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N-succinimidyl 4-(5-nitro-pyridin-2-yldithio)-pentanoate

  CAS No.: 663598-85-4   Cat No.: BADC-00484   Purity: ≥98% 4.5  

N-succinimidyl 4-(5-nitro-pyridin-2-yldithio)-pentanoate is a disulfide-based ADC linker with NHS ester activity, facilitating efficient payload attachment and controlled cleavage within tumor cells. This enhances antibody-drug conjugate stability and targeted drug delivery.

N-succinimidyl 4-(5-nitro-pyridin-2-yldithio)-pentanoate

Structure of 663598-85-4

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ADC Linker
Molecular Formula
C13H13N3O6S2
Molecular Weight
371.39
Shipping
Room temperature, or blue ice upon request.

* For research and manufacturing use only. We do not sell to patients.

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Popular Publications Citing BOC Sciences Products
Synonyms
(2,5-dioxopyrrolidin-1-yl) 4-[(5-nitropyridin-2-yl)disulfanyl]butanoate;
IUPAC Name
Canonical SMILES
C1CC(=O)N(C1=O)OC(=O)CCCSSC2=NC=C(C=C2)[N+](=O)[O-]
InChI
InChI=1S/C13H13N3O6S2/c17-11-5-6-12(18)15(11)22-13(19)2-1-7-23-24-10-4-3-9(8-14-10)16(20)21/h3-4,8H,1-2,5-7H2
InChIKey
WAXTZXRJMOUNSA-UHFFFAOYSA-N
Appearance
Soild powder
Shipping
Room temperature, or blue ice upon request.
1. Oxidizing potential of endosomes and lysosomes limits intracellular cleavage of disulfide-based antibody-drug conjugates
Lewis Gazzard, Suzie J Scales, Xiaohui Wen, Christopher Nelson, Cary D Austin, Richard H Scheller Proc Natl Acad Sci U S A . 2005 Dec 13;102(50):17987-92. doi: 10.1073/pnas.0509035102.
Antibody-drug conjugate therapy entails targeted killing of cancer cells with cytotoxic compounds covalently linked to tumor-specific antibodies and shows promise in the treatment of several human cancers. Current antibody-drug conjugate designs that incorporate a disulfide linker between the antibody and cytotoxic drug are inspired by indirect evidence suggesting that the redox potential within the endosomal system is reducing. It is presumed that antigen-dependent endocytosis leads to disulfide linker reduction and intracellular release of free drug, but direct demonstration of such a mechanism is lacking. To determine whether the disulfide N-succinimidyl 4-(2-pyridyldithio)pentanoate (SPP) linker would be reduced during endocytic recycling of the anti-HER2 antibody trastuzumab (Herceptin, Genentech), we synthesized a trastuzumab-SPP-Rhodamine red conjugate and developed a linker cleavage assay by using the self-quenching property of this fluorophore. In breast carcinoma SKBr3 cells, no SPP linker cleavage was observed, as detected by fluorescence dequenching upon internalization. By contrast, the conjugate did display fluorescence dequenching when diverted to the lysosomal pathway by geldanamycin, an effect partly due to proteolytic degradation rather than disulfide reduction. To understand why linker reduction was inefficient, we measured redox potentials of endocytic compartments by expressing a redox-sensitive variant of GFP fused to various endocytic proteins. Unexpectedly, we found that recycling endosomes, late endosomes, and lysosomes are not reducing, but oxidizing and comparable with conditions in the endoplasmic reticulum. These results suggest that intracellular reduction is unlikely to account for the potency of disulfide-linked antibody-drug conjugates.

The molarity calculator equation

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

The dilution calculator equation

Concentration (start) × Volume (start) = Concentration (final) × Volume (final)

This equation is commonly abbreviated as: C1V1 = C2V2

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