Expedited Development through Parallel Reaction Screening: Application to PTC-Mediated Knoevenagel Condensation

Corona, J.; Davis, Roman; Kedia, Sandeep B.; Mitchell, Mark B.

doi:10.1021/op100026u

Cited by 12 publications

(5 citation statements)

References 5 publications

(7 reference statements)

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“…Chemical compounds were sourced as in Supplementary file 1B . Pro-INDY and GSK-626616 were synthesized as previously described ( Corona et al, 2010 ; Ogawa et al, 2010 ).…”

Section: Methodsmentioning

confidence: 99%

The kinase DYRK1A reciprocally regulates the differentiation of Th17 and regulatory T cells

Khor

Gagnon

Goel

et al. 2015

eLife

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The balance between Th17 and T regulatory (Treg) cells critically modulates immune homeostasis, with an inadequate Treg response contributing to inflammatory disease. Using an unbiased chemical biology approach, we identified a novel role for the dual specificity tyrosine-phosphorylation-regulated kinase DYRK1A in regulating this balance. Inhibition of DYRK1A enhances Treg differentiation and impairs Th17 differentiation without affecting known pathways of Treg/Th17 differentiation. Thus, DYRK1A represents a novel mechanistic node at the branch point between commitment to either Treg or Th17 lineages. Importantly, both Treg cells generated using the DYRK1A inhibitor harmine and direct administration of harmine itself potently attenuate inflammation in multiple experimental models of systemic autoimmunity and mucosal inflammation. Our results identify DYRK1A as a physiologically relevant regulator of Treg cell differentiation and suggest a broader role for other DYRK family members in immune homeostasis. These results are discussed in the context of human diseases associated with dysregulated DYRK activity.DOI: http://dx.doi.org/10.7554/eLife.05920.001

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“…Chemical compounds were sourced as in Supplementary file 1B . Pro-INDY and GSK-626616 were synthesized as previously described ( Corona et al, 2010 ; Ogawa et al, 2010 ).…”

Section: Methodsmentioning

confidence: 99%

The kinase DYRK1A reciprocally regulates the differentiation of Th17 and regulatory T cells

Khor

Gagnon

Goel

et al. 2015

eLife

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“…When GO was incorporated into the DEX mixture solution, no sol–gel transition was observed, although the G ′ (<20 Pa) was slightly higher than G ″, which indicated that the KC reaction was hampered owing to the existence of GO. It has been demonstrated that the KC reaction in aqueous solution could be greatly affected by the pH. , Herein, in order to explain this finding, benzaldehyde and cyanoacetate group-modified methoxy poly(ethylene glycol)s (termed as mPEG-BA and mPEG-CA, respectively) were synthesized as model compounds (Figure S5) and the UV–vis absorbance spectra of 5% mixed polymer solution at pH 5.6 were measured (Figure S6a). It was found that when the mixture reacted at pH 5.6, the absorbance of the benzaldehyde group in mPEG-BA at 256 nm ( A 1 ) and the absorbance at 305 nm ( A 2 ) corresponding to the newly formed CC double bond showed negligible changes after 30 min, indicating that the reaction was significantly hampered under acidic conditions.…”

Section: Resultsmentioning

confidence: 99%

Histidine-Triggered GO Hybrid Hydrogels for Microfluidic 3D Printing

Ding

Shang

et al. 2022

ACS Nano

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Graphene oxide (GO) hydrogels have provided tremendous opportunities in designing and fabricating complex constructs for diverse applications, while their 3D printing without photocuring is still a challenging task due to their low viscosity, uncontrollable gelation, and low interfacial tension. Here, we report a histidine-assisted printing strategy to prepare GO hybrid hydrogels through the microfluidic 3D printing technique. We found that the GO additive could significantly hamper the Knoevenagel condensation (KC) reaction between benzaldehyde and cyanoacetate group-functionalized polymers to form a hydrogel, while these GO mixed solutions were rapidly solidified into a hydrogel when histidine was added. This fascinating phenomenon enabled us to prepare low-viscosity GO mixed polymer solutions as printable inks and generate hydrogel microfibers in histidine solutions. The hydrogel fibers could support cell survival and be further constructed into complex 3D structures through microfluidic 3D printing techniques. Moreover, due to the addition of GO, the microfibers exhibited excellent electrical conductivity and could sense the motion changes and convert these stimuli as electrical resistance signals. This strategy adds an option for the design and application of 3D printable aqueous GO inks in many fields.

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“…GSK workers sought to optimize the PTC-mediated aldol condensation between an aromatic aldehyde and thiazalone 144 to generate aldol adducts 145 and 146 , which upon acidification yielded olefin 147 (Scheme ). They employed a D-optimal design to probe the impact of the qualitative factors of solvent (2-BuOH, toluene, 2-MeTHF, MIBK, i- PrOAc), Lewis acid (none, Sc(OTf) 3 , Y(OTf) 3 , Yb(OTf) 3 ), base (50% NaOH, 2 N NaOH (with and without brine), 50% K 2 CO 3 , 25% KHCO 3 ), and phase-transfer agent (Aliquat 128, ( n- Bu) 4 NHSO 4 , BnEt 3 NCl).…”

Section: Review Of Selected Doe Manuscripts Published In Oprd From 20...mentioning

confidence: 99%

Design of Experiments (DoE) and Process Optimization. A Review of Recent Publications

Weissman

Anderson²

2014

Org. Process Res. Dev.

400

268

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Expedited Development through Parallel Reaction Screening: Application to PTC-Mediated Knoevenagel Condensation

Cited by 12 publications

References 5 publications

The kinase DYRK1A reciprocally regulates the differentiation of Th17 and regulatory T cells

The kinase DYRK1A reciprocally regulates the differentiation of Th17 and regulatory T cells

Histidine-Triggered GO Hybrid Hydrogels for Microfluidic 3D Printing

Design of Experiments (DoE) and Process Optimization. A Review of Recent Publications

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