ChemicalBook > CAS DataBase List > (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

(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
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(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)
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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

ChemScene
Product number
CS-6022
Product name
Soblidotin
Purity
99.64%
Packaging
1mg
Price
$168
Updated
2021/12/16
ChemScene
Product number
CS-6022
Product name
Soblidotin
Purity
99.64%
Packaging
5mg
Price
$420
Updated
2021/12/16
American Custom Chemicals Corporation
Product number
API0004192
Product name
SOBLIDOTIN
Purity
95.00%
Packaging
5MG
Price
$500.49
Updated
2021/12/16
ChemScene
Product number
CS-6022
Product name
Soblidotin
Purity
99.64%
Packaging
10mg
Price
$600
Updated
2021/12/16
ChemScene
Product number
CS-6022
Product name
Soblidotin
Purity
99.64%
Packaging
25mg
Price
$1200
Updated
2021/12/16
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(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

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(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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149606-27-9, (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-butanamideRelated Search:

(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 4,9-dioxo-5,10-diazatetradecane Butanamide, 3-methyl-N-(4-oxo-4-(propylamino)butyl)- 2-(4-Aminopentyl(ethyl)amino)ethanol dolastatin 10

  • TZT 1027
  • Soblidotin
  • Auristatin PE
  • TZT-1027(Soblidotin)
  • (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
  • 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-
  • Soblidotin (Auristatin PE)
  • TZT1027,inhibit,Microtubule/Tubulin,Inhibitor,TZT 1027,Soblidotin
  • Soblidotin, 10 mM in DMSO
  • 149606-27-9
  • C39H67N5O6