7370-58-3Relevant academic research and scientific papers
Selenosulfides Tethered to gem-Dimethyl Esters: A Robust and Highly Versatile Framework for H2S Probe Development
Suarez, S. Israel,Ambrose, Rynne,Kalk, Madison A.,Lukesh, John C.
, p. 15736 - 15740 (2019)
Selenosulfides coupled to gem-dimethyl esters provide an exceptional platform for H2S probe development. With the sulfur half being nonessential to its high reactivity and selectivity towards H2S, we highlight the unique flexibility of our design by improving its biocompatibility and tissue specificity through structural modifications of its sulfide moiety.
Novel multi-stimuli responsive functionalized PEG-based co-delivery nanovehicles toward sustainable treatments of multidrug resistant tumor
Xu, Jingwen,Yan, Xiangji,Ge, Xin,Zhang, Mingzhen,Dang, Xugang,Yang, Yan,Xu, Feng,Luo, Yanling,Li, Guoliang
, p. 1297 - 1314 (2021)
The efficacy of ongoing anticancer treatment is often compromised by some barriers, such as low drug content, nonspecific release of drug delivery system, and multidrug resistance (MDR) effect of tumors. Herein, in the research a novel functionalized PEG-based polymer cystine-(polyethylene glycol)2-b-(poly(2-methacryloyloxyethyl ferrocenecarboxylate)2) (Cys-(PEG45)2-b-(PMAOEFC)2) with multi-stimuli sensitive mechanism was constructed, in which doxorubicin (DOX) was chemical bonded through Schiff base structure to provide acid labile DOX prodrug (DOX)2-Cys-(PEG45)2-b-(PMAOEFC)2. Afterwards, paclitaxel (PTX) and its diselenide bond linked PTX dimer were encapsulated into the prodrug through physical loading, to achieve pH and triple redox responsive (DOX)2-Cys-(PEG45)2-b-(PMAOEFC)2@PTXand (DOX)2-Cys-(PEG45)2-b-(PMAOEFC)2@PTX?dimerwith ultrahigh drugs content. The obtained nanovehicles could self-assemble into globular micelles with good stability based on fluorescence spectra and TEM observation. Moreover, there was a remarkable “reassembly-disassembly” behavior caused by phase transition of micelles under the mimic cancerous physiological environment. DOX and PTX could be on-demand released in acid and redox stress mode, respectively. Meanwhile,in vivoanticancer studies revealed the significant tumor inhibition of nanoformulas. This work offered facile strategies to fabricate drug nanaovehicles with tunable drug content and types, it has a profound significance in overcoming MDR effect, which provided more options for sustainable cancer treatment according to the desired drug dosage and the stage of tumor growth.
Fabrication of redox-responsive Bi(mPEG-PLGA)-Se2 micelles for doxorubicin delivery
Birhan, Yihenew Simegniew,Hailemeskel, Balkew Zewge,Mekonnen, Tefera Worku,Hanurry, Endiries Yibru,Darge, Haile Fentahun,Andrgie, Abegaz Tizazu,Chou, Hsiao-Ying,Lai, Juin-Yih,Hsiue, Ging-Ho,Tsai, Hsieh-Chih
, (2019)
Stimuli-responsive polymeric nanostructures have emerged as potential drug carriers for cancer therapy. Herein, we synthesized redox-responsive diselenide bond containing amphiphilic polymer, Bi(mPEG-PLGA)-Se2 from mPEG-PLGA and 3,3′-diselanediyldipropanoic acid (DSeDPA) using DCC/DMAP as coupling agents. Due to its amphiphilic nature, Bi(mPEG-PLGA)-Se2 self-assembled in to stable micelles in aqueous solution with a hydrodynamic size of 123.9 ± 0.85 nm. The Bi(mPEG-PLGA)-Se2 micelles exhibited DOX-loading content (DLC) of 6.61 wt% and encapsulation efficiency (EE) of 54.9%. The DOX-loaded Bi(mPEG-PLGA)-Se2 micelles released 73.94% and 69.54% of their cargo within 72 h upon treatment with 6 mM GSH and 0.1% H2O2, respectively, at pH 7.4 and 37 °C. The MTT assay results demonstrated that Bi(mPEG-PLGA)-Se2 was devoid of any inherent toxicity and the DOX-loaded micelles showed pronounced antitumor activities against HeLa cells, 44.46% of cells were viable at maximum dose of 7.5 μg/mL. The cellular uptake experiment further confirmed the internalization of DOX-loaded Bi(mPEG-PLGA)-Se2 micelles and endowed redox stimuli triggered drug release in cytosol and nuclei of cancer cells. Overall, the results suggested that the smart, biocompatible Bi(mPEG-PLGA)-Se2 copolymer could serve as potential drug delivery biomaterial for the controlled release of hydrophobic drugs in cancer cells.
NIR responsive cross-linked micelles, drug delivery carrier targeting cancer cell and method for preparing the same
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Paragraph 0192-0194, (2020/07/28)
The present invention relates to: a cross-linked micelle having a cancer cell target function in response to near infrared rays; a drug delivery carrier comprising the same; and a method for manufacturing the same. The drug delivery carrier having the cancer cell target function that induces drug release by using near infrared rays can be easily manufactured by a click reaction, and actively releases drugs from the outside by specifically targeting cancer cells, thereby being able to specifically kill cancer cells. Therefore, the drug delivery carrier can be usefully used in the pharmaceutical field.COPYRIGHT KIPO 2020
Synthesis of functionalized organoselenium materials: Selenides and diselenides containing cholesterol
Frizon, Tiago E.,Rafique, Jamal,Saba, Sumbal,Bechtold, Ivan H.,Gallardo, Hugo,Braga, Antonio L.
supporting information, p. 3470 - 3476 (2015/06/08)
Abstract A simple and efficient procedure for the synthesis of three new series of chalcogen liquid crystals, based on selenides and diselenides, containing cholesterol in their structure, is described. Thermal and liquid crystalline properties were investigated by POM, DSC, TGA and XRD scattering. Six of the nine molecules synthesized showed liquid crystal properties, with smectic mesomorphism. All the compounds presented good thermal stability. The smectic mesomorphism was confirmed through XRD analysis. The morphology of the surface of the films was investigated by using atomic force microscopy (AFM). All prepared diselenides showed good glutathione peroxidase like activity and one of the diselenides was 3.3 times more active than the standard Ebselen.
Synthesis and biological evaluation of 2-picolylamide-based diselenides with non-bonded interactions
Rafique, Jamal,Saba, Sumbal,Canto, Rmulo Faria Santos,Frizon, Tiago Elias Allievi,Hassan, Waseem,Waczuk, Emily Pansera,Jan, Maryam,Back, Davi Fernando,Rocha, Joo Batista Teixeira Da,Braga, Antonio Luiz
, p. 10095 - 10109 (2015/08/06)
In this paper, we report the synthesis and biological evaluation of picolylamide-based diselenides with the aim of developing a new series of diselenides with O???Se non-bonded interactions. The synthesis of diselenides was performed by a simple and efficient synthetic route. All the products were obtained in good yields and their structures were determined by 1H-NMR, 13C-NMR and HRMS. All these new compounds showed promising activities when tested in different antioxidant assays. These amides exhibited strong thiol peroxidase-like (TPx) activity. In fact one of the compounds showed 4.66 times higher potential than the classical standard i.e., diphenyl diselenide. The same compound significantly inhibited iron (Fe)-induced thiobarbituric acid reactive species (TBARS) production in rat's brain homogenate. In addition, the X-ray structure of the most active compound showed non-bonded interaction between the selenium and the oxygen atom that are in close proximity and may be responsible for the increased antioxidant activity. The present study provides evidence about the possible biochemical influence of nonbonding interactions on organochalcogens potency.
Synthesis and biological evaluation of new nitrogen-containing diselenides
Nascimento, Vanessa,Ferreira, Natasha L.,Canto, R?mulo F.S.,Schott, Karen L.,Waczuk, Emily P.,Sancineto, Luca,Santi, Claudio,Rocha, Jo?o B.T.,Braga, Antonio L.
, p. 131 - 139 (2015/02/19)
The antioxidant properties of organoselenium compounds have been extensively investigated with the aim of developing new drugs, since oxidative stress is responsible for a variety of chronic human diseases. Herein, we reported the synthesis of new nitrogen-containing diselenides by a simple and efficient synthetic route. The products were obtained in good to excellent yields and their identification and characterization were achieved by NMR and HRMS techniques. The new derivatives may represent promising structures with different biological activities, which can act against oxidative stress through diverse mechanisms of action. The glutathione peroxidase-like assay (GPx-like activity) of the new synthesized compounds indicated that they reduced H2O2to water at the expense of PhSH. The best results were obtained with diselenide 2b, which was 9 times more active than the standard organoselenium drug ebselen and, in contrast, this compound was not reduced by hepatic TrxR. All of the new compounds inhibited Fe(II)-induced TBARS.
Diselenides and Allyl Selenides as Glutathione Peroxidase Mimetics. Remarkable Activity of Cyclic Seleninates Produced in Situ by the Oxidation of Allyl ω-Hydroxyalkyl Selenides
Back, Thomas G.,Moussa, Ziad
, p. 13455 - 13460 (2007/10/03)
A series of aliphatic diselenides and selenides containing coordinating substituents was tested for glutathione peroxidase (GPx)-like catalytic activity in a model system in which the reduction of tert-butyl hydroperoxide with benzyl thiol to afford dibenzyl disulfide and tert-butyl alcohol was performed under standard conditions and monitored by HPLC. Although the diselenides showed generally poor catalytic activity, allyl selenides proved more effective. In particular, allyl 3-hydroxypropyl selenide (25) rapidly generated 1,2-oxaselenolane Se-oxide (31) in situ by a series of oxidation and [2,3]sigmatropic rearrangement steps. The remarkably active cyclic seleninate 31 proved to be the true catalyst, reacting with the thiol via a postulated mechanism in which the thioseleninate 32 is first produced, followed by further thiolysis to selenenic acid 33 and oxidation-dehydration to regenerate 31. In contrast to catalysis with GPx, formation of the corresponding selenenyl sulfide 34 comprises a competing deactivation pathway in the catalytic cycle of 31, as a separate experiment revealed that authentic 34 was a much less effective catalyst than 31. 1,2-Oxaselenane Se-oxide (37), the six-membered homologue of 31, was formed similarly from allyl 4-hydroxybutyl selenide (26), but proved a less effective catalyst than 31. Compounds 31 and 37 are the first examples of unsubstituted monocyclic seleninate esters.
Selenium compounds
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, (2008/06/13)
Selenium compounds, and a method of their preparation, are disclosed which have a structure that renders the compounds useful in immunoassays or in competitive protein binding assays wherein either radio-labeled selenium compounds or nonradioactive selenium compounds are used respectively, with radiologic or fluorometric analysis. One class of these compounds have the generalized structural formula of: STR1 wherein: X is hydrogen or oxo; R1 and R2, together, are ethylene, trimethylene, or 5,6-phenylene; R3 is alkylene of 1 to 6 carbons; R4 is alkyl or isoalkyl of 1 to 6 carbons, phenyl or benzyl; or R3 and R4 together are 1,2,3-propanetriyl; And n is 1 or 2. The compounds in the aforementioned structure are N-pyrrolidine derivatives wherein R1 and R2 together are ethylene; N-succinimdyl derivatives when R1 and R2 together are ethylene and the X groups are oxo groups; N-phthalimidyl derivatives when R1 and R2 are 5,6-phenylene and the X groups are oxo; and N-piperidyl compounds when R1 and R2 together are trimethylene. Another class of these compounds has the generic formula: STR2 wherein: R3, R4 and n are as previously defined.
