Seco-DUBA
- Product Name
- Seco-DUBA
- CAS No.
- 1227961-59-2
- Chemical Name
- Seco-DUBA
- Synonyms
- SYD985;Seco-DUBA;Benzamide, N-[2-[[(1S)-1-(chloromethyl)-1,2-dihydro-5-hydroxy-9-methyl-3H-benz[e]indol-3-yl]carbonyl]imidazo[1,2-a]pyridin-6-yl]-4-hydroxy-
- CBNumber
- CB48129965
- Molecular Formula
- C29H23ClN4O4
- Formula Weight
- 526.97
- MOL File
- 1227961-59-2.mol
Seco-DUBA Property
- Density
- 1.47±0.1 g/cm3(Predicted)
- pka
- 8.08±0.15(Predicted)
- form
- Solid
- color
- Light yellow to brown
Seco-DUBA Chemical Properties,Usage,Production
Uses
Seco-DUBA is a inactive prodrug form of duocarmycin (DUBA) containing two hydroxyl groups, which can each be used for coupling to an antibody via a linker. Seco-DUBA can be used in the synthesis of antibody-drug conjugates (ADCs).
Definition
Duocarmycins (DUMs; A, B1, B2, C1, C2, D1, D2 and SA) are members of an extremely potent group of antitumor antibiotics isolated from Streptomyces sp. The pharmacophore consists of a cyclopropa[c]pyrrolo[3,2-e]indole (CPI) moiety. DUMs B1, B2, C1, C2, D1 and D2 were a seco-type of DUM A and chemically more stable than DUM A[1].
in vitro
Seco-DUBA (SK-BR-3 cells; 0.0001 pM~0.01 nM; 144 hours) dose-dependent reduces cell viability and shows equally potent and efficacious as DUBA[1].
Seco-DUBA causes SK-BR-3 (IC50=0.09), SK-OV-3 (IC50=0.43), and SW620 (IC50=0.09) cells to exhibit highly sensitive.
Seco-DUBA (89 μg/kg; i.v.) is likely converted to DUBA almost instantaneously[2].
target
Humanized IgG1, HER-2
Humanized IgG1, 5 T4
Humanized IgG1, CD22
Mouse IgG1; CD56
References
[1] Choi T, et al. Structural Influence of Indole C5-N-Substitutents on the Cytotoxicity
of seco-Duocarmycin Analogs. Archives of Pharmacal Research, 2011; 34: 357–367.
[2] Elgersma R, et al. Design, Synthesis, and Evaluation of Linker-Duocarmycin Payloads: Toward Selection of HER2-Targeting Antibody–Drug Conjugate SYD985. Molecular Pharmaceutics, 2015; 12: 1813–1835.
Seco-DUBA Preparation Products And Raw materials
Raw materials
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