Skip to Content
MilliporeSigma
  • Structural factors affecting affinity of cytotoxic oxathiole-fused chalcones toward tubulin.

Structural factors affecting affinity of cytotoxic oxathiole-fused chalcones toward tubulin.

European journal of medicinal chemistry (2014-12-03)
Marek T Konieczny, Anita Buɬakowska, Danuta Pirska, Wojciech Konieczny, Andrzej Skladanowski, Michal Sabisz, Marek Wojciechowski, Krzysztof Lemke, Anna Pieczykolan, Wojciech Strożek
ABSTRACT

Synthesis, in vitro cytotoxic activity, and interaction with tubulin of (E)-1-(6-alkoxybenzo[d][1,3]oxathiol-5-yl)-3-phenylprop-2-en-1-one derivatives (2) are described. Some of the compounds demonstrated cytotoxic activity at submicromolar concentrations, and the activity could be related to interaction with tubulin at the colchicine binding site. Interaction of selected derivatives with tubulin was evaluated using molecular modeling, and two different modes of the interaction were identified. The proposed models demonstrate how particular structural fragments participate in binding to the tubulin and explain the importance of the fragments for cytotoxic activity. It was demonstrated that concerning binding to tubulin, the 6-alkoxybenzoxathiole ring can be considered as structural equivalent of trimethoxyphenyl motif of colchicine, podophyllotoxin or combretastatin A4. The observation opened new ways of rational modifications of several groups of tubulin binders.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Chloroform, suitable for HPLC
Sign Into View Organizational & Contract Pricing
SKUPack SizeAvailabilityPriceQuantity
1 vial
Estimated to ship on March 24, 2025
$168.00
5 vials
Estimated to ship on March 24, 2025
$572.00
Sigma-Aldrich
Chloroform, ACS reagent, ≥99.8%, contains 0.5-1.0% ethanol as stabilizer
Sign Into View Organizational & Contract Pricing
SKUPack SizeAvailabilityPriceQuantity
1 vial
Estimated to ship on March 24, 2025
$168.00
5 vials
Estimated to ship on March 24, 2025
$572.00
Sigma-Aldrich
Chloroform, SAJ super special grade, ≥99.0%
Sign Into View Organizational & Contract Pricing
SKUPack SizeAvailabilityPriceQuantity
1 vial
Estimated to ship on March 24, 2025
$168.00
5 vials
Estimated to ship on March 24, 2025
$572.00
Sigma-Aldrich
Chloroform, SAJ first grade, ≥99.0%, contains 0.4-0.8% ethanol
Sign Into View Organizational & Contract Pricing
SKUPack SizeAvailabilityPriceQuantity
1 vial
Estimated to ship on March 24, 2025
$168.00
5 vials
Estimated to ship on March 24, 2025
$572.00
Sigma-Aldrich
Chloroform, JIS 300, ≥99.0%, for residue analysis
Sign Into View Organizational & Contract Pricing
SKUPack SizeAvailabilityPriceQuantity
1 vial
Estimated to ship on March 24, 2025
$168.00
5 vials
Estimated to ship on March 24, 2025
$572.00
Sigma-Aldrich
Chloroform, JIS special grade, ≥99.0%
Sign Into View Organizational & Contract Pricing
SKUPack SizeAvailabilityPriceQuantity
1 vial
Estimated to ship on March 24, 2025
$168.00
5 vials
Estimated to ship on March 24, 2025
$572.00
Sigma-Aldrich
Chloroform, ≥99%, PCR Reagent, contains amylenes as stabilizer
Sign Into View Organizational & Contract Pricing
SKUPack SizeAvailabilityPriceQuantity
1 vial
Estimated to ship on March 24, 2025
$168.00
5 vials
Estimated to ship on March 24, 2025
$572.00
Sigma-Aldrich
Chloroform, ACS reagent, ≥99.8%, contains amylenes as stabilizer
Sign Into View Organizational & Contract Pricing
SKUPack SizeAvailabilityPriceQuantity
1 vial
Estimated to ship on March 24, 2025
$168.00
5 vials
Estimated to ship on March 24, 2025
$572.00
Sigma-Aldrich
Chloroform, anhydrous, contains amylenes as stabilizer, ≥99%
Sign Into View Organizational & Contract Pricing
SKUPack SizeAvailabilityPriceQuantity
1 vial
Estimated to ship on March 24, 2025
$168.00
5 vials
Estimated to ship on March 24, 2025
$572.00
Sigma-Aldrich
Chloroform, anhydrous, ≥99%, contains 0.5-1.0% ethanol as stabilizer
Sign Into View Organizational & Contract Pricing
SKUPack SizeAvailabilityPriceQuantity
1 vial
Estimated to ship on March 24, 2025
$168.00
5 vials
Estimated to ship on March 24, 2025
$572.00
Supelco
Chloroform, analytical standard
Sign Into View Organizational & Contract Pricing
SKUPack SizeAvailabilityPriceQuantity
1 vial
Estimated to ship on March 24, 2025
$168.00
5 vials
Estimated to ship on March 24, 2025
$572.00
Sigma-Aldrich
Chloroform, ReagentPlus®, ≥99.8%, contains 0.5-1.0% ethanol as stabilizer
Sign Into View Organizational & Contract Pricing
SKUPack SizeAvailabilityPriceQuantity
1 vial
Estimated to ship on March 24, 2025
$168.00
5 vials
Estimated to ship on March 24, 2025
$572.00
Sigma-Aldrich
Chloroform, HPLC Plus, for HPLC, GC, and residue analysis, ≥99.9%, contains 0.5-1.0% ethanol as stabilizer
Sign Into View Organizational & Contract Pricing
SKUPack SizeAvailabilityPriceQuantity
1 vial
Estimated to ship on March 24, 2025
$168.00
5 vials
Estimated to ship on March 24, 2025
$572.00
Sigma-Aldrich
Chloroform, HPLC Plus, for HPLC, GC, and residue analysis, ≥99.9%, contains amylenes as stabilizer
Sign Into View Organizational & Contract Pricing
SKUPack SizeAvailabilityPriceQuantity
1 vial
Estimated to ship on March 24, 2025
$168.00
5 vials
Estimated to ship on March 24, 2025
$572.00
Sigma-Aldrich
Chloroform, suitable for HPLC, ≥99.8%, amylene stabilized
Sign Into View Organizational & Contract Pricing
SKUPack SizeAvailabilityPriceQuantity
1 vial
Estimated to ship on March 24, 2025
$168.00
5 vials
Estimated to ship on March 24, 2025
$572.00
Sigma-Aldrich
Chloroform, suitable for HPLC, ≥99.8%, contains 0.5-1.0% ethanol as stabilizer
Sign Into View Organizational & Contract Pricing
SKUPack SizeAvailabilityPriceQuantity
1 vial
Estimated to ship on March 24, 2025
$168.00
5 vials
Estimated to ship on March 24, 2025
$572.00
Sigma-Aldrich
Chloroform, contains ethanol as stabilizer, ACS reagent, ≥99.8%
Sign Into View Organizational & Contract Pricing
SKUPack SizeAvailabilityPriceQuantity
1 vial
Estimated to ship on March 24, 2025
$168.00
5 vials
Estimated to ship on March 24, 2025
$572.00
Sigma-Aldrich
Chloroform, puriss. p.a., reag. ISO, reag. Ph. Eur., 99.0-99.4% (GC)
Sign Into View Organizational & Contract Pricing
SKUPack SizeAvailabilityPriceQuantity
1 vial
Estimated to ship on March 24, 2025
$168.00
5 vials
Estimated to ship on March 24, 2025
$572.00
Sigma-Aldrich
Chloroform, contains 100-200 ppm amylenes as stabilizer, ≥99.5%
Sign Into View Organizational & Contract Pricing
SKUPack SizeAvailabilityPriceQuantity
1 vial
Estimated to ship on March 24, 2025
$168.00
5 vials
Estimated to ship on March 24, 2025
$572.00
Sigma-Aldrich
Chloroform, biotech. grade, ≥99.8%, contains 0.5-1.0% ethanol as stabilizer
Sign Into View Organizational & Contract Pricing
SKUPack SizeAvailabilityPriceQuantity
1 vial
Estimated to ship on March 24, 2025
$168.00
5 vials
Estimated to ship on March 24, 2025
$572.00
Sigma-Aldrich
Chloroform, ACS spectrophotometric grade, ≥99.8%, contains 0.5-1.0% ethanol as stabilizer
Sign Into View Organizational & Contract Pricing
SKUPack SizeAvailabilityPriceQuantity
1 vial
Estimated to ship on March 24, 2025
$168.00
5 vials
Estimated to ship on March 24, 2025
$572.00
Sigma-Aldrich
Chloroform, contains ethanol as stabilizer, meets analytical specification of BP, 99-99.4% (GC)
Sign Into View Organizational & Contract Pricing
SKUPack SizeAvailabilityPriceQuantity
1 vial
Estimated to ship on March 24, 2025
$168.00
5 vials
Estimated to ship on March 24, 2025
$572.00
Sigma-Aldrich
Chloroform, contains amylenes as stabilizer, ACS reagent, ≥99.8%
Sign Into View Organizational & Contract Pricing
SKUPack SizeAvailabilityPriceQuantity
1 vial
Estimated to ship on March 24, 2025
$168.00
5 vials
Estimated to ship on March 24, 2025
$572.00
Supelco
Chloroform, Pharmaceutical Secondary Standard; Certified Reference Material
Sign Into View Organizational & Contract Pricing
SKUPack SizeAvailabilityPriceQuantity
1 vial
Estimated to ship on March 24, 2025
$168.00
5 vials
Estimated to ship on March 24, 2025
$572.00
Supelco
Chloroform, suitable for HPLC, ≥99.8%, contains 0.5-1.0% ethanol as stabilizer
Sign Into View Organizational & Contract Pricing
SKUPack SizeAvailabilityPriceQuantity
1 vial
Estimated to ship on March 24, 2025
$168.00
5 vials
Estimated to ship on March 24, 2025
$572.00
Sigma-Aldrich
β-D-Allose, rare aldohexose sugar
Sign Into View Organizational & Contract Pricing
SKUPack SizeAvailabilityPriceQuantity
1 vial
Estimated to ship on March 24, 2025
$168.00
5 vials
Estimated to ship on March 24, 2025
$572.00
Sigma-Aldrich
Colchicine, BioReagent, suitable for plant cell culture, ≥95% (HPLC)
Sign Into View Organizational & Contract Pricing
SKUPack SizeAvailabilityPriceQuantity
1 vial
Estimated to ship on March 24, 2025
$168.00
5 vials
Estimated to ship on March 24, 2025
$572.00
Sigma-Aldrich
Colchicine, ≥95% (HPLC), powder
Sign Into View Organizational & Contract Pricing
SKUPack SizeAvailabilityPriceQuantity
1 vial
Estimated to ship on March 24, 2025
$168.00
5 vials
Estimated to ship on March 24, 2025
$572.00
Colchicine, (European Pharmacopoeia (EP) Reference Standard)
Sign Into View Organizational & Contract Pricing
SKUPack SizeAvailabilityPriceQuantity
1 vial
Estimated to ship on March 24, 2025
$168.00
5 vials
Estimated to ship on March 24, 2025
$572.00
Supelco
Residual Solvent - Chloroform, Pharmaceutical Secondary Standard; Certified Reference Material
Sign Into View Organizational & Contract Pricing
SKUPack SizeAvailabilityPriceQuantity
1 vial
Estimated to ship on March 24, 2025
$168.00
5 vials
Estimated to ship on March 24, 2025
$572.00