Disease relevance of PENICILLANIC ACID

• Penicillanic acid sulfone: nature of irreversible inactivation of RTEM beta-lactamase from Escherichia coli [1].
• Mecillinam, a novel penicillanic acid derivative with unusual activity against gram-negative bacteria [2].
• Sensitivity of Yersinia pseudotuberculosis and Yersinia enterocolitica strains to a 6-beta-amidino penicillanic acid derivative [3].
• The concentrations for these penicillanic acid derivatives in prostatic interstitial fluid were above the minimal inhibitory concentrations for most of the commonly encountered gram-negative bacteria encountered in prostatitis [4].
• Tazobactam, a non-amino penicillanic acid sulfone, is a new beta-lactamase inhibitor and acts synergistically with piperacillin against clinical isolates of beta-lactamase-producing Bacteroides fragilis [5].

High impact information on PENICILLANIC ACID

• The ab initio quantum mechanical/molecular mechanical (QM/MM) calculations, augmented by extensive molecular dynamics simulations reported herein, describe the serine acylation mechanism for the class A TEM-1 beta-lactamase with penicillanic acid as substrate [6].
• Amdinocillin is a beta-amidino penicillanic acid derivative that binds specifically to penicillin-binding protein 2 [7].
• Beta-Secondary and solvent deuterium kinetic isotope effects have been determined for the steady-state kinetic parameters V/K and V for turnover of a depsipeptide substrate, m-[[(phenylacetyl)glycyl]-oxy]benzoic acid, and of a beta-lactam substrate, penicillanic acid, by three typical class A beta-lactamases and a class C beta-lactamase [8].
• An argument is presented to rationalize these observations on the basis of the leaving ability of thiolate, sulfenate, and sulfinate from the acyl-enzyme intermediates of penicillanic acid (2), the penicillanic acid S-oxides (3 and 4), and sulbactam, respectively [9].
• Cloning, characterization of the acyl-CoA:6-amino penicillanic acid acyltransferase gene of Aspergillus nidulans and linkage to the isopenicillin N synthase gene [10].

Biological context of PENICILLANIC ACID

• Sulbactam ([CP45,899] penicillanic acid sulfone) inhibits many of the beta-lactamases commonly found to be the cause of penicillin resistance [11].

Associations of PENICILLANIC ACID with other chemical compounds

• Two genes, pcbC and penDE (also named ips and aat, respectively) encoding the enzymes isopenicillin N synthase and acyl-CoA:6-amino penicillanic acid (6-APA) acyltransferase, which are involved in the penicillin biosynthetic pathway in Penicillium chrysogenum, were cloned [12].
• YTR 830, now known as tazobactam, is a new penicillanic acid sulfone beta-lactamase inhibitor [13].
• Beta-lactamase inhibition by acetylmethylene penicillanic acid compared to that of clavulanate and sulbactam [14].
• A series of 2 beta-[(4-substituted)-1,2,3-triazol-1-yl] methyl penicillanic acid sulfones was synthesized as beta-lactamase inhibitors [15].

Gene context of PENICILLANIC ACID

• Synthesis and biological evaluation of 6-bromo-6-substituted penicillanic acid derivatives as beta-lactamase inhibitors [16].

Analytical, diagnostic and therapeutic context of PENICILLANIC ACID

• A prospective, randomized, double-blinded study was undertaken to evaluate the effectiveness of Sulbactam (a new semisynthetic, injectable penicillanic acid sulfone) to inhibit beta-lactamase activity of bacteria in infections of the soft tissue [17].

References