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07985

Sigma-Aldrich

6-Aminofluorescein

BioReagent, suitable for fluorescence, ~95% (HPLC)

Synonym(s):

Fluoresceinamine isomer II

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About This Item

Empirical Formula (Hill Notation):
C20H13NO5
CAS Number:
51649-83-3
Molecular Weight:
347.32
Beilstein:
51708
EC Number:
257-334-7
MDL number:
MFCD00005051
UNSPSC Code:
12171500
PubChem Substance ID:
329748535
NACRES:
NA.32

product line

BioReagent

Assay

~95% (HPLC)

form

powder

impurities

≤5% 5-aminofluorescein

mp

285 °C (dec.) (lit.)

solubility

DMSO: soluble
acetone: soluble
methanol: soluble

fluorescence

λex 490 nm; λem 520 nm in 0.1 M Tris pH 9.0

suitability

suitable for fluorescence

SMILES string

Nc1ccc2C(=O)OC3(c4ccc(O)cc4Oc5cc(O)ccc35)c2c1

InChI

1S/C20H13NO5/c21-10-1-4-13-16(7-10)20(26-19(13)24)14-5-2-11(22)8-17(14)25-18-9-12(23)3-6-15(18)20/h1-9,22-23H,21H2

InChI key

YOAWSYSKQHLFPM-UHFFFAOYSA-N

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Application

6-Aminofluorescein has been demonstrated to be useful fluorescent labeling reagent for fullerene-based liposome nanostructures termed ‘buckysomes′. 6-aminofluorescein dissolved in 0.1 N NaOH can be quantified from a maximum absorbance at 490 nm. Decarboxylated 6-aminofluorescein dissolved 6 N HCl (prepare by constant boiling at 110° C for 24 h) can be quantified from a maximum absorbance at 454 nm. Aldehyde groups are formed by oxidateive damage to proteins, which can be detected by conjugation to decarboxylated 6-aminofluorescein.

Other Notes

Note: Do not confuse with fluorescamine.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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I Climent et al.
Analytical biochemistry, 182(2), 226-232 (1989-11-01)
Oxidative modification of proteins is implicated in a number of physiologic and pathologic processes. Metal-catalyzed oxidative modification usually causes inactivation of enzymes and the appearance of carbonyl groups in amino acid side chains of the protein. We describe use of
K C Ingham et al.
Biochimica et biophysica acta, 670(2), 181-189 (1981-09-29)
A method for covalent attachment of a fluorescent molecule to the carbohydrate moieties of glycoproteins is described. The glycoproteins were oxidized with periodate under mild conditions selective for sialic acid (Van Lenten, L. and Ashwell, G. (1971) J. Biol. Chem.
Miju Kim et al.
ACS nano, 9(8), 8269-8278 (2015-07-15)
Polyelectrolyte microcapsules represent versatile stimuli-responsive structures that enable the encapsulation, protection, and release of active agents. Their conventional preparation methods, however, tend to be time-consuming, yield low encapsulation efficiency, and seldom allow for the dual incorporation of hydrophilic and hydrophobic
Thapakorn Tree-Udom et al.
ACS applied materials & interfaces, 7(43), 23993-24000 (2015-10-16)
Although computer simulation and cell culture experiments have shown that elongated spherical particles can be taken up into cells more efficiently than spherical particles, experimental investigation on effects of these different shapes over the particle-membrane association has never been reported.
Thomas Tigges et al.
Small (Weinheim an der Bergstrasse, Germany), 11(35), 4540-4548 (2015-06-06)
Patchy particles are next generation colloidal building blocks for self-assembly and find further use as (bio) sensors. Progress in this direction crucially depends on developing straightforward preparation pathways able to provide patchy particles with highest uniformity and integrating precise, orthogonal

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