Dorsomorphin

  • CAT Number: I006518
  • CAS Number: 866405-64-3 (free base)
  • Molecular Formula: C24H25N5O
  • Molecular Weight: 399.498
  • Purity: ≥95%
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Dorsomorphin, also known as BML-275 , is a selective small molecule inhibitor of BMP signaling, which promotes cardiomyogenesis in embryonic stem cells. Dorsomorphin reverses the mesenchymal phenotype of breast cancer initiating cells by inhibition of bone morphogenetic protein signaling.

Catalog Number I006518
CAS Number 866405-64-3 (free base)
Synonyms

Dorsomorphin; Compound C BML275; BML-275; BML 275;6-(4-(2-(piperidin-1-yl)ethoxy)phenyl)-3-(pyridin-4-yl)pyrazolo[1,5-a]pyrimidine

Molecular Formula

C24H25N5O

Purity 95%
Target BMP inhibitor
Solubility Soluble in DMSO, not in water
Storage 0 - 4°C for short term or -20 °C for long term
IUPAC Name 6-[4-(2-piperidin-1-ylethoxy)phenyl]-3-pyridin-4-ylpyrazolo[1,5-a]pyrimidine
InChI InChI=1S/C24H25N5O/c1-2-12-28(13-3-1)14-15-30-22-6-4-19(5-7-22)21-16-26-24-23(17-27-29(24)18-21)20-8-10-25-11-9-20/h4-11,16-18H,1-3,12-15H2
InChIKey XHBVYDAKJHETMP-UHFFFAOYSA-N
SMILES C1CCN(CC1)CCOC2=CC=C(C=C2)C3=CN4C(=C(C=N4)C5=CC=NC=C5)N=C3
Reference

</br>1:Erratum to: Ambivalent effects of compound C (dorsomorphin) on inflammatory response in LPS-stimulated rat primary microglial cultures. Łabuzek K, Liber S, Gabryel B, Bułdak Ł, Okopień B.Naunyn Schmiedebergs Arch Pharmacol. 2017 Mar;390(3):327-328. doi: 10.1007/s00210-017-1348-5. No abstract available. PMID: 28160017 </br>2:Dorsomorphin homologue 1, a highly selective small-molecule bone morphogenetic protein inhibitor, suppresses medial artery calcification. Lin T, Wang XL, Zettervall SL, Cai Y, Guzman RJ.J Vasc Surg. 2016 Jun 30. pii: S0741-5214(16)30090-8. doi: 10.1016/j.jvs.2016.03.462. [Epub ahead of print] PMID: 27374065 </br>3:Dual Inhibition of Activin/Nodal/TGF-β and BMP Signaling Pathways by SB431542 and Dorsomorphin Induces Neuronal Differentiation of Human Adipose Derived Stem Cells. Madhu V, Dighe AS, Cui Q, Deal DN.Stem Cells Int. 2016;2016:1035374. doi: 10.1155/2016/1035374. Epub 2015 Dec 20. PMID: 26798350 Free PMC Article</br>4:Small molecules dorsomorphin and LDN-193189 inhibit myostatin/GDF8 signaling and promote functional myoblast differentiation. Horbelt D, Boergermann JH, Chaikuad A, Alfano I, Williams E, Lukonin I, Timmel T, Bullock AN, Knaus P.J Biol Chem. 2015 Feb 6;290(6):3390-404. doi: 10.1074/jbc.M114.604397. Epub 2014 Nov 3. PMID: 25368322 Free PMC Article</br>5:Differential cellular responses induced by dorsomorphin and LDN-193189 in chemotherapy-sensitive and chemotherapy-resistant human epithelial ovarian cancer cells. Ali JL, Lagasse BJ, Minuk AJ, Love AJ, Moraya AI, Lam L, Arthur G, Gibson SB, Morrison LC, Werbowetski-Ogilvie TE, Fu Y, Nachtigal MW.Int J Cancer. 2015 Mar 1;136(5):E455-69. doi: 10.1002/ijc.29220. Epub 2014 Sep 26. PMID: 25227893 Free Article</br>6:Dorsomorphin reverses the mesenchymal phenotype of breast cancer initiating cells by inhibition of bone morphogenetic protein signaling. Garulli C, Kalogris C, Pietrella L, Bartolacci C, Andreani C, Falconi M, Marchini C, Amici A.Cell Signal. 2014 Feb;26(2):352-62. doi: 10.1016/j.cellsig.2013.11.022. Epub 2013 Nov 23. PMID: 24280125 </br>7:Dorsomorphin promotes survival and germline competence of zebrafish spermatogonial stem cells in culture. Wong TT, Collodi P.PLoS One. 2013 Aug 1;8(8):e71332. doi: 10.1371/journal.pone.0071332. Print 2013. PMID: 23936500 Free PMC Article</br>8:Synthesis and structure-activity relationships of a novel and selective bone morphogenetic protein receptor (BMP) inhibitor derived from the pyrazolo[1.5-a]pyrimidine scaffold of dorsomorphin: the discovery of ML347 as an ALK2 versus ALK3 selective MLPCN probe. Engers DW, Frist AY, Lindsley CW, Hong CC, Hopkins CR.Bioorg Med Chem Lett. 2013 Jun 1;23(11):3248-52. doi: 10.1016/j.bmcl.2013.03.113. Epub 2013 Apr 11. PMID: 23639540 Free PMC Article</br>9:Bioanalytical method development, validation and quantification of dorsomorphin in rat plasma by LC-MS/MS. Karthikeyan K, Mahat MY, Chandrasekaran S, Gopal K, Franklin PX, Sivakumar BJ, Singh G, Narayanan S, Gopalan B, Khan AA.Biomed Chromatogr. 2013 Aug;27(8):1018-26. doi: 10.1002/bmc.2899. Epub 2013 Mar 21. PMID: 23526253 </br>10:Dorsomorphin stimulates neurite outgrowth in PC12 cells via activation of a protein kinase A-dependent MEK-ERK1/2 signaling pathway. Kudo TA, Kanetaka H, Mizuno K, Ryu Y, Miyamoto Y, Nunome S, Zhang Y, Kano M, Shimizu Y, Hayashi H.Genes Cells. 2011 Nov;16(11):1121-32. doi: 10.1111/j.1365-2443.2011.01556.x. Epub 2011 Oct 12. PMID: 21988724 Free Article

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