Home Aminos Cyclo[(2Z)-2-amino-2-butenoyl-L-valyl-(3S,4E)-3-hydroxy-7-mercapto-4-heptenoyl-D-valyl-D-cysteinyl], cyclic (3→5)-disulfide

Cyclo[(2Z)-2-amino-2-butenoyl-L-valyl-(3S,4E)-3-hydroxy-7-mercapto-4-heptenoyl-D-valyl-D-cysteinyl], cyclic (3→5)-disulfide

CAS No.:
128517-07-7
Catalog Number:
AG000Y5C
Molecular Formula:
C24H36N4O6S2
Molecular Weight:
540.6958
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
1mg
99%
1 week
United States
$240
- +
5mg
99%
1 week
United States
$473
- +
10mg
99%
1 week
United States
$807
- +
Product Description
Catalog Number:
AG000Y5C
Chemical Name:
Cyclo[(2Z)-2-amino-2-butenoyl-L-valyl-(3S,4E)-3-hydroxy-7-mercapto-4-heptenoyl-D-valyl-D-cysteinyl], cyclic (3→5)-disulfide
CAS Number:
128517-07-7
Molecular Formula:
C24H36N4O6S2
Molecular Weight:
540.6958
MDL Number:
MFCD18433404
IUPAC Name:
(1S,4S,7Z,10S,16E,21R)-7-ethylidene-4,21-di(propan-2-yl)-2-oxa-12,13-dithia-5,8,20,23-tetrazabicyclo[8.7.6]tricos-16-ene-3,6,9,19,22-pentone
InChI:
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
SMILES:
C/C=C/1\NC(=O)[C@H]2CSSCC/C=C/[C@@H](OC(=O)[C@@H](NC1=O)C(C)C)CC(=O)N[C@@H](C(=O)N2)C(C)C
UNII:
CX3T89XQBK
Properties
Complexity:
905  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
4  
Defined Bond Stereocenter Count:
2  
Exact Mass:
540.208g/mol
Formal Charge:
0
Heavy Atom Count:
36  
Hydrogen Bond Acceptor Count:
8  
Hydrogen Bond Donor Count:
4  
Isotope Atom Count:
0
Molecular Weight:
540.694g/mol
Monoisotopic Mass:
540.208g/mol
Rotatable Bond Count:
2  
Topological Polar Surface Area:
193A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
2.2  
Literature
Title Journal
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Gene expression profiling induced by histone deacetylase inhibitor, FK228, in human esophageal squamous cancer cells. Oncology reports 20070901
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FK228 inhibits Hsp90 chaperone function in K562 cells via hyperacetylation of Hsp70. Biochemical and biophysical research communications 20070518
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The use of histone deacetylase inhibitor FK228 and DNA hypomethylation agent 5-azacytidine in human bladder cancer therapy. International journal of cancer 20070415
Low concentrations of the histone deacetylase inhibitor, depsipeptide, enhance the effects of gemcitabine and docetaxel in hormone refractory prostate cancer cells. Oncology reports 20070401
The histone deacetylase inhibitors depsipeptide and MS-275, enhance TRAIL gene therapy of LNCaP prostate cancer cells without adverse effects in normal prostate epithelial cells. Cancer gene therapy 20070301
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HDAC inhibitors and cardiac safety. Clinical cancer research : an official journal of the American Association for Cancer Research 20070201
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Signal therapy of human pancreatic cancer and NF1-deficient breast cancer xenograft in mice by a combination of PP1 and GL-2003, anti-PAK1 drugs (Tyr-kinase inhibitors). Cancer letters 20070108
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Apoptosis induced by depsipeptide FK228 coincides with inhibition of survival signaling in lung cancer cells. Cancer journal (Sudbury, Mass.) 20070101
Systemic co-administration of depsipeptide selectively targets transfection enhancement to specific tissues and cell types. Gene therapy 20061201
Histone deacetylase inhibitor FK228 is a potent inducer of human fetal hemoglobin. American journal of hematology 20061201
The histone deacetylase inhibitor FK228 distinctly sensitizes the human leukemia cells to retinoic acid-induced differentiation. Annals of the New York Academy of Sciences 20061201
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Pleiotropic role of histone deacetylases in the regulation of human adult erythropoiesis. British journal of haematology 20061001
Bmf contributes to histone deacetylase inhibitor-mediated enhancing effects on apoptosis after ionizing radiation. Apoptosis : an international journal on programmed cell death 20060801
Histone deacetylase inhibitors enhance phosphorylation of histone H2AX after ionizing radiation. International journal of radiation oncology, biology, physics 20060701
Cardiac safety, risk management, and oncology drug development. Clinical cancer research : an official journal of the American Association for Cancer Research 20060615
Cardiac studies in patients treated with depsipeptide, FK228, in a phase II trial for T-cell lymphoma. Clinical cancer research : an official journal of the American Association for Cancer Research 20060615
Depsipeptide-resistant KU812 cells show reversible P-glycoprotein expression, hyper-acetylated histones, and modulated gene expression profile. Leukemia research 20060601
Defining the role of gene regulation in resistance to HDAC inhibitors--mechanisms beyond P-glycoprotein. Leukemia research 20060601
Synergistic induction of folate receptor beta by all-trans retinoic acid and histone deacetylase inhibitors in acute myelogenous leukemia cells: mechanism and utility in enhancing selective growth inhibition by antifolates. Cancer research 20060601
Histone post-translational modification: from discovery to the clinic. IDrugs : the investigational drugs journal 20060601
A phase II study of depsipeptide in refractory metastatic renal cell cancer. Clinical genitourinary cancer 20060601
A histone deacetylase inhibitor enhances recombinant adeno-associated virus-mediated gene expression in tumor cells. Molecular therapy : the journal of the American Society of Gene Therapy 20060401
Increased MDR1 expression in normal and malignant peripheral blood mononuclear cells obtained from patients receiving depsipeptide (FR901228, FK228, NSC630176). Clinical cancer research : an official journal of the American Association for Cancer Research 20060301
Up-regulation of MDR1 and induction of doxorubicin resistance by histone deacetylase inhibitor depsipeptide (FK228) and ATRA in acute promyelocytic leukemia cells. Blood 20060215
Histone deacetylase inhibitor FR901228 enhances the antitumor effect of telomerase-specific replication-selective adenoviral agent OBP-301 in human lung cancer cells. Experimental cell research 20060201
Histone deacetylase inhibitor FK228 suppresses the Ras-MAP kinase signaling pathway by upregulating Rap1 and induces apoptosis in malignant melanoma. Oncogene 20060126
Bmf is a possible mediator in histone deacetylase inhibitors FK228 and CBHA-induced apoptosis. Cell death and differentiation 20060101
Involvement of P-glycoprotein and MRP1 in resistance to cyclic tetrapeptide subfamily of histone deacetylase inhibitors in the drug-resistant osteosarcoma and Ewing's sarcoma cells. International journal of cancer 20060101
Histone deacetylase inhibitor depsipeptide (FK228) induces apoptosis in leukemic cells by facilitating mitochondrial translocation of Bax, which is enhanced by the proteasome inhibitor bortezomib. Acta haematologica 20060101
Histone deacetylase inhibitors in cancer therapy. Cancer investigation 20060101
Cancer cells become susceptible to natural killer cell killing after exposure to histone deacetylase inhibitors due to glycogen synthase kinase-3-dependent expression of MHC class I-related chain A and B. Cancer research 20051201
Effect of the histone deacetylase inhibitor depsipeptide on B-cell differentiation in both TEL-AML1-positive and negative childhood acute lymphoblastic leukemia. Haematologica 20051201
Inhibition of histone deacetylase suppresses osteoclastogenesis and bone destruction by inducing IFN-beta production. Journal of immunology (Baltimore, Md. : 1950) 20051101
Histone deacetylase inhibitor FK228 activates tumor suppressor Prdx1 with apoptosis induction in esophageal cancer cells. Clinical cancer research : an official journal of the American Association for Cancer Research 20051101
Antitumor effects of histone deacetylase inhibitor on Ewing's family tumors. International journal of cancer 20050920
A putative role for histone deacetylase in the differentiation of human erythroid cells. International journal of oncology 20050901
Signal therapy of breast cancers by the HDAC inhibitor FK228 that blocks the activation of PAK1 and abrogates the tamoxifen-resistance. Cancer biology & therapy 20050901
Depletion of mutant p53 and cytotoxicity of histone deacetylase inhibitors. Cancer research 20050815
Enhanced transgene expression in urothelial cancer gene therapy with histone deacetylase inhibitor. The Journal of urology 20050801
Synergistic induction of DOC-2/DAB2 gene expression in transitional cell carcinoma in the presence of GATA6 and histone deacetylase inhibitor. Cancer research 20050715
Accumulation of hypoxia-inducible factor-1alpha is limited by transcription-dependent depletion. Oncogene 20050714
Effects of histone deacetylase inhibitor FR901228 on the expression level of telomerase reverse transcriptase in oral cancer. Cancer chemotherapy and pharmacology 20050701
Chemoresistance to depsipeptide FK228 [(E)-(1S,4S,10S,21R)-7-[(Z)-ethylidene]-4,21-diisopropyl-2-oxa-12,13-dithia-5,8,20,23-tetraazabicyclo[8,7,6]-tricos-16-ene-3,6,9,22-pentanone] is mediated by reversible MDR1 induction in human cancer cell lines. The Journal of pharmacology and experimental therapeutics 20050701
Significant growth suppression of synovial sarcomas by the histone deacetylase inhibitor FK228 in vitro and in vivo. Cancer letters 20050628
Involvement of the tumor necrosis factor (TNF)/TNF receptor system in leukemic cell apoptosis induced by histone deacetylase inhibitor depsipeptide (FK228). Journal of cellular physiology 20050501
Interference of CREB-dependent transcriptional activation by expanded polyglutamine stretches--augmentation of transcriptional activation as a potential therapeutic strategy for polyglutamine diseases. Journal of neurochemistry 20050501
Inhibitors of histone deacetylases alter kinetochore assembly by disrupting pericentromeric heterochromatin. Cell cycle (Georgetown, Tex.) 20050501
Efflux of depsipeptide FK228 (FR901228, NSC-630176) is mediated by P-glycoprotein and multidrug resistance-associated protein 1. The Journal of pharmacology and experimental therapeutics 20050401
Depsipeptide (FR901228) enhances the cytotoxic activity of TRAIL by redistributing TRAIL receptor to membrane lipid rafts. Molecular therapy : the journal of the American Society of Gene Therapy 20050401
Signal therapy of NF1-deficient tumor xenograft in mice by the anti-PAK1 drug FK228. Cancer biology & therapy 20050401
Sequential 5-Aza 2'-deoxycytidine/depsipeptide FK228 treatment induces tissue factor pathway inhibitor 2 (TFPI-2) expression in cancer cells. Oncogene 20050331
[Histone deacetylase inhibitors as a new generation of anti-cancer agents]. Postepy higieny i medycyny doswiadczalnej (Online) 20050311
Suppression of phosphatidylinositol 3-kinase/Akt signaling pathway is a determinant of the sensitivity to a novel histone deacetylase inhibitor, FK228, in lung adenocarcinoma cells. Oncology reports 20050301
Marker genes to predict sensitivity to FK228, a histone deacetylase inhibitor. Biochemical pharmacology 20050215
A phase 1 and pharmacodynamic study of depsipeptide (FK228) in chronic lymphocytic leukemia and acute myeloid leukemia. Blood 20050201
Distinct roles of the ERK pathway in modulating apoptosis of Ras-transformed and non-transformed cells induced by anticancer agent FR901228. FEBS letters 20050103
Sensitization of osteosarcoma cells to death receptor-mediated apoptosis by HDAC inhibitors through downregulation of cellular FLIP. Cell death and differentiation 20050101
Identification of cytochrome P450 enzymes involved in the metabolism of FK228, a potent histone deacetylase inhibitor, in human liver microsomes. Biological & pharmaceutical bulletin 20050101
The histone deacetylase inhibitor FR901228 induces caspase-dependent apoptosis via the mitochondrial pathway in small cell lung cancer cells. Molecular cancer therapeutics 20041101
[A histone deacetylase inhibitor and tumor suppressing gene p53 induction synergistically induce apoptosis of cancer cells]. [Hokkaido igaku zasshi] The Hokkaido journal of medical science 20041101
Selective efficacy of depsipeptide in a xenograft model of Epstein-Barr virus-positive lymphoproliferative disorder. Journal of the National Cancer Institute 20041006
Histone deacetylase inhibitor suppression of autoantibody-mediated arthritis in mice via regulation of p16INK4a and p21(WAF1/Cip1) expression. Arthritis and rheumatism 20041001
Determination of the cyclic depsipeptide FK228, a histone deacetylase inhibitor, by liquid chromatography-mass spectrometry. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20040925
Potentiation of androgen receptor transcriptional activity by inhibition of histone deacetylation--rescue of transcriptionally compromised mutants. The Journal of endocrinology 20040901
[Violacein: a molecule of biological interest originating from the soil-borne bacterium Chromobacterium violaceum]. La Revue de medecine interne 20040901
Plasma and cerebrospinal fluid pharmacokinetics of depsipeptide (FR901228) in nonhuman primates. Cancer chemotherapy and pharmacology 20040701
Effects of demethylating agent 5-aza-2(')-deoxycytidine and histone deacetylase inhibitor FR901228 on maspin gene expression in oral cancer cell lines. Oral oncology 20040701
Histone deacetylase inhibitors FK228, N-(2-aminophenyl)-4-[N-(pyridin-3-yl-methoxycarbonyl)amino- methyl]benzamide and m-carboxycinnamic acid bis-hydroxamide augment radiation-induced cell death in gastrointestinal adenocarcinoma cells. International journal of cancer 20040610
Histone deacetylase inhibitors restore radioiodide uptake and retention in poorly differentiated and anaplastic thyroid cancer cells by expression of the sodium/iodide symporter thyroperoxidase and thyroglobulin. Endocrinology 20040601
Histone deacetylase inhibitor, FK228, induces apoptosis and suppresses cell proliferation of human glioblastoma cells in vitro and in vivo. Acta neuropathologica 20040601
Enhancement of radiation sensitivity of human squamous carcinoma cells by histone deacetylase inhibitors. Radiation research 20040601
Synergistic effect of histone deacetylase inhibitors FK228 and m-carboxycinnamic acid bis-hydroxamide with proteasome inhibitors PSI and PS-341 against gastrointestinal adenocarcinoma cells. Clinical cancer research : an official journal of the American Association for Cancer Research 20040601
Impact of novel histone deacetylase inhibitors, CHAP31 and FR901228 (FK228), on adenovirus-mediated transgene expression. The journal of gene medicine 20040501
Analysis of histone deacetylase inhibitor, depsipeptide (FR901228), effect on multiple myeloma. British journal of haematology 20040401
FR901228, a novel histone deacetylase inhibitor, induces cell cycle arrest and subsequent apoptosis in refractory human pancreatic cancer cells. International journal of oncology 20040301
Genomic surgery for lung cancer. The Journal of surgical research 20040301
Abrogation of p21 expression by flavopiridol enhances depsipeptide-mediated apoptosis in malignant pleural mesothelioma cells. Clinical cancer research : an official journal of the American Association for Cancer Research 20040301
Lack of preventive efficacy of FK228, a histone deacetylase inhibitor, against N-butyl-N-(4-hydroxybutyl) nitrosamine-induced urinary bladder carcinogenesis in p53+/- and p53+/+ mice. Anticancer research 20040101
A review of depsipeptide and other histone deacetylase inhibitors in clinical trials. Current pharmaceutical design 20040101
Depsipeptide enhances imatinib mesylate-induced apoptosis of Bcr-Abl-positive cells and ectopic expression of cyclin D1, c-Myc or active MEK abrogates this effect. Anticancer research 20040101
FR901228 induces tumor regression associated with induction of Fas ligand and activation of Fas signaling in human osteosarcoma cells. Oncogene 20031218
The histone deacetylase inhibitor FK228 preferentially enhances adenovirus transgene expression in malignant cells. Clinical cancer research : an official journal of the American Association for Cancer Research 20031101
Antitumor efficacy of FK228, a novel histone deacetylase inhibitor, depends on the effect on expression of angiogenesis factors. Biochemical pharmacology 20030915
Novel mechanisms of apoptosis induced by histone deacetylase inhibitors. Cancer research 20030801
Depsipeptide (FR901228) induces histone acetylation and inhibition of histone deacetylase in chronic lymphocytic leukemia cells concurrent with activation of caspase 8-mediated apoptosis and down-regulation of c-FLIP protein. Blood 20030715
Effects of FK228, a novel histone deacetylase inhibitor, on tumor growth and expression of p21 and c-myc genes in vivo. Cancer letters 20030610
Depsipeptide (FR901228) inhibits proliferation and induces apoptosis in primary and metastatic human uveal melanoma cell lines. Investigative ophthalmology & visual science 20030601
Histone deacetylase inhibitors activate p21(WAF1) expression via ATM. Cancer research 20030601
Preclinical evaluation of antineoplastic activity of inhibitors of DNA methylation (5-aza-2'-deoxycytidine) and histone deacetylation (trichostatin A, depsipeptide) in combination against myeloid leukemic cells. Leukemia research 20030501
Enhancement of depsipeptide-mediated apoptosis of lung or esophageal cancer cells by flavopiridol: activation of the mitochondria-dependent death-signaling pathway. The Journal of thoracic and cardiovascular surgery 20030501
Antiproliferative effects of the histone deacetylase inhibitor FR901228 on small-cell lung cancer lines and drug-resistant sublines. International journal of cancer 20030320
Interaction of 5-aza-2'-deoxycytidine and depsipeptide on antineoplastic activity and activation of 14-3-3sigma, E-cadherin and tissue inhibitor of metalloproteinase 3 expression in human breast carcinoma cells. Anti-cancer drugs 20030301
A novel combination of suicide gene therapy and histone deacetylase inhibitor for treatment of malignant melanoma. Cancer gene therapy 20030301
Depsipeptide (FR 901228) promotes histone acetylation, gene transcription, apoptosis and its activity is enhanced by DNA methyltransferase inhibitors in AML1/ETO-positive leukemic cells. Leukemia 20030201
Inhibition of hypoxia-induced angiogenesis by FK228, a specific histone deacetylase inhibitor, via suppression of HIF-1alpha activity. Biochemical and biophysical research communications 20030103
Identification of thiols and glutathione conjugates of depsipeptide FK228 (FR901228), a novel histone protein deacetylase inhibitor, in the blood. Rapid communications in mass spectrometry : RCM 20030101
Profiling of cyclic hexadepsipeptides roseotoxins synthesized in vitro and in vivo: a combined tandem mass spectrometry and quantum chemical study. European journal of mass spectrometry (Chichester, England) 20030101
Effects of FK228, a novel histone deacetylase inhibitor, on human lymphoma U-937 cells in vitro and in vivo. Biochemical pharmacology 20021001
A histone deacetylase inhibitor enhances killing of undifferentiated thyroid carcinoma cells by p53 gene therapy. The Journal of clinical endocrinology and metabolism 20021001
FR901228, an inhibitor of histone deacetylases, increases the cellular responsiveness to IL-6 type cytokines by enhancing the expression of receptor proteins. Oncogene 20020912
FK228 (depsipeptide) as a natural prodrug that inhibits class I histone deacetylases. Cancer research 20020901
Histone deacetylase inhibitors all induce p21 but differentially cause tubulin acetylation, mitotic arrest, and cytotoxicity. Molecular cancer therapeutics 20020901
FR-901228 Fujisawa/National Cancer Institute. Current opinion in investigational drugs (London, England : 2000) 20020901
38th annual meeting of the American Society of Clinical Oncology. Clinical lymphoma 20020601
Regulation of activation-induced receptor activator of NF-kappaB ligand (RANKL) expression in T cells. European journal of immunology 20020401
Histone deacetylase inhibitor FR901228 enhances adenovirus infection of hematopoietic cells. Blood 20020315
Differential modulation of signaling pathways and apoptosis of ras-transformed 10T1/2 cells by the depsipeptide FR901228. The Journal of pharmacology and experimental therapeutics 20020301
Histone deacetylase inhibitors: a new class of potential therapeutic agents for cancer treatment. Clinical cancer research : an official journal of the American Association for Cancer Research 20020301
Phase I trial of the histone deacetylase inhibitor, depsipeptide (FR901228, NSC 630176), in patients with refractory neoplasms. Clinical cancer research : an official journal of the American Association for Cancer Research 20020301
Histone deacetylase inhibitor FK228 inhibits tumor angiogenesis. International journal of cancer 20020120
A phase I trial of depsipeptide (FR901228) in patients with advanced cancer. Journal of experimental therapeutics & oncology 20020101
Inhibitor of histone deacetylation, depsipeptide (FR901228), in the treatment of peripheral and cutaneous T-cell lymphoma: a case report. Blood 20011101
Inhibitors of histone deacetylase as new anticancer agents. Current medicinal chemistry 20011001
Enhanced adenovirus transgene expression in malignant cells treated with the histone deacetylase inhibitor FR901228. Cancer research 20010901
Low concentrations of the histone deacetylase inhibitor, depsipeptide (FR901228), increase expression of the Na(+)/I(-) symporter and iodine accumulation in poorly differentiated thyroid carcinoma cells. The Journal of clinical endocrinology and metabolism 20010701
In vivo effects of a histone deacetylase inhibitor, FK228, on human acute promyelocytic leukemia in NOD / Shi-scid/scid mice. Japanese journal of cancer research : Gann 20010501
Construction of gene therapy vectors targeting thyroid cells: enhancement of activity and specificity with histone deacetylase inhibitors and agents modulating the cyclic adenosine 3',5'-monophosphate pathway and demonstration of activity in follicular and anaplastic thyroid carcinoma cells. The Journal of clinical endocrinology and metabolism 20010201
Induction of MAGE-3 expression in lung and esophageal cancer cells. The Annals of thoracic surgery 20010101
Sequential 5-Aza-2 deoxycytidine-depsipeptide FR901228 treatment induces apoptosis preferentially in cancer cells and facilitates their recognition by cytolytic T lymphocytes specific for NY-ESO-1. Journal of immunotherapy (Hagerstown, Md. : 1997) 20010101
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