Application of Pyrrolobenzodiazepines in Antibody Drug Conjugates

Zhang, Ning; Han, Amy

doi:10.1002/9781119627784.ch13

Cited by 2 publications

(2 citation statements)

References 134 publications

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“…Also, the N10-C11 amide group-possessing PBDs exhibit considerable cytotoxicity in various cancer cell lines acting as noncovalent binders . A number of naturally occurring and synthetic PBDs have been studied in clinical trials, and nowadays, the PBDs are considered a privileged warhead scaffold in the development of antibody–drug conjugates (ADCs). − Structurally, several naturally occurring PBDs possess an exocyclic alkylidene group at the C2 position. Studies in synthetic PBD series also reveal that this alkylidene substituent is crucial for the superior cytotoxicity of these compounds …”

Section: Introductionmentioning

confidence: 99%

Stereoselective Olefination with Sterically Demanding Julia–Kocienski Reagents: Total Synthesis of Oxo-prothracarcin, Oxo-tomaymycin, and Boseongazepine B

et al. 2022

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Total syntheses of three pyrrolo[1,4]benzodiazepine anticancer antibiotic family members oxo-prothracarcin, oxo-tomaymycin, and boseongazepine B are described. The total syntheses feature late-stage stereoselective olefination employing modified Julia–Kocienski reagents that can be conveniently prepared in only two steps and allows for a significant reduction in the number of linear steps. Detailed density functional theory (DFT) studies explain the stereochemical outcome of the key step.

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Section: Introductionmentioning

confidence: 99%

Stereoselective Olefination with Sterically Demanding Julia–Kocienski Reagents: Total Synthesis of Oxo-prothracarcin, Oxo-tomaymycin, and Boseongazepine B

et al. 2022

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“…4 Although with limited success, several naturally occurring PBDs have been evaluated in clinical trials for cancer treatment. 5 Nowadays PBDs are mainly studied as toxic payloads in antibody–drug conjugate (ADC) development 6–8 and in 2021 the FDA approved the first PBD payload containing ADC (brand name Zynlonta®) 9 for the treatment of large B-cell lymphoma. 10…”

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confidence: 99%