Thiostrepton

Thiostrepton

Names
Other names Alaninamide, Bryamycin, Thiactin
Identifiers
CAS Number	1393-48-2 Y
3D model (Jmol)	Interactive image
ECHA InfoCard	100.014.304
PubChem CID	16130278
InChI InChI=1S/C72H85N19O18S5/c1-14-26(3)47-63(105)78-30(7)57(99)75-28(5)56(98)76-31(8)58(100)91-72-19-18-40(66-85-43(22-111-66)59(101)77-29(6)55(97)74-27(4)54(73)96)81-52(72)42-21-112-67(83-42)49(34(11)109-69(107)41-20-37(32(9)92)36-16-17-39(79-47)51(95)50(36)80-41)89-60(102)44-24-113-68(86-44)53(71(13,108)35(12)94)90-62(104)45-23-110-65(84-45)38(15-2)82-64(106)48(33(10)93)88-61(103)46-25-114-70(72)87-46/h15-17,20-22,24-26,30-35,39,45,47-49,51-53,79,92-95,108H,4-6,14,18-19,23H2,1-3,7-13H3,(H2,73,96)(H,74,97)(H,75,99)(H,76,98)(H,77,101)(H,78,105)(H,82,106)(H,88,103)(H,89,102)(H,90,104)(H,91,100)/b38-15-/t26-,30-,31-,32-,33+,34+,35+,39+,45+,47-,48-,49-,51-,52+,53+,71+,72+/m0/s1 Key: NSFFHOGKXHRQEW-AIHSUZKVSA-N
SMILES C[C@@H](O)[C@@](C)(O)[C@@H](C2=NC6=CS2)NC(C1CSC(/C(NC([C@@H](NC(C3=CS[C@]([C@]4(NC([C@@H](NC(C(NC([C@H](C)NC%10=O)=O)=C)=O)C)=O)C(C5=CSC([C@H]([C@@H](C)OC(C8=CC([C@H](C)O)=C(C=CC(N[C@]([H])%10[C@H](CC)C)[C@@H]9O)C9=N8)=O)NC6=O)=N5)N=C(C7=NC(C(NC(C(NC(C(N)=O)=C)=O)=C)=O)=CS7)CC4)=N3)=O)[C@@H](C)O)=O)=C/C)=N1)=O
Properties
Chemical formula	C72H85N19O18S5
Molar mass	1664.83 g/mol
Appearance	White to off-white powder
Melting point	246 to 256 °C (475 to 493 °F; 519 to 529 K)
Solubility in water	Insoluble
Solubility in other solvents	Soluble in CHCl3, CH2Cl2, dioxane, pyridine, glacial acetic acid, DMF. Practically insoluble in the lower alcohols, nonpolar organic solvents, diluted aqueous acids or bases. May be dissolved by methanolic acid or base, but with decomposition.
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
Infobox references

Thiostrepton is a natural cyclic oligopeptide antibiotic of the thiopeptide class, derived from several strains of streptomycetes, such as Streptomyces azureus and Streptomyces laurentii. Thiostrepton is a natural product of the ribosomally synthesized and post-translationally modified peptide (RiPP) class.

Thiostrepton was discovered by Donovick et al. who described its antibacterial properties in 1955.Dorothy Crowfoot Hodgkin solved the structure of thiostrepton in 1970. Early in 1978, Bycroft and Gowland proposed the biosynthesis of thiostrepton, which was still unclear until 2009. Several studies of thiopeptide biosynthesis have been contemporarily published in 2009 and two of them (Liao et al. and Kelly et al.) included the similar biosynthesis of thiostrepton: it's ribosomally synthesized from thiostrepton biosynthetic genes (tsr genes) and posttranslational modification is needed.

A total synthesis of Thiostrepton was completed by K.C. Nicolaou, et al. in 2004.

Thiostrepton has been used in veterinary medicine in mastitis caused by gram-negative organisms and in dermatologic disorders. It is mostly used in complex ointments containing neomycin, nystatin, Thiostrepton and topical steroids. It is also active against gram-positive bacteria. It is notable that ointments for human usage contain neomycin, nystatin, and topical steroids, but no Thiostrepton.

Thiostrepton was reported (in 2008) to exhibit activity against breast cancer cells through targeting the transcription factor forkhead box M1 (FOXM1)., also in 2011. It has also been shown to circumvent acquired cisplatin resistance in breast cancer cells under in invitro conditions.