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Chapter 6 : Antibiotics and Synthetic Antibacterial Agents

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Antibiotics and Synthetic Antibacterial Agents, Page 1 of 2

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Abstract:

In this chapter, the antibiotics and synthetic antibacterials are grouped on the basis of their chemical structure and by mechanism of action. Substructure groups are the penicillins, the cephalosporins, the carbapenems, the monobactams, and the β-lactam derivatives clavulanic acid, sulbactam and tazobactam, which are β-lactamase inhibitors. Fosfomycin [L-(cis)-1,2-epoxypropylphosphonic acid] (formerly known as phosphonomycin) is a naturally occurring antibiotic obtained from species of Streptomyces. The nitrofurans are a class of synthetic antibacterial agents characterized by the presence of a 5-nitro-2-furanoyl group. Some of the antibiotics that interfere with the biosynthesis of peptidoglycan are β-lactams (penicillins, cephalosporins, cephamycins, monobactams, and carbapenems), glycopeptides (vancomycin and teicoplanin), D-cycloserine, fosfomycin, and bacitracin. The bactericidal activity of the polymyxins and cationic antimicrobial peptides results from their interaction with the bacterial cytoplasmic membrane, causing gross disorganization of its structure. For growth and multiplication, microorganisms conduct a variety of biochemical and metabolic processes to obtain energy and new cell material. All industrial microbiology processes require the initial isolation of microorganisms from nature. Antibiotic-producing microorganisms are subjected to extensive genetic manipulations and modifications before they are used for antibiotic-manufacturing purposes. Nonpolar antibiotics are usually purified by solvent extraction procedures; water-soluble compounds are commonly purified by ion-exchange methods or chemical precipitation.

Citation: Mascaretti O. 2003. Antibiotics and Synthetic Antibacterial Agents, p 97-106. In Bacteria versus Antibacterial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555817794.ch6
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Figures

Image of Figure 6.1
Figure 6.1

Chemical structures of penicillins and cephalosporins.

Citation: Mascaretti O. 2003. Antibiotics and Synthetic Antibacterial Agents, p 97-106. In Bacteria versus Antibacterial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555817794.ch6
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Image of Figure 6.2
Figure 6.2

Chemical structure of gentamicin, an amino-glycoside antibiotic.

Citation: Mascaretti O. 2003. Antibiotics and Synthetic Antibacterial Agents, p 97-106. In Bacteria versus Antibacterial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555817794.ch6
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Image of Figure 6.3
Figure 6.3

Chemical structure of erythromycin A.

Citation: Mascaretti O. 2003. Antibiotics and Synthetic Antibacterial Agents, p 97-106. In Bacteria versus Antibacterial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555817794.ch6
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Image of Figure 6.4
Figure 6.4

Chemical structure of telithromycin. (Source: Hoechst Marion Roussel.)

Citation: Mascaretti O. 2003. Antibiotics and Synthetic Antibacterial Agents, p 97-106. In Bacteria versus Antibacterial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555817794.ch6
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Image of Figure 6.5
Figure 6.5

Chemical structure of tetracycline.

Citation: Mascaretti O. 2003. Antibiotics and Synthetic Antibacterial Agents, p 97-106. In Bacteria versus Antibacterial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555817794.ch6
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Image of Figure 6.6
Figure 6.6

Chemical structure of clindamycin.

Citation: Mascaretti O. 2003. Antibiotics and Synthetic Antibacterial Agents, p 97-106. In Bacteria versus Antibacterial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555817794.ch6
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Image of Figure 6.7
Figure 6.7

Chemical structure of rifampin.

Citation: Mascaretti O. 2003. Antibiotics and Synthetic Antibacterial Agents, p 97-106. In Bacteria versus Antibacterial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555817794.ch6
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Image of Figure 6.8
Figure 6.8

Chemical structure of vancomycin. aa, amino acid.

Citation: Mascaretti O. 2003. Antibiotics and Synthetic Antibacterial Agents, p 97-106. In Bacteria versus Antibacterial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555817794.ch6
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Image of Figure 6.9
Figure 6.9

Chemical structure of chloramphenicol.

Citation: Mascaretti O. 2003. Antibiotics and Synthetic Antibacterial Agents, p 97-106. In Bacteria versus Antibacterial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555817794.ch6
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Image of Figure 6.10
Figure 6.10

Chemical structure of polymyxin B1.

Citation: Mascaretti O. 2003. Antibiotics and Synthetic Antibacterial Agents, p 97-106. In Bacteria versus Antibacterial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555817794.ch6
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Image of Figure 6.11
Figure 6.11

Chemical structures of the methanesulfonates (mesylates) of quinupristin and dalfopristin.

Citation: Mascaretti O. 2003. Antibiotics and Synthetic Antibacterial Agents, p 97-106. In Bacteria versus Antibacterial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555817794.ch6
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Image of Figure 6.12
Figure 6.12

Chemical structure of mupirocin.

Citation: Mascaretti O. 2003. Antibiotics and Synthetic Antibacterial Agents, p 97-106. In Bacteria versus Antibacterial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555817794.ch6
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Image of Figure 6.13
Figure 6.13

Chemical structure of D-cycloserine.

Citation: Mascaretti O. 2003. Antibiotics and Synthetic Antibacterial Agents, p 97-106. In Bacteria versus Antibacterial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555817794.ch6
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Image of Figure 6.14
Figure 6.14

Chemical structure of fosfomycin.

Citation: Mascaretti O. 2003. Antibiotics and Synthetic Antibacterial Agents, p 97-106. In Bacteria versus Antibacterial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555817794.ch6
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Image of Figure 6.15
Figure 6.15

Chemical structure of linezolid.

Citation: Mascaretti O. 2003. Antibiotics and Synthetic Antibacterial Agents, p 97-106. In Bacteria versus Antibacterial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555817794.ch6
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Image of Figure 6.16
Figure 6.16

Chemical structure of ciprofloxacin.

Citation: Mascaretti O. 2003. Antibiotics and Synthetic Antibacterial Agents, p 97-106. In Bacteria versus Antibacterial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555817794.ch6
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Image of Figure 6.17
Figure 6.17

Chemical structure of sulfamethoxazole.

Citation: Mascaretti O. 2003. Antibiotics and Synthetic Antibacterial Agents, p 97-106. In Bacteria versus Antibacterial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555817794.ch6
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Image of Figure 6.18
Figure 6.18

Chemical structure of trimethoprim.

Citation: Mascaretti O. 2003. Antibiotics and Synthetic Antibacterial Agents, p 97-106. In Bacteria versus Antibacterial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555817794.ch6
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Image of Figure 6.19
Figure 6.19

Chemical structures of metronidazole and furazolidone.

Citation: Mascaretti O. 2003. Antibiotics and Synthetic Antibacterial Agents, p 97-106. In Bacteria versus Antibacterial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555817794.ch6
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Image of Figure 6.20
Figure 6.20

Schematic representation of the sites of action of antibacterial agents on a gram-negative bacterial cell.

Citation: Mascaretti O. 2003. Antibiotics and Synthetic Antibacterial Agents, p 97-106. In Bacteria versus Antibacterial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555817794.ch6
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Image of Figure 6.21
Figure 6.21

Strain improvement. Conventional strain improvement engineers the metabolism in a random manner. The mutated strains have to be screened or selected for the desired end point. Metabolic engineering with molecular genetic tools uses a preexisting knowledge database to produce strains that have directed and precise changes. Reprinted from A. Khetan and W.-S. Hu, p. 717–724, in A. L. Demain and J. E. Davies (ed.), Manual of Industrial Microbiology and Biotechnology, 2nd ed. (ASM Press, Washington, D.C., 1999), with permission from the publisher.

Citation: Mascaretti O. 2003. Antibiotics and Synthetic Antibacterial Agents, p 97-106. In Bacteria versus Antibacterial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555817794.ch6
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References

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1. Aharonowitz, Y.,, and G. Cohen. 1981. The microbiological production of pharmaceuticals. Sci. Am., 245:141152.
2. Borders, D., 1993. Antibiotics (survey), p. 107118. In M. Howe-Grant (ed.), Chemotherapeutics and Disease Control (Encyclopedia Reprint Series). John Wiley & Sons, Inc., New York, N.Y.
3. Demain, A. L.,, and J. E. Davies (ed.). 1999. Manual of Industrial Microbiology and Biotechnology, 2nd ed. ASM Press, Washington, D.C.
4. Demain, A.,, and N. A. Solomon. 1981. Industrial microbiology. Sci. Am. 245:6775.
5. Gaden, E. L. 1981. Production methods in industrial microbiology. Sci. Am. 245:181196.
6. Hopwood, D. A. 1981. The genetic programming of industrial microorganisms. Sci. Am. 245:91102.
7. Lal, R.,, R. Khanna,, H. Kaur,, M. Monisha,, N. Dhingra,, S. Lal,, K. H. Gaterman,, R. Eichenlaub,, and P. K. Ghosh. 1996. Engineering antibiotic producers to overcome the limitations of classical strain improvement programs. Crit. Rev. Microbiol. 22:201255.
8. Madigan, M. T.,, J. M. Martinko,, and J. Parker. 2000. Brock Biology of Microorganisms, 9th ed. Prentice-Hall, Upper Saddle River, N.J.
9. Phaff, H. J. 1981. Industrial microorganisms. Sci. Am. 245:7789.
10. Strohl, W. R. 1997. Biotechnology of Antibiotics, 2nd ed. Marcel Dekker, Inc., New York, N.Y.

Tables

Generic image for table
Table 6.1

Some industrial microorganisms that produce antibiotics

Citation: Mascaretti O. 2003. Antibiotics and Synthetic Antibacterial Agents, p 97-106. In Bacteria versus Antibacterial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555817794.ch6

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