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806005

Sigma-Aldrich

APN-Amine HCl

95%

Synonym(s):

3-(4-(4-(Aminomethyl)-1H-1,2,3-triazol-1-yl)phenyl)propiolonitrile hydrochloride

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About This Item

Empirical Formula (Hill Notation):
C12H10N5Cl
Molecular Weight:
259.69
UNSPSC Code:
12352200
PubChem Substance ID:
329768982

Quality Level

100

Assay

95%

form

powder

reaction suitability

reagent type: cross-linking reagent

storage temp.

2-8°C

SMILES string

N#CC#CC1=CC=C(N2C=C(CN)N=N2)C=C1.[H]Cl

InChI

1S/C12H9N5.ClH/c13-7-1-2-10-3-5-12(6-4-10)17-9-11(8-14)15-16-17;/h3-6,9H,8,14H2;1H

InChI key

JZGAUVVBWJHLGN-UHFFFAOYSA-N

Application

APN-Amine is a bifunctional crosslinker for thiol-to-carboxyl coupling. The coupling can be performed with high selectivity in biological medium using mild reaction conditions. The amino group readily reacts with activated carboxylic acids (e.g. NHS-esters) in basic conditions to produce stable amide bonds. The APN group can be used for coupling with free thiols (e.g. labeling of free cysteines in proteins).

Other Notes

Standard protein labeling procedure (cysteine labeling):
  • Dissolve the protein in the appropriate buffer* with pH 6.5-9.0 (e.g. PBS) at 1-10 mg/mL concentration.
  • Apply the appropriate amount of the stock solution of the reagent (1-5 molar eq. per free cysteine residue).
  • Incubate at room temperature for 2 hours.
  • If necessary, purify the protein conjugate using size exclusion chromatography or ultrafiltration.
*Note: avoid thiol-containing buffers.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

806005-50MG:4548174013700
806005-VAR:
806005-BULK:

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Sergii Kolodych et al.
Bioconjugate chemistry, 26(2), 197-200 (2015-01-24)
Amine-to-thiol coupling is the most common route for the preparation of antibody-drug conjugates (ADC). It is usually achieved by using heterobifunctional reagents possessing an activated ester at one end and a maleimide group at the other. However, maleimide-based conjugates were

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