Myoseverin | CAS#267402-71-1

MedKoo Cat#: 526266 | Name: Myoseverin

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Description:

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

Myoseverin is an inducer of the reversible fission of multinucleated myotubes into mononucleated fragments, affecting the expression of a variety of growth factor, immunomodulatory, extracellular matrix-remodeling, and stress response genes, consistent with the activation of pathways involved in wound healing and tissue regeneration.

Chemical Structure

Myoseverin

CAS#267402-71-1

Theoretical Analysis

MedKoo Cat#: 526266

Name: Myoseverin

CAS#: 267402-71-1

Chemical Formula: C24H28N6O2

Exact Mass: 432.2274

Molecular Weight: 432.53

Elemental Analysis: C, 66.65; H, 6.53; N, 19.43; O, 7.40

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 225.00
10mg	USD 385.00

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Related CAS #

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Synonym

Myoseverin

IUPAC/Chemical Name

2-N,6-N-Bis[(4-methoxyphenyl)methyl]-9-propan-2-ylpurine-2,6-diamine

InChi Key

IDCOTQWQVPRTNK-UHFFFAOYSA-N

InChi Code

InChI=1S/C24H28N6O2/c1-16(2)30-15-27-21-22(25-13-17-5-9-19(31-3)10-6-17)28-24(29-23(21)30)26-14-18-7-11-20(32-4)12-8-18/h5-12,15-16H,13-14H2,1-4H3,(H2,25,26,28,29)

SMILES Code

CC(C)N(C=N1)C2=C1C(NCC3=CC=C(OC)C=C3)=NC(NCC4=CC=C(OC)C=C4)=N2

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

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

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Myoseverina, a microtubule-binding molecule, induces the reversible fission of multinucleated myotubes into mononucleated fragments.

In vitro activity:

A new microtubule-binding molecule, myoseverin, was identified from a library of 2,6,9-trisubstituted purines in a morphological differentiation screen. Myoseverin induces the reversible fission of multinucleated myotubes into mononucleated fragments. Myotube fission promotes DNA synthesis and cell proliferation after removal of the compound and transfer of the cells to fresh growth medium. Transcriptional profiling and biochemical analysis indicate that myoseverin alone does not reverse the biochemical differentiation process. Instead, myoseverin affects the expression of a variety of growth factor, immunomodulatory, extracellular matrix-remodeling, and stress response genes, consistent with the activation of pathways involved in wound healing and tissue regeneration. Reference: Nat Biotechnol. 2000 Mar;18(3):304-8. https://pubmed.ncbi.nlm.nih.gov/10700146/

In vivo activity:

TBD

	Solvent	mg/mL	mM
Solubility
	DMF	3.3	7.63
	DMSO	87.0	201.04
	DMSO:PBS (pH 7.2) (1:2)	0.3	0.76
	Ethanol	11.1	25.56

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 432.53 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:

1. Ng DC, Gebski BL, Grounds MD, Bogoyevitch MA. Myoseverin disrupts sarcomeric organization in myocytes: an effect independent of microtubule assembly inhibition. Cell Motil Cytoskeleton. 2008 Jan;65(1):40-58. doi: 10.1002/cm.20242. PMID: 17948234. 2. Rosania GR, Chang YT, Perez O, Sutherlin D, Dong H, Lockhart DJ, Schultz PG. Myoseverin, a microtubule-binding molecule with novel cellular effects. Nat Biotechnol. 2000 Mar;18(3):304-8. doi: 10.1038/73753. PMID: 10700146.

In vitro protocol:

In vivo protocol:

TBD

1: Kim WH, Jung DW, Kim J, Im SH, Hwang SY, Williams DR. Small molecules that recapitulate the early steps of urodele amphibian limb regeneration and confer multipotency. ACS Chem Biol. 2012 Apr 20;7(4):732-43. doi: 10.1021/cb200532v. Epub 2012 Feb 9. PubMed PMID: 22270490. 2: Jung DW, Williams DR. Novel chemically defined approach to produce multipotent cells from terminally differentiated tissue syncytia. ACS Chem Biol. 2011 Jun 17;6(6):553-62. doi: 10.1021/cb2000154. Epub 2011 Feb 28. PubMed PMID: 21322636. 3: Kim YK, Ha HH, Lee JS, Bi X, Ahn YH, Hajar S, Lee JJ, Chang YT. Control of muscle differentiation by a mitochondria-targeted fluorophore. J Am Chem Soc. 2010 Jan 20;132(2):576-9. doi: 10.1021/ja906862g. PubMed PMID: 20020712. 4: Popowycz F, Schneider C, Debonis S, Skoufias DA, Kozielski F, Galmarini CM, Joseph B. Synthesis and antiproliferative evaluation of pyrazolo[1,5-a]-1,3,5-triazine myoseverin derivatives. Bioorg Med Chem. 2009 May 1;17(9):3471-8. doi: 10.1016/j.bmc.2009.03.007. Epub 2009 Mar 10. PubMed PMID: 19349183. 5: Dvorák Z, Modrianský M, Vrba J, Ulrichová J, Krystof V, Stýskala J, Pávek P. Evaluation of novel microtubules interfering agents myoseverin, tubulyzine and E2GG in primary cultures of rat hepatocytes. Gen Physiol Biophys. 2007 Sep;26(3):173-80. PubMed PMID: 18063844. 6: Ng DC, Gebski BL, Grounds MD, Bogoyevitch MA. Myoseverin disrupts sarcomeric organization in myocytes: an effect independent of microtubule assembly inhibition. Cell Motil Cytoskeleton. 2008 Jan;65(1):40-58. PubMed PMID: 17948234. 7: Krystof V, Moravcová D, Paprskárová M, Barbier P, Peyrot V, Hlobilková A, Havlícek L, Strnad M. Synthesis and biological activity of 8-azapurine and pyrazolo[4,3-d]pyrimidine analogues of myoseverin. Eur J Med Chem. 2006 Dec;41(12):1405-11. Epub 2006 Sep 22. PubMed PMID: 16996651. 8: Park HE, Baek SH, Min J, Chang YT, Kang DK, Chang SI, Joe YA. Myoseverin is a potential angiogenesis inhibitor by inhibiting endothelial cell function and endothelial progenitor cell differentiation. DNA Cell Biol. 2006 Sep;25(9):514-22. PubMed PMID: 16989574. 9: Vismara C, Bacchetta R, Di Muzio A, Mantecca P, Tarca S, Vailati G, Colombo R. Determination of myoseverin embryotoxic potential by using FETAX. Birth Defects Res B Dev Reprod Toxicol. 2006 Aug;77(4):257-67. PubMed PMID: 16929549. 10: Duckmanton A, Kumar A, Chang YT, Brockes JP. A single-cell analysis of myogenic dedifferentiation induced by small molecules. Chem Biol. 2005 Oct;12(10):1117-26. PubMed PMID: 16242654. 11: Hines J. Small molecules driving myotube fission. Chem Biol. 2005 Oct;12(10):1058-60. Review. PubMed PMID: 16242647. 12: Imokawa Y, Gates PB, Chang YT, Simon HG, Brockes JP. Distinctive expression of Myf5 in relation to differentiation and plasticity of newt muscle cells. Int J Dev Biol. 2004 Jun;48(4):285-91. PubMed PMID: 15300509. 13: El Fahime E, Bouchentouf M, Benabdallah BF, Skuk D, Lafreniere JF, Chang YT, Tremblay JP. Tubulyzine, a novel tri-substituted triazine, prevents the early cell death of transplanted myogenic cells and improves transplantation success. Biochem Cell Biol. 2003 Apr;81(2):81-90. PubMed PMID: 12870872. 14: Moon HS, Jacobson EM, Khersonsky SM, Luzung MR, Walsh DP, Xiong W, Lee JW, Parikh PB, Lam JC, Kang TW, Rosania GR, Schier AF, Chang YT. A novel microtubule destabilizing entity from orthogonal synthesis of triazine library and zebrafish embryo screening. J Am Chem Soc. 2002 Oct 2;124(39):11608-9. PubMed PMID: 12296721. 15: Brockes JP, Kumar A. Plasticity and reprogramming of differentiated cells in amphibian regeneration. Nat Rev Mol Cell Biol. 2002 Aug;3(8):566-74. Review. PubMed PMID: 12154368. 16: Perez OD, Chang YT, Rosania G, Sutherlin D, Schultz PG. Inhibition and reversal of myogenic differentiation by purine-based microtubule assembly inhibitors. Chem Biol. 2002 Apr;9(4):475-83. PubMed PMID: 11983336. 17: Chang YT, Wignall SM, Rosania GR, Gray NS, Hanson SR, Su AI, Merlie J Jr, Moon HS, Sangankar SB, Perez O, Heald R, Schultz PG. Synthesis and biological evaluation of myoseverin derivatives: microtubule assembly inhibitors. J Med Chem. 2001 Dec 20;44(26):4497-500. PubMed PMID: 11741468. 18: Rosania GR, Chang YT, Perez O, Sutherlin D, Dong H, Lockhart DJ, Schultz PG. Myoseverin, a microtubule-binding molecule with novel cellular effects. Nat Biotechnol. 2000 Mar;18(3):304-8. PubMed PMID: 10700146.