MC1568
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MedKoo CAT#: 406487

CAS#: 852475-26-4

Description: MC1568 is a class II-specific histone deacetylase inhibitor. MC1568 suppress IL-8 expression in human melanoma cells. Treatment of IEC-18 cells with specific inhibitors of class IIa HDACs, including MC1568, prevented cell cycle progression, DNA synthesis, and proliferation induced in response to G protein-coupled receptor/PKD1 activation.

Chemical Structure

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MC1568
CAS# 852475-26-4
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 406487
Name: MC1568
CAS#: 852475-26-4
Chemical Formula: C17H15FN2O3
Exact Mass: 314.11
Molecular Weight: 314.311
Elemental Analysis: C, 64.96; H, 4.81; F, 6.04; N, 8.91; O, 15.27

Price and Availability

Size Price Availability Quantity
50mg USD 450 2 Weeks
100mg USD 850 2 weeks
200mg USD 1550 2 weeks
500mg USD 2750 2 weeks
1g USD 3750 2 weeks
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Synonym: MC-1568; MC 1568; MC1568.

IUPAC/Chemical Name: (E)-3-(5-((E)-3-(3-fluorophenyl)-3-oxoprop-1-en-1-yl)-1-methyl-1H-pyrrol-2-yl)-N-hydroxyacrylamide

InChi Key: QQDIFLSJMFDTCQ-FIFLTTCUSA-N

InChi Code: InChI=1S/C17H15FN2O3/c1-20-14(5-6-15(20)8-10-17(22)19-23)7-9-16(21)12-3-2-4-13(18)11-12/h2-11,23H,1H3,(H,19,22)/b9-7+,10-8+

SMILES Code: O=C(NO)/C=C/C1=CC=C(/C=C/C(C2=CC=CC(F)=C2)=O)N1C

Appearance: Solid powder

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

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

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Product Data:
Product Data
Instruction:
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Biological target: MC1568 is a selective class II (IIa) histone deacetylase (HDAC II) inhibitor, used for cancer research.
In vitro activity: MC1568 and MC1575 inhibited IL-8 levels and cell proliferation in either unstimulated or PMA-stimulated melanoma cells. Reference: Pigment Cell Melanoma Res. 2013 Mar;26(2):193-204. https://pubmed.ncbi.nlm.nih.gov/23176534/
In vivo activity: Analyses of the pancreas of class IIa HDAC mutant mice revealed an increased pool of insulin-producing β-cells in Hdac5(-/-) and Hdac9(-/-) mice and an increased pool of somatostatin-producing δ-cells in Hdac4(-/-) and Hdac5(-/-) mice. Treatment of pancreatic explants with the selective class IIa HDAC inhibitor MC1568 enhances expression of Pax4, a key factor required for proper β-and δ-cell differentiation and amplifies endocrine β- and δ-cells. Reference: Diabetes. 2011 Nov;60(11):2861-71. https://pubmed.ncbi.nlm.nih.gov/21953612/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMF 0.5 1.59
DMSO 18.2 58.01
DMSO:PBS (pH 7.2) (1:2) 0.3 0.95

Preparing Stock Solutions

The following data is based on the product molecular weight 314.31 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Venza I, Visalli M, Oteri R, Cucinotta M, Teti D, Venza M. Class II-specific histone deacetylase inhibitors MC1568 and MC1575 suppress IL-8 expression in human melanoma cells. Pigment Cell Melanoma Res. 2013 Mar;26(2):193-204. doi: 10.1111/pcmr.12049. Epub 2013 Jan 7. Erratum in: Pigment Cell Melanoma Res. 2013 Sep;26(5):761. PMID: 23176534. 2. Nebbioso A, Dell'Aversana C, Bugge A, Sarno R, Valente S, Rotili D, Manzo F, Teti D, Mandrup S, Ciana P, Maggi A, Mai A, Gronemeyer H, Altucci L. HDACs class II-selective inhibition alters nuclear receptor-dependent differentiation. J Mol Endocrinol. 2010 Oct;45(4):219-28. doi: 10.1677/JME-10-0043. Epub 2010 Jul 16. PMID: 20639404. 3. Lenoir O, Flosseau K, Ma FX, Blondeau B, Mai A, Bassel-Duby R, Ravassard P, Olson EN, Haumaitre C, Scharfmann R. Specific control of pancreatic endocrine β- and δ-cell mass by class IIa histone deacetylases HDAC4, HDAC5, and HDAC9. Diabetes. 2011 Nov;60(11):2861-71. doi: 10.2337/db11-0440. Epub 2011 Sep 27. PMID: 21953612; PMCID: PMC3198089. 4. Nebbioso A, Manzo F, Miceli M, Conte M, Manente L, Baldi A, De Luca A, Rotili D, Valente S, Mai A, Usiello A, Gronemeyer H, Altucci L. Selective class II HDAC inhibitors impair myogenesis by modulating the stability and activity of HDAC-MEF2 complexes. EMBO Rep. 2009 Jul;10(7):776-82. doi: 10.1038/embor.2009.88. Epub 2009 Jun 5. Erratum in: EMBO Rep. 2020 Dec 3;21(12):e51028. PMID: 19498465; PMCID: PMC2693879.
In vitro protocol: 1. Venza I, Visalli M, Oteri R, Cucinotta M, Teti D, Venza M. Class II-specific histone deacetylase inhibitors MC1568 and MC1575 suppress IL-8 expression in human melanoma cells. Pigment Cell Melanoma Res. 2013 Mar;26(2):193-204. doi: 10.1111/pcmr.12049. Epub 2013 Jan 7. Erratum in: Pigment Cell Melanoma Res. 2013 Sep;26(5):761. PMID: 23176534. 2. Nebbioso A, Dell'Aversana C, Bugge A, Sarno R, Valente S, Rotili D, Manzo F, Teti D, Mandrup S, Ciana P, Maggi A, Mai A, Gronemeyer H, Altucci L. HDACs class II-selective inhibition alters nuclear receptor-dependent differentiation. J Mol Endocrinol. 2010 Oct;45(4):219-28. doi: 10.1677/JME-10-0043. Epub 2010 Jul 16. PMID: 20639404.
In vivo protocol: 1. Lenoir O, Flosseau K, Ma FX, Blondeau B, Mai A, Bassel-Duby R, Ravassard P, Olson EN, Haumaitre C, Scharfmann R. Specific control of pancreatic endocrine β- and δ-cell mass by class IIa histone deacetylases HDAC4, HDAC5, and HDAC9. Diabetes. 2011 Nov;60(11):2861-71. doi: 10.2337/db11-0440. Epub 2011 Sep 27. PMID: 21953612; PMCID: PMC3198089. 2. Nebbioso A, Manzo F, Miceli M, Conte M, Manente L, Baldi A, De Luca A, Rotili D, Valente S, Mai A, Usiello A, Gronemeyer H, Altucci L. Selective class II HDAC inhibitors impair myogenesis by modulating the stability and activity of HDAC-MEF2 complexes. EMBO Rep. 2009 Jul;10(7):776-82. doi: 10.1038/embor.2009.88. Epub 2009 Jun 5. Erratum in: EMBO Rep. 2020 Dec 3;21(12):e51028. PMID: 19498465; PMCID: PMC2693879.

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1: Colarossi L, Memeo L, Colarossi C, Aiello E, Iuppa A, Espina V, Liotta L, Mueller C. Inhibition of histone deacetylase 4 increases cytotoxicity of docetaxel in gastric cancer cells. Proteomics Clin Appl. 2014 Dec;8(11-12):924-31. doi: 10.1002/prca.201400058. Epub 2014 Oct 22. PubMed PMID: 25091122.

2: Collins LM, Adriaanse LJ, Theratile SD, Hegarty SV, Sullivan AM, O'Keeffe GW. Class-IIa Histone Deacetylase Inhibition Promotes the Growth of Neural Processes and Protects Them Against Neurotoxic Insult. Mol Neurobiol. 2014 Jul 29. [Epub ahead of print] PubMed PMID: 25065734.

3: Sinnett-Smith J, Ni Y, Wang J, Ming M, Young SH, Rozengurt E. Protein kinase D1 mediates class IIa histone deacetylase phosphorylation and nuclear extrusion in intestinal epithelial cells: role in mitogenic signaling. Am J Physiol Cell Physiol. 2014 May 15;306(10):C961-71. doi: 10.1152/ajpcell.00048.2014. Epub 2014 Mar 19. PubMed PMID: 24647541; PubMed Central PMCID: PMC4024715.

4: Kumar P, Tripathi S, Pandey KN. Histone deacetylase inhibitors modulate the transcriptional regulation of guanylyl cyclase/natriuretic peptide receptor-a gene: interactive roles of modified histones, histone acetyltransferase, p300, AND Sp1. J Biol Chem. 2014 Mar 7;289(10):6991-7002. doi: 10.1074/jbc.M113.511444. Epub 2014 Jan 22. PubMed PMID: 24451378; PubMed Central PMCID: PMC3945360.

5: Fleming CL, Ashton TD, Gaur V, McGee SL, Pfeffer FM. Improved synthesis and structural reassignment of MC1568: a class IIa selective HDAC inhibitor. J Med Chem. 2014 Feb 13;57(3):1132-5. doi: 10.1021/jm401945k. Epub 2014 Jan 30. PubMed PMID: 24450497.

6: Poljak M, Lim R, Barker G, Lappas M. Class I to III histone deacetylases differentially regulate inflammation-induced matrix metalloproteinase 9 expression in primary amnion cells. Reprod Sci. 2014 Jun;21(6):804-13. doi: 10.1177/1933719113518990. Epub 2014 Jan 15. PubMed PMID: 24429678; PubMed Central PMCID: PMC4016730.

7: Ishikawa S, Hayashi H, Kinoshita K, Abe M, Kuroki H, Tokunaga R, Tomiyasu S, Tanaka H, Sugita H, Arita T, Yagi Y, Watanabe M, Hirota M, Baba H. Statins inhibit tumor progression via an enhancer of zeste homolog 2-mediated epigenetic alteration in colorectal cancer. Int J Cancer. 2014 Dec 1;135(11):2528-36. doi: 10.1002/ijc.28672. Epub 2014 Jan 6. PubMed PMID: 24346863; PubMed Central PMCID: PMC4233976.

8: Busbee PB, Nagarkatti M, Nagarkatti PS. Natural indoles, indole-3-carbinol and 3,3'-diindolymethane, inhibit T cell activation by staphylococcal enterotoxin B through epigenetic regulation involving HDAC expression. Toxicol Appl Pharmacol. 2014 Jan 1;274(1):7-16. doi: 10.1016/j.taap.2013.10.022. Epub 2013 Nov 5. PubMed PMID: 24200994; PubMed Central PMCID: PMC3874587.

9: Usui T, Morita T, Okada M, Yamawaki H. Histone deacetylase 4 controls neointimal hyperplasia via stimulating proliferation and migration of vascular smooth muscle cells. Hypertension. 2014 Feb;63(2):397-403. doi: 10.1161/HYPERTENSIONAHA.113.01843. Epub 2013 Oct 28. PubMed PMID: 24166750.

10: Fu X, Zhao JX, Liang J, Zhu MJ, Foretz M, Viollet B, Du M. AMP-activated protein kinase mediates myogenin expression and myogenesis via histone deacetylase 5. Am J Physiol Cell Physiol. 2013 Oct 15;305(8):C887-95. doi: 10.1152/ajpcell.00124.2013. Epub 2013 Aug 7. PubMed PMID: 23926128; PubMed Central PMCID: PMC3798682.

11: Koppel I, Timmusk T. Differential regulation of Bdnf expression in cortical neurons by class-selective histone deacetylase inhibitors. Neuropharmacology. 2013 Dec;75:106-15. doi: 10.1016/j.neuropharm.2013.07.015. Epub 2013 Aug 2. PubMed PMID: 23916482.

12: Spallotta F, Tardivo S, Nanni S, Rosati JD, Straino S, Mai A, Vecellio M, Valente S, Capogrossi MC, Farsetti A, Martone J, Bozzoni I, Pontecorvi A, Gaetano C, Colussi C. Detrimental effect of class-selective histone deacetylase inhibitors during tissue regeneration following hindlimb ischemia. J Biol Chem. 2013 Aug 9;288(32):22915-29. doi: 10.1074/jbc.M113.484337. Epub 2013 Jul 7. PubMed PMID: 23836913; PubMed Central PMCID: PMC3743470.

13: Mannaerts I, Eysackers N, Onyema OO, Van Beneden K, Valente S, Mai A, Odenthal M, van Grunsven LA. Class II HDAC inhibition hampers hepatic stellate cell activation by induction of microRNA-29. PLoS One. 2013;8(1):e55786. doi: 10.1371/journal.pone.0055786. Epub 2013 Jan 31. PubMed PMID: 23383282; PubMed Central PMCID: PMC3561334.

14: Wang G, He J, Zhao J, Yun W, Xie C, Taub JW, Azmi A, Mohammad RM, Dong Y, Kong W, Guo Y, Ge Y. Class I and class II histone deacetylases are potential therapeutic targets for treating pancreatic cancer. PLoS One. 2012;7(12):e52095. doi: 10.1371/journal.pone.0052095. Epub 2012 Dec 14. PubMed PMID: 23251689; PubMed Central PMCID: PMC3522644.

15: Venza I, Visalli M, Oteri R, Cucinotta M, Teti D, Venza M. Class II-specific histone deacetylase inhibitors MC1568 and MC1575 suppress IL-8 expression in human melanoma cells. Pigment Cell Melanoma Res. 2013 Mar;26(2):193-204. doi: 10.1111/pcmr.12049. Epub 2013 Jan 7. Erratum in: Pigment Cell Melanoma Res. 2013 Sep;26(5):761. PubMed PMID: 23176534.

16: Leontovyč I, Koblas T, Pektorova L, Zacharovova K, Berkova Z, Saudek F. The effect of epigenetic factors on differentiation of pancreatic progenitor cells into insulin-producing cells. Transplant Proc. 2011 Nov;43(9):3212-6. doi: 10.1016/j.transproceed.2011.10.025. PubMed PMID: 22099760.

17: Lenoir O, Flosseau K, Ma FX, Blondeau B, Mai A, Bassel-Duby R, Ravassard P, Olson EN, Haumaitre C, Scharfmann R. Specific control of pancreatic endocrine β- and δ-cell mass by class IIa histone deacetylases HDAC4, HDAC5, and HDAC9. Diabetes. 2011 Nov;60(11):2861-71. doi: 10.2337/db11-0440. Epub 2011 Sep 27. PubMed PMID: 21953612; PubMed Central PMCID: PMC3198089.

18: Colussi C, Rosati J, Straino S, Spallotta F, Berni R, Stilli D, Rossi S, Musso E, Macchi E, Mai A, Sbardella G, Castellano S, Chimenti C, Frustaci A, Nebbioso A, Altucci L, Capogrossi MC, Gaetano C. Nε-lysine acetylation determines dissociation from GAP junctions and lateralization of connexin 43 in normal and dystrophic heart. Proc Natl Acad Sci U S A. 2011 Feb 15;108(7):2795-800. doi: 10.1073/pnas.1013124108. Epub 2011 Jan 31. PubMed PMID: 21282606; PubMed Central PMCID: PMC3041095.

19: Nebbioso A, Dell'Aversana C, Bugge A, Sarno R, Valente S, Rotili D, Manzo F, Teti D, Mandrup S, Ciana P, Maggi A, Mai A, Gronemeyer H, Altucci L. HDACs class II-selective inhibition alters nuclear receptor-dependent differentiation. J Mol Endocrinol. 2010 Oct;45(4):219-28. doi: 10.1677/JME-10-0043. Epub 2010 Jul 16. PubMed PMID: 20639404.

20: Spallotta F, Rosati J, Straino S, Nanni S, Grasselli A, Ambrosino V, Rotili D, Valente S, Farsetti A, Mai A, Capogrossi MC, Gaetano C, Illi B. Nitric oxide determines mesodermic differentiation of mouse embryonic stem cells by activating class IIa histone deacetylases: potential therapeutic implications in a mouse model of hindlimb ischemia. Stem Cells. 2010 Mar 31;28(3):431-42. doi: 10.1002/stem.300. Erratum in: Stem Cells. 2014 Jun;32(6):1688-9. PubMed PMID: 20073046.