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Merck

55865

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:
129273-26-3
Molecular Weight:
658.78
NACRES:
NA.25
PubChem Substance ID:
57651557
UNSPSC Code:
12352108
MDL number:
MFCD02093394

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Product Name

Digoxigenin NHS-ester, ≥80% (HPLC)

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

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 key

KHNDABJZSPPYLE-FUGFVFQCSA-N

assay

≥80% (HPLC)

form

solid

shipped in

wet ice

storage temp.

−20°C

Quality Level

200

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This Item
113330540011542315481
Digoxigenin NHS-ester ≥80% (HPLC)

Sigma-Aldrich

55865

Digoxigenin NHS-ester

Digoxigenin-3-O-methylcarbonyl-ε-aminocaproic acid-N-hydroxysuccinimide ester >90% (elementary analysis), pkg of 5 mg, powder, pH range 2-13

Roche

11333054001

Digoxigenin-3-O-methylcarbonyl-ε-aminocaproic acid-N-hydroxysuccinimide ester

Boc-Gly-OSu ≥99.0% (T)

Sigma-Aldrich

15423

Boc-Gly-OSu

Boc-Phe-OSu ≥98.0% (HPLC)

Sigma-Aldrich

15481

Boc-Phe-OSu

assay

≥80% (HPLC)

assay

>90% (elementary analysis)

assay

≥99.0% (T)

assay

≥98.0% (HPLC)

form

solid

form

powder

form

solid

form

solid

Quality Level

200

Quality Level

100

Quality Level

200

Quality Level

100

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

shipped in

wet ice

shipped in

-

shipped in

-

shipped in

-

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[1][2] 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
GHS06,GHS08

signalword

Danger

Hazard Classifications

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

Storage Class

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

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
BCCN1891
BCCM3603
BCCM0721
BCCM0773
BCCJ7940

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R Antolovic et al.
The Journal of biological chemistry, 273(26), 16259-16264 (1998-06-20)
Searching for a binding protein in blood, which may be involved in the specific transport of cardiac glycosides to their receptor sites on the sodium pump, we isolated a cardiac glycoside-binding protein (CGBG) of 26 kDa from the globulin fraction
R Antolovic et al.
FEBS letters, 368(1), 169-172 (1995-07-10)
The digoxigenin derivative N-hydroxysuccinimidyl digoxigenin-3-O-methylcarbonyl-epsilon-aminocaproate (HDMA) has been shown to covalently label the ouabain binding site of the Na,K-ATPase epsilon subunit [Antolovic et al. (1995) Eur. J. Biochem. 227, 61-67]. In the present study we observed both, labeling and inactivation
Silke Metz et al.
Proceedings of the National Academy of Sciences of the United States of America, 108(20), 8194-8199 (2011-05-04)
Bispecific antibodies that bind cell-surface targets as well as digoxigenin (Dig) were generated for targeted payload delivery. Targeting moieties are IgGs that bind the tumor antigens Her2, IGF1R, CD22, or LeY. A Dig-binding single-chain Fv was attached in disulfide-stabilized form
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+
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)
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