Vc-seco-DUBA
Vc-seco-DUBA Basic information
- Product Name:
- Vc-seco-DUBA
- Synonyms:
-
- 4-((2S,5S)-13-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)-5-isopropyl-4,7-dioxo-2-(3-ureidopropyl)-8,11-dioxa-3,6-diazatridecanamido)benzyl (2-(((((S)-1-(chloromethyl)-3-(6-(4-hydroxybenzamido)imidazo[1,2-a]pyridine-2-carbonyl)-9-methyl-2,3-dihydro-1H-benzo[e]indol-5-yl)oxy)carbonyl)(2-(2-hydroxyethoxy)ethyl)amino)ethyl)(methyl)carbamate
- Vc-seco-DUBA
- 4-((2S,5S)-13-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)-5-isopropyl-4,7-dioxo-2-(3-ureidopropyl)-8,11-dioxa-3,6-diazatridecanamido)benzyl (2-(((((S)-1-(chloromethyl)-3-(6-(4-hydroxybenzamido)imidazo[1,2-a]pyridine-2-carbonyl)-9-methyl-2,3-dihydro-1H-benzo[e]
- MGC018
- L-Ornithinamide, N-[[2-[2-(2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl)ethoxy]ethoxy]carbonyl]-L-valyl-N5-(aminocarbonyl)-N-[4-[7-[[[(1S)-1-(chloromethyl)-2,3-dihydro-3-[[6-[(4-hydroxybenzoyl)amino]imidazo[1,2-a]pyridin-2-yl]carbonyl]-9-methyl-1H-benz[e]indol-5-yl]oxy]carbonyl]-12-hydroxy-4-methyl-3-oxo-2,...
- Vc-seco-DUBA (SYD985)/Duocarmazine
- (S)-1-(chloromethyl)-3-(6-(4-hydroxybenzamido)imidazo[1,2-a]pyridine-2-carbonyl)-9-methyl-2,3-dihydro-1H-benzo[e]indol-5-yl (2-((((4-((2S,5S)-13-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)-5-isopropyl-4,7-dioxo-2-(3-ureidopropyl)-8,11-dioxa-3,6-diazatridecanamido)benzyl)oxy)carbonyl)(methyl)amino)ethyl)(2-(2-hydroxyethoxy)ethyl)carbamate
- 2-[2-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)ethoxy]ethyl N-[(1S)-1-{[(1S)-4-(carbamoylamino)-1-[(4-{[({2-[({[(1S)-1-(chloromethyl)-3-[6-(4-hydroxybenzamido)imidazo[1,2-a]pyridine-2-carbonyl]-9-methyl-1H,2H,3H-benzo[e]indol-5-yl]oxy}carbonyl)[2-(2-hydroxyethoxy)ethyl]amino]ethyl}(methyl)carbamoyl)oxy]methyl}phenyl)carbamoyl]butyl]carbamoyl}-2-methylpropyl]carbamate
- CAS:
- 1345681-58-4
- MF:
- C65H75ClN12O17
- MW:
- 1331.81
- EINECS:
- 813-138-9
- Mol File:
- 1345681-58-4.mol
Vc-seco-DUBA Chemical Properties
- Density
- 1.43±0.1 g/cm3(Predicted)
- solubility
- DMSO : 146.67 mg/mL (110.13 mM; ultrasonic and warming and heat to 60°C)
- pka
- 8.08±0.15(Predicted)
- form
- Solid
- color
- Off-white to light yellow
Vc-seco-DUBA Usage And Synthesis
Description
Vc-seco-DUBA is a novel HER2-targeting antibody–drug conjugate used in the treatment of cancer. Trastuzumab duocarmycin, also known as SYD985, is a new HER2-targeted ADC with a cleavable payload (vc-seco-DUBA) conjugated with trastuzumab[1].
Uses
Vc-seco-DUBA, a cleavable linker-duocarmycin payload, could used to synthsis SYD985 with trastuzumab.
Hazard
Vc-seco-DUBA is Danger.
H340 (100%): May cause genetic defects [Danger Germ cell mutagenicity]
H351 (100%): Suspected of causing cancer [Warning Carcinogenicity]
H373 (100%): Causes damage to organs through prolonged or repeated exposure [Warning Specific target organ toxicity, repeated exposure]
Cytotoxicity
SYD985 ( based on trastuzumab and Vc-seco-DUBA) and T-DM1 induced similar ADCC in the presence of peripheral blood lymphocytes (PBL) against EOC cell lines with differential HER2/neu expression. In contrast, SYD985 was 3 to 42 fold more cytotoxic in the absence of PBL when compared to T-DM1 (p<0.0001). Unlike T-DM1, SYD985 induced efficient bystander killing of HER2/neu 0/1+ tumor cells when admixed with HER2/neu 3+ EOC cells. In vivo studies confirmed that SYD985 is significantly more active than T-DM1 against HER2/neu 3+ EOC xenografts[2].
References
[1] Ubink R, et al. Unraveling the interaction between carboxylesterase 1c and the antibody-drug conjugate SYD985: improved translational PKPD by using CES1c knockout mice. Molecular Cancer Therapeutics, 2018; 17: 2389–2398.
[2] Menderes G, et al. SYD985, a novel duocarmycin-based HER2-targeting antibody-drug conjugate, shows promising antitumor activity in epithelial ovarian carcinoma with HER2/Neu expression. Gynecologic Oncology, 2017; 146: 179-186.
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