SPP - CAS 341498-08-6
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SPP - CAS 341498-08-6 Catalog number: BADC-00678

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Category
ADCs Linker
Product Name
SPP
CAS
341498-08-6
Catalog Number
BADC-00678
Molecular Formula
C14H16N2O4S2
Molecular Weight
340.42
SPP

Ordering Information

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BADC-00678 -- $-- Inquiry

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Synonyms
N-succinimidyl 4-(2-pyridyldithio)pentanoate; (2,5-dioxopyrrolidin-1-yl) 4-(pyridin-2-yldisulfanyl)pentanoate
Canonical SMILES
CC(CCC(=O)ON1C(=O)CCC1=O)SSC2=CC=CC=N2
InChI
InChI=1S/C14H16N2O4S2/c1-10(21-22-11-4-2-3-9-15-11)5-8-14(19)20-16-12(17)6-7-13(16)18/h2-4,9-10H,5-8H2,1H3
InChIKey
GTBCXYYVWHFQRS-UHFFFAOYSA-N
LogP
2.53570
PSA
127.17000
Shipping
Room temperature
Pictograms
Irritant
Signal Word
Warning
In Vivo
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, redox potentials of endocytic compartments by expressing a redox-sensitive variant of GFP fused to various endocytic proteins was measured. Unexpectedly, it was found that recycling endosomes, late endosomes, and lysosomes are not reducing, but oxidizing and comparable with conditions in the endoplasmic reticulum.
NCT NumberCondition Or DiseasePhaseStart DateSponsorStatus
NCT00184080Non-Hodgkin's LymphomaPhase 22014-05-21University of Southern CaliforniaCompleted
NCT00299806HypertensionPhase 32016-11-18NovartisCompleted
NCT00376636HypertensionPhase 22007-10-30Speedel Pharma Ltd.Completed
NCT00344110HypertensionPhase 32016-11-18NovartisCompleted
NCT00299832HypertensionPhase 32016-11-18NovartisCompleted
1.Metabolites of antibody-maytansinoid conjugates: characteristics and in vitro potencies
Widdison W, Wilhelm S, Veale K, Costoplus J, Jones G, Audette C, Leece B, Bartle L, Kovtun Y, Chari R
Several antibody-maytansinoid conjugates (AMCs) are in clinical trials for the treatment of various cancers. Each of these conjugates can be metabolized by tumor cells to give cytotoxic maytansinoid metabolites that can kill targeted cells. In preclinical studies in mice, the cytotoxic metabolites initially formed in vivo are further processed in the mouse liver to give several oxidized metabolic species. In this work, the primary AMC metabolites were synthesized and incubated with human liver microsomes (HLMs) to determine if human liver would likely give the same metabolites as those formed in mouse liver. The results of these HLM metabolism studies as well as the subsequent syntheses of the resulting HLM oxidation products are presented. Syntheses of the minor impurities formed during the conjugation of AMCs were also conducted to determine their cytotoxicities and to establish how these impurities would be metabolized by HLM.
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