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Synthesis of a fluorescent xanthenic derivative useful for labeling amine residues

Synthesis of a fluorescent xanthenic derivative useful for labeling amine residues
Synthesis of a fluorescent xanthenic derivative useful for labeling amine residues
The 2,5-dioxopyrrolidin-1-yl-4-(3-hydroxy-6-oxo-6H-xanthen-9-yl)-3-methylbenzoate has been synthesized as an amine-reactive derivative able to yield stable covalently labeled biopolymers. The new derivative has been used to label polyribocytidilic acid (5'), poly(C), amine residues. TG-II-poly(C) exhibits monoexponential decay at the physiological pH range. In addition, both steady-state fluorescence intensity and fluorescence decay are also sensitive to solution pH. The large decrease in steady-state fluorescence upon hybridization allows it to be used as a nucleic acid probe in a homogeneous assay format. In summary, we report an efficient synthesis to obtain labeled RNA from commercially available materials in excellent yields.
1520-6106
10082-10085
Crovetto, Luis
45d4cd97-3fe5-4498-a861-bc06492eb09d
Rios, Ramon
609bedf2-e886-4d62-a676-a32b6f8c1441
Alvarez-Pez, Jose M.
6970f24c-ecb5-418b-9847-f7a6be1d91f2
Paredes, Jose M.
56f39307-ce21-4a3c-9ec5-61dfc850ab43
Lozano-Velez, Patricia
36ebc008-4edd-4d96-8c7f-dff9b8bc9e0b
del Valle, Carmen
88e4fadf-3726-48bd-a65f-e06e3b005d04
Talavera, Eva M.
e0319787-e90f-48dd-b89f-5c631bbe15a1
Crovetto, Luis
45d4cd97-3fe5-4498-a861-bc06492eb09d
Rios, Ramon
609bedf2-e886-4d62-a676-a32b6f8c1441
Alvarez-Pez, Jose M.
6970f24c-ecb5-418b-9847-f7a6be1d91f2
Paredes, Jose M.
56f39307-ce21-4a3c-9ec5-61dfc850ab43
Lozano-Velez, Patricia
36ebc008-4edd-4d96-8c7f-dff9b8bc9e0b
del Valle, Carmen
88e4fadf-3726-48bd-a65f-e06e3b005d04
Talavera, Eva M.
e0319787-e90f-48dd-b89f-5c631bbe15a1

Crovetto, Luis, Rios, Ramon, Alvarez-Pez, Jose M., Paredes, Jose M., Lozano-Velez, Patricia, del Valle, Carmen and Talavera, Eva M. (2008) Synthesis of a fluorescent xanthenic derivative useful for labeling amine residues. The Journal of Physical Chemistry B, 112 (33), 10082-10085. (doi:10.1021/jp803970c). (PMID:18637685)

Record type: Article

Abstract

The 2,5-dioxopyrrolidin-1-yl-4-(3-hydroxy-6-oxo-6H-xanthen-9-yl)-3-methylbenzoate has been synthesized as an amine-reactive derivative able to yield stable covalently labeled biopolymers. The new derivative has been used to label polyribocytidilic acid (5'), poly(C), amine residues. TG-II-poly(C) exhibits monoexponential decay at the physiological pH range. In addition, both steady-state fluorescence intensity and fluorescence decay are also sensitive to solution pH. The large decrease in steady-state fluorescence upon hybridization allows it to be used as a nucleic acid probe in a homogeneous assay format. In summary, we report an efficient synthesis to obtain labeled RNA from commercially available materials in excellent yields.

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More information

e-pub ahead of print date: 19 July 2008
Published date: 2008
Organisations: Chemistry

Identifiers

Local EPrints ID: 347772
URI: http://eprints.soton.ac.uk/id/eprint/347772
ISSN: 1520-6106
PURE UUID: 5615ccd4-5278-4a40-a774-d8df76923290
ORCID for Ramon Rios: ORCID iD orcid.org/0000-0002-3843-8521

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Date deposited: 30 Jan 2013 09:42
Last modified: 03 Dec 2019 01:38

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Contributors

Author: Luis Crovetto
Author: Ramon Rios ORCID iD
Author: Jose M. Alvarez-Pez
Author: Jose M. Paredes
Author: Patricia Lozano-Velez
Author: Carmen del Valle
Author: Eva M. Talavera

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