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55865

Sigma-Aldrich

Digoxigenin NHS-ester

≥80% (HPLC)

Synonym(s):

ε-(Digoxigenin-3-0-acetamido)caproic acid N-hydroxysuccinimide ester, DIG NHS

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About This Item

Empirical Formula (Hill Notation):
C35H50N2O10
CAS Number:
Molecular Weight:
658.78
MDL number:
UNSPSC Code:
12352108
PubChem Substance ID:
NACRES:
NA.25

Assay

≥80% (HPLC)

form

solid

shipped in

wet ice

storage temp.

−20°C

SMILES string

[H][C@]12CC[C@]3([H])[C@]([H])(C[C@@H](O)[C@]4(C)[C@H](CC[C@]34O)C5=CC(=O)OC5)[C@@]1(C)CC[C@@H](C2)OCC(=O)NCCCCCC(=O)ON6C(=O)CCC6=O

InChI

1S/C35H50N2O10/c1-33-13-11-23(45-20-28(39)36-15-5-3-4-6-31(42)47-37-29(40)9-10-30(37)41)17-22(33)7-8-25-26(33)18-27(38)34(2)24(12-14-35(25,34)44)21-16-32(43)46-19-21/h16,22-27,38,44H,3-15,17-20H2,1-2H3,(H,36,39)/t22-,23+,24-,25-,26+,27-,33+,34+,35+/m1/s1

InChI key

KHNDABJZSPPYLE-FUGFVFQCSA-N

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Application

Digoxigenin NHS-ester has been used in the preparation of streptavidin-digoxigenin conjugate and digoxin-recombinant Ara h1 (peanut component) conjugate for enzyme-linked immunosorbent assay (ELISA) analysis.

Biochem/physiol Actions

Digoxigenin NHS-ester is an activated ester that reacts with amino groups under mild conditions, attaching the digoxigenin moiety to proteins or 5′-amino substituted oligonucleotides Digoxigenin labeling is used to immuno-tag molecules for detection using anti-digoxigenin antibodies with high affinities and specificity.
Digoxigenin, an aglycon, is a pharmacologically active plant toxin. It is less potent than digoxin. It is used in lower doses to treat heart conditions. Digoxigenin is usually conjugated to another payload which reduces its remaining activity or accessibility to tissues. Since digoxigenin is permanently bound and entirely covered by the capture modules, it cannot be used as an active entity.

Pictograms

Skull and crossbonesHealth hazard

Signal Word

Danger

Hazard Statements

Hazard Classifications

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

Storage Class Code

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

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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A. Decarie et al.
Biochemica, 20-20 (1996)
Demonstration of a specific transport protein for cardiac glycosides in bovine blood.
R Antolovic et al.
Annals of the New York Academy of Sciences, 834, 618-620 (1997-12-24)
B Ahlemeyer et al.
European journal of biochemistry, 205(1), 269-275 (1992-04-01)
Digital-imaging fluorescence microscopy with fura-2 allows the determination of intracellular calcium concentration ([Ca2+]i) in single cells. At a cell density of 10(5) cells/petri dish 44% of the chick embryo heart cells had a high [Ca2+]i of 99.4 +/- 7.1 nM
Isotype-specific agglutination-PCR (ISAP): A sensitive and multiplex method for measuring allergen-specific IgE.
Cheng-Ting Tsai et al.
The Journal of allergy and clinical immunology, 141(5), 1901-1904 (2017-12-19)
R Antolovic et al.
European journal of biochemistry, 227(1-2), 61-67 (1995-01-15)
Na+/K(+)-ATPase from pig kidney is inactivated by protein-reactive N-hydroxysuccinimidyl derivatives of digoxigenin. Like digoxigenin, its protein-reactive derivatives N-hydroxysuccinimidyl digoxigenin-3-methylcarbonyl-epsilon-aminocaproate (HDMA), 3-amino-3-deoxydigoxigenin hemisuccinimide succinimidyl ester (ADHS), 3-iodoacetylamino-3-deoxydigoxigenin (IAD) and digoxigenin-3-O-succinyl-[2-(N-maleimido)]ethylamide (DSME) inhibited the sodium pump in the presence of Na+, Mg2+

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