FSL0879

Structure

• InChI=1S/C21H39N7O12/c1-5-21(36,4-30)16(40-17-9(26-2)13(34)10(31)6(3-29)38-17)18(37-5)39-15-8(28-20(24)25)11(32)7(27-19(22)23)12(33)14(15)35/h4-18,26,29,31-36H,3H2,1-2H3,(H4,22,23,27)(H4,24,25,28)
• InChIKey=UCSJYZPVAKXKNQ-UHFFFAOYSA-N

Synonyms

• 57-92-1
• Streptomycin
• Streptomycin-A

Origin

Streptomyces griseus

Biological activities

Inhibition of bacterial protein synthesis

Therapeutic

Antibacterial
Antituberculosis

Target

30S ribosomal protein S12

Assay information

Binding to ribosomal protein S12, a 30S subunit of the bacterial ribosome, causing protein synthesis inhibition
Antibacterial activity against Gram-(+) strains (MIC [μg/ml]: S. aureus, 0.125; B. subtilis, 0.25; E. coli, 1.0; P. aeruginosa, 0.5; M. kansasii, 3.13; M. intracellulare, 12.5)
Inhibition of the binding of the Tat protein to mRNA with IC₅₀ of 9.5 μM

References

• Med. Chem. Res., 22: 5789-5797 (2013)
• Holberger LE, Hayes CS
  Ribosomal protein S12 and aminoglycoside antibiotics modulate A-site mRNA cleavage and transfer-messenger RNA activity in Escherichia coli.
  J Biol Chem, 284(46): 32188-32200 (2009)  19776006  doi: 10.1074/jbc.M109.062745
• Sharma D, Cukras AR, Rogers EJ, Southworth DR, Green R
  Mutational analysis of S12 protein and implications for the accuracy of decoding by the ribosome.
  J Mol Biol, 374(4): 1065-1076 (2007)  17967466  doi: 10.1016/j.jmb.2007.10.003
• Tassew N, Thompson M
  Binding affinity and inhibitory potency of neomycin and streptomycin on the Tat peptide interaction with HIV-1 TAR RNA detected by on-line acoustic wave sensor.
  Org Biomol Chem, 1(19): 3268-3270 (2003)  14584788
• Okachi R, Niino H, Kitaura K, Mineura K, Nakamizo Y, Murayama Y, Ono T, Nakamizo A
  Synthesis and antibacterial activity of 2,2'-dithiobis(benzamide) derivatives against Mycobacterium species.
  J Med Chem, 28(12): 1772-1779 (1985)  3934384
• KUEHL FA Jr, PECK RL
  Streptomyces antibiotics; isolation of streptomycin.
  J Am Chem Soc, 68: 1460-1462 (1946)  20994955