18992-11-5Relevant academic research and scientific papers
Tumor selectivity and transcriptional activation by azelaic bishydroxamic acid in human melanocytic cells
Parsons,Hansen,Fairlie,West,Danoy,Sturm,Dunn,Pedley,Ablett
, p. 1719 - 1724 (1997)
Azelaic bishydroxamic acid (ABHA), a potent differentiating agent for lymphoid cells, was selectively toxic for 5 human tumor cell lines and transformed human melanocytes and keratinocytes (dose for 37% survival, D37, 30-100 μg/mL) compared with normal cells (melanocytes, fibroblasts; D37 > 300 μg/mL). Dendritic morphology was the only indicator found for increased differentiation, markers for the pigmentation pathway being unchanged or inhibited by ABHA. In contrast to hexamethylene bisacetamide and azelaic acid. ABHA significantly increased the HIV LTR, SV40 and c-fos promoter activities during a 24 hr treatment. Metallothionein promoter activity was enhanced by 5 hr treatment with ABHA in a sensitive melanoma cell line (MM96L) but was inhibited in a more resistant line (HeLa); c-fos promoter activity was inhibited in HeLa during this time. Transcription from a p53 binding response element was inhibited in MM96L by a 24 hr ABHA treatment but enhanced in HeLa. ABHA may represent a structural prototype for designing more potent and selective anti-melanoma agents.
Conformational behaviour of hydroxamic acids: Ab initio and structural studies
Brown, David A.,Coogan, Raymond A.,Fitzpatrick, Noel J.,Glass, William K.,Abukshima, Dau E.,Shiels, Loreto,Ahlgren, Markku,Smolander, Kimmo,Pakkanen, Tuula T.,Pakkanen, Tapani A.,Peraekylae, Mikael
, p. 2673 - 2679 (1996)
The conformational behaviour of a series of monohydroxamic acids, p-RC6H4CONR 'OH (R = Me, R' = H Me; R = MeO, R' = H, Me; R = NO2, R' = H), and a series of dihydroxamic acids, (CH2)n (CONR'OH)2 (n = 3-8, 10, R' = H and n = 7, R' = Me), in methanol, DMSO and chloroform and in the solid state has been examined using IR and NMR spectroscopy. X-Ray crystal structure determinations of p-MeC6H4CONMeOH and the monohydrate of glutarodihydroxamic acid (n = 3) together with ab initio molecular orbital calculations for several hydrated and unhydrated hydroxamic acids have been performed. Hydrogen bonding effects are shown to be important in both the so id state and solution. The cis(Z) conformation of the hydroxamate group(s) (CONHOH) is preferentially stabilized by hydrogen bonding with water molecules.
A FACILE SYNTHESIS OF ALIPHATIC DIHYDROXAMIC ACIDS OF GENERAL FORMULA RONR'-CO-(CH2)n-CO-NR'OR
Brown, D. A.,Geraty, R. A.,Glennon, J. D.,Choileain, N. Ni
, p. 1159 - 1164 (2007/10/02)
Synthesis of dihydroxamic acids using dicarboxylic acids and N,N'-carbonyldiimidazole.
