31499-54-4Relevant articles and documents
Alkene–Azide 1,3-Dipolar Cycloaddition as a Trigger for Ultrashort Peptide Hydrogel Dissolution
Dadhwal, Sumit,Fairhall, Jessica M.,Goswami, Shailesh K.,Hook, Sarah,Gamble, Allan B.
, p. 1143 - 1150 (2019)
An alkene–azide 1,3-dipolar cycloaddition between trans-cyclooctene (TCO) and an azide-capped hydrogel that promotes rapid gel dissolution is reported. Using an ultrashort aryl azide-capped peptide hydrogel (PhePhe), we have demonstrated proof-of-concept where upon reaction with TCO, the hydrogel undergoes a gel–sol transition via 1,2,3-triazoline degradation and 1,6-self-immolation of the generated aniline. The potential application of this as a general trigger in sustained drug delivery is demonstrated through release of encapsulated cargo (doxorubicin). Administration of TCO resulted in 87 % of the cargo being released in 10 h, compared to 13–14 % in the control gels. This is the first example of a potential bioorthogonal-triggered hydrogel dissolution using a traditional click-type reaction. This type of stimulus could be extended to other aryl azide-capped hydrogels.
Molecular isomerization triggered by H2S to an NIR accessible first direct visualization of Ca2+-dependent production in living HeLa cells
Wen, Ying,Huo, Fangjun,Wang, Junping,Yin, Caixia
, p. 6855 - 6860 (2019)
Few studies determined the role of intracellular labile Ca2+ in H2S homeostasis. Undoubtedly, fluorescent probes are powerful tools for exploring the question because of their unique advantages: non-destruction, visualization, and mu
Synthesis and antitumor activity of 1-substituted 1,2,3-triazole-mollugin derivatives
Hu, Jiang-Miao,Li, Hong-Mei,Liu, Shou-Jin,Luo, Han,Lv, Yong-Feng,Zhang, Hong
, (2021/06/11)
A new series of mollugin-1,2,3-triazole derivatives were synthesized using a copper(I)-catalyzed Huisgen 1,3-dipolar cycloaddition reaction of corresponding O-propargylated mollugin with aryl azides. All the compounds were evaluated for their cytotoxicity on five human cancer cell lines (HL-60, A549, SMMC-7721, SW480, and MCF-7) using MTS assays. Among the synthesized series, most of them showed cytotoxicity and most of all, compounds 14 and 17 exhibited significant cytotoxicity of all five cancer cell lines.
SELECTIVE DRUG RELEASE FROM INTERNALIZED CONJUGATES OF BIOLOGICALLY ACTIVE COMPOUNDS
-
Paragraph 0609-0610, (2021/04/01)
The invention relates to conjugates of biologically active compounds, wherein such a conjugate is comprised of a sequence of amino acids containing a tripeptide that confers selective cleavage by tumor tissue homogenate for release of free drug and/or imp
Small Molecule Control of Morpholino Antisense Oligonucleotide Function through Staudinger Reduction
Chen, James K.,Darrah, Kristie,Deiters, Alexander,Lukasak, Bradley,Tsang, Michael,Wesalo, Joshua
supporting information, p. 18665 - 18671 (2021/11/16)
Conditionally activated, caged morpholino antisense agents (cMOs) are tools that enable the temporal and spatial investigation of gene expression, regulation, and function during embryonic development. Cyclic MOs are conformationally gated oligonucleotide analogs that do not block gene expression until they are linearized through the application of an external trigger, such as light or enzyme activity. Here, we describe the first examples of small molecule-responsive cMOs, which undergo rapid and efficient decaging via a Staudinger reduction. This is enabled by a highly flexible linker design that offers opportunities for the installation of chemically activated, self-immolative motifs. We synthesized cyclic cMOs against two distinct, developmentally relevant genes and demonstrated phosphine-triggered knockdown of gene expression in zebrafish embryos. This represents the first report of a small molecule-triggered antisense agent for gene knockdown, adding another bioorthogonal entry to the growing arsenal of gene knockdown tools.
