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Aminoglycosides

Aminoglycosides: Streptomycin, Neomycin, Kanamycin

1 of 26
AMINOGLYCOSIDES:
Streptomycin, Neomycin,
Kanamycin
Introduction
Aminoglycoside is a medicinal and bacteriologic category of traditional Gram-negative
antibacterial medications that inhibit protein synthesis and contain as a portion of the molecule
an amino-modified glycoside (sugar).
The term can also refer more generally to any organic molecule that contains amino sugar
substructures.
Aminoglycoside antibiotics display bactericidal activity against Gram-negative aerobes and
some anaerobic bacilli where resistance has not yet arisen but generally not against Gram-
positive and anaerobic Gram-negative bacteria.
The first aminoglycoside, streptomycin, was isolated in 1943 from Streptomyces griseus by
Albert Schatz and Selman A. Waksan (reported in 1944).
It was a seminal discovery in the history of antibiotics since streptomycin was the first
effective treatment for tuberculosis as well as the first useful antibiotic derived from a
bacterial source.
Streptomycin lacks the common 2-deoxystreptamine moiety present in most other members of
this class. Other examples include the deoxystreptamine-containing agents kanamycin,
tobramycin, gentamicin, and neomycin.
2-Deoxystreptamine
Aminoglycosides

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Aminoglycosides

  • 2. Introduction Aminoglycoside is a medicinal and bacteriologic category of traditional Gram-negative antibacterial medications that inhibit protein synthesis and contain as a portion of the molecule an amino-modified glycoside (sugar). The term can also refer more generally to any organic molecule that contains amino sugar substructures.
  • 3. Aminoglycoside antibiotics display bactericidal activity against Gram-negative aerobes and some anaerobic bacilli where resistance has not yet arisen but generally not against Gram- positive and anaerobic Gram-negative bacteria. The first aminoglycoside, streptomycin, was isolated in 1943 from Streptomyces griseus by Albert Schatz and Selman A. Waksan (reported in 1944).
  • 4. It was a seminal discovery in the history of antibiotics since streptomycin was the first effective treatment for tuberculosis as well as the first useful antibiotic derived from a bacterial source. Streptomycin lacks the common 2-deoxystreptamine moiety present in most other members of this class. Other examples include the deoxystreptamine-containing agents kanamycin, tobramycin, gentamicin, and neomycin.
  • 14. Aminoglycosides that are derived from bacteria of the Streptomyces genus are named with the suffix -mycin, whereas those that are derived from Micromonospora are named with the suffix -micin.
  • 15. Mechanism of action Aminoglycosides binds to specific 30S-subunit ribosomal proteins. Protein synthesis is inhibited by them in at least three ways: ①They block the formation of initiation 70S ribosomal mRNA complex; ②They induce misreading of mRNA causes incorporation of incorrect amino acids into peptide resulting in a non-functional or abnormal protein synthesis. ③ They inhibit the combination of the releasing factor with the site A on ribosome prevent the synthesized peptide chain releasing from the 70S ribosomal mRNA complex and the 70S ribosomal mRNA complex dissociating into 30S and 50S subunits.
  • 22. SAR The aminoglycosides consist of two or more amino sugars joined in glycoside linkage to a highly substituted 1,3-diaminocyclo hexane (aminocyclitol), which is a centrally placed ring. The ring is a 2-deoxy streptamine in all aminoglycosides except streptomycin and dihydrostreptomycin, where it is streptidine.  In kanamycin and gentamycin families, two amino sugars are attached to 2-deoxy streptamine.  In streptomycin, two amino sugars are att ached to strepidine.  In neomycin family, there are amino sugars attached to 2-deoxy streptamine.
  • 23. - The aminoglycoside antibiotics contain two important structural features. They are amino sugar portion and centrally placed hexose ring, which is either 2-deoxystreptamine or streptidine. Amino sugar portion i. The bacterial inactivating enzymes targets C-6 and C-2 position and the substitution with methyl group at C-6 increases the enzyme resistance. ii. Cleavage of 3-hydroxyl or the 4-hydroxyl or both groups does not affect the activity.
  • 24. Centrally placed hexose ring (aminocyclitol ring)
  • 25. i. Various modifications at C-1 amino group have been tested. The acylation (e.g. amikacyn) and ethylation (e.g. 1-N-ethylsisomycin) though does not increase the activity helps to retain the antibacterial potency. ii. In sisomicin series, 2-hydroxylation and 5-deoxygenation result in the increased inhibition of bacterial inactivating enzyme systems. Thus, very few modifications of the central ring are possible, which do not violate the activity spectrum of aminoglycosides. https://www.youtube.com/watch?v=JbHp7CAyldc https://www.youtube.com/watch?v=ffZpkYHOxTg