BML-284 | CAS# 853220-52-7 | Wnt Activator

MedKoo Cat#: 573455 | Name: BML-284

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Description:

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

BML-284 is a Wnt canonical signaling activator and tubulin polymerization inhibitor. Treatment of Xenopus embryos with AMBMP leads to defects similar to the MT depolymerizing drug nocodazole, including a failure to generate or polarize cilia (depending on the timing of treatment) and a loss of the cell movements associated with radial intercalation. The dramatic effect AMBMP has on basic MT based cellular functions suggests that its usefulness as a Wnt regulator is questionable. Moreover, it may be an important new tool for experimental or pharmacological manipulation of MTs.

Chemical Structure

BML-284

CAS#853220-52-7 (free base)

Theoretical Analysis

MedKoo Cat#: 573455

Name: BML-284

CAS#: 853220-52-7 (free base)

Chemical Formula: C19H18N4O3

Exact Mass: 350.1400

Molecular Weight: 350.30

Elemental Analysis: C, 65.13; H, 5.18; N, 15.99; O, 13.70

Price and Availability

Size	Price	Availability	Quantity
10mg	USD 350.00	2 Weeks
50mg	USD 750.00	2 Weeks

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Related CAS #

853220-52-7 (free base) 2095432-75-8 (HCl)

Synonym

AMBMP; Wnt Agonist; BML284; BML-284; BML 284; Wnt agonist 1;

IUPAC/Chemical Name

N4-(1,3-Benzodioxol-5-ylmethyl)-6-(3-methoxyphenyl)-2,4-pyrimidinediamine

InChi Key

FABQUVYDAXWUQP-UHFFFAOYSA-N

InChi Code

InChI=1S/C19H18N4O3/c1-24-14-4-2-3-13(8-14)15-9-18(23-19(20)22-15)21-10-12-5-6-16-17(7-12)26-11-25-16/h2-9H,10-11H2,1H3,(H3,20,21,22,23)

SMILES Code

NC1=NC(C2=CC=CC(OC)=C2)=CC(NCC3=CC=C(OCO4)C4=C3)=N1

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

>3 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:

Wnt canonical signaling activator; also tubulin polymerization inhibitor.

In vitro activity:

Treatment of RPE1 cells with AMBMP shows a rapid dose response effect on MT growth in the nanomolar range immediately upon drug addition (Figure 1a.-b., Supplemental Movie 1). This is apparent based on both the decrease in colorimetric changes (Fig 1a) as well as a quantification of comet length (Fig 1b). Furthermore, a dose of 10μM completely abolishes all MT growth (Figure 1c. and e., Supplemental Movie 2). The rapid effect of the drug treatment (seconds) suggests that the drug’s effects are mediated via binding MTs or MT associated proteins rather than via transcriptional regulation of the Wnt pathway. Reference: Cytoskeleton (Hoboken). 2018 Oct; 75(10): 450–457. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6322664/

In vivo activity:

C3KO mice were treated with AMBMP for 2 weeks, receiving daily doses ranging from 3 to 30 mg/kg and administered via s.c. and i.p. routes of delivery, based on the results of preliminary PK and efficacy testing. AMBMP treatment at 7.5–15.0 mg/kg (i.p.) was most efficacious, based on fiber type and fiber size measurements. Cage-side observations did not reveal any obvious toxicity (e.g., weight loss, loss of grooming, loss of activity) in mice treated for 2 weeks with AMBMP (Figure S4). Reference: Cell Rep Med. 2020 Oct 20; 1(7): 100122. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7659555/

	Solvent	mg/mL	mM
Solubility
	DMSO	38.7	99.99

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 350.30 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. Werner M, Del Castillo U, Ventrella R, Brotslaw E, Mitchell B. The small molecule AMBMP disrupts microtubule growth, ciliogenesis, cell polarity, and cell migration. Cytoskeleton (Hoboken). 2018 Oct;75(10):450-457. doi: 10.1002/cm.21496. PMID: 30315640; PMCID: PMC6322664. 2. Wang H, Graves MW 2nd, Zhou H, Gu Z, Lamont RJ, Scott DA. 2-Amino-4-(3,4-(methylenedioxy)benzylamino)-6-(3-methoxyphenyl)pyrimidine is an anti-inflammatory TLR-2, -4 and -5 response mediator in human monocytes. Inflamm Res. 2016 Jan;65(1):61-9. doi: 10.1007/s00011-015-0891-0. Epub 2015 Nov 27. PMID: 26613980; PMCID: PMC4703520. 3. Liu J, Campagna J, John V, Damoiseaux R, Mokhonova E, Becerra D, Meng H, McNally EM, Pyle AD, Kramerova I, Spencer MJ. A Small-Molecule Approach to Restore a Slow-Oxidative Phenotype and Defective CaMKIIβ Signaling in Limb Girdle Muscular Dystrophy. Cell Rep Med. 2020 Oct 20;1(7):100122. doi: 10.1016/j.xcrm.2020.100122. PMID: 33205074; PMCID: PMC7659555. 4. Xia Z, Qi W, Xiaofeng G, Jiguang K, Hongfei H, Yuchen Z, Yihan Z, Yan W, Nannan L, Yiwei L, Hongsheng B, Xiaobai L. AMBMP activates WNT pathway and alleviates stress-induced behaviors in maternal separation and chronic stress models. Eur J Pharmacol. 2020 Aug 15;881:173192. doi: 10.1016/j.ejphar.2020.173192. Epub 2020 May 12. PMID: 32413348.

In vitro protocol:

In vivo protocol:

1. Liu J, Campagna J, John V, Damoiseaux R, Mokhonova E, Becerra D, Meng H, McNally EM, Pyle AD, Kramerova I, Spencer MJ. A Small-Molecule Approach to Restore a Slow-Oxidative Phenotype and Defective CaMKIIβ Signaling in Limb Girdle Muscular Dystrophy. Cell Rep Med. 2020 Oct 20;1(7):100122. doi: 10.1016/j.xcrm.2020.100122. PMID: 33205074; PMCID: PMC7659555. 2. Xia Z, Qi W, Xiaofeng G, Jiguang K, Hongfei H, Yuchen Z, Yihan Z, Yan W, Nannan L, Yiwei L, Hongsheng B, Xiaobai L. AMBMP activates WNT pathway and alleviates stress-induced behaviors in maternal separation and chronic stress models. Eur J Pharmacol. 2020 Aug 15;881:173192. doi: 10.1016/j.ejphar.2020.173192. Epub 2020 May 12. PMID: 32413348.

1: Xia Z, Qi W, Xiaofeng G, Jiguang K, Hongfei H, Yuchen Z, Yihan Z, Yan W, Nannan L, Yiwei L, Hongsheng B, Xiaobai L. AMBMP activates WNT pathway and alleviates stress-induced behaviors in maternal separation and chronic stress models. Eur J Pharmacol. 2020 Aug 15;881:173192. doi: 10.1016/j.ejphar.2020.173192. Epub 2020 May 12. PMID: 32413348. 2: Werner M, Del Castillo U, Ventrella R, Brotslaw E, Mitchell B. The small molecule AMBMP disrupts microtubule growth, ciliogenesis, cell polarity, and cell migration. Cytoskeleton (Hoboken). 2018 Oct;75(10):450-457. doi: 10.1002/cm.21496. PMID: 30315640; PMCID: PMC6322664. 3: Denicol AC, Dobbs KB, McLean KM, Carambula SF, Loureiro B, Hansen PJ. Canonical WNT signaling regulates development of bovine embryos to the blastocyst stage. Sci Rep. 2013;3:1266. doi: 10.1038/srep01266. Epub 2013 Feb 12. PMID: 23405280; PMCID: PMC3569626. 4: Wang H, Graves MW 2nd, Zhou H, Gu Z, Lamont RJ, Scott DA. 2-Amino-4-(3,4-(methylenedioxy)benzylamino)-6-(3-methoxyphenyl)pyrimidine is an anti-inflammatory TLR-2, -4 and -5 response mediator in human monocytes. Inflamm Res. 2016 Jan;65(1):61-9. doi: 10.1007/s00011-015-0891-0. Epub 2015 Nov 27. PMID: 26613980; PMCID: PMC4703520. 5: Şahin İO, Özkul Y, Dündar M. Current and Future Therapeutic Strategies for Limb Girdle Muscular Dystrophy Type R1: Clinical and Experimental Approaches. Pathophysiology. 2021 May 18;28(2):238-249. doi: 10.3390/pathophysiology28020016. PMID: 35366260; PMCID: PMC8830477. 6: Liu J, Campagna J, John V, Damoiseaux R, Mokhonova E, Becerra D, Meng H, McNally EM, Pyle AD, Kramerova I, Spencer MJ. A Small-Molecule Approach to Restore a Slow-Oxidative Phenotype and Defective CaMKIIβ Signaling in Limb Girdle Muscular Dystrophy. Cell Rep Med. 2020 Oct 20;1(7):100122. doi: 10.1016/j.xcrm.2020.100122. PMID: 33205074; PMCID: PMC7659555. 7: Tribulo P, Leão BCDS, Lehloenya KC, Mingoti GZ, Hansen PJ. Consequences of endogenous and exogenous WNT signaling for development of the preimplantation bovine embryo. Biol Reprod. 2017 Jun 1;96(6):1129-1141. doi: 10.1093/biolre/iox048. PMID: 28575156; PMCID: PMC5803770. 8: Ma X, Hu X, Zhu Y, Jin H, Hu G, Ding L, Ning S. Sesamol inhibits proliferation, migration and invasion of triple negative breast cancer via inactivating Wnt/β-catenin signaling. Biochem Pharmacol. 2022 Dec;206:115299. doi: 10.1016/j.bcp.2022.115299. Epub 2022 Oct 13. PMID: 36244446. 9: Fukuda Y, Sano O, Kazetani K, Yamamoto K, Iwata H, Matsui J. Tubulin is a molecular target of the Wnt-activating chemical probe. BMC Biochem. 2016 May 20;17(1):9. doi: 10.1186/s12858-016-0066-9. PMID: 27207629; PMCID: PMC4873989. 10: Narcisi R, Arikan OH, Lehmann J, Ten Berge D, van Osch GJ. Differential Effects of Small Molecule WNT Agonists on the Multilineage Differentiation Capacity of Human Mesenchymal Stem Cells. Tissue Eng Part A. 2016 Nov;22(21-22):1264-1273. doi: 10.1089/ten.TEA.2016.0081. Epub 2016 Oct 17. PMID: 27633010.