StemRegenin 1 | CAS#1227633-49-9 | AHR antagonist

MedKoo Cat#: 531295 | Name: StemRegenin 1

Description:

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

StemReginin 1 is an aryl hydrocarbon receptor (AHR) antagonist (IC50 = 127 nM). StemReginin 1 exhibits no inhibitory activity against a panel of 61 kinases and preferentially inhibits human AHR. StemReginin 1 promotes the expansion of CD34+ cells ex vivo. In hematopoietic stem cell (HSC) culture, the compound induces a 50-fold increase in CD34-expressing cells, and HSCs cultured with StemReginin 1 show increased engraftment in mice. Combination of StemReginin 1 with DMOG increases the proportion of primitive HSCs and improves long-term engraftment. The product also promotes expansion of human promyelocytic leukemia cell line NB4.

Chemical Structure

StemRegenin 1

CAS#1227633-49-9

Theoretical Analysis

MedKoo Cat#: 531295

Name: StemRegenin 1

CAS#: 1227633-49-9

Chemical Formula: C24H23N5OS

Exact Mass: 429.1623

Molecular Weight: 429.54

Elemental Analysis: C, 67.11; H, 5.40; N, 16.30; O, 3.72; S, 7.46

Price and Availability

Size	Price	Availability
50mg	USD 450.00	2 Weeks
100mg	USD 750.00	2 Weeks
200mg	USD 1,250.00	2 Weeks
500mg	USD 1,950.00	2 Weeks
1g	USD 2,950.00	2 Weeks
2g	USD 5,250.00	2 Weeks

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Synonym

StemRegenin 1; StemRegenin-1; StemRegenin1; SR1; SR-1; SR 1;

IUPAC/Chemical Name

4-[2-[[2-benzo[b]thien-3-yl-9-(1-methylethyl)-9H-purin-6-yl]amino]ethyl]-phenol

InChi Key

BGFHMYJZJZLMHW-UHFFFAOYSA-N

InChi Code

InChI=1S/C24H23N5OS/c1-15(2)29-14-26-21-23(25-12-11-16-7-9-17(30)10-8-16)27-22(28-24(21)29)19-13-31-20-6-4-3-5-18(19)20/h3-10,13-15,30H,11-12H2,1-2H3,(H,25,27,28)

SMILES Code

OC1=CC=C(CCNC2=C3N=CN(C(C)C)C3=NC(C4=CSC5=CC=CC=C54)=N2)C=C1

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:

StemRegenin 1 is a potent AHR antagonist with IC50 of 127 nM.

In vitro activity:

StemRegenin 1 promoted the ex vivo expansion of CD34+ cells. Culture of hematopoietic stem cells with SR1 led to a 50-fold increase in cells expressing CD34 and a 17-fold increase in cells that retain the ability to engraft immunodeficient mice. Mechanistic studies show that SR1 acts by antagonizing the aryl hydrocarbon receptor. Reference: Science. 2010 Sep 10;329(5997):1345-8. https://pubmed.ncbi.nlm.nih.gov/20688981/

In vivo activity:

StemRegenin 1 may help increase patient survival after irradiation because it modulated the radioresponse of hematopoietic stem/progenitor cells. Treatment with StemRegenin 1 after irradiation of C57BL/6 mice significantly mitigated TBI-induced death (80% survival vs. 30% saline treatment survival) with enhanced recovery of peripheral blood cell counts. Reference: Biomedicines. 2023 Mar 8;11(3):824. https://pubmed.ncbi.nlm.nih.gov/36979803/

	Solvent	mg/mL	mM
Solubility
	DMSO	62.5	145.50

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 429.54 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. Koide R, Kulkeaw K, Tanaka Y, Swain A, Nakanishi Y, Sugiyama D. Aryl Hydrocarbon Receptor Antagonist StemRegenin 1 Promotes the Expansion of Human Promyelocytic Leukemia Cell Line, NB4. Anticancer Res. 2016 Jul;36(7):3635-43. PMID: 27354634. 2. Boitano AE, Wang J, Romeo R, Bouchez LC, Parker AE, Sutton SE, Walker JR, Flaveny CA, Perdew GH, Denison MS, Schultz PG, Cooke MP. Aryl hydrocarbon receptor antagonists promote the expansion of human hematopoietic stem cells. Science. 2010 Sep 10;329(5997):1345-8. doi: 10.1126/science.1191536. Epub 2010 Aug 5. Erratum in: Science. 2011 May 6;332(6030):664. PMID: 20688981; PMCID: PMC3033342. 3. Hwang YJ, Shin DY, Kim MJ, Jang H, Kim S, Yang H, Jang WI, Park S, Shim S, Lee SB. StemRegenin 1 Mitigates Radiation-Mediated Hematopoietic Injury by Modulating Radioresponse of Hematopoietic Stem/Progenitor Cells. Biomedicines. 2023 Mar 8;11(3):824. doi: 10.3390/biomedicines11030824. PMID: 36979803; PMCID: PMC10045038. 4. Koide R, Kulkeaw K, Tanaka Y, Swain A, Nakanishi Y, Sugiyama D. Aryl Hydrocarbon Receptor Antagonist StemRegenin 1 Promotes the Expansion of Human Promyelocytic Leukemia Cell Line, NB4. Anticancer Res. 2016 Jul;36(7):3635-43. PMID: 27354634.

In vitro protocol:

In vivo protocol:

1. Hwang YJ, Shin DY, Kim MJ, Jang H, Kim S, Yang H, Jang WI, Park S, Shim S, Lee SB. StemRegenin 1 Mitigates Radiation-Mediated Hematopoietic Injury by Modulating Radioresponse of Hematopoietic Stem/Progenitor Cells. Biomedicines. 2023 Mar 8;11(3):824. doi: 10.3390/biomedicines11030824. PMID: 36979803; PMCID: PMC10045038. 2. Koide R, Kulkeaw K, Tanaka Y, Swain A, Nakanishi Y, Sugiyama D. Aryl Hydrocarbon Receptor Antagonist StemRegenin 1 Promotes the Expansion of Human Promyelocytic Leukemia Cell Line, NB4. Anticancer Res. 2016 Jul;36(7):3635-43. PMID: 27354634.

1: Trikha P, Moseman J, Thakkar A, Campbell AL, Elmas E, Foltz JA, Chakravarti N, Fitch J, Mardis E, Lee D. Defining the AHR regulated transcriptome in NK cells reveal gene expression program relevant to development and function. Blood Adv. 2021 Sep 24:bloodadvances.2021004533. doi: 10.1182/bloodadvances.2021004533. Epub ahead of print. PMID: 34559190. 2: Zhu X, Sun Q, Tan WS, Cai H. Reducing TGF-β1 cooperated with StemRegenin 1 promoted the expansion ex vivo of cord blood CD34+ cells by inhibiting AhR signalling. Cell Prolif. 2021 Mar;54(3):e12999. doi: 10.1111/cpr.12999. Epub 2021 Jan 31. PMID: 33522060; PMCID: PMC7941221. 3: Wu Q, Zheng J, Dou C, Qi S. Forkhead Box M1 promotes the growth and tube formation of human malignant meningioma cells via the aryl hydrocarbon receptor signaling pathway. Folia Neuropathol. 2020;58(3):223-236. doi: 10.5114/fn.2020.100065. PMID: 33099292. 4: Marx-Blümel L, Marx C, Weise F, Frey J, Perner B, Schlingloff G, Lindig N, Hampl J, Sonnemann J, Brauer D, Voigt A, Singh S, Beck B, Jäger UM, Wang ZQ, Beck JF, Schober A. Biomimetic reconstruction of the hematopoietic stem cell niche for in vitro amplification of human hematopoietic stem cells. PLoS One. 2020 Jun 22;15(6):e0234638. doi: 10.1371/journal.pone.0234638. PMID: 32569325; PMCID: PMC7307768. 5: Sica RA, Terzioglu MK, Mahmud D, Mahmud N. Mechanistic Basis of ex Vivo Umbilical Cord Blood Stem Progenitor Cell Expansion. Stem Cell Rev Rep. 2020 Aug;16(4):628-638. doi: 10.1007/s12015-020-09981-w. PMID: 32424674. 6: Jin H, Ji C, Ren F, Aniagu S, Tong J, Jiang Y, Chen T. AHR-mediated oxidative stress contributes to the cardiac developmental toxicity of trichloroethylene in zebrafish embryos. J Hazard Mater. 2020 Mar 5;385:121521. doi: 10.1016/j.jhazmat.2019.121521. Epub 2019 Oct 25. PMID: 31699484. 7: Singh J, Chen ELY, Xing Y, Stefanski HE, Blazar BR, Zúñiga-Pflücker JC. Generation and function of progenitor T cells from StemRegenin-1-expanded CD34+ human hematopoietic progenitor cells. Blood Adv. 2019 Oct 22;3(20):2934-2948. doi: 10.1182/bloodadvances.2018026575. PMID: 31648315; PMCID: PMC6849952. 8: Xie SZ, Garcia-Prat L, Voisin V, Ferrari R, Gan OI, Wagenblast E, Kaufmann KB, Zeng AGX, Takayanagi SI, Patel I, Lee EK, Jargstorf J, Holmes G, Romm G, Pan K, Shoong M, Vedi A, Luberto C, Minden MD, Bader GD, Laurenti E, Dick JE. Sphingolipid Modulation Activates Proteostasis Programs to Govern Human Hematopoietic Stem Cell Self-Renewal. Cell Stem Cell. 2019 Nov 7;25(5):639-653.e7. doi: 10.1016/j.stem.2019.09.008. Epub 2019 Oct 17. PMID: 31631013; PMCID: PMC6838675. 9: Heo JS, Lim JY, Pyo S, Yoon DW, Lee D, Ren WX, Lee SG, Kim GJ, Kim J. Environmental Benzopyrene Attenuates Stemness of Placenta-Derived Mesenchymal Stem Cells via Aryl Hydrocarbon Receptor. Stem Cells Int. 2019 Jan 13;2019:7414015. doi: 10.1155/2019/7414015. PMID: 30766605; PMCID: PMC6350590. 10: Gentil M, Hugues P, Desterke C, Telliam G, Sloma I, Souza LEB, Baykal S, Artus J, Griscelli F, Guerci A, Johnson-Ansah H, Foudi A, Bennaceur-Griscelli A, Turhan AG. Aryl hydrocarbon receptor (AHR) is a novel druggable pathway controlling malignant progenitor proliferation in chronic myeloid leukemia (CML). PLoS One. 2018 Aug 9;13(8):e0200923. doi: 10.1371/journal.pone.0200923. PMID: 30091999; PMCID: PMC6084853. 11: Bock KW. From TCDD-mediated toxicity to searches of physiologic AHR functions. Biochem Pharmacol. 2018 Sep;155:419-424. doi: 10.1016/j.bcp.2018.07.032. Epub 2018 Jul 26. PMID: 30055148. 12: Tao L, Togarrati PP, Choi KD, Suknuntha K. StemRegenin 1 selectively promotes expansion of Multipotent Hematopoietic Progenitors derived from Human Embryonic Stem Cells. J Stem Cells Regen Med. 2017 Dec 18;13(2):75-79. doi: 10.46582/jsrm.1302011. PMID: 29391752; PMCID: PMC5786649. 13: Hoogstad-van Evert JS, Cany J, van den Brand D, Oudenampsen M, Brock R, Torensma R, Bekkers RL, Jansen JH, Massuger LF, Dolstra H. Umbilical cord blood CD34+ progenitor-derived NK cells efficiently kill ovarian cancer spheroids and intraperitoneal tumors in NOD/SCID/IL2Rgnull mice. Oncoimmunology. 2017 May 11;6(8):e1320630. doi: 10.1080/2162402X.2017.1320630. PMID: 28919991; PMCID: PMC5593716. 14: Psatha N, Georgolopoulos G, Phelps S, Papayannopoulou T. Brief Report: A Differential Transcriptomic Profile of Ex Vivo Expanded Adult Human Hematopoietic Stem Cells Empowers Them for Engraftment Better than Their Surface Phenotype. Stem Cells Transl Med. 2017 Oct;6(10):1852-1858. doi: 10.1002/sctm.17-0048. Epub 2017 Aug 11. PMID: 28801972; PMCID: PMC6430062. 15: Dant TA, Lin KL, Bruce DW, Montgomery SA, Kolupaev OV, Bommiasamy H, Bixby LM, Woosley JT, McKinnon KP, Gonzalez FJ, Blazar BR, Vincent BG, Coghill JM, Serody JS. T-cell expression of AhR inhibits the maintenance of pTreg cells in the gastrointestinal tract in acute GVHD. Blood. 2017 Jul 20;130(3):348-359. doi: 10.1182/blood-2016-08-734244. Epub 2017 May 26. PMID: 28550042; PMCID: PMC5520467. 16: Jackson CS, Durandt C, Janse van Rensburg I, Praloran V, Brunet de la Grange P, Pepper MS. Targeting the aryl hydrocarbon receptor nuclear translocator complex with DMOG and Stemregenin 1 improves primitive hematopoietic stem cell expansion. Stem Cell Res. 2017 May;21:124-131. doi: 10.1016/j.scr.2017.04.007. Epub 2017 Apr 20. PMID: 28445828. 17: Kiernan J, Damien P, Monaghan M, Shorr R, McIntyre L, Fergusson D, Tinmouth A, Allan D. Clinical Studies of Ex Vivo Expansion to Accelerate Engraftment After Umbilical Cord Blood Transplantation: A Systematic Review. Transfus Med Rev. 2017 Jul;31(3):173-182. doi: 10.1016/j.tmrv.2016.12.004. Epub 2016 Dec 23. PMID: 28087163. 18: Lawicki S, Covin RB, Powers AA. The Kidd (JK) Blood Group System. Transfus Med Rev. 2017 Jul;31(3):165-172. doi: 10.1016/j.tmrv.2016.10.003. Epub 2016 Nov 9. PMID: 28065763. 19: Baron F, Nagler A. Novel strategies for improving hematopoietic reconstruction after allogeneic hematopoietic stem cell transplantation or intensive chemotherapy. Expert Opin Biol Ther. 2017 Feb;17(2):163-174. doi: 10.1080/14712598.2017.1269167. Epub 2016 Dec 21. PMID: 27927023. 20: Koide R, Kulkeaw K, Tanaka Y, Swain A, Nakanishi Y, Sugiyama D. Aryl Hydrocarbon Receptor Antagonist StemRegenin 1 Promotes the Expansion of Human Promyelocytic Leukemia Cell Line, NB4. Anticancer Res. 2016 Jul;36(7):3635-43. PMID: 27354634.