<i>Fluorescent Silica Nanoparticles</i>

Mader, Heike Sabine; Li, Xiaohua; Saleh, Sayed M.; Link, Martin; Kele, Péter; Wolfbeis, Otto S.

doi:10.1196/annals.1430.053

Cited by 65 publications

(51 citation statements)

References 27 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…The blue phenoxazinium azide 1 and the red coumarin azide 2 represent examples of two structurally different but novel types of fluorophores (35). A common feature of both dyes is the instability under strongly basic conditions that are typically used for DNA workup.…”

Section: Discussionmentioning

confidence: 99%

Comparison of a Nucleosidic vs Non-Nucleosidic Postsynthetic “Click” Modification of DNA with Base-Labile Fluorescent Probes

et al. 2009

Self Cite

View full text Add to dashboard Cite

The azides 1 and 2 bearing a phenoxazinium and a coumarin fluorophore, respectively, were applied in postsynthetic "click"-type bioconjugation and coupled to oligonucleotides modified with alkyne groups using two alternative approaches: (i) as a nucleotide modification at the 2′-position of uridine and (ii) as a nucleotide substitution using (S)-(-)-3-amino-1,2-propanediol as an acyclic linker between the phosphodiester bridges. The corresponding alkynylated phosporamidites 3 and 6 were used as DNA building blocks for the preparation of alkyne-bearing DNA duplexes. The base pairs adjacent to the site of modification and the base opposite to it were varied in the DNA sequences. The modified duplexes were investigated by UV/vis absorption spectroscopy (including melting temperatures) and fluorescence spectroscopy in order to study the different optical properties of the two chromophores and to evaluate their potential for bioanalytical applications. The sequence-selective fluorescence quenching of phenoxazinium 1 differs only slightly and does not depend on the type of modification, meaning whether it has been attached to the 2′-position of uridine or as DNA base surrogate using the acyclic glycol linker. The 2′-chromophore-modified uridine still recognizes adenine as the counterbase, and the duplexes exhibit a sufficient thermal stability that is comparable to that of unmodified duplexes. Thus, the application of the 2′-modification site of uridine is preferred in comparison to glycol-assisted DNA base surrogates. Accordingly, the coumarin dye azide 2 was attached only to the 2′-position of uridine. The significant Stokes shift of ∼100 nm and the good quantum yields make the coumarin chromophore a powerful fluorescent label for nucleic acids.

show abstract

Section: Discussionmentioning

confidence: 99%

Comparison of a Nucleosidic vs Non-Nucleosidic Postsynthetic “Click” Modification of DNA with Base-Labile Fluorescent Probes

et al. 2009

Self Cite

View full text Add to dashboard Cite

show abstract

“…[6,20] The known synthon 4 was then used to link the maleinimido group to the azido-modified fluorophores. The reaction of 4 with the azidophenoxazines 1-3 is characterized by high yields, easy work-up, and proceeds in aqueous solvent at room temperature to give the thiol-reactive labels 5-7 shown in Figure 2.…”

Section: Synthesis Of Azido-modified Oxazinesmentioning

confidence: 99%

“…As a result, in vitro click chemistry has been used for labeling biomolecules, [2] hormones, [3] and for in-vivo tumor cell targeting [4] with either fluorophores, radiomarkers, spin labels, or nanoparticles made from gold [5] or silica. [6] The success of click chemistry is especially striking in the case of labeling glycans and glycoconjugates. [7] Site-specific labeling of proteins is of particular interest because it has several advantages over random labeling.…”

Section: Introductionmentioning

confidence: 99%

Click Chemistry Based Method for the Preparation of Maleinimide‐Type Thiol‐Reactive Labels

Link

Kleim

et al. 2010

Eur J Org Chem

Self Cite

View full text Add to dashboard Cite

Maleinimides are widely used to label proteins and to derivatize thiols. The so‐called click reaction was shown to allow the efficient introduction of the maleinimido group into azido‐modified fluorophores (benzoxazines) by reacting them with an alkyne‐modified maleinimide to yield new thiol‐reactive fluorescent labels 5–7. The reaction proceeds under mild experimental conditions and provides a new strategy with which to introduce the maleimide group, as exemplified here for fluorophores. Conceivably, it may be extended to radioactive, electro‐active, isotopic, or spin labels. Previously reported methods for the formation of such maleinimides starting from open‐ring precursors require rather harsh conditions. The new benzoxazines 5–7 are characterized by a fairly long and flexible linker between the chromophore and the maleinimide functional group, and their fluorescence can be photoexcited with diode lasers (which are preferred light sources in fluorometry). They were conjugated to: (a) the aminothiol cysteamine, (b) the peptide glutathione, and (c) to human serum albumin. The fluorescence of the phenoxazinone 5 is strongly solvatochromic, which suggests its use as a polarity‐sensitive probe.

show abstract

“…After the production of a fluorescent indicator, it is incorporated into a solid support for the preparation of an indicator material, such as silica mesoporous solids [15] or silica nanoparticles, [16] from which fluorescent sensors are prepared.…”

Section: Introductionmentioning

confidence: 99%

Detection of Contaminants of High Environmental Impact by Means of Fluorogenic Probes

García‐Calvo

Calvo-Gredilla

Ibáñez-Llorente

et al. 2016

The Chemical Record

View full text Add to dashboard Cite

This personal account describes our contribution to the design of selective fluorogenic probes for contaminants of high environmental impact. For this purpose, we have developed a new family of highly versatile fluorogenic reagents that were able to show large differences in their fluorescence in the presence of selected analytes. They were used in the preparation of fluorogenic probes for the detection of contaminants of high environmental impact which currently have no good solutions: phosphorylating agents, such as chemical weapons; methyl mercury(II); the cyanide anion; amino-acid metabolites, such as doping substances; and biogenic amine mimics, such as drugs of abuse and recreational drugs. The development of new materials for specific sensing was achieved by anchoring selected probes to silica nanomaterials, suitable for the selective detection of organic analytes in water for immediate application to toxicological or environmental purposes.

show abstract

Fluorescent Silica Nanoparticles

Cited by 65 publications

References 27 publications

Comparison of a Nucleosidic vs Non-Nucleosidic Postsynthetic “Click” Modification of DNA with Base-Labile Fluorescent Probes

Comparison of a Nucleosidic vs Non-Nucleosidic Postsynthetic “Click” Modification of DNA with Base-Labile Fluorescent Probes

Click Chemistry Based Method for the Preparation of Maleinimide‐Type Thiol‐Reactive Labels

Detection of Contaminants of High Environmental Impact by Means of Fluorogenic Probes

Contact Info

Product

Resources

About