T511293
(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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A propos de cet article
Formule empirique (notation de Hill) :
C11H11FN2O5
Numéro CAS:
Poids moléculaire :
270.21
UNSPSC Code:
12352200
PubChem Substance ID:
MDL number:
NACRES:
NA.21
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reaction suitability
reaction type: click chemistry
SMILES string
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
InChI key
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.
Other Notes
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.
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.
signalword
Danger
hcodes
Hazard Classifications
Acute Tox. 2 Dermal - Acute Tox. 2 Inhalation - Acute Tox. 2 Oral
Classe de stockage
6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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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
Lingluo Chu et al.
Molecular cell, 79(6), 902-916 (2020-08-10)
A long-standing conundrum is how mitotic chromosomes can compact, as required for clean separation to daughter cells, while maintaining close parallel alignment of sister chromatids. Pursuit of this question, by high resolution 3D fluorescence imaging of living and fixed mammalian