Skip to Content
MilliporeSigma
  • Synthesis and characterization of the anticancer and metal binding properties of novel pyrimidinylhydrazone derivatives.

Synthesis and characterization of the anticancer and metal binding properties of novel pyrimidinylhydrazone derivatives.

Journal of inorganic biochemistry (2015-01-16)
Veronika F S Pape, Dóra Türk, Pál Szabó, Michael Wiese, Eva A Enyedy, Gergely Szakács
ABSTRACT

Three novel pyrimidinylhydrazones substituted at either the aromatic moiety or at the imine carbon atom were synthesized and characterized by standard analytical methods. All compounds were found to be toxic in the micro- to submicromolar range against a diverse panel of cancer cell lines including multidrug resistant (MDR) derivatives expressing P-glycoprotein (Pgp). UV-visible spectrophotometry experiments demonstrated that the most active compound (3) forms highly stable complexes with iron(III) and copper(II) in a wide pH range with a stronger preference towards iron(III). The redox activity of the iron and copper complexes of ligand 3 was investigated using cyclic voltammetry and was tested with cellular reductants. The impact of reactive oxygen species (ROS) on the mechanism of toxicity was assessed using the ROS-sensitive cell permeable dye 2',7'-dichlorofluorescin diacetate (DCFDA). Our results demonstrate that the studied pyrimidinylhydrazones form redox-active iron and copper complexes that are capable of producing intracellular ROS, which might lead to cellular damage and cell death in cancer cells regardless of their resistance status.

MATERIALS
Product Number
Brand
Product Description

Supelco
L-Ascorbic acid, analytical standard
Sign Into View Organizational & Contract Pricing
Sigma-Aldrich
L-Ascorbic acid, puriss. p.a., ≥99.0% (RT)
Sign Into View Organizational & Contract Pricing
Sigma-Aldrich
L-Ascorbic acid, suitable for cell culture, suitable for plant cell culture, ≥98%
Sign Into View Organizational & Contract Pricing
Sigma-Aldrich
L-Ascorbic acid, FCC, FG
Sign Into View Organizational & Contract Pricing
Supelco
Potassium hydroxide concentrate, 0.1 M KOH in water (0.1N), Eluent concentrate for IC
Sign Into View Organizational & Contract Pricing
USP
Acetylcysteine, United States Pharmacopeia (USP) Reference Standard
Sign Into View Organizational & Contract Pricing
Acetylcysteine, European Pharmacopoeia (EP) Reference Standard
Sign Into View Organizational & Contract Pricing
SAFC
HEPES
Sign Into View Organizational & Contract Pricing
Sigma-Aldrich
2′,7′-Dichlorodihydrofluorescein diacetate, ≥97%
Sign Into View Organizational & Contract Pricing
Sigma-Aldrich
L-Ascorbic acid, powder, suitable for cell culture, γ-irradiated
Sign Into View Organizational & Contract Pricing
Sigma-Aldrich
L-Ascorbic acid, meets USP testing specifications
SKU
Pack Size
Availability
Price
Quantity
Sigma-Aldrich
L-Ascorbic acid, reagent grade, crystalline
SKU
Pack Size
Availability
Price
Quantity
Sigma-Aldrich
L-Ascorbic acid, reagent grade
SKU
Pack Size
Availability
Price
Quantity
Sigma-Aldrich
HEPES, BioPerformance Certified, ≥99.5% (titration), suitable for cell culture
SKU
Pack Size
Availability
Price
Quantity
Sigma-Aldrich
HEPES, BioXtra, suitable for mouse embryo cell culture, ≥99.5% (titration)
SKU
Pack Size
Availability
Price
Quantity
Sigma-Aldrich
HEPES, BioXtra, pH 5.0-6.5 (1 M in H2O), ≥99.5% (titration)
SKU
Pack Size
Availability
Price
Quantity
Sigma-Aldrich
L-Ascorbic acid, BioXtra, ≥99.0%, crystalline
SKU
Pack Size
Availability
Price
Quantity
Sigma-Aldrich
L-Ascorbic acid, ACS reagent, ≥99%
SKU
Pack Size
Availability
Price
Quantity
Sigma-Aldrich
L-Ascorbic acid, puriss. p.a., ACS reagent, reag. ISO, Ph. Eur., 99.7-100.5% (oxidimetric)
SKU
Pack Size
Availability
Price
Quantity
Sigma-Aldrich
L-Ascorbic acid, 99%
SKU
Pack Size
Availability
Price
Quantity
Sigma-Aldrich
L-Ascorbic acid, tested according to Ph. Eur.
SKU
Pack Size
Availability
Price
Quantity
Sigma-Aldrich
HEPES, BioUltra, for molecular biology, ≥99.5% (T)
SKU
Pack Size
Availability
Price
Quantity
Sigma-Aldrich
L-Ascorbic acid, BioUltra, ≥99.5% (RT)
SKU
Pack Size
Availability
Price
Quantity
Supelco
L-Ascorbic acid, certified reference material, TraceCERT®, Manufactured by: Sigma-Aldrich Production GmbH, Switzerland
SKU
Pack Size
Availability
Price
Quantity
Glutathione, European Pharmacopoeia (EP) Reference Standard
SKU
Pack Size
Availability
Price
Quantity
Supelco
Glutathione, Pharmaceutical Secondary Standard; Certified Reference Material
SKU
Pack Size
Availability
Price
Quantity
SAFC
HEPES
SKU
Pack Size
Availability
Price
Quantity
Sigma-Aldrich
HEPES, anhydrous, free-flowing, Redi-Dri, ≥99.5%
SKU
Pack Size
Availability
Price
Quantity
Supelco
HEPES, Pharmaceutical Secondary Standard; Certified Reference Material
SKU
Pack Size
Availability
Price
Quantity
Sigma-Aldrich
Amyloid Protein Non-Aβ Component, ≥80% (HPLC)
SKU
Pack Size
Availability
Price
Quantity