Siomycin A

Siomycin A is a thiopeptide antibiotic and is a Forkhead box M1(FOXM1) selective inhibitor without affecting other members of the Forkhead box family. Siomycin A has anti-tumor and promotes apoptosis.

Product information

CAS Number: 12656-09-6

Molecular Weight: 1648.84

Formula: C71H81N19O18S5

Chemical Name: N-(1-carbamoyleth-1-en-1-yl)-2-({2-[(1R, 11Z, 15S, 18S, 25S, 26R, 35R, 37S, 46S, 53S, 59S)-18-[(2S, 3R)-2, 3-dihydroxybutan-2-yl]-11-ethylidene-59-hydroxy-8-[(1R)-1-hydroxyethyl]-60-[(1S)-1-hydroxyethyl]-26, 46-dimethyl-40, 43-dimethylidene-6, 9, 16, 23, 28, 38, 41, 44, 47-nonaoxo-37-(propan-2-yl)-27-oxa-3, 13, 20, 56-tetrathia-7, 10, 17, 24, 30, 36, 39, 42, 45, 48, 52, 58, 62, 63, 64-pentadecaazanonacyclo[23.23.9.2, .1, .1, .1, .1, .1, .0, ]tetrahexaconta-2(64), 4, 12(63), 19(62), 21, 29(61), 30, 32(60), 33, 51, 54, 57-dodecaen-51-yl]-1, 3-thiazol-4-yl}formamido)prop-2-enamide

Smiles: C[C@](O)([C@@H]1NC(=O)[C@H]2CSC(=N2)/C(=C/C)/NC(=O)C(NC(=O)C2=CSC(=N2)[C@@]23CCC(=N[C@@H]2C2=CSC(=N2)[C@@H](NC(=O)C2=CSC1=N2)[C@@H](C)OC(=O)C1=CC([C@H](C)O)=C2C=C[C@@H](N[C@@H](C(C)C)C(=O)NC(=C)C(=O)NC(=C)C(=O)N[C@@H](C)C(=O)N3)[C@H](O)C2=N1)C1=NC(=CS1)C(=O)NC(=C)C(=O)NC(=C)C(N)=O)[C@@H](C)O)[C@@H](C)O

InChiKey: AKFVOKPQHFBYCA-WAHIHXRRSA-N

InChi: InChI=1S/C71H81N19O18S5/c1-14-37-64-83-44(22-109-64)61(103)89-52(70(13,107)34(12)93)67-85-43(23-112-67)59(101)88-48-33(11)108-68(106)40-19-36(31(9)91)35-15-16-38(50(94)49(35)79-40)78-46(25(2)3)62(104)77-29(7)56(98)74-27(5)55(97)75-30(8)57(99)90-71(69-86-45(24-113-69)60(102)87-47(32(10)92)63(105)81-37)18-17-39(80-51(71)41-20-111-66(48)82-41)65-84-42(21-110-65)58(100)76-28(6)54(96)73-26(4)53(72)95/h14-16,19-21,23-25,30-34,38,44,46-48,50-52,78,91-94,107H,4-7,17-18,22H2,1-3,8-13H3,(H2,72,95)(H,73,96)(H,74,98)(H,75,97)(H,76,100)(H,77,104)(H,81,105)(H,87,102)(H,88,101)(H,89,103)(H,90,99)/b37-14-/t30-,31-,32+,33+,34+,38+,44+,46-,47?,48-,50-,51+,52+,70+,71+/m0/s1

Technical Data

Appearance: Solid Power

Purity: ≥98% (or refer to the Certificate of Analysis)

Solubility: Soluble in DMSO

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical or refer to Certificate of Analysis

Storage Condition: Dry, dark and -20 ^oC for 1 year or refer to the Certificate of Analysis.

Shelf Life: ≥12 months if stored properly.

Stock Solution Storage: 0 - 4 ^oC for 1 month or refer to the Certificate of Analysis.

Drug Formulation: To be determined

HS Tariff Code: 382200

How to use

In Vitro:

Siomycin A (0-10 µM; 24-72 hours; K562, MCF7 and MiaPaCa-2 cells) treatment markedly reduces cell viability in a dose-dependent and a time-dependent association in K562, MCF7 and MiaPaCa-2 cells. Among the three cell lines, the IC50 of the human leukemia K562 cells is the lowest at 6.25 µM at 24 h, while that for the human pancreatic cancer MiaPaCa-2 cells is 6.38 µM. However, the IC50 of the human pancreatic cancer MiaPaCa-2 cells at 48 and 72 h are the lowest of the three cell lines, which are 0.76 and 0.54 µM, respectively. Siomycin A (0-10 µM; MiaPaCa-2 cells) treatment has potent proapoptotic effect in MiaPaCa-2 cells. Siomycin A (0-10 µM; 24 hours; MiaPaCa-2 cells) treatment significantly reduces the expression levels of MMP-2, MMP-9 and α-tubulin protein in the MiaPaCa-2 cells.

In Vivo:

Siomycin A (1 µM; subcutaneous injection; for 4 weeks; male Balb/c nude mice) pretreatment decreases tumour growth in an in vivo mouse model.

References:

1. Wang B, et al. Effects and mechanism of siomycin A on the growth and apoptosis of MiaPaCa-2 cancer cells. Oncol Lett. 2019 Sep;18(3):2869-2876.
2. Kim H, et al. Forkhead box M1 (FOXM1) transcription factor is a key oncogenic driver of aggressive human meningioma progression. Neuropathol Appl Neurobiol. 2019 Jun 9.

Products are for research use only. Not for human use.