovsky, Ron,Pendrak, Israil
, p. 1541 - 1542 (1996)
The reported calpain inhibitor cystamidin A (1a, pyrrole-3-propanamide) and a regioisomer, pyrrole-2-propanamide (1b) have been synthesized from the corresponding pyrrolecarboxaldehydes. The previously assigned structure of cystamidin A is confirmed. However, neither synthetic cystamidin A nor regioisomer 1b inhibits recombinant human calpain I.
BODI-Pt, a Green-Light-Activatable and Carboplatin-Based Platinum(IV) Anticancer Prodrug with Enhanced Activation and Cytotoxicity
Chen, Shu,Deng, Zhiqin,Matsuda, Yudai,Tse, Man-Kit,Yao, Houzong,Zhu, Guangyu
, (2020/09/02)
Platinum drugs are widely used in clinics to treat various types of cancer. However, a number of severe side effects induced by the nonspecific binding of platinum drugs to normal tissues limit their clinical use. The conversion of platinum(II) drugs into more inert platinum(IV) derivatives is a promising strategy to solve this problem. Some platinum(IV) prodrugs, such as carboplatin-based tetracarboxylatoplatinum(IV) prodrugs, are not easily reduced to active platinum(II) species, leading to low cytotoxicity in vitro. In this study, we report the design and synthesis of a carboplatin-based platinum(IV) prodrug functionalized with a boron dipyrromethene (bodipy) ligand at the axial position, and the ligand acts as a photoabsorber to photoactivate the platinum(IV) prodrug. This compound, designated as BODI-Pt, is highly stable in the dark but quickly activated under irradiation to release carboplatin and the axial ligands. A cytotoxic study reveals that BODI-Pt is effective under irradiation, with cytotoxicity 11 times higher than that in the dark and 39 times higher than that of carboplatin in MCF-7 cells. Moreover, BODI-Pt has been proven to kill cancer cells by binding to the genomic DNA, arresting the cell cycle at the G2/M phase, inducing oncosis, and generating ROS upon irradiation. In summary, we report a green-light-activatable and carboplatin-based Pt(IV) prodrug with improved cytotoxicity against cancer cells, and our strategy can be used as a promising way to effectively activate carboplatin-based platinum(IV) prodrugs.
FLUORESCENT ENDOPLASMIC RETICULUM TRACKERS FOR LIVE CELL IMAGING OF PATHOGENIC YEAST
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Paragraph 0071, (2020/03/23)
Particular 1,2,3-triazole- and 1,2,4-triazole-based compounds can be used as fluorescent probes. The compounds can optionally be substituted with one or two fluorine atoms. The compounds are effective as specific endoplasmatic reticulum (ER)-trackers for live cell imaging in a fungal cell, such as a pathogenic yeast. Compositions including the fluorescent probes can be used in methods for tracking the endoplasmic reticulum in a fungal cell.
18F-Labeled BODIPY Dye: A Potential Prosthetic Group for Brain Hybrid PET/Optical Imaging Agents
Kim, Hyunjung,Kim, Kyul,Son, Sang-Hyun,Choi, Joon Young,Lee, Kyung-Han,Kim, Byung-Tae,Byun, Youngjoo,Choe, Yearn Seong
, p. 1445 - 1451 (2019/03/26)
There are few hybrid positron emission tomography (PET)/fluorescence imaging agents available for brain imaging. For this purpose, BODIPY dye is very attractive because one of its fluorine atoms can be readily exchanged with 18F, and it can be modified to produce red-shifted fluorescence. In this study, therefore, we synthesized and investigated a 18F-labeled red-shifted BODIPY dye as a prosthetic group for brain hybrid PET/optical imaging agents and determined the optimal dose of this radioligand for hybrid imaging. The red-shifted BODIPY dye (1) was synthesized, and one of its fluorine atoms was exchanged with 18F using SnCl4 in high yield. Partition coefficients of 18F-labeled BODIPY dye ([18F]1) and 1 were measured using its radioactivity and fluorescence, respectively, which were shown to be suitable for brain penetration. Optimal dose for hybrid imaging was determined by analysis of PET/CT and optical images of Balb/C nude mice injected with [18F]1 and 1, respectively. Hybrid PET/optical images of mice injected with optimal dose of [18F]1 showed strong radioactivity and fluorescence signal in the brain at 2 min after injection, with rapid clearance by 30 min. Tissue distribution data confirmed the in vivo and ex vivo PET/optical imaging data, indicating desirable brain pharmacokinetics of the radioligand. Taken together, the results of this study suggest that [18F]1 can be widely used as a prosthetic group for brain hybrid PET/optical imaging agents.
A Synthetic Approach for the Rapid Preparation of BODIPY Conjugates and their use in Imaging of Cellular Drug Uptake and Distribution
Krajcovicova, Sona,Stankova, Jarmila,Dzubak, Petr,Hajduch, Marian,Soural, Miroslav,Urban, Milan
, p. 4957 - 4966 (2018/03/21)
A solid-phase synthetic (SPS) method was developed for the preparation of BODIPY-labeled bioactive compounds that allows for fast and simple synthesis of conjugates for use in fluorescent microscopy. The approach was used to visualize cellular uptake and
KETONE INHIBITORS OF LYSINE GINGIPAIN
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Paragraph 0278; 0357, (2018/04/12)
The present invention provides compounds according to Formula (I) as described herein, and their use for inhibiting the lysine gingipain protease (Kgp) from the bacterium Porphyromonas gingivalis. Also described are gingipain activity probe compounds and methods for assaying gingipain activity are also described, as well as methods for the treatment of disorders associated with P. gingivalis infection, including brain disorders such as Alzheimer's disease.
Rate of Lipid Peroxyl Radical Production during Cellular Homeostasis Unraveled via Fluorescence Imaging
Greene, Lana E.,Lincoln, Richard,Cosa, Gonzalo
, p. 15801 - 15811 (2017/11/14)
Reactive oxygen species (ROS) and their associated byproducts have been traditionally associated with a range of pathologies. It is now believed, however, that at basal levels these molecules also have a beneficial cellular function in the form of cell signaling and redox regulation. Critical to elucidating their physiological role is the opportunity to visualize and quantify the production of ROS with spatiotemporal accuracy. Armed with a newly developed, extremely sensitive fluorogenic α-tocopherol analogue (H4BPMHC), we report herein the observation of steady concentrations of lipid peroxyl radicals produced in live cell imaging conditions. Imaging studies with H4BPMHC indicate that the rate of production of lipid peroxyl radicals in HeLa cells under basal conditions is 33 nM/h within the cell. Our work further provides indisputable evidence on the antioxidant role of Vitamin E, as lipid peroxidation was suppressed in HeLa cells both under basal conditions and in the presence of Haber-Weiss chemistry, generated by the presence of cumyl hydroperoxide and Cu2+ in solution, when supplemented with the α-tocopherol surrogate, PMHC (2,2,5,7,8-pentamethyl-6-hydroxy-chromanol, an α-tocopherol analogue lacking the phytyl tail). H4BPMHC has the sensitivity needed to detect trace changes in oxidative status within the lipid membrane, underscoring the opportunity to illuminate the physiological relevance of lipid peroxyl radical production during cell homeostasis and disease.
Novel fluorescent anthracene-bodipy dyads displaying sensitivity to pH and turn-on behaviour towards Cu(II) ions
Vanessa Saura,Isabel Burguete,Galindo, Francisco,Luis, Santiago V.
, p. 3013 - 3024 (2017/04/10)
Three bichromophoric compounds containing anthracene and bodipy moieties connected by different spacers have been synthesized and fully characterized. The set of spacers comprises a variety of bridges (short and flexible 1,2-diaminoethane in compound 1a, long and flexible 1,8-diaminooctane in compound 1b and short and rigid piperazine in compound 1c). The new compounds show interchromophoric communication via Electronic Energy Transfer (EET). When anthracene is excited, the energy is efficiently transferred to the bodipy moiety. The emission of the acceptor is partially quenched in dyad 1a but remarkably not in 1b and 1c. In an aqueous environment, the fluorescence of the new compounds display sensitivity to pH (emissive at acidic values and non-emissive at neutral ones), a typical behaviour of photoinduced electron-transfer (PET) probes, but with remarkable differences in the pKa of each compound, attributable to the nature of the linker. Additionally, the behaviour in the presence of several metallic cations (Cu2+, Ni2+, Cd2+, Zn2+) has been studied, and a turn-on response towards Cu2+ in water at neutral pH has been found.
Tunable BODIPY derivatives amenable to 'click' and peptide chemistry
Hansen, Anna Mette,Sewell, Alan L.,Pedersen, Rasmus H.,Long, De-Liang,Gadegaard, Nikolaj,Marquez, Rodolfo
, p. 8527 - 8533 (2013/09/02)
Novel azido- and amino-functionalised fluorescent probes based on the BODIPY framework have been developed. The probes can be easily and cheaply synthesised, exhibit the highly desirable BODIPY fluorescent properties, and are amenable to 'click' and pepti
Synthesis of 3′-BODIPY-labeled active esters of nucleotides and a chemical primer extension assay on beads
Giessler, Kerstin,Griesser, Helmut,Goehringer, Daniela,Sabirov, Thomas,Richert, Clemens
supporting information; experimental part, p. 3611 - 3620 (2010/09/08)
A solution-phase synthesis of active esters of 3′-fluoropho:relabeled deoxynucleoside 5′-monophosphates was developed for thymine and cytosine as nucleobases by using two different: BODIPY dyes. Starting from the respective 2′-amino2′,3′-dideoxynucleoside
