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292 Chemistry and Biology of Beta-Lactams
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FIGURE 9.20 Cumulative MIC distributions for Enterobacteriaceae (181 strains) (a) and P. aeruginosa (206 strains) (b).
Adapted with permission from Page MGP et al. (2010).
development of some promising new clinical candidates in the eld of neurodegenerative diseases and
the treatment of hemostasis. In terms of their antibacterial activity, there is still room for improvement
and a broadening of their spectrum of action, particularly in Gram-positive bacteria and PBPs that are
drug insensitive, as well as to increase the stability of their beta-lactamase enzymes.
It is known that monobactams are natural antibiotic compounds that are characterized by the presence
of a monocyclic ring structure. In other words, the compounds are monocyclic, beta-lactam antibiotics
that are produced by bacteria. It should be noted that the beta-lactam ring is not fused to another ring, contrary to what is found in most other beta-lactams.
164
There are many natural soil inhabitants that produce
293Medicinal Activities of Beta-Lactams as Antibacterials
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FIGURE 9.21 Bactericidal action of BAL30072 and comparators against representative strains of P. aeruginosa, E.
cloacae, and S. maltophilia. Adapted with permission from Page MGP et al. (2010).
these monocyclic beta-lactams, which include Chromobacterium, Agrobacterium, Gluconobacter,
Flexibacter, and Pseudomonas species that are present in the soil. These bacteria produce compounds
that exhibit weak antimicrobial activity, but through the modication of the chemical side chains, it
is possible to improve both the spectrum and the stability of the compounds produced by these bacteria. Only Gram-negative aerobic bacteria can be effectively treated with monobactams, for example,
Neisseria and Pseudomonas. In order to treat MDR microorganisms, the use of siderophore-conjugated
monobactams is promising.
There is no cross-reactivity between monobactam antibiotics and penicillin, but there has been some
cross-reactivity with cephalosporin antibiotics, especially ceftazidime, which has an identical side chain
to aztreonam, although it is untested. The risk of seizures being triggered by monobactams is slightly
lower than the risk of seizures being triggered by penicillin in patients with a history of seizures.
As a monocyclic beta-lactam containing an N1-sulfonic acid substituent, aztreonam originated from
a novel antibiotic isolated from the New Jersey Pine Barrens and is the only monobactam to have been
approved for therapeutic use. The drug is effective against aerobic enteric bacteria and P. aeruginosa,
165
294 Chemistry and Biology of Beta-Lactams
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FIGURE 9.22 Effects of the addition after 60 min of incubation of BAL30072 (MIC=0.25 µg/mL) (a) and aztreonam
(MIC=0.06 µg/mL) (b) on the optical density of growing E. coli W3110 cultures. Adapted with permission from Page MGP
et al. (2010).
with MICs of greater than 50 µg/mL against S. aureus, S. pneumoniae, and E. faecalis.
to PBP3 in Gram-negative rods, with weaker binding to PBP1a, leading to lamentation followed by
cell lysis. It is important to note that aztreonam was stable to hydrolysis by all of the common betalactamases when it was rst introduced to clinical practice; however, the introduction of ESBLs and serine carbapenemase has since made it less effective against MDR beta-lactamases producing organisms
(Figure 9.19).
167
for the hydrolysis of monobactams by MBLs, thus making this monobactam a good candidate for use
in combination therapy with a serine beta-lactamase inhibitor to treat infections caused by multi-betalactamase-producing bacteria.
It has been shown that BAL30072 is a novel monosulfactam with an N1-O-sulfate group, a 3-dihydropyridone siderophore substituent for improved activity, and a 4-gem-dimethyl substitution on the ring of
the azetidinone.
against a number of nonfermentative bacteria. The increased penetration of BAL30072 via iron uptake
mechanisms has resulted in it being more potent against some Gram-negative bacteria than other betalactams; it has an 8- to 256-fold better activity against Acinetobacter spp. and Burkholderia spp. than imipenem (Figures 9.20 –9.22). This drug is susceptible to hydrolysis by ESBLs and many carbapenemases,
166
It binds tightly
There is, however, some evidence that the monobactam nucleus is not a good substrate
168
Compared to aztreonam, the spectrum of its activity is similar, but it also has activity
295Medicinal Activities of Beta-Lactams as Antibacterials
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and it has shown synergistic activity when it has been combined with beta-lactamase inhibitors
meropenem.
170, 171
Similar to aztreonam, it is stable to hydrolysis by MBLs; additionally, in comparison
169
or
to aztreonam, it was hydrolyzed 3000-fold less efciently by the KPC-2 serine carbapenemase.
9.7 Conclusion
A comprehensive review of the beta-lactam antibiotics that are currently in use as well as a look ahead
to several new compounds that are in the process of being developed is presented here. Due to the widespread therapeutic dependence on these effective and safe antibiotics, beta-lactam resistance continues to
increase, especially among Gram-negative organisms, as a result of the widespread use of these antibiotics. Beta-lactamases are one of the most prevalent and one of the most damaging resistance mechanisms
among Gram-negative pathogens. Beta-lactamases are chromosomally encoded enzymes that may be
produced at high levels, as well as transferable enzymes that travel through mobile elements between
species. As a countermeasure to the emergence of resistance, perhaps the most promising prospect is the
development of new classes of beta-lactamase inhibitors, which will provide protection for some of the
most important antibiotics in clinical practice, for the time being at least.
Acknowledgments
AD is grateful to CEA-Grenoble, Joseph Fourier University, University of Göttingen, and University of
California, Los Angeles, for their support. BKB is grateful to the US NIH, the US NCI, Texas Kleberg
Foundation, Stevens Institute of Technology, University of Texas MD Anderson Cancer Center, University
of Texas-Pan American, and Community Health Systems of Texas for their nancial and moral support
to his research. AD and BKB are also grateful to their current employer, Prince Mohammad Bin Fahd
University.
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