Soblidotin - ≥99% , Tubulin inhibitor, CAS No.149606-27-9, Tubulin inhibitor

CAS: 149606-27-9 Cat. No.: S649813 Molecular Weight: 701.98 PubChem CID: 6918315

GRADE & PURITY ≥99%

Synonyms

Soblidotin | NCGC00509861-02 | UNII-DQC51A0WQH | (2S)-2-[[(2S)-2-(Dimethylamino)-3-methylbutanoyl]amino]-N-[(3R,4S,5S)-3-methoxy-1-[(2S)-2-[(1R,2R)-1-methoxy-2-methyl-3-oxo-3-(2-phenylethylamino)propyl]pyrrolidin-1-yl]-5-methyl-1-oxoheptan-4-yl]-N,3-dimet

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Soblidotin (Auristatin PE) is a novel synthetic Dolastatin 10 derivative and inhibitor of tubulin polymerization.

In Vitro

Soblidotin (Auristatin PE) is a novel synthetic dolastatin 10 derivative that inhibits tubulin polymerization. Soblidotin (Auristatin PE) exhibits antitumor activity against p-glycoprotein-overexpressing cell lines established from colon cancer H116 and breast cancer-resistant protein-positive cell lines established from lung cancer PC-6, and is more potent than Vincristine, Paclitaxel, and Docetaxel against these cell lines. Soblidotin (Auristatin PE) is a synthetic analog of dolastatin 10 which inhibits the growth of several tumoral cell lines and induces caspase-3-dependent apoptosis. Soblidotin (Auristatin PE) also shows antitumoral activity in Vincristine-, Docetaxel-, and Paclitaxel-resistant tumors, which makes it a potential chemotherapy drug for use in tumors which do not respond to other microtubule inhibitors. MCE has not independently confirmed the accuracy of these methods. They are for reference only.

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 . 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. Mice bearing subcutaneous HT-29 tumors (200 mm 3 ) 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. MCE has not independently confirmed the accuracy of these methods. They are for reference only.

Form:Solid

IC50& Target:Tubulin

Specifications

Synonyms

Soblidotin | NCGC00509861-02 | UNII-DQC51A0WQH | (2S)-2-[[(2S)-2-(Dimethylamino)-3-methylbutanoyl]amino]-N-[(3R, 4S, 5S)-3-methoxy-1-[(2S)-2-[(1R, 2R)-1-methoxy-2-methyl-3-oxo-3-(2-phenylethylamino)propyl]pyrrolidin-1-yl]-5-methyl-1-oxoheptan-4-yl]-N, 3-dimet

Specifications & Purity

≥99%

Biochemical and Physiological Mechanisms

Soblidotin (Auristatin PE) is a novel synthetic Dolastatin 10 derivative and inhibitor of tubulin polymerization.

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Action Type

INHIBITOR

Mechanism of action

Tubulin inhibitor

Purity

≥99%

Product Properties

• ALogP: 5.2

Names and Identifiers

• Canonical Smiles: CC[C@H](C)[C@@H]([C@@H](CC(=O)N1CCC[C@H]1[C@@H]([C@@H](C)C(=O)NCCC2=CC=CC=C2)OC)OC)N(C)C(=O)[C@H](C(C)C)NC(=O)[C@H](C(C)C)N(C)C
• IUPAC Name: (2S)-2-[[(2S)-2-(dimethylamino)-3-methylbutanoyl]amino]-N-[(3R,4S,5S)-3-methoxy-1-[(2S)-2-[(1R,2R)-1-methoxy-2-methyl-3-oxo-3-(2-phenylethylamino)propyl]pyrrolidin-1-yl]-5-methyl-1-oxoheptan-4-yl]-N,3-dimethylbutanamide
• InChIKey: DZMVCVHATYROOS-ZBFGKEHZSA-N
• INCHI: 1S/C39H67N5O6/c1-13-27(6)35(43(10)39(48)33(25(2)3)41-38(47)34(26(4)5)42(8)9)31(49-11)24-32(45)44-23-17-20-30(44)36(50-12)28(7)37(46)40-22-21-29-18-15-14-16-19-29/h14-16,18-19,25-28,30-31,33-36H,13,17,20-24H2,1-12H3,(H,40,46)(H,41,47)/t27-,28+,30-,31
• Isomeric SMILES: CC[C@H](C)[C@@H]([C@@H](CC(=O)N1CCC[C@H]1[C@@H]([C@@H](C)C(=O)NCCC2=CC=CC=C2)OC)OC)N(C)C(=O)[C@H](C(C)C)NC(=O)[C@H](C(C)C)N(C)C
• PubChem CID: 6918315
• Molecular Weight: 701.98

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Class Peptidomimetics
      • Subclass Hybrid peptides

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Class: Peptidomimetics
• Subclass: Hybrid peptides
• Intermediate Tree Nodes: Not available
• Direct Parent: Hybrid peptides
• Alternative Parents: Dipeptides Valine and derivatives N-acyl-alpha amino acids and derivatives Alpha amino acid amides N-acylpyrrolidines Benzene and substituted derivatives N-acyl amines Tertiary carboxylic acid amides Trialkylamines Secondary carboxylic acid amides Dialkyl ethers Azacyclic compounds Organopnictogen compounds Carbonyl compounds Hydrocarbon derivatives Organic oxides
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: Hybrid peptide - Alpha-dipeptide - N-acyl-alpha amino acid or derivatives - Valine or derivatives - Alpha-amino acid amide - Alpha-amino acid or derivatives - N-acylpyrrolidine - Monocyclic benzene moiety - Fatty amide - Fatty acyl - Benzenoid - N-acyl-amine - Tertiary carboxylic acid amide - Pyrrolidine - Carboxamide group - Tertiary aliphatic amine - Tertiary amine - Secondary carboxylic acid amide - Amino acid or derivatives - Carboxylic acid derivative - Dialkyl ether - Ether - Azacycle - Organoheterocyclic compound - Organic oxygen compound - Organic nitrogen compound - Hydrocarbon derivative - Carbonyl group - Organic oxide - Amine - Organopnictogen compound - Organooxygen compound - Organonitrogen compound - Aromatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as hybrid peptides. These are compounds containing at least two different types of amino acids (alpha, beta, gamma, delta) linked to each other through a peptide bond.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Mechanisms of Action

Chemical and Physical Properties

• Solubility: DMSO : 100 mg/mL (142.45 mM; Need ultrasonic) H2O : <0.1 mg/mL (insoluble)
• Molecular Weight: 702.000 g/mol
• XLogP3: 5.200
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 20
• Exact Mass: 701.509 Da
• Monoisotopic Mass: 701.509 Da
• Topological Polar Surface Area: 121.000 Ų
• Heavy Atom Count: 50
• Formal Charge: 0
• Complexity: 1060.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 8
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1