Olinone | CAS#1770789-37-1 | BET inhibitor

MedKoo Cat#: 407401 | Name: Olinone

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Olinone is a potent and selective inhibitor of bromodomain of BET proteins. Olinone enhances oligodendrocyte differentiation, contrasting the reverse process triggered by broad BD1/BD2-targeting inhibitors.

Chemical Structure

Olinone

CAS#1770789-37-1

Theoretical Analysis

MedKoo Cat#: 407401

Name: Olinone

CAS#: 1770789-37-1

Chemical Formula: C17H21N3O2

Exact Mass: 299.1634

Molecular Weight: 299.37

Elemental Analysis: C, 68.20; H, 7.07; N, 14.04; O, 10.69

Price and Availability

Size	Price	Availability
5mg	USD 350.00	2 Weeks
10mg	USD 550.00	2 Weeks
25mg	USD 950.00	2 Weeks

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Related CAS #

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Synonym

Olinone

IUPAC/Chemical Name

N-[4-(1-Oxo-1,2,3,4-tetrahydro-pyrido[4,3-b]indol-5-yl)-butyl]-acetamide

InChi Key

RYVLOOXFFIFQEN-UHFFFAOYSA-N

InChi Code

InChI=1S/C17H21N3O2/c1-12(21)18-9-4-5-11-20-14-7-3-2-6-13(14)16-15(20)8-10-19-17(16)22/h2-3,6-7H,4-5,8-11H2,1H3,(H,18,21)(H,19,22)

SMILES Code

CC(NCCCCN1C(CCN2)=C(C2=O)C3=C1C=CC=C3)=O

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

More Info

Bromodomains (BrDs), a conserved structural module in chromatin-associated proteins, are well known for recognizing ε-N-acetyl lysine residues on histones. One of the most relevant BrDs is BRD4, a tandem BrD containing protein (BrD1 and BrD2) that plays a critical role in numerous diseases including cancer. Growing evidence shows that the two BrDs of BRD4 have different biological functions; hence selective ligands that can be used to study their functions are of great interest.

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Olinone is a potent and selective inhibitor of bromodomain of BET proteins.

In vitro activity:

This study shows that selective chemical inhibition of the first bromodomain of BET proteins using the small-molecule inhibitor, Olinone, accelerated the progression of mouse primary oligodendrocyte progenitors toward differentiation, whereas inhibition of both bromodomains of BET proteins hindered differentiation. Reference: Chem Biol. 2014 Jul 17;21(7):841-854. https://pubmed.ncbi.nlm.nih.gov/24954007/

In vivo activity:

TBD

Preparing Stock Solutions

The following data is based on the product molecular weight 299.37 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.

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:

Gacias M, Gerona-Navarro G, Plotnikov AN, Zhang G, Zeng L, Kaur J, Moy G, Rusinova E, Rodriguez Y, Matikainen B, Vincek A, Joshua J, Casaccia P, Zhou MM. Selective chemical modulation of gene transcription favors oligodendrocyte lineage progression. Chem Biol. 2014 Jul 17;21(7):841-854. doi: 10.1016/j.chembiol.2014.05.009. Epub 2014 Jun 19. PMID: 24954007; PMCID: PMC4104156.

In vitro protocol:

In vivo protocol:

TBD

1: Hilton-Proctor JP, Ilyichova O, Zheng Z, Jennings IG, Johnstone RW, Shortt J, Mountford SJ, Scanlon MJ, Thompson PE. Synthesis and elaboration of N-methylpyrrolidone as an acetamide fragment substitute in bromodomain inhibition. Bioorg Med Chem. 2019 Dec 15;27(24):115157. doi: 10.1016/j.bmc.2019.115157. Epub 2019 Oct 28. PMID: 31727451. 2: Rodríguez Y, Gerona-Navarro G, Osman R, Zhou MM. In silico design and molecular basis for the selectivity of Olinone toward the first over the second bromodomain of BRD4. Proteins. 2020 Mar;88(3):414-430. doi: 10.1002/prot.25818. Epub 2019 Oct 21. PMID: 31587361; PMCID: PMC6982606. 3: Zhao L, Li J, Fu Y, Zhang M, Wang B, Ouellette J, Shahi PK, Pattnaik BR, Watters JJ, Wong WT, Guo LW. Photoreceptor protection via blockade of BET epigenetic readers in a murine model of inherited retinal degeneration. J Neuroinflammation. 2017 Jan 19;14(1):14. doi: 10.1186/s12974-016-0775-4. PMID: 28103888; PMCID: PMC5248448. 4: Chiang CM. Nonequivalent response to bromodomain-targeting BET inhibitors in oligodendrocyte cell fate decision. Chem Biol. 2014 Jul 17;21(7):804-6. doi: 10.1016/j.chembiol.2014.07.003. PMID: 25036774; PMCID: PMC4137397. 5: Gacias M, Gerona-Navarro G, Plotnikov AN, Zhang G, Zeng L, Kaur J, Moy G, Rusinova E, Rodriguez Y, Matikainen B, Vincek A, Joshua J, Casaccia P, Zhou MM. Selective chemical modulation of gene transcription favors oligodendrocyte lineage progression. Chem Biol. 2014 Jul 17;21(7):841-854. doi: 10.1016/j.chembiol.2014.05.009. Epub 2014 Jun 19. PMID: 24954007; PMCID: PMC4104156. 6: Fujimura M, Tachibana H, Myou S, Kita T, Matsuda T. Bronchoprotective effect of an intrabronchial administration of cilostazol powder and a nebulized PDE1 and PDE4 inhibitor KF19514 in guinea pigs. Int Arch Allergy Immunol. 1998 Jul;116(3):220-7. doi: 10.1159/000023948. PMID: 9693270. 7: Kitani M, Miyamoto G, Nagasawa M, Yamada T, Matsubara J, Uchida M, Odomi M. Biotransformation of the novel inotropic agent toborinone (OPC-18790) in rats and dogs. Evidence for the formation of novel glutathione and two cysteine conjugates. Drug Metab Dispos. 1997 Jun;25(6):663-74. PMID: 9193867. 8: Fujimura M, Kita T, Myou S, Tachibana H, Matsuda T. Bronchoprotective effects of KF-19514 and cilostazol in guinea pigs in vivo. Eur J Pharmacol. 1997 May 26;327(1):57-63. doi: 10.1016/s0014-2999(97)89678-1. PMID: 9185836. 9: Itoh S, Mori T, Yoshida K, Fujiki H, Tominaga M, Yabuuchi Y. Cardiovascular effects of the combination of OPC-18790 and dopamine in halothane-anesthetized dogs. Jpn J Pharmacol. 1995 Nov;69(3):229-37. doi: 10.1254/jjp.69.229. PMID: 8699631. 10: Norman MH, Rigdon GC, Navas F 3rd, Cooper BR. Cyclic benzamides as mixed dopamine D2/serotonin 5-HT2 receptor antagonists: potential atypical antipsychotic agents. J Med Chem. 1994 Aug 5;37(16):2552-63. doi: 10.1021/jm00042a008. PMID: 7914539. 11: Tanaka T, Ishikawa T, Hagiwara M, Onoda K, Itoh H, Hidaka H. Effects of cilostazol, a selective cAMP phosphodiesterase inhibitor on the contraction of vascular smooth muscle. Pharmacology. 1988;36(5):313-20. doi: 10.1159/000138400. PMID: 2841693. 12: Miyamoto G, Sasabe H. Pharmacokinetics of a new positive inotropic agent, 3, 4-dihydro-6-[4-(3,4-dimethoxybenzoyl)-1-piperazinyl]-2(1H)-qu inolinone (OPC-8212), in the rat, rabbit, beagle dog and rhesus monkey. Arzneimittelforschung. 1984;34(3A):394-402. PMID: 6540095. 13: Hashimoto K, Yabuuchi Y, Yamashita S, Mori T. Positive inotropic effect of 3, 4-dihydro-6-[4-(3,4-dimethoxybenzoyl)-1-piperazinyl]-2(1H)-qu inolinone (OPC-8212) in the dog with experimentally-induced right-sided heart failure. Arzneimittelforschung. 1984;34(3A):390-3. PMID: 6540094. 14: Schwartz A, Wallick ET, Lee SW, Wang T, Hosakawa T, Whitmer KR, Matlib MA. Studies on the mechanism of action of 3, 4-dihydro-6-[4-(3,4-dimethoxybenzoyl)-1-piperazinyl]-2(1H)-qu inolinone (OPC-8212), a new positive inotropic drug. Enzyme activities and Ca2+ transport processes of sarcolemma and intracellular organelles. Arzneimittelforschung. 1984;34(3A):384-9. PMID: 6540093. 15: Endo M. The effect of a new positive inotropic agent, 3, 4-dihydro-6-[4-(3,4-dimethoxybenzoyl)-1-piperazinyl]-2(1H)-qu inolinone (OPC-8212), on thin bundles of skinned fibers from cardiac muscle. Arzneimittelforschung. 1984;34(3A):380-3. PMID: 6540092. 16: Satoh H, Hashimoto K. Effect of 3, 4-dihydro-6-[4-(3,4-dimethoxybenzoyl)-1-piperazinyl]-2(1H)-qu inolinone (OPC-8212) on the membrane currents of rabbit sino-atrial node cells. Arzneimittelforschung. 1984;34(3A):376-80. PMID: 6540091. 17: Lathrop DA, Schwartz A. Electro-mechanical effects of 3, 4-dihydro-6-[4-(3,4-dimethoxybenzoyl)-1-piperazinyl]-2(1H)-qu inolinone (OPC-8212), a new positive inotropic agent. Isolated adult canine Purkinje strands and ventricular trabeculae. Arzneimittelforschung. 1984;34(3A):371-5. PMID: 6540090.