Reactions of 7-aminocoumarins leading to alkylidenebenzopyrans

Kirpichenok, M. A.; Gorozhankin, S. K.; Грандберг, И. И.

doi:10.1007/bf00475593

Cited by 5 publications

(27 citation statements)

References 6 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The photophysical characterization of the dicyanocoumarincaged model compounds (1)(2)(3)(4)(5)(6)w as carriedo ut in ad egassed 1:1( v/v) mixture of Tris buffer (20 mm,p H7.5) and MeCN. The UV/Vis absorption and emission spectra of the compounds are shown in Figure 1, and their photophysical properties are reported in Table 1.…”

Section: Absorption and Emission Properties Of Dicyanocoumarin Derivamentioning

confidence: 99%

“…Table 1. Photophysical parameters for dicyanocoumarin-caged model compounds (1)(2)(3)(4)(5)(6)a nd for the corresponding photoreleasedc oumarina lcohol derivatives (12 and 16). [a] Compound [a] Absorption Emission l max [nm] [b] e(l max ) [mM À1 cm À1 ] [c] l Em [nm] [d] Dn…”

Section: Absorption and Emission Properties Of Dicyanocoumarin Derivamentioning

confidence: 99%

“…Recently, the modification of the carbonyl group of the lactone in the N , N ‐diethylamino(coumarin 4‐yl)methyl platform has been proved to be a valuable way to further shift the wavelength of maximum absorption, which can be exploited to trigger uncaging with blue, cyan, or green light . Indeed, dicyanomethylenecoumarin derivatives, which are obtained by conjugating two nitrile groups through position 2 of the coumarin moiety, are particularly attractive as they exhibit a maximum absorption around 500 nm in the 7‐diethylamino series (487 nm in a coumarin derivative containing a benzyloxymethyl group at position 4 described by Jullien and co‐workers and 475 nm when this position was occupied by a methyl as described by Granberg and colleagues). Uncaging of dicyanocoumarin‐caged cyclic morpholino oligonucleotides has been exploited in the context of gene silencing by Deiters’ and Chen's group, and very recently we have described the synthesis of a dicyanocoumarin‐caged RGD peptide for photocontrolled‐targeted drug delivery .…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Sequential Uncaging with Green Light can be Achieved by Fine‐Tuning the Structure of a Dicyanocoumarin Chromophore

et al. 2017

View full text Add to dashboard Cite

We report the synthesis and photochemical properties of a series of dicyanocoumarinylmethyl (DEAdcCM)‐ and dicyanocoumarinylethyl (DEAdcCE)‐based photocages of carboxylic acids and amines with absorption maximum around 500 nm. Photolysis studies with green light have demonstrated that the structure of the coumarin chromophore as well as the nature of the leaving group and the type of bond to be photocleaved (ester or carbamate) have a strong influence on the rate and efficiency of the uncaging process. These experimental observations were also supported by DFT calculations. Such differences in deprotection kinetics have been exploited to sequentially photolyze two dicyanocoumarin‐caged model compounds (e.g., benzoic acid and ethylamine), and open the way to increasing the number of functional levels that can be addressed with light in a single system, particularly when combining dicyanocoumarin caging groups with other photocleavable protecting groups, which remain intact under green light irradiation.

show abstract

Section: Absorption and Emission Properties Of Dicyanocoumarin Derivamentioning

confidence: 99%

Section: Absorption and Emission Properties Of Dicyanocoumarin Derivamentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Sequential Uncaging with Green Light can be Achieved by Fine‐Tuning the Structure of a Dicyanocoumarin Chromophore

et al. 2017

View full text Add to dashboard Cite

show abstract

“…1D NMR (1H, 13 C and 19 F), MS and selected 2D NMR spectra. This material is available free of charge via the Internet at http://pubs.acs.org.…”

Section: Supporting Informationmentioning

confidence: 99%

“…8,13 This modification has also been incorporated in coumarin-caged cyclic morpholino oligonucleotides by Deiters, Chen and collaborators for sequential gene silencing, 14 as well as by us in a caged cyclic RGD peptide for applications in photocontrolled targeted therapies.…”

Section: Introductionmentioning

confidence: 99%

Development of Green/Red-Absorbing Chromophores Based on a Coumarin Scaffold That Are Useful as Caging Groups

et al. 2017

View full text Add to dashboard Cite

show abstract

Visible-to-NIR-Light Activated Release: From Small Molecules to Nanomaterials

et al. 2020

View full text Add to dashboard Cite

Photoactivatable (alternatively, photoremovable, photoreleasable, or photocleavable) protecting groups (PPGs), also known as caged or photocaged compounds, are used to enable non-invasive spatiotemporal photochemical control over the release of species of interest. Recent years have seen the development of PPGs activatable by biologically and chemically benign visible and near-infrared (NIR) light. These long-wavelength-absorbing moieties expand the applicability of this powerful method and its accessibility to non-specialist users. This review comprehensively covers organic and transition metal-containing photoactivatable compounds (complexes) that absorb in the visible- and NIR-range to release various leaving groups and gasotransmitters (carbon monoxide, nitric oxide, and hydrogen sulfide). The text also covers visible- and NIR-light-induced photosensitized release using molecular sensitizers, quantum dots, and upconversion and second-harmonic nanoparticles, as well as release via photodynamic (photooxygenation by singlet oxygen) and photothermal effects. Release from photoactivatable polymers, micelles, vesicles, and photoswitches, along with the related emerging field of photopharmacology, is discussed at the end of the review.

show abstract

Reactions of 7-aminocoumarins leading to alkylidenebenzopyrans

Cited by 5 publications

References 6 publications

Sequential Uncaging with Green Light can be Achieved by Fine‐Tuning the Structure of a Dicyanocoumarin Chromophore

Sequential Uncaging with Green Light can be Achieved by Fine‐Tuning the Structure of a Dicyanocoumarin Chromophore

Development of Green/Red-Absorbing Chromophores Based on a Coumarin Scaffold That Are Useful as Caging Groups

Visible-to-NIR-Light Activated Release: From Small Molecules to Nanomaterials

Contact Info

Product

Resources

About