(2S)-2-[[(2S)-2-dimethylamino-3-methyl-butanoyl]amino]-N-[(3R,4S,5S)-3 -methoxy-1-[(3R)-3-[(1R,2R)-1-methoxy-2-(phenethylcarbamoyl)propyl]pyr rolidin-1-yl]-5-methyl-1-oxo-heptan-4-yl]-N,3-dimethyl-butanamide
- Product Name
- (2S)-2-[[(2S)-2-dimethylamino-3-methyl-butanoyl]amino]-N-[(3R,4S,5S)-3 -methoxy-1-[(3R)-3-[(1R,2R)-1-methoxy-2-(phenethylcarbamoyl)propyl]pyr rolidin-1-yl]-5-methyl-1-oxo-heptan-4-yl]-N,3-dimethyl-butanamide
- CAS No.
- 149606-27-9
- Chemical Name
- (2S)-2-[[(2S)-2-dimethylamino-3-methyl-butanoyl]amino]-N-[(3R,4S,5S)-3 -methoxy-1-[(3R)-3-[(1R,2R)-1-methoxy-2-(phenethylcarbamoyl)propyl]pyr rolidin-1-yl]-5-methyl-1-oxo-heptan-4-yl]-N,3-dimethyl-butanamide
- Synonyms
- TZT 1027;Soblidotin;Auristatin PE;TZT-1027(Soblidotin);Soblidotin, 10 mM in DMSO;Soblidotin (Auristatin PE);TZT1027,inhibit,Microtubule/Tubulin,Inhibitor,TZT 1027,Soblidotin;L-Valinamide, N,N-dimethyl-L-valyl-N-[(1S,2R)-2-methoxy-4-[(2S)-2-[(1R,2R)-1-methoxy-2-methyl-3-oxo-3-[(2-phenylethyl)amino]propyl]-1-pyrrolidinyl]-1-[(1S)-1-methylpropyl]-4-oxobutyl]-N-methyl-;(2S)-2-[[(2S)-2-dimethylamino-3-methyl-butanoyl]amino]-N-[(3R,4S,5S)-3 -methoxy-1-[(3R)-3-[(1R,2R)-1-methoxy-2-(phenethylcarbamoyl)propyl]pyr rolidin-1-yl]-5-methyl-1-oxo-heptan-4-yl]-N,3-dimethyl-butanamide
- CBNumber
- CB81253823
- Molecular Formula
- C39H67N5O6
- Formula Weight
- 701.98
- MOL File
- 149606-27-9.mol
(2S)-2-[[(2S)-2-dimethylamino-3-methyl-butanoyl]amino]-N-[(3R,4S,5S)-3 -methoxy-1-[(3R)-3-[(1R,2R)-1-methoxy-2-(phenethylcarbamoyl)propyl]pyr rolidin-1-yl]-5-methyl-1-oxo-heptan-4-yl]-N,3-dimethyl-butanamide Property
- Melting point:
- 73-79 °C
- Boiling point:
- 843.4±65.0 °C(Predicted)
- Density
- 1.064±0.06 g/cm3(Predicted)
- storage temp.
- Store at -20°C,unstable in solution, ready to use.
- form
- Solid
- pka
- 13.95±0.46(Predicted)
- color
- White to off-white
- Water Solubility
- Water : < 0.1 mg/mL (insoluble)
N-Bromosuccinimide Price
- Product number
- CS-6022
- Product name
- Soblidotin
- Purity
- 99.64%
- Packaging
- 1mg
- Price
- $168
- Updated
- 2021/12/16
- Product number
- CS-6022
- Product name
- Soblidotin
- Purity
- 99.64%
- Packaging
- 5mg
- Price
- $420
- Updated
- 2021/12/16
- Product number
- API0004192
- Product name
- SOBLIDOTIN
- Purity
- 95.00%
- Packaging
- 5MG
- Price
- $500.49
- Updated
- 2021/12/16
- Product number
- CS-6022
- Product name
- Soblidotin
- Purity
- 99.64%
- Packaging
- 10mg
- Price
- $600
- Updated
- 2021/12/16
- Product number
- CS-6022
- Product name
- Soblidotin
- Purity
- 99.64%
- Packaging
- 25mg
- Price
- $1200
- Updated
- 2021/12/16
(2S)-2-[[(2S)-2-dimethylamino-3-methyl-butanoyl]amino]-N-[(3R,4S,5S)-3 -methoxy-1-[(3R)-3-[(1R,2R)-1-methoxy-2-(phenethylcarbamoyl)propyl]pyr rolidin-1-yl]-5-methyl-1-oxo-heptan-4-yl]-N,3-dimethyl-butanamide Chemical Properties,Usage,Production
Uses
Soblidotin (Auristatin PE) is a novel synthetic Dolastatin 10 derivative and inhibitor of tubulin polymerization.
Definition
ChEBI: Soblidotin is a tetrapeptide derivative of dolastatin 10. It is an inhibitor of tubulin polymerization which exhibits potent antitumor activity. It has a role as a microtubule-destabilising agent, an antineoplastic agent and an apoptosis inducer. It is functionally related to a 2-phenylethylamine and a L-valine.
in vivo
Intravenous injection of Auristatin PE (TZT-1027) has been shown to potently inhibit the growth of P388 leukemic cells and several solid tumors in mice, and to prolong the survival of the animals, and its antitumor efficacy has been shown to be superior or comparable to that of the reference agents Dolastatin 10, Cisplatin, Vincristine, and 5-Fluorouracil. Furthermore, in xenograft models, Auristatin PE reduces intratumoral blood perfusion 1 to >24 h after its administration, thereby producing hemorrhagic necrosis of the tumors[1]. Auristatin PE (Soblidotin) shows antivascular effects in tumoral models overexpressing VEGF and in murine colon tumors, with an increase in vascular permeability, vessel closure, and widespread hemorrhage[2]. Mice bearing subcutaneous HT-29 tumors (200 mm3) are dosed every 7 days with Auristatin PE (0.5 or 1.0 mg/kg) for a total of four cycles. Under such conditions, Auristatin PE (TZT-1027) inhibits the growth of HT-29 xenografts in a dose-dependent manner. Coadministration of Auristatin PE does not interfere with the PD184352-induced suppression of ERK1/2 phosphorylation. Immunostaining for Ki-67 as a marker for proliferating cells confirmed that the number of such cells in tumor sections is decreased greatly at 24 hours after the initial dosing with PD184352 compared with that apparent for vehicle-treated tumors. Auristatin PE treatment alone increases the number of TUNEL-positive cells in HT-29 xenografts by 24 hours in a dose-dependent manner, and this effect is enhanced by coadministration of PD184352[3].
References
[1] Yamamoto N, et al. Phase I study of TZT-1027, a novel synthetic dolastatin 10 derivative and inhibitor of tubulin polymerization, given weekly to advanced solid tumor patients for 3 weeks. Cancer Sci. 2009 Feb;100(2):316-21. DOI:10.1111/j.1349-7006.2008.01023.x
[2] Fanale D, et al. Stabilizing versus destabilizing the microtubules: a double-edge sword for an effective cancer treatment option? Anal Cell Pathol (Amst). 2015;2015:690916. DOI:10.1155/2015/690916
[3] Watanabe K, et al. Blockade of the extracellular signal-regulated kinase pathway enhances the therapeutic efficacy of microtubule-destabilizing agents in human tumor xenograft models. Clin Cancer Res. 2010 Feb 15;16(4):1170-8. DOI:10.1158/1078-0432.CCR-09-2482
(2S)-2-[[(2S)-2-dimethylamino-3-methyl-butanoyl]amino]-N-[(3R,4S,5S)-3 -methoxy-1-[(3R)-3-[(1R,2R)-1-methoxy-2-(phenethylcarbamoyl)propyl]pyr rolidin-1-yl]-5-methyl-1-oxo-heptan-4-yl]-N,3-dimethyl-butanamide Preparation Products And Raw materials
Raw materials
Preparation Products
(2S)-2-[[(2S)-2-dimethylamino-3-methyl-butanoyl]amino]-N-[(3R,4S,5S)-3 -methoxy-1-[(3R)-3-[(1R,2R)-1-methoxy-2-(phenethylcarbamoyl)propyl]pyr rolidin-1-yl]-5-methyl-1-oxo-heptan-4-yl]-N,3-dimethyl-butanamide Suppliers
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