GS-9219
GS-9219 is a prodrug of the acyclic nucleoside phosphonate analogue 9-(2-phosphonylmethoxyethyl)guanine (PMEG) with potential antineoplastic activity. Formulated to selectively accumulate in lymphocytes, nucleotide analogue GS 9219 is converted to its active metabolite, PMEG diphosphate (PMEGpp), via enzymatic hydrolysis, deamination, and phosphorylation; subsequently, PMEGpp is incorporated into nascent DNA chains by DNA polymerases, which may result in the termination of DNA synthesis, S-phase cell cycle arrest, and the induction of apoptosis in susceptible lymphoma cell populations.
1: Thamm DH, Vail DM, Kurzman ID, Babusis D, Ray AS, Sousa-Powers N, Tumas DB. GS-9219/VDC-1101--a prodrug of the acyclic nucleotide PMEG has antitumor activity in spontaneous canine multiple myeloma. BMC Vet Res. 2014 Jan 25;10:30. doi: 10.1186/1746-6148-10-30. PubMed PMID: 24460928; PubMed Central PMCID: PMC3904015.
2: Frey CR, Andrei G, Votruba I, Cannizzaro C, Han B, Fung W, Hung M, Liu X, Geleziunas R, Fiten P, Opdenakker G, Snoeck R, Cihlar T. Mutations in adenosine deaminase-like (ADAL) protein confer resistance to the antiproliferative agents N6-cyclopropyl-PMEDAP and GS-9219. Anticancer Res. 2013 May;33(5):1899-912. PubMed PMID: 23645737.
3: Tsai CY, Ray AS, Tumas DB, Keating MJ, Reiser H, Plunkett W. Targeting DNA repair in chronic lymphocytic leukemia cells with a novel acyclic nucleotide analogue, GS-9219. Clin Cancer Res. 2009 Jun 1;15(11):3760-9. doi: 10.1158/1078-0432.CCR-08-2848. Epub 2009 May 12. PubMed PMID: 19435836.
4: Vail DM, Thamm DH, Reiser H, Ray AS, Wolfgang GH, Watkins WJ, Babusis D, Henne IN, Hawkins MJ, Kurzman ID, Jeraj R, Vanderhoek M, Plaza S, Anderson C, Wessel MA, Robat C, Lawrence J, Tumas DB. Assessment of GS-9219 in a pet dog model of non-Hodgkin's lymphoma. Clin Cancer Res. 2009 May 15;15(10):3503-10. doi: 10.1158/1078-0432.CCR-08-3113. Epub 2009 May 5. PubMed PMID: 19417014.
5: Reiser H, Wang J, Chong L, Watkins WJ, Ray AS, Shibata R, Birkus G, Cihlar T, Wu S, Li B, Liu X, Henne IN, Wolfgang GH, Desai M, Rhodes GR, Fridland A, Lee WA, Plunkett W, Vail D, Thamm DH, Jeraj R, Tumas DB. GS-9219--a novel acyclic nucleotide analogue with potent antineoplastic activity in dogs with spontaneous non-Hodgkin's lymphoma. Clin Cancer Res. 2008 May 1;14(9):2824-32. doi: 10.1158/1078-0432.CCR-07-2061. PubMed PMID: 18451250.
6: Preclinical data expected for nucleotide GS 9219. AIDS Patient Care STDS. 2007 Apr;21(4):289-90. PubMed PMID: 17506142.
2: Frey CR, Andrei G, Votruba I, Cannizzaro C, Han B, Fung W, Hung M, Liu X, Geleziunas R, Fiten P, Opdenakker G, Snoeck R, Cihlar T. Mutations in adenosine deaminase-like (ADAL) protein confer resistance to the antiproliferative agents N6-cyclopropyl-PMEDAP and GS-9219. Anticancer Res. 2013 May;33(5):1899-912. PubMed PMID: 23645737.
3: Tsai CY, Ray AS, Tumas DB, Keating MJ, Reiser H, Plunkett W. Targeting DNA repair in chronic lymphocytic leukemia cells with a novel acyclic nucleotide analogue, GS-9219. Clin Cancer Res. 2009 Jun 1;15(11):3760-9. doi: 10.1158/1078-0432.CCR-08-2848. Epub 2009 May 12. PubMed PMID: 19435836.
4: Vail DM, Thamm DH, Reiser H, Ray AS, Wolfgang GH, Watkins WJ, Babusis D, Henne IN, Hawkins MJ, Kurzman ID, Jeraj R, Vanderhoek M, Plaza S, Anderson C, Wessel MA, Robat C, Lawrence J, Tumas DB. Assessment of GS-9219 in a pet dog model of non-Hodgkin's lymphoma. Clin Cancer Res. 2009 May 15;15(10):3503-10. doi: 10.1158/1078-0432.CCR-08-3113. Epub 2009 May 5. PubMed PMID: 19417014.
5: Reiser H, Wang J, Chong L, Watkins WJ, Ray AS, Shibata R, Birkus G, Cihlar T, Wu S, Li B, Liu X, Henne IN, Wolfgang GH, Desai M, Rhodes GR, Fridland A, Lee WA, Plunkett W, Vail D, Thamm DH, Jeraj R, Tumas DB. GS-9219--a novel acyclic nucleotide analogue with potent antineoplastic activity in dogs with spontaneous non-Hodgkin's lymphoma. Clin Cancer Res. 2008 May 1;14(9):2824-32. doi: 10.1158/1078-0432.CCR-07-2061. PubMed PMID: 18451250.
6: Preclinical data expected for nucleotide GS 9219. AIDS Patient Care STDS. 2007 Apr;21(4):289-90. PubMed PMID: 17506142.
| Chemical | |
|---|---|
| CAS Num | 859209-74-8 |
| Chemical Formula | C21H35N8O6P |
| Molecular Weight | 526.53 |
| IUPAC Chemical Name | (2S,2'S)-diethyl 2,2'-((((2-(2-amino-6-(cyclopropylamino)-9H-purin-9-yl)ethoxy)methyl)phosphoryl)bis(azanediyl))dipropanoate |
| Exact Mass | 526.24172 |
| Elemental Analysis | C, 47.90; H, 6.70; N, 21.28; O, 18.23; P, 5.88 |
| Synonym | GS 9219; GS9219; GS-9219. |
| Solubility | Soluble in DMSO, not in water |
| SMILES Code | O=P(N[C@@H](C)C(OCC)=O)(N[C@@H](C)C(OCC)=O)COCCN1C=NC2=C(NC3CC3)N=C(N)N=C12 |
| Biological | |
| Targets and Effects | N/A |
| Pathways | Apoptosis |
| Physical | |
| 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). |
| Shelf Life | >2 years if stored properly |
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