Synthesis, Characterization and Evaluation of Cytotoxic Activities of Novel Aziridinyl Phosphonic Acid Derivatives

New aziridine 2-phosphonic acids were prepared by monohydrolysis of the aziridine 2-phosphonates that were obtained by the modified Gabriel-Cromwell reaction of vinyl phosphonate or alpha-tosylvinyl phosphonate with a primary amine or a chiral amine. The cellular cytotoxicity of these compounds was tested against the HCT-116 colorectal cancer cell lines and the CCD-18Co normal colon fibroblast lines using the MTT assay. Three of the synthesized phosphonic acid derivatives 2e (ethyl hydrogen {(2S)-1-[(1S)-1-(naphthalen-2-yl)ethyl]aziridin-2-yl}phosphonate), 2h (ethyl hydrogen (1-benzylaziridin-2-yl)phosphonate), and 2i (ethyl hydrogen (1-cyclohexylaziridin-2-yl)phosphonate) showed higher cytotoxicity than the reference cancer treatment agent etoposide. Cell death was through a robust induction of apoptosis even more effectively than etoposide, a well-known apoptosis inducing agent.


Cyclization of RGD Peptides by Suzuki-Miyaura Cross-Coupling
Kemker, Isabell; Schnepel, Christian; Schroeder, David C.; Marıon, Antoıne; Sewald, Norbert (American Chemical Society (ACS), 2019-08-22)
Halogenated L- or D-tryptophan obtained by biocatalytic halogenation was incorporated into RGD peptides together with a variety of alkyl or aryl boronic acids. Suzuki-Miyaura cross-coupling either in solution or on-resin results in side chain-to-tail-cyclized RGD peptides, for example, with biaryl moieties, providing a new dimension of structure-activity relationships. An array of RGD peptides differing in macrocycle size, the presence of D-amino acid, N-methylation, or connectivity between the indole moiet...
Synthesis and characterization of a new soluble conducting polymer and its electrochromic device
Varis, Serhat; Ak, Metin; Tanyeli, Cihangir; Akhmedov, Idris Mecidoglu; Toppare, Levent Kamil (Elsevier BV, 2006-12-01)
A mixture of isomers 2,5-di(4-methyl-thiophen-2-yl)-1-(4-nitrophenyl)-1H-pyrrole, 2-(4-methyl-thiophen-2-yl)-5-(3-methyl-thiophen-2-yl)1-(4-nitrophenyl)-1H-pyrrole and 2,5-di(3-methyl-thiophen-2-yl)-1-(4-nitrophenyl)-1H-pyrrole (Me-SNS(NO2)) were synthesized. Resulting monomers were polymerized chemically, producing soluble polymers in common organic solvents. The average molecular weight has been determined by gel permeation chromatography (GPC) as Mn = 5.6 x 10(3) for the chemically synthesized polymer. T...
ARINC, E; Güray, Nülüfer Tülün; SAPLAKOGLU, U; Adalı, Orhan (Elsevier BV, 1992-01-01)
1. Two forms of soluble NADH cytochrome b5 reductase were purified from human erythrocytes. Two distinct fractions both having the NADH cytochrome b5 reductase activity eluted from the second DEAE-cellulose column were further purified by ultrafiltration and 5'-ADP-agarose affinity chromatography.
Bioproduction, structure elucidation and in vitro antiproliferative effect of eumelanin pigment from Streptomyces parvus BSB49
Bayram, Sinan; Dengiz, Çağatay; GERÇEK, Yusuf Can; ÇETİN, İdil; TOPÇUL, Mehmet Rıfkı (Springer Science and Business Media LLC, 2020-01-01)
In this study, the structure of the purified extracellular eumelanin pigment isolated from Streptomyces spp. was elucidated by detailed analysis via two different spectroscopic techniques (FT-IR and NMR). In vitro antiproliferative effects of eumelanin were evaluated on HeLa cell line. These experiments were carried out with the evaluation of the parameters including cell viability, cell index, and mitotic index. With the cell viability and cell index, IC50 concentration of eumelanin was determined as 10 μM...
Chemoselective Immobilization of Proteins by Microcontact Printing and Bio-orthogonal Click Reactions
Tolstyka, Zachary P.; Richardson, Wade; Bat, Erhan; Stevens, Caitlin J.; Parra, Dayanara P.; Dozier, Jonathan K.; Distefano, Mark D.; Dunn, Bruce; Maynard, Heather D. (Wiley, 2013-12-16)
Herein, a combination of microcontact printing of functionalized alkanethiols and site-specific modification of proteins is utilized to chemoselectively immobilize proteins onto gold surfaces, either by oxime- or copper-catalyzed alkyne-azide click chemistry. Two molecules capable of click reactions were synthesized, an aminooxy-functionalized alkanethiol and an azide-functionalized alkanethiol, and self-assembled monolayer (SAM) formation on gold was confirmed by IR spectroscopy. The alkanethiols were then...
Citation Formats
R. Khan, S. Ulusan, S. Banerjee, and Ö. Doğan, “Synthesis, Characterization and Evaluation of Cytotoxic Activities of Novel Aziridinyl Phosphonic Acid Derivatives,” CHEMISTRY & BIODIVERSITY, pp. 0–0, 2019, Accessed: 00, 2020. [Online]. Available: