153870-20-3Relevant academic research and scientific papers
Synthesis of reactive polymers for acrolein capture using AGET ATRP
Beringer, Laura T.,Li, Shaohua,Gilmore, Gary,Lister, John,Averick, Saadyah
, p. 3776 - 3781 (2015)
Acrolein is a toxic metabolite of the anticancer agent cyclophosphamide (CP). Current strategies to mitigate acrolein toxicity are insufficient, and in this brief article, we report the synthesis of well-defined low molecular weight block copolymers using activators generated by electron transfer atom transfer radical polymerization (AGET ATRP) capable of reacting with the cytotoxic small molecule acrolein. Acrolein reactivity was introduced into the block copolymers via incorporation of either (a) aminooxy or (b) sulfhydryl groups. The cytoprotective effect of the polymers was compared to sodium 2-sulfanylethanesulfonate (mesna) the current gold standard for protection from CP urotoxicity, and we found that the polymers bearing sulfhydryl moieties demonstrated superior cytoprotective activity.
Exhaustive glycosylation, pegylation, and glutathionylation of a [G4]-ene48 dendrimer via photoinduced thiol-ene coupling
Conte, Mauro Lo,Robb, Maxwell J.,Hed, Yvonne,Marra, Alberto,Malkoch, Michael,Hawker, Craig J.,Dondoni, Alessandro
, p. 4468 - 4475 (2011)
The use of free-radical thiol-ene coupling (TEC) for the introduction of carbohydrate, poly(ethylene glycol), and peptide fragments at the periphery of an alkene functional dendrimer has been reported in this article. Four different sugar thiols including glucose, mannose, lactose, and sialic acid, two PEGylated thiols, and the natural tripeptide glutathione were reacted with a fourth generation alkene functional dendrimer [G4]-ene48 on irradiation at λmax 365 nm. In all cases, the 1H NMR spectra of the crude reaction mixture revealed the complete disappearance of alkene proton signals indicating the quantitative conversion of all 48 alkene groups of the dendrimer. With one exception only, all dendrimer conjugates were isolated in high yields (70-94%), validating the high efficiency of multiple TEC reactions on a single substrate. All isolated and purified compounds were analyzed by matrix assisted laser desorption ionization-time of flight (MALDI-TOF) spectrometry and gave spectra consistent with the assigned structure.
Hetero-Click Conjugation of Oligonucleotides with Glycosides Using Bifunctional Phosphoramidites
Meyer, Albert,No?l, Mathieu,Vasseur, Jean-Jacques,Morvan, Fran?ois
, p. 2921 - 2927 (2015)
Two phosphoramidite derivatives, 1 and 2, each bearing two orthogonal functions: alkyne/thioacetyl or alkyne/tosyl, respectively, were synthesized and used to generate heteroglyco 5′-oligonucleotide conjugates. After coupling, the first conjugation was pe
Targeting Colorectal Cancer with Conjugates of a Glucose Transporter Inhibitor and 5-Fluorouracil
Chang, Chun-Kai,Chiu, Pei-Fang,Yang, Hui-Yi,Juang, Yu-Pu,Lai, Yen-Hsun,Lin, Tzung-Sheng,Hsu, Lih-Ching,Yu, Linda Chia-Hui,Liang, Pi-Hui
supporting information, p. 4450 - 4461 (2021/05/06)
Overexpression of glucose transporters (GLUTs) in colorectal cancer cells is associated with 5-fluorouracil (1, 5-FU) resistance and poor clinical outcomes. We designed and synthesized a novel GLUT-targeting drug conjugate, triggered by glutathione in the tumor microenvironment, that releases 5-FU and GLUTs inhibitor (phlorizin (2) and phloretin (3)). Using an orthotopic colorectal cancer mice model, we showed that the conjugate exhibited better antitumor efficacy than 5-FU, with much lower exposure of 5-FU during treatment and without significant side effects. Our study establishes a GLUT-targeting theranostic incorporating a disulfide linker between the targeting module and cytotoxic payload as a potential antitumor therapy.
A New Strategy for the Solid-Phase Synthesis of 5'-Thiolated Oligodeoxynucleotides
Kuijpers, Will H. A.,Boeckel, Constant A. A. van
, p. 10931 - 10944 (2007/10/02)
A novel procedure is described for the introduction of a masked thiol function at the 5'-terminus of oligodeoxynucleotides.An acetyl-protected thiol linker phosphoramidite has been prepared which can be coupled efficiently to fully protected oligonucleoti
