RG108 | CAS#48208-26-0 | DNA methyltransferase inhibitor

MedKoo Cat#: 406615 | Name: RG108

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Description:

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

RG108 is a non-nucleoside DNA methyltransferase inhibitor (DNMT inhibitor). RG108 led to a significant dose and time dependent growth inhibition and apoptosis induction in LNCaP, 22Rv1 and DU145. LNCaP and 22Rv1 also displayed decreased DNMT activity, DNMT1 expression and global DNA methylation. Interestingly, chronic treatment with RG108 significantly decreased GSTP1, APC and RAR-β2 promoter hypermethylation levels, although mRNA reexpression was only attained for GSTP1 and APC. RG108 is an effective tumor growth suppressor in most PCa cell lines tested.

Chemical Structure

RG108

CAS#48208-26-0

Theoretical Analysis

MedKoo Cat#: 406615

Name: RG108

CAS#: 48208-26-0

Chemical Formula: C19H14N2O4

Exact Mass: 334.0954

Molecular Weight: 334.33

Elemental Analysis: C, 68.26; H, 4.22; N, 8.38; O, 19.14

Price and Availability

Size	Price	Availability	Quantity
10mg	USD 150.00
25mg	USD 250.00
50mg	USD 450.00
100mg	USD 650.00
200mg	USD 950.00
500mg	USD 1,650.00
1g	USD 2,350.00
2g	USD 3,950.00
5g	USD 6,450.00

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Synonym

RG108; RG-108; RG 108; N-Phthalyl-L-tryptophan.

IUPAC/Chemical Name

(S)-2-(1,3-dioxoisoindolin-2-yl)-3-(1H-indol-3-yl)propanoic acid.

InChi Key

HPTXLHAHLXOAKV-INIZCTEOSA-N

InChi Code

InChI=1S/C19H14N2O4/c22-17-13-6-1-2-7-14(13)18(23)21(17)16(19(24)25)9-11-10-20-15-8-4-3-5-12(11)15/h1-8,10,16,20H,9H2,(H,24,25)/t16-/m0/s1

SMILES Code

O=C(O)[C@H](CC1=CNC2=CC=CC=C12)N3C(C4=CC=CC=C4C3=O)=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

Product Data

Product Data

Instruction

View handling instruction

Biological target:

RG108 is a non-nucleoside DNA methyltransferases (DNMTs) inhibitor (IC50=115 nM) that blocks the DNMTs active site. RG108 causes demethylation and reactivation of tumor suppressor genes, but it does not affect the methylation of centromeric satellite sequences.

In vitro activity:

This study proposes that RG108 could be used for epigenetic modulation, because it promotes epigenetic activation of NANOG and OCT4 without affecting the viability of human bone marrow-derived mesenchymal stem cells. RG108 is a stronger modulator of epigenetic machinery enzymes than DMSO. Reference: PLoS One. 2018 Dec 3;13(12):e0207873. https://pubmed.ncbi.nlm.nih.gov/30507955/

In vivo activity:

Inhibition of DNA methyltransferase activity via RG108 significantly attenuated auditory brainstem response threshold elevation, hair cell damage, and the loss of auditory synapses. RG108 protected against noise-induced hearing loss, protected against noise-induced hair cell loss and auditory neural damage, and attenuated oxidative stress-induced DNA damage and subsequent apoptosis-mediated cell loss in the cochlea after noise exposure. Reference: Cell Biol Toxicol. 2021 Oct;37(5):751-771. https://pubmed.ncbi.nlm.nih.gov/33723744/

	Solvent	mg/mL	mM
Solubility
	DMSO	100.0	299.11

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 334.33 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. Assis RIF, Wiench M, Silvério KG, da Silva RA, Feltran GDS, Sallum EA, Casati MZ, Nociti FH Jr, Andia DC. RG108 increases NANOG and OCT4 in bone marrow-derived mesenchymal cells through global changes in DNA modifications and epigenetic activation. PLoS One. 2018 Dec 3;13(12):e0207873. doi: 10.1371/journal.pone.0207873. PMID: 30507955; PMCID: PMC6277091. 2. Yang L, Hou J, Cui XH, Suo LN, Lv YW. RG108 induces the apoptosis of endometrial cancer Ishikawa cell lines by inhibiting the expression of DNMT3B and demethylation of HMLH1. Eur Rev Med Pharmacol Sci. 2017 Nov;21(22):5056-5064. doi: 10.26355/eurrev_201711_13818. PMID: 29228451. 3. Zheng Z, Zeng S, Liu C, Li W, Zhao L, Cai C, Nie G, He Y. The DNA methylation inhibitor RG108 protects against noise-induced hearing loss. Cell Biol Toxicol. 2021 Oct;37(5):751-771. doi: 10.1007/s10565-021-09596-y. Epub 2021 Mar 15. PMID: 33723744; PMCID: PMC8490244. 4. Zhai Y, Zhang Z, Yu H, Su L, Yao G, Ma X, Li Q, An X, Zhang S, Li Z. Dynamic Methylation Changes of DNA and H3K4 by RG108 Improve Epigenetic Reprogramming of Somatic Cell Nuclear Transfer Embryos in Pigs. Cell Physiol Biochem. 2018;50(4):1376-1397. doi: 10.1159/000494598. Epub 2018 Oct 24. PMID: 30355946.

In vitro protocol:

In vivo protocol:

1. Zheng Z, Zeng S, Liu C, Li W, Zhao L, Cai C, Nie G, He Y. The DNA methylation inhibitor RG108 protects against noise-induced hearing loss. Cell Biol Toxicol. 2021 Oct;37(5):751-771. doi: 10.1007/s10565-021-09596-y. Epub 2021 Mar 15. PMID: 33723744; PMCID: PMC8490244. 2. Zhai Y, Zhang Z, Yu H, Su L, Yao G, Ma X, Li Q, An X, Zhang S, Li Z. Dynamic Methylation Changes of DNA and H3K4 by RG108 Improve Epigenetic Reprogramming of Somatic Cell Nuclear Transfer Embryos in Pigs. Cell Physiol Biochem. 2018;50(4):1376-1397. doi: 10.1159/000494598. Epub 2018 Oct 24. PMID: 30355946.

1: Kong FX, Liu H, Xu T, Li SJ, Li W, Lu H, Ma NN, Wang YL, Shi JH, Yang YR, Wang FL. RG108 attenuates acute kidney injury by inhibiting P38 MAPK/FOS and JNK/JUN pathways. Int Immunopharmacol. 2024 Sep 11;142(Pt A):113077. doi: 10.1016/j.intimp.2024.113077. Epub ahead of print. PMID: 39265353. 2: Asgharian R, Hashemi A, Javeri A, Fakhr Taha M. DNA Methyltransferase Inhibition by RG108 Improves Stemness and Multipotential Differentiation of Human Adipose Tissue-derived Stem Cells. Iran J Biotechnol. 2024 Apr 1;22(2):e3863. doi: 10.30498/ijb.2024.435096.3863. PMID: 39220336; PMCID: PMC11364923. 3: Li L, Pang W, Xu L, Zhang Y, Zhang H, Zhu L, Li Y, Lin H, Mo L, Liu Y, Wang L, Yang P. Inhibition of DNMT1 attenuates experimental food allergy. Mol Immunol. 2024 Sep;173:71-79. doi: 10.1016/j.molimm.2024.07.009. Epub 2024 Jul 26. PMID: 39067087. 4: Lyu TJ, Qiu X, Wang Y, Zhang L, Dai Y, Wang X, Zhao S, Xiang M, Cui L, Cheng S, Liu Y, Gu H, Jiang Y, Meng X, Wang Y, Zhao X, Wang X, Li Q, Wang M, Jiang Y, Xu Z, Huang X, Li H, Wang Y, Li Z. DNMT3A dysfunction promotes neuroinflammation and exacerbates acute ischemic stroke. MedComm (2020). 2024 Jul 14;5(7):e652. doi: 10.1002/mco2.652. PMID: 39006763; PMCID: PMC11246610. 5: Tang YW, Jiang MY, Cao JW, Wan F. Triptolide decreases podocytes permeability by regulating TET2-mediated hydroxymethylation of ZO-1. Exp Biol Med (Maywood). 2024 May 31;249:10051. doi: 10.3389/ebm.2024.10051. PMID: 38881848; PMCID: PMC11176508. 6: Liu J, Ruan M, Liu Y, Hong X, Zhang L, Zhang Q. Identification of 3-(9H-carbazol-9-yl)-2-(1,3-dioxoisoindolin-2-yl)propanoic acids as promising DNMT1 inhibitors. Eur J Med Chem. 2024 Aug 5;274:116538. doi: 10.1016/j.ejmech.2024.116538. Epub 2024 May 27. PMID: 38823264. 7: Ghosh K, Zhou JJ, Shao JY, Chen SR, Pan HL. DNA demethylation in the hypothalamus promotes transcription of Agtr1a and Slc12a2 and hypertension development. J Biol Chem. 2024 Feb;300(2):105597. doi: 10.1016/j.jbc.2023.105597. Epub 2023 Dec 29. PMID: 38160798; PMCID: PMC10830874. 8: Renard T, Martinet B, De Souza Araujo N, Aron S. DNA methylation extends lifespan in the bumblebee Bombus terrestris. Proc Biol Sci. 2023 Dec 6;290(2012):20232093. doi: 10.1098/rspb.2023.2093. Epub 2023 Dec 6. PMID: 38052245; PMCID: PMC10697797. 9: Zuzina AB, Vinarskaya AK, Balaban PM. DNA Methylation Inhibition Reversibly Impairs the Long-Term Context Memory Maintenance in Helix. Int J Mol Sci. 2023 Sep 14;24(18):14068. doi: 10.3390/ijms241814068. PMID: 37762369; PMCID: PMC10531757. 10: Roato I, Baima G, Orrico C, Mosca Balma A, Alotto D, Romano F, Ferracini R, Aimetti M, Mussano F. Senescent Markers Expressed by Periodontal Ligament- Derived Stem Cells (PDLSCs) Harvested from Patients with Periodontitis Can Be Rejuvenated by RG108. Biomedicines. 2023 Sep 14;11(9):2535. doi: 10.3390/biomedicines11092535. PMID: 37760976; PMCID: PMC10526252. 11: Cho CC, Lin CJ, Huang HH, Yang WZ, Fei CY, Lin HY, Lee MS, Yuan HS. Mechanistic Insights into Harmine-Mediated Inhibition of Human DNA Methyltransferases and Prostate Cancer Cell Growth. ACS Chem Biol. 2023 Jun 16;18(6):1335-1350. doi: 10.1021/acschembio.3c00065. Epub 2023 May 15. PMID: 37188336; PMCID: PMC10278071. 12: Zhang D, Sun Y, Lei M, Wang Y, Cai C. Deciphering the potential ability of RG108 in cisplatin-induced HEI-OC1 ototoxicity: a research based on RNA-seq and molecular biology experiment. Hereditas. 2023 Apr 24;160(1):18. doi: 10.1186/s41065-023-00283-y. PMID: 37088824; PMCID: PMC10124021. 13: Heyob KM, Khuhro Z, Khan AQ, Brown D, Tipple TE, Rogers LK. Effects of DNA methylase inhibitors in a murine model of severe BPD. Respir Physiol Neurobiol. 2023 Jul;313:104060. doi: 10.1016/j.resp.2023.104060. Epub 2023 Apr 7. PMID: 37031925. 14: Poon CH, Liu Y, Pak S, Zhao RC, Aquili L, Tipoe GL, Leung GK, Chan YS, Yang S, Fung ML, Wu EX, Lim LW. Prelimbic Cortical Stimulation with L-methionine Enhances Cognition through Hippocampal DNA Methylation and Neuroplasticity Mechanisms. Aging Dis. 2023 Feb 1;14(1):112-135. doi: 10.14336/AD.2022.0706. PMID: 36818556; PMCID: PMC9937711. 15: Roszkowski L, Jaszczyk B, Plebańczyk M, Ciechomska M. S100A8 and S100A12 Proteins as Biomarkers of High Disease Activity in Patients with Rheumatoid Arthritis That Can Be Regulated by Epigenetic Drugs. Int J Mol Sci. 2022 Dec 31;24(1):710. doi: 10.3390/ijms24010710. PMID: 36614150; PMCID: PMC9820830. 16: Solntseva SV, Nikitin VP, Kozyrev SA, Nikitin PV. DNA methylation inhibition participates in the anterograde amnesia key mechanism through the suppression of the transcription of genes involved in memory formation in grape snails. Behav Brain Res. 2023 Feb 2;437:114118. doi: 10.1016/j.bbr.2022.114118. Epub 2022 Sep 16. PMID: 36116736. 17: Sosnowski P, Sass P, Słonimska P, Płatek R, Kamińska J, Baczyński Keller J, Mucha P, Peszyńska-Sularz G, Czupryn A, Pikuła M, Piotrowski A, Janus Ł, Rodziewicz-Motowidło S, Skowron P, Sachadyn P. Regenerative Drug Discovery Using Ear Pinna Punch Wound Model in Mice. Pharmaceuticals (Basel). 2022 May 16;15(5):610. doi: 10.3390/ph15050610. PMID: 35631437; PMCID: PMC9145447. 18: He Y, Zheng Z, Liu C, Li W, Zhao L, Nie G, Li H. Inhibiting DNA methylation alleviates cisplatin-induced hearing loss by decreasing oxidative stress-induced mitochondria-dependent apoptosis via the LRP1-PI3K/AKT pathway. Acta Pharm Sin B. 2022 Mar;12(3):1305-1321. doi: 10.1016/j.apsb.2021.11.002. Epub 2021 Nov 9. PMID: 35530135; PMCID: PMC9069410. 19: Ushio R, Hiroi M, Matsumoto A, Mori K, Yamamoto N, Ohmori Y. Enhanced Cytotoxic Effects in Human Oral Squamous Cell Carcinoma Cells Treated with Combined Methyltransferase Inhibitors and Histone Deacetylase Inhibitors. Biomedicines. 2022 Mar 24;10(4):763. doi: 10.3390/biomedicines10040763. PMID: 35453513; PMCID: PMC9029187. 20: Moshfegh C, Rambow SG, Domenig SA, Pieńkowska-Schelling A, Bleul U, Vogel V. Differentiation of mouse embryonic stem cells into cells with spermatogonia-like morphology with chemical intervention-dependent increased gene expression of LIM homeobox 1 (Lhx1). Stem Cell Res. 2022 May;61:102780. doi: 10.1016/j.scr.2022.102780. Epub 2022 Apr 4. PMID: 35395624.