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Chapter 29 : Coumarin Antibiotics: Novobiocin, Coumermycin, and Clorobiocin

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Coumarin Antibiotics: Novobiocin, Coumermycin, and Clorobiocin, Page 1 of 2

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Abstract:

This chapter provides an overview about coumarin antibiotics such as novobiocin, coumermycin, and clorobiocin. Novobiocin was the first antibacterial agent of this chemical class to be described. Two other chemical entities have been described in this chapter: the coumermycin complex and clorobiocin. Clorobiocin is composed of an 8-amino chlorocoumarin nucleus, a sugar (L-noviose substituted with a 5-methyl-1H-pyrrole-2-carboxylic moiety), and a benzoic chain identical to that of novobiocin. Two products are identical to coumermycin A (sugordomycin D-1a and sugordomycin D-1d). BL-C43 is active against gram-positive cocci and bacilli and against certain fastidious gram-negative bacilli, such as , , , and gram-negative cocci such as . It is inactive against and nonfermentative gram-negative bacilli. This molecule appears to be slightly less active in vitro than novobiocin, but it is more active than lincomycin or erythromycin A. The determination of susceptibility by the antibiotic sensitivity test method involves disks with a dose of 5 µg. Antibacterial activities of natural coumarinic acid derivatives are listed in this chapter. Novobiocin binds to the 24-kDa protein fragment and stabilizes the structure so as to prevent the binding of triphosphate nucleosides. This reduces the pool of available enzymes and inhibits the hydrolysis of ATP. Novobiocin is well absorbed by the gastrointestinal tract. Less than 3% of the administered dose is eliminated in the urine; the drug is mainly eliminated in the bile. Concentrations in the feces are high.

Citation: Bryskier A, Klich M. 2005. Coumarin Antibiotics: Novobiocin, Coumermycin, and Clorobiocin, p 816-825. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch29
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Citation: Bryskier A, Klich M. 2005. Coumarin Antibiotics: Novobiocin, Coumermycin, and Clorobiocin, p 816-825. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch29
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Citation: Bryskier A, Klich M. 2005. Coumarin Antibiotics: Novobiocin, Coumermycin, and Clorobiocin, p 816-825. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch29
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Citation: Bryskier A, Klich M. 2005. Coumarin Antibiotics: Novobiocin, Coumermycin, and Clorobiocin, p 816-825. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch29
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Citation: Bryskier A, Klich M. 2005. Coumarin Antibiotics: Novobiocin, Coumermycin, and Clorobiocin, p 816-825. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch29
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Citation: Bryskier A, Klich M. 2005. Coumarin Antibiotics: Novobiocin, Coumermycin, and Clorobiocin, p 816-825. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch29
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Citation: Bryskier A, Klich M. 2005. Coumarin Antibiotics: Novobiocin, Coumermycin, and Clorobiocin, p 816-825. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch29
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Citation: Bryskier A, Klich M. 2005. Coumarin Antibiotics: Novobiocin, Coumermycin, and Clorobiocin, p 816-825. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch29
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Citation: Bryskier A, Klich M. 2005. Coumarin Antibiotics: Novobiocin, Coumermycin, and Clorobiocin, p 816-825. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch29
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Citation: Bryskier A, Klich M. 2005. Coumarin Antibiotics: Novobiocin, Coumermycin, and Clorobiocin, p 816-825. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch29
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Citation: Bryskier A, Klich M. 2005. Coumarin Antibiotics: Novobiocin, Coumermycin, and Clorobiocin, p 816-825. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch29
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Citation: Bryskier A, Klich M. 2005. Coumarin Antibiotics: Novobiocin, Coumermycin, and Clorobiocin, p 816-825. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch29
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References

/content/book/10.1128/9781555815929.ch29
1. Drusano GL,, Townsend RJ,, Walsh TJ,, Forrest A,, Antal EJ,, Standiford HC, 1986, Steady-state serum pharmacokinetics of novobiocin and rifampin alone and in combination, Antimicrob Agents Chemother, 30, 4245.
2. Ferroud D,, Collard J,, Klich M,, Dupuis-Hamelin C,, Mauvais P,, Lassaigne P,, Bonnefoy A,, Musicki B, 1999, Synthesis and biological evaluation of coumarin carboxylic acids as inhibitors of gyrase B: l-rhamnose as an effective substitute for l-noviose, Bioorg Med Chem Lett, 9, 28812886.
3. Galm U,, Heller S,, Shapiro S,, Page M,, Li S-M,, Heide L, 2004, Antimicrobial and DNA gyrase-inhibitory activities of novel clorobiocin derivatives produced by mutasynthesis, Antimicrob Agents Chemother, 48, 13071312.
4. Laurin P,, Ferroud D,, Klich M,, Dupuis-Hamelin C,, Mauvais P,, Lassaigne P,, Bonnefoy A,, Musicki B, 1999, Synthesis and in vitro evaluation of novel highly potent coumarin inhibitors of gyrase B, Bioorg Med Chem Lett, 9, 20792084.
5. Laurin P,, Ferroud D,, Schio L,, Klich M,, Dupuis-Hamelin C,, Mauvais P,, Lassaigne P,, Bonnefoy A,, Musicki B, 1999, Structure activity relationship in two series of aminoalkyl substituted coumarin inhibitors of gyrase B, Bioorg Med Chem Lett, 9, 28752880.
6. Meyer CE, 1964, Rubradirin, a new antibiotic. II. Isolation and characterization, Antimicrob Agents Chemother, 10, 9799.
7. Musicki B,, Periers A-M,, Laurin P,, Ferroud D,, Benedetti Y,, Lachaud S, et al, 2000, Improved antibacterial activities of coumarinic antibiotics bearing 5,5′-dialkylnoviose: biological activity of RU 79115, Bioorg Med Chem Lett, 10, 16951699.
8. Periers A-M,, Laurin P,, Ferroud D,, Haesslein J-L,, Klich M,, Dupuis-Hamelin C,, Mauvais P,, Lassaigne P,, Bonnefoy A,, Musicki B, 2000, Coumarin inhibitors of gyrase B with N-propargyloxy-carbamate as an effective pyrrole bioisostere, Bioorg Med Chem Lett, 10, 161165.
9. Shen G,, Yu XM,, Blagg SJ, 2000, Syntheses of photolabile novobiocin analogues, Bioorg Med Chem Lett, 14, 59035906.
10. Yun B-G,, Huang W,, Hartson SD,, Matts RL, 2004, Novobiocin induces a distinct conformation of Hsp90 and alters Hsp90-cochaperone-client interactions, Biochemistry, 43, 82178229.

Tables

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Table 1

Citation: Bryskier A, Klich M. 2005. Coumarin Antibiotics: Novobiocin, Coumermycin, and Clorobiocin, p 816-825. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch29
Generic image for table
Table 2

Citation: Bryskier A, Klich M. 2005. Coumarin Antibiotics: Novobiocin, Coumermycin, and Clorobiocin, p 816-825. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch29
Generic image for table
Table 3

Citation: Bryskier A, Klich M. 2005. Coumarin Antibiotics: Novobiocin, Coumermycin, and Clorobiocin, p 816-825. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch29
Generic image for table
Table 4

Citation: Bryskier A, Klich M. 2005. Coumarin Antibiotics: Novobiocin, Coumermycin, and Clorobiocin, p 816-825. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch29
Generic image for table
Table 5

Citation: Bryskier A, Klich M. 2005. Coumarin Antibiotics: Novobiocin, Coumermycin, and Clorobiocin, p 816-825. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch29
Generic image for table
Table 6

Citation: Bryskier A, Klich M. 2005. Coumarin Antibiotics: Novobiocin, Coumermycin, and Clorobiocin, p 816-825. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch29
Generic image for table
Table 7

Citation: Bryskier A, Klich M. 2005. Coumarin Antibiotics: Novobiocin, Coumermycin, and Clorobiocin, p 816-825. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch29
Generic image for table
Table 8

Citation: Bryskier A, Klich M. 2005. Coumarin Antibiotics: Novobiocin, Coumermycin, and Clorobiocin, p 816-825. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch29
Generic image for table
Table 9

Citation: Bryskier A, Klich M. 2005. Coumarin Antibiotics: Novobiocin, Coumermycin, and Clorobiocin, p 816-825. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch29
Generic image for table
Table 10

Citation: Bryskier A, Klich M. 2005. Coumarin Antibiotics: Novobiocin, Coumermycin, and Clorobiocin, p 816-825. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch29
Generic image for table
Table 11

Citation: Bryskier A, Klich M. 2005. Coumarin Antibiotics: Novobiocin, Coumermycin, and Clorobiocin, p 816-825. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch29
Generic image for table
Table 12

Citation: Bryskier A, Klich M. 2005. Coumarin Antibiotics: Novobiocin, Coumermycin, and Clorobiocin, p 816-825. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch29
Generic image for table
Table 13

Citation: Bryskier A, Klich M. 2005. Coumarin Antibiotics: Novobiocin, Coumermycin, and Clorobiocin, p 816-825. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch29
Generic image for table
Table 14

Citation: Bryskier A, Klich M. 2005. Coumarin Antibiotics: Novobiocin, Coumermycin, and Clorobiocin, p 816-825. In Bryskier, M.D. A (ed), Antimicrobial Agents. ASM Press, Washington, DC. doi: 10.1128/9781555815929.ch29

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