Indibulin - CAS 204205-90-3
Catalog number: 204205-90-3
Category: Inhibitor
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Molecular Formula:
C22H16ClN3O2
Molecular Weight:
389.83
COA:
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Targets:
Microtubule/Tubulin
Description:
Indibulin, also called D 24851, estabilizes tubulin polymerization (IC50 = 0.3 μM) and induces tumor cell cycle arrest and apoptosis. In vitro: blocking cell cycle progression at metaphase; In vivo: induce complete tumor remission in the Yoshida AH13 rat sarcoma model
Brife Description:
Estabilizes tubulin polymerization; Induces tumor cell cycle arrest and apoptosis
Appearance:
Off-white solid
Synonyms:
2-[1-[(4-chlorophenyl)methyl]indol-3-yl]-2-oxo-N-pyridin-4-ylacetamide; D 24851; D-24851; indibulin; N-(pyridin-4-yl)-(1-(4-chlorobenzyl)indol-3-yl)glycoxylamide; N-(pyridin-4-yl)-(1-(4-chlorobenzyl)indol-3-yl)glyoxylamide
Solubility:
Soluble to 25 mM in DMSO
Storage:
Store in a cool and dry place and at 0 - 4℃ for short term (days to weeks) or -60℃ for long term (months to years).
MSDS:
Inquire
Density:
1.310 g/cm3
InChIKey:
SOLIIYNRSAWTSQ-UHFFFAOYSA-N
InChI:
1S/C22H16ClN3O2/c23-16-7-5-15(6-8-16)13-26-14-19(18-3-1-2-4-20(18)26)21(27)22(28)25-17-9-11-24-12-10-17/h1-12,14H,13H2,(H,24,25,28)
Canonical SMILES:
C1=CC=C2C(=C1)C(=CN2CC3=CC=C(C=C3)Cl)C(=O)C(=O)NC4=CC=NC=C4
1.[Molecular dynamics simulation of the tubulin dimer with cytostatics].
Varzhabetian LR, Glazachev DV, Nazarian KB. Mol Biol (Mosk). 2012 Mar-Apr;46(2):348-53.
Colchicin, podophylotoxin and indibulin are natural cytostatics that are used in the treatment of neoplasms. But applications of those compounds are rather restricted due to the high toxicity and low specificity. It seems very promising to investigate possibility to design new analogs of the above mentioned drugs that will possess higher cytostatic activity and less toxicity. For this purpose we see computer modeling experiments of tubulin and above mentioned compounds interaction as a powerful approach to design new artificial cytostatics with desired properties. In the current study the CHARMM software of protein-ligand interaction molecular dynamics method has been used. Particularly the following strategy has been applied. Molecules of the cytostatits have been positioned at several random positions around binding sites of tubulin and after energy minimization several binding sites have been identified on the tubulin macromolecule. In these binding sites structural changes that may be responsible for tubulin polymerization have been detected.
2.Side chain modifications of (indol-3-yl)glyoxamides as antitumor agents.
Antoine M1, Marchand P, Le Baut G, Czech M, Baasner S, Gunther E. J Enzyme Inhib Med Chem. 2008 Oct;23(5):686-95. doi: 10.1080/14756360802207998 .
New series of analogues of N-(pyridin-4-yl)-2-[1-(4-chlorobenzyl)-indol-3-yl]glyoxamide D-24851 were synthesized, characterized and tested for their in vitro anticancer properties. In the first series, an amino acid spacer was introduced in the glyoxamide chain of D-24851. In the second series, the glyoxamide chain was moved to positions 4 and 5 of indole skeleton. These new compounds were tested on four cancer cell lines (KB, SK-OV-3, NCI-H460 and SF-268), with promising activity for the glycine derivative.
3.Dose-finding and pharmacokinetic study of orally administered indibulin (D-24851) to patients with advanced solid tumors.
Oostendorp RL1, Witteveen PO, Schwartz B, Vainchtein LD, Schot M, Nol A, Rosing H, Beijnen JH, Voest EE, Schellens JH. Invest New Drugs. 2010 Apr;28(2):163-70. doi: 10.1007/s10637-009-9244-6. Epub 2009 Apr 30.
Indibulin (ZIO-301/D-24851) is an orally applied small molecule with antitumor activity based upon destabilization of microtubule polymerization. The purpose of this phase I study was to determine the maximum tolerated dose (MTD) as well as the dose limiting toxicity (DLT), the pharmacokinetics, safety and tolerability of orally administered indibulin as capsule formulation in patients with advanced solid tumors. Patients received a single dose of indibulin. Seven dose-levels were evaluated: 100 mg, 150 mg, 250 mg, 350 mg and 600 mg once daily (QD), 450 mg and 600 mg twice daily (BID). After a washout period, patients received indibulin at the pre-defined daily dose for 14 days every 3 weeks (multiple dose part). A total of 28 patients entered the study. Indibulin administered as capsules was generally well tolerated. The MTD was not reached. There was a disproportionate increase of the area under the plasma concentration-time curve (AUC) with dose, with declining AUC corrected for dose starting at the 250 mg dose-level.
4.Design, synthesis and cytotoxicity of novel podophyllotoxin derivatives.
Yu PF1, Chen H, Wang J, He CX, Cao B, Li M, Yang N, Lei ZY, Cheng MS. Chem Pharm Bull (Tokyo). 2008 Jun;56(6):831-4.
A series of novel podophyllotoxin derivatives were designed using association strategy and synthesized by coupling either podophyllotoxin (1) or 4beta-amino podophyllotoxin (3) with substituted indol-3-yl-glyoxyl chlorides. Their structures were identified using spectroscopic techniques. These novel derivatives have been evaluated for cytotoxicity in vitro against four human cancer cell lines with comparison to the parent compounds 1, 3 and indibulin (2). Some of the compounds (7a, 7c) showed comparable cytotoxicity to that of podophyllotoxin.
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