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T511293

Sigma-Aldrich

(2′S)-2′-Deoxy-2′-fluoro-5-ethynyluridine, (F-ara-EdU)

AldrichCPR

Synonyme(s) :

1-(2-Deoxy-2-fluoro-β-D-arabinofuranosyl)-5-ethynyl-2,4(1H,3H)-pyrimidinedione

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About This Item

Formule empirique (notation de Hill):
C11H11FN2O5
Numéro CAS:
95740-26-4
Poids moléculaire :
270.21
Numéro MDL:
MFCD22417248
Code UNSPSC :
12352200
ID de substance PubChem :
329826809

Niveau de qualité

100

Capacité de réaction

reaction type: click chemistry

Chaîne SMILES 

OC[C@H]1O[C@H]([C@@H](F)[C@@H]1O)N2C=C(C#C)C(=O)NC2=O

InChI

1S/C11H11FN2O5/c1-2-5-3-14(11(18)13-9(5)17)10-7(12)8(16)6(4-15)19-10/h1,3,6-8,10,15-16H,4H2,(H,13,17,18)/t6-,7+,8-,10-/m1/s1

Clé InChI

YEEGMPUOCRQFRV-IBCQBUCCSA-N

Application

A probe for DNA synthesis in vivo that is less toxic than both EdU and BrdU. Ideally suited for metabolic DNA labeling when prolonged cell survival and undisturbed cell cycle progression are required.

Autres remarques

Please note that Sigma-Aldrich provides this product to early discovery researchers as part of a collection of unique chemicals. Sigma-Aldrich does not collect analytical data for this product. Buyer assumes responsibility to confirm product identity and/or purity. All sales are final.

NOTWITHSTANDING ANY CONTRARY PROVISION CONTAINED IN SIGMA-ALDRICH′S STANDARD TERMS AND CONDITIONS OF SALE OR AN AGREEMENT BETWEEN SIGMA-ALDRICH AND BUYER, SIGMA-ALDRICH SELLS THIS PRODUCT "AS-IS" AND MAKES NO REPRESENTATION OR WARRANTY WHATSOEVER WITH RESPECT TO THIS PRODUCT, INCLUDING ANY (A) WARRANTY OF MERCHANTABILITY; (B) WARRANTY OF FITNESS FOR A PARTICULAR PURPOSE; OR (C) WARRANTY AGAINST INFRINGEMENT OF INTELLECTUAL PROPERTY RIGHTS OF A THIRD PARTY; WHETHER ARISING BY LAW, COURSE OF DEALING, COURSE OF PERFORMANCE, USAGE OF TRADE OR OTHERWISE.

Pictogrammes

Skull and crossbones
GHS06

Mention d'avertissement

Danger

Mentions de danger

H300 + H310 + H330

Classification des risques

Acute Tox. 2 Dermal - Acute Tox. 2 Inhalation - Acute Tox. 2 Oral

Code de la classe de stockage

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

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Lot/Batch Number

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Consulter la Bibliothèque de documents

Anne B Neef et al.
Proceedings of the National Academy of Sciences of the United States of America, 108(51), 20404-20409 (2011-12-07)
Commonly used metabolic labels for DNA, including 5-ethynyl-2'-deoxyuridine (EdU) and BrdU, are toxic antimetabolites that cause DNA instability, necrosis, and cell-cycle arrest. In addition to perturbing biological function, these properties can prevent metabolic labeling studies where subsequent tissue survival is
Florence D D'Orazi et al.
The Journal of comparative neurology, 528(17), 2816-2830 (2020-04-29)
A major challenge in regenerative medicine is replacing cells lost through injury or disease. While significant progress has been made, much remains unknown about the accuracy of native regenerative programs in cell replacement. Here, we capitalized on the regenerative capacity
Sameer S Chopra et al.
Cell systems, 10(1), 66-81 (2019-12-10)
Frequent mutation of PI3K/AKT/mTOR signaling pathway genes in human cancers has stimulated large investments in targeted drugs but clinical successes are rare. As a result, many cancers with high PI3K pathway activity, such as triple-negative breast cancer (TNBC), are treated

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