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PubMed1983

Induction of DNA strand breaks and chromosome abnormalities by an imide derivative of 3-nitro-1,8-naphthalic acid (mitonafide) in Chinese hamster ovary cells.

Mitonafide (5-nitro-2-(2-dimethylaminoethyl)-benzo- [de]isoquinoline-1,3-dione hydrochloride), a new candidate as an anticancer or antiviral agent, inhibited the incorporation of DNA precursors into the acid-insoluble fractions of cultured Chinese hamster ovary (CHO) cells and also into CHO cells made permeable (i.e., "permeabilized") that were supplemented with ATP and deoxynucleoside triphosphates. Mitonafide enhanced the degradation of previously incorporated [3H]thymidine and increased the amount of DNA recovered in fractions containing single-stranded DNA after alkaline denaturation and hydroxyapatite chromatography. At concentrations of 0.01 and 1.0 microM, respectively, mitonafide increased the frequency of sister chromatid exchanges and chromosome aberrations in CHO cells. The inhibition of DNA synthesis in a permeabilized cell system suggested that mitonafide acted on the DNA-synthesizing apparatus without requiring metabolic conversion and interfered with DNA synthesis independent of the cellular metabolism of DNA precursors. Mitonafide induced DNA strand breaks and chromosome abnormalities in cultured cells.

Animals↗
PubMed2003

Chiral inversion of the second generation IMiD CC-4047 (ACTIMID ) in human plasma and phosphate-buffered saline.

CC-4047 is a racemic second-generation immunomodulatory drug currently in clinical development for various oncologic indications. It has potent effects on key cytokines including tumor necrosis factor-alpha, interleukin (IL-10), and interferon (IFN-gamma). The S-isomer of CC-4047 has been reported to be the more potent enantiomer of the racemate. In this article we report on the rapid racemization of the S-isomer of CC-4047 in human plasma and phosphate-buffered saline. These results support the further development of the racemate instead of the S-isomer.

Adjuvants, Immunologic↗
PubMed2006

Highly functionalized glyco-conjugated hexahydroazepindiones from saccharide imides via the Norrish type II reaction.

Starting from readily available protected 6-tosylates of D-glucose and D-mannose in both their pyranoside and furanoside forms as well as 6-tosylates of alpha-D-galactopyranose, the corresponding primary succinimido derivatives were obtained in good yield by nucleophilic displacement with potassium succinimide. These imido sugars were photochemically transformed into hexahydroazepindione derivatives such as by means of a Norrish type II reaction. As expected, the intramolecular alkylation proceeded via an 1,6 H-abstraction leading to a stabilized diradical. The regiochemistry of the photoreaction was controlled by configurational, conformational and electronic features and was sometimes influenced by the protecting groups. Using this route, a facile approach to a novel class of highly functionalized sugar derived heterocycles was developed.

Alkylation↗
PubMed2005

Nanoparticles fabricated by selective reaction of Fe100-xPtx alloy films during imidization of polyamic acid.

Nanoparticles with different morphology and composition were fabricated inside a polyimide (PI) matrix based on selectively oxidizing a layer of Fe(100-x)Pt(x) alloy metal film sandwiched between two PI precursor layers. Gamma-Fe2O3, Pt, and Fe3Pt nanoparticles were formed in a monolayer between two PI layers, depending on the alloy film composition and curing conditions. These particles were well-crystallized and sized between 4 and 10 nm. X-ray photoelectron spectroscopy confirmed that Fe in the film preferentially reacted with the organic matrix whereas Pt remained metallic throughout the curing process, which enabled fabrication of particles different morphology and composition. This process can be easily extended to other alloy films, which provides an opportunity to fabricate nanoparticles relatively easily with desired composition and morphology embedded in an inert organic matrix.

Journal Article↗