A tunable synthesis of indigoids: targeting indirubin through temperature

Shriver, James A.; Kaller, Kaylie S.; Kinsey, Ally L.; Wang, Katelyn R.; Sterrenberg, Summer R.; Vors, Madison K. Van; Cheek, Joshua T.; Horner, John S.

doi:10.1039/d2ra00400c

Cited by 6 publications

(2 citation statements)

References 29 publications

(71 reference statements)

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“…The colorful indigo derivatives exhibited maximum absorbance at 570–650 nm, while indirubin derivatives showed an absorption band between 510 and 580 nm, depending on the identity and location of the substituents. These results are well consistent with previously reported spectroscopic parameters [ [45] , [46] , [47] ].…”

Section: Resultssupporting

confidence: 94%

Enzymatic synthesis of indigo derivatives by tuning P450 BM3 peroxygenases

Sun

Liu

et al. 2023

Synthetic and Systems Biotechnology

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Section: Resultssupporting

confidence: 94%

Enzymatic synthesis of indigo derivatives by tuning P450 BM3 peroxygenases

Sun

Liu

et al. 2023

Synthetic and Systems Biotechnology

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“…Over the past decade, there has been a significant amount of attention given to the pharmacological activities of these compounds in relation to their anticancer properties, especially indirubin which has demonstrated significant antileukemia activity [8,9]. The anticancer properties of indirubin and its analogues are mainly manifested by inhibiting the proliferation of cancer cells, promoting cell apoptosis and inhibiting the migration and invasion of tumor cells [10][11][12][13].…”

Section: Introductionmentioning

confidence: 99%

STK214947, a novel indole alkaloids, inhibits HeLa and SK-HEP-1 cells survival and EMT process by bloking the Notch3 and Akt signals

Xu,

Yuan,

Liu

et al. 2024

Anti-Cancer Drugs

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Apoptosis and epithelial-to-mesenchymal transition (EMT) are closely associated with tumor survival and metastasis. These are the basic events in tumor occurrence and progression. STK214947 is an indole alkaloid with a skeleton that is similar to that of indirubin. Indole alkaloids have attracted considerable attention because of their antitumor activity. However, the relationship between STK214947 and these basic events remains unknown. In this study, the effects of STK214947 on inducing apoptosis and reversing the EMT process in tumor cells were confirmed. Mild concentrations of STK214947 inhibited tumor cell migration by reversing EMT and significantly regulated the expression of EMT-related proteins, including Notch3, E-cadherin, N-cadherin and vimentin. In addition, STK214947 in high concentration could induce apoptosis by down-regulating Notch3, p-Akt/Akt, and NF-κB, and upregulating Caspase 3. These findings support the further development of STK214947 as a potential antitumor small molecule that targets Notch3 and Akt signal transduction in cancer.

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A Blueprint for Transforming Indigos to Photoresponsive Molecular Tools

Huang

Hecht

2023

Chemistry A European J

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Indigo, one of the most ancient and abundant dyes in human history, has recently emerged as a potential functional motif due to its intriguing photochemical properties. This review aims to provide insights into both the preparation of these molecules and their utilization in molecular systems. First, the synthesis of the indigo core as well as available methods to derivatize indigo are described to outline synthetic strategies to build the desired molecular structures. Then, the photochemical behavior of indigos is discussed, with particular focus on E-Z photoisomerization and photoinduced electron transfer. Connections between the molecular structures and their photochemical properties are highlighted and serve as guiding principles for designing indigos to be applied as photoresponsive tools.

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A tunable synthesis of indigoids: targeting indirubin through temperature

Abstract: Selectivity of indigoid synthesis shifts from indigo to indirubin at reduced temperatures across a range of substrates.

Cited by 6 publications

References 29 publications

Enzymatic synthesis of indigo derivatives by tuning P450 BM3 peroxygenases

Enzymatic synthesis of indigo derivatives by tuning P450 BM3 peroxygenases

STK214947, a novel indole alkaloids, inhibits HeLa and SK-HEP-1 cells survival and EMT process by bloking the Notch3 and Akt signals

A Blueprint for Transforming Indigos to Photoresponsive Molecular Tools

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