GS-9219
featured

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

MedKoo CAT#: 201452

CAS#: 859209-74-8

Description: 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.


Chemical Structure

img
GS-9219
CAS# 859209-74-8

Theoretical Analysis

MedKoo Cat#: 201452
Name: GS-9219
CAS#: 859209-74-8
Chemical Formula: C21H35N8O6P
Exact Mass: 526.24172
Molecular Weight: 526.53
Elemental Analysis: C, 47.90; H, 6.70; N, 21.28; O, 18.23; P, 5.88

Price and Availability

Size Price Availability Quantity
Bulk inquiry

Synonym: GS 9219; GS9219; GS-9219.

IUPAC/Chemical Name: (2S,2'S)-diethyl 2,2'-((((2-(2-amino-6-(cyclopropylamino)-9H-purin-9-yl)ethoxy)methyl)phosphoryl)bis(azanediyl))dipropanoate

InChi Key: ANSPEDQTHURSFQ-KBPBESRZSA-N

InChi Code: InChI=1S/C21H35N8O6P/c1-5-34-19(30)13(3)27-36(32,28-14(4)20(31)35-6-2)12-33-10-9-29-11-23-16-17(24-15-7-8-15)25-21(22)26-18(16)29/h11,13-15H,5-10,12H2,1-4H3,(H2,27,28,32)(H3,22,24,25,26)/t13-,14-/m0/s1

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

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

Preparing Stock Solutions

The following data is based on the product molecular weight 526.53 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.

Recalculate based on batch purity %
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

Molarity Calculator

Calculate the mass, volume, or concentration required for a solution.
=
x
x
g/mol

*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

Reconstitution Calculator

The reconstitution calculator allows you to quickly calculate the volume of a reagent to reconstitute your vial. Simply enter the mass of reagent and the target concentration and the calculator will determine the rest.

=
÷

Dilution Calculator

Calculate the dilution required to prepare a stock solution.
x
=
x

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.

GS-9219

10.0mg / Not available


Additional Information

GS-9219 was designed as a cytotoxic agent that preferentially targets lymphoid cells.  In lymphocytes, GS-9219 is converted to its active metabolite, PMEG diphosphate, via enzymic hydrolysis, deamination, and phosphorylation. GS-9219 has substantial antiproliferative activity against activated lymphocytes and hematopoietic tumor cell lines. In contrast, resting lymphocytes and solid tumor lines were less sensitive to GS-9219. GS-9219, but not PMEG, depleted the germinal centers in lymphoid tissues of normal beagle dogs at doses that were tolerated. In addn., GS-9219 displayed significant in vivo efficacy in five dogs with spontaneous NHL after a single administration, with either no or low-grade adverse events.  GS-9219 may have utility for the treatment of NHL.