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SML1175

Sigma-Aldrich

Romidepsin

≥98% (HPLC), powder, histone deacetylase inhibitor

Sinónimos:

Cyclo[(2Z)-2-amino-2-butenoyl-L-valyl-(3S,4E)-3-hydroxy-7-mercapto-4-heptenoyl-D-valyl-D-cysteinyl] cyclic (35)-disulfide, Depsipeptide, FK228, FR901228, L-Valine, N-((3S,4E)-3-hydroxy-7-mercapto-1-oxo-4-heptenyl)-D-valyl-D-cysteinyl-(2Z)-2-amino-2-butenoxyl-, (4-1)-lactone, cyclic (1-2)-disulfide

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About This Item

Fórmula empírica (notación de Hill):
C24H36N4O6S2
Número de CAS:
128517-07-7
Peso molecular:
540.70
MDL number:
MFCD18433404
UNSPSC Code:
12352200
PubChem Substance ID:
329825701
NACRES:
NA.77

product name

Romidepsin, ≥98% (HPLC)

Quality Level

100

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 25 mg/mL, clear

storage temp.

−20°C

SMILES string

O=C(N/C(C(N[C@@H](C(C)C)C(O[C@@]1([H])CC2=O)=O)=O)=C\C)[C@@H](CSSCC/C=C/1)NC([C@H](N2)C(C)C)=O

InChI

1S/C24H36N4O6S2/c1-6-16-21(30)28-20(14(4)5)24(33)34-15-9-7-8-10-35-36-12-17(22(31)25-16)26-23(32)19(13(2)3)27-18(29)11-15/h6-7,9,13-15,17,19-20H,8,10-12H2,1-5H3,(H,25,31)(H,26,32)(H,27,29)(H,28,30)/b9-7+,16-6-/t15-,17-,19-,20+/m1/s1

InChI key

OHRURASPPZQGQM-GCCNXGTGSA-N

Gene Information

human ... HDAC1(3065) , HDAC10(83933) , HDAC11(79885) , HDAC2(3066) , HDAC3(8841) , HDAC4(9759) , HDAC5(10014) , HDAC6(10013) , HDAC7(51564) , HDAC8(55869) , HDAC9(9734)

Biochem/physiol Actions

Romidepsin is a very potent natural prodrug inhibitor of HDAC1 and HDAC2 that is converted to active form by glutathione. Romidepsin has IC50 values of 36 nM and 47 nM for HDAC1 and HDAC2, respectively. Romidepsin kills lymphoma cell lines overexpressing Bcl-2 and Bcl-XL, and has been approved for the treatment for cutaneous T-cell lymphoma (CTCL) and peripheral T-cell lymphoma, and a variety of other cancers.
Romidepsin promotes apoptosis, while hindering tumor growth in glioma models.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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A phase I/II trial of the histone deacetylase inhibitor romidepsin for adults with recurrent malignant glioma: North American Brain Tumor Consortium Study 03-03.
Iwamoto F M, et al.
Neuro-Oncology, 13(5), 509-516 (2011)
Anna Otte et al.
International journal of oncology, 49(6), 2453-2463 (2016-10-18)
Chemotherapeutic drug testing of SCCOHT-1 and BIN-67 tumor cells revealed synergistic growth-inhibition of >95% in vitro with a combination of foretinib and FK228. Application of this drug combination in vivo in NODscid mice-induced SCCOHT-1GFP tumors was associated with ~6-fold reduction in
Florencia Cayrol et al.
Nature communications, 8, 14290-14290 (2017-01-31)
Peripheral T-cell lymphomas (PTCL) are aggressive diseases with poor response to chemotherapy and dismal survival. Identification of effective strategies to target PTCL biology represents an urgent need. Here we report that PTCL are sensitive to transcription-targeting drugs, and, in particular
Sina Jostes et al.
Journal of cellular and molecular medicine, 21(7), 1300-1314 (2016-12-28)
Type II testicular germ cell cancers (TGCT) are the most frequently diagnosed tumours in young men (20-40 years) and are classified as seminoma or non-seminoma. TGCTs are commonly treated by orchiectomy and chemo- or radiotherapy. However, a subset of metastatic
Rosie M Butler et al.
The Journal of investigative dermatology, 139(9), 1975-1984 (2019-03-27)
FK228 (romidepsin) and suberoylanilide hydroxamic acid (vorinostat) are histone deacetylase inhibitors (HDACi) approved by the US Food and Drug Administration for cutaneous T-cell lymphoma (CTCL), including the leukemic subtype Sézary syndrome. This study investigates RAD23B and STAT3 gene perturbations in
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