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PubMed1998

Antimalarial activities of polyhydroxyphenyl and hydroxamic acid derivatives.

Several known mammalian ribonucleotide reductase inhibitors featuring a polyhydroxyphenyl and/or hydroxamate moiety as the active group were screened for potency in inhibiting growth of the malaria parasite Plasmodium falciparum. Compounds containing a 2,3- or 3,4-dihydroxyphenyl group as well as benzohydroxamate appear to be the most effective inhibitors of the malaria parasite.

Animals↗
PubMed1967

Iron-chelating hydroxamic acid (schizokinen) active in initiation of cell division in Bacillus megaterium.

Bacillus megaterium ATCC 19213 secretes a cell division-initiating "schizokinen" (SK) which accumulates during its culture cycle to a concentration inversely proportional to the iron added to a sucrose-mineral salts medium. Secreted SK was purified from culture filtrates as a red Fe (III) chelate, and a fraction with similar biological properties was obtained from whole cells. Infrared spectra of SK, and analyses of unhydrolyzed and acid-hydrolyzed preparations indicated it to be a secondary hydroxamate; visible absorption maxima of the ferric complex showed pH dependency typical of ferric monohydroxamates. Schizokinen preparations from cultures grown at "normal" and at low Fe concentrations were similar biologically and in certain of their chemical properties, but their R(F) values and infrared spectra suggested nonidentity. Significant lag reduction of B. megaterium was effected by 0.2 mmug of SK per ml; the Fe (III)-SK chelate and "iron-free" SK were equally effective. A 50-mmug amount produced half-maximal growth response of the siderochrome auxotroph, Arthrobacter JG-9. Schizokinen also overcame ferrimycin A inhibition of three Bacillus species. These properties relate the B. megaterium schizokinen to the trihydroxamate siderochromes, although SK appears to be a monohydroxamate.

Bacillus megaterium↗
PubMed2005

Synthesis and structure-activity relationships of beta- and alpha-piperidine sulfone hydroxamic acid matrix metalloproteinase inhibitors with oral antitumor efficacy.

alpha-Piperidine-beta-sulfone hydroxamate derivatives were explored that are potent for matrix metalloproteinases (MMP)-2, -9, and -13 and are sparing of MMP-1. The investigation of the beta-sulfones subsequently led to the discovery of hitherto unknown alpha-sulfone hydroxamates that are superior to the corresponding beta-sulfones in potency for target MMPs, selectivity vs MMP-1, and exposure when dosed orally. alpha-Piperidine-alpha-sulfone hydroxamate 35f (SC-276) was advanced through antitumor and antiangiogenesis assays and was selected for development. Compound 35f demonstrates excellent antitumor activity vs MX-1 breast tumor in mice when dosed orally as monotherapy or in combination with paclitaxel.

Administration, Oral↗
PubMed2004

Peptidyl hydroxamic acids as methionine aminopeptidase inhibitors.

A new class of methionine aminopeptidase (MetAP) inhibitors, which contain an internal hydroxamate (N-acyl-N-alkylhydroxylamine) core as the metal-chelating group, has been designed, synthesized, and tested. The compounds exhibited reversible, competitive inhibition against Escherichia coli MetAP as well as human MetAP-1 and MetAP-2. The most potent inhibitor had a K(i) value of 2.5 microM and >20-fold selectivity toward E. coli MAP.

Aminopeptidases↗
PubMed1988

A new group of antibiotics, hydroxamic acid antimycotic antibiotics. I. Precursor-initiated changes in productivity and biosynthesis of neoenactins NL1 and NL2.

Neoenactins (NEs) are L-serine-containing antifungal antibiotics produced by Streptoverticillium olivoreticuli. The effect of supplementation of individual amino acids on the production of NEs by this organism was examined from both quantitative and qualitative view points by using a nitrogen source-restricted medium. L-Alanine, L-arginine, L-glutamine, L-histidine, L-lysine and L-proline increased significantly the total productivity of NEs without changing the production ratio of the congeners. The supplementation of L-norvaline, L-isoleucine, L-leucine and L-valine to the culture medium resulted in selective enhancement of the production of NEs A, B1, B2, and M1, respectively, while significant change was not observed in terms of overall production of NEs. When L-norleucine was employed as an amino acid supplement, new NE congeners, named NEs NL1 and NL2, were preferentially produced; but the amount of NEs produced was not markedly affected.

Amino Acids↗