MedKoo Cat#: 406615 Name: RG108 CAS#: 48208-26-0 Chemical Formula: C19H14N2O4 Exact Mass: 334.09536 Molecular Weight: 334.32546 Elemental Analysis: C, 68.26; H, 4.22; N, 8.38; O, 19.14
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
Technical Data
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).
Harmonized System Code: 293490
Additional Information
References
1: Asgatay S, Champion C, Marloie G, Drujon T, Senamaud-Beaufort C, Ceccaldi A, Erdmann A, Rajavelu A, Schambel P, Jeltsch A, Lequin O, Karoyan P, Arimondo PB, Guianvarc\'h D. Synthesis and evaluation of analogues of N-phthaloyl-l-tryptophan
(RG108) as inhibitors of DNA methyltransferase 1. J Med Chem. 2014 Jan 23;57(2):421-34. doi: 10.1021/jm401419p. Epub 2014 Jan 9. PubMed PMID: 24328113.
2: Graça I, Sousa EJ, Baptista T, Almeida M, Ramalho-Carvalho J, Palmeira C, Henrique R, Jerónimo C. Anti-tumoral effect of the non-nucleoside DNMT inhibitor RG108 in human prostate cancer cells. Curr Pharm Des. 2014;20(11):1803-11. PubMed PMID: 23888969.
3: Savickiene J, Treigyte G, Jazdauskaite A, Borutinskaite VV, Navakauskiene R. DNA methyltransferase inhibitor RG108 and histone deacetylase inhibitors cooperate to enhance NB4 cell differentiation and E-cadherin re-expression by chromatin remodelling. Cell Biol Int. 2012 Nov 1;36(11):1067-78. doi: 10.1042/CBI20110649. PubMed PMID: 22845560.
4: Savickiene J, Treigyte G, Borutinskaite VV, Navakauskiene R. Antileukemic activity of combined epigenetic agents, DNMT inhibitors zebularine and RG108 with HDAC inhibitors, against promyelocytic leukemia HL-60 cells. Cell Mol Biol Lett. 2012 Dec;17(4):501-25. Epub 2012 Jul 20. PubMed PMID: 22820861.
5: Braun J, Boittiaux I, Tilborg A, Lambert D, Wouters J. The dicyclo-hexyl-amine salt of RG108 (N-phthalyl-l-tryptophan), a potential epigenetic modulator. Acta Crystallogr Sect E Struct Rep Online. 2010 Nov 13;66(Pt 12):o3175-6. doi: 10.1107/S160053681004626X. PubMed PMID: 21589471; PubMed Central PMCID: PMC3011641.
6: Schirrmacher E, Beck C, Brueckner B, Schmitges F, Siedlecki P, Bartenstein P, Lyko F, Schirrmacher R. Synthesis and in vitro evaluation of biotinylated RG108: a high affinity compound for studying binding interactions with human DNA methyltransferases. Bioconjug Chem. 2006 Mar-Apr;17(2):261-6. PubMed PMID: 16536454.