Streptothricin

Streptothricins are a group of antibiotics in the aminoglycoside class.^[1] The first antibiotic in the group was isolated from Streptomyces lavendulae in 1942.^[2] It was later determined to be a mixture of closely-related compounds, and is now known as nourseothricin. Although initial interest was positive because it appeared to be the first broad-spectrum antibiotic, meaning it was effective against both Gram-positive and Gram-negative bacteria, it never found clinical use due to toxicity.^[3] However, because of the increasing need for new antibiotics due to resistance to existing antibiotics, there is a current interest in developing new drugs based on the chemical scaffold of the streptothricins.^[1][4][5]

Streptothricin

Streptothricin F
Identifiers
CAS Number	D: 3776-36-1 E: 3776-38-3 F: 3808-42-2
3D model (JSmol)	D: Interactive image E: Interactive image F: Interactive image
ChEBI	E: CHEBI:67576 F: CHEBI:26789
ChEMBL	D: ChEMBL4447098 E: ChEMBL1801945 F: ChEMBL4448608
KEGG	F: C19785
PubChem CID	D: 165157 E: 160718 F: 197034
CompTox Dashboard (EPA)	E: DTXSID70929491 F: DTXSID20191489
InChI D: InChI=1S/C37H70N14O11/c38-9-1-5-19(39)13-25(54)44-10-2-6-20(40)14-26(55)45-11-3-7-21(41)15-27(56)46-12-4-8-22(42)16-28(57)48-31-32(58)33(62-36(43)60)24(18-52)61-35(31)51-37-49-29-23(53)17-47-34(59)30(29)50-37/h19-24,29-33,35,52-53,58H,1-18,38-42H2,(H2,43,60)(H,44,54)(H,45,55)(H,46,56)(H,47,59)(H,48,57)(H2,49,50,51)/t19-,20-,21-,22-,23+,24+,29+,30-,31+,32-,33-,35+/m0/s1 Key: UZMKRCMBWWXPBP-CSVBCEEXSA-N E: InChI=1S/C25H46N10O9/c26-5-1-3-11(27)7-15(38)30-6-2-4-12(28)8-16(39)32-19-20(40)21(44-24(29)42)14(10-36)43-23(19)35-25-33-17-13(37)9-31-22(41)18(17)34-25/h11-14,17-21,23,36-37,40H,1-10,26-28H2,(H2,29,42)(H,30,38)(H,31,41)(H,32,39)(H2,33,34,35)/t11-,12-,13+,14+,17+,18-,19+,20-,21-,23+/m0/s1 Key: SCHKAKNJXBPJHD-SNQQVPMJSA-N F: InChI=1S/C19H34N8O8/c20-3-1-2-7(21)4-10(30)24-13-14(31)15(35-18(22)33)9(6-28)34-17(13)27-19-25-11-8(29)5-23-16(32)12(11)26-19/h7-9,11-15,17,28-29,31H,1-6,20-21H2,(H2,22,33)(H,23,32)(H,24,30)(H2,25,26,27)/t7-,8+,9+,11+,12-,13+,14-,15-,17+/m0/s1 Key: NRAUADCLPJTGSF-VLSXYIQESA-N
SMILES D: C1[C@H]([C@@H]2[C@@H](C(=O)N1)N=C(N2)N[C@H]3[C@@H]([C@@H]([C@H]([C@H](O3)CO)OC(=O)N)O)NC(=O)C[C@H](CCCNC(=O)C[C@H](CCCNC(=O)C[C@H](CCCNC(=O)C[C@H](CCCN)N)N)N)N)O E: C1[C@H]([C@@H]2[C@@H](C(=O)N1)N=C(N2)N[C@H]3[C@@H]([C@@H]([C@H]([C@H](O3)CO)OC(=O)N)O)NC(=O)C[C@H](CCCNC(=O)C[C@H](CCCN)N)N)O F: C1[C@H]([C@@H]2[C@@H](C(=O)N1)N=C(N2)N[C@H]3[C@@H]([C@@H]([C@H]([C@H](O3)CO)OC(=O)N)O)NC(=O)C[C@H](CCCN)N)O
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

References

1. Franck, Ezabelle; Crofts, Terence S. (2024). "History of the streptothricin antibiotics and evidence for the neglect of the streptothricin resistome". npj Antimicrobials and Resistance. 2. doi:10.1038/s44259-023-00020-5.
2. Waksman, S. A. & Woodruff, H. B. (1942). "Streptothricin, a new selective bacteriostatic and bactericidal agent, particularly active against Gram-negative bacteria". Proc. Soc. Exp. Biol. Med. 49 (2): 207–210. doi:10.3181/00379727-49-13515.{{cite journal}}: CS1 maint: multiple names: authors list (link)
3. STANLEY AR (1946). "Proceedings of Local Branches of the Society of American Bacteriologists". Journal of Bacteriology. 52 (3): 399–404. doi:10.1128/JB.52.3.399-404.1946. PMID 21065179.
4. Morgan, Christopher E.; Kang, Yoon-Suk; Green, Alex B.; Smith, Kenneth P.; Dowgiallo, Matthew G.; Miller, Brandon C.; Chiaraviglio, Lucius; Truelson, Katherine A.; Zulauf, Katelyn E.; Rodriguez, Shade; Kang, Anthony D.; Manetsch, Roman; Yu, Edward W.; Kirby, James E. (2023). "Streptothricin F is a bactericidal antibiotic effective against highly drug-resistant gram-negative bacteria that interacts with the 30S subunit of the 70S ribosome". PLOS Biology. 21 (5): e3002091. doi:10.1371/journal.pbio.3002091. PMC 10187937. PMID 37192172.
5. "Forgotten Antibiotic From Decades Past Could Be a Superbug Killer". October 30, 2024.