GGTI-298 TFA
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MedKoo CAT#: 206802

CAS#: 1217457-86-7 (TFA)

Description: GGTI-298 is a potent geranylgeranyltransferase-I (GGTase-I) inhibitor with potential antitumor actrivity. GGTI-298 disrupts MAP kinase activation and G(1)-S transition in Ki-Ras-overexpressing transformed adrenocortical cells. GGTI-298 induces hypophosphorylation of retinoblastoma and partner switching of cyclin-dependent kinase inhibitors. A potential mechanism for GGTI-298 antitumor activity. GGTI-298 arrests human tumor cells in G0/G1 and induces p21(WAF1/CIP1/SDI1) in a p53-independent manner. GGTI-298 induces G0-G1 block and apoptosis whereas FTI-277 causes G2-M enrichment in A549 cells.


Price and Availability

Size Price Shipping out time Quantity
100mg USD 850 Same day
200mg USD 1450 Same day
500mg USD 2150 Same day
1g USD 3250 Same day
2g USD 4850 Same day
5g USD 7950 2 weeks
Inquire bulk and customized quantity

Pricing updated 2020-10-27. Prices are subject to change without notice.

GGTI-298 TFA, purity > 98%, is in stock. The same day shipping out after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 206802
Name: GGTI-298 TFA
CAS#: 1217457-86-7 (TFA)
Chemical Formula: C29H34F3N3O5S
Exact Mass:
Molecular Weight: 593.6622
Elemental Analysis: C, 58.67; H, 5.77; F, 9.60; N, 7.08; O, 13.47; S, 5.40


Related CAS #: 205590-41-6 (HCl)   180977-44-0 (free base)   1217457-86-7 (TFA)  

Synonym: GGTI-298 TFA; GGTI-298 trifluoride salt; GGTI-298; GGTI 298; GGTI298.

IUPAC/Chemical Name: methyl (4-(((R)-2-amino-3-mercaptopropyl)amino)-2-(naphthalen-1-yl)benzoyl)-L-leucinate 2,2,2-trifluoroacetate

InChi Key: WALKWJPZELDSKT-UFABNHQSSA-N

InChi Code: InChI=1S/C27H33N3O3S.C2HF3O2/c1-17(2)13-25(27(32)33-3)30-26(31)23-12-11-20(29-15-19(28)16-34)14-24(23)22-10-6-8-18-7-4-5-9-21(18)22;3-2(4,5)1(6)7/h4-12,14,17,19,25,29,34H,13,15-16,28H2,1-3H3,(H,30,31);(H,6,7)/t19-,25+;/m1./s1

SMILES Code: CC(C)C[C@H](NC(C1=CC=C(NC[C@@H](N)CS)C=C1C2=C3C=CC=CC3=CC=C2)=O)C(OC)=O.O=C(O)C(F)(F)F


Technical Data

Appearance:
White to off-white solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Certificate of Analysis:

Safety Data Sheet (SDS):

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


References

1: Chu UB, Duellman T, Weaver SJ, Tao Y, Yang J. Endothelial protective genes induced by statin are mimicked by ERK5 activation as triggered by a drug combination of FTI-277 and GGTI-298. Biochim Biophys Acta. 2015 Jul;1850(7):1415-25. doi: 10.1016/j.bbagen.2015.03.011. PubMed PMID: 25829196; PubMed Central PMCID: PMC4465438.

2: Allal C, Pradines A, Hamilton AD, Sebti SM, Favre G. Farnesylated RhoB prevents cell cycle arrest and actin cytoskeleton disruption caused by the geranylgeranyltransferase I inhibitor GGTI-298. Cell Cycle. 2002 Nov-Dec;1(6):430-7. PubMed PMID: 12548020.

3: Lau CP, Wong KC, Huang L, Li G, Tsui SK, Kumta SM. A mouse model of luciferase-transfected stromal cells of giant cell tumor of bone. Connect Tissue Res. 2015 Nov;56(6):493-503. doi: 10.3109/03008207.2015.1075519. PubMed PMID: 26327464.

4: Mazet JL, Padieu M, Osman H, Maume G, Mailliet P, Dereu N, Hamilton AD, Lavelle F, Sebti SM, Maume BF. Combination of the novel farnesyltransferase inhibitor RPR130401 and the geranylgeranyltransferase-1 inhibitor GGTI-298 disrupts MAP kinase activation and G(1)-S transition in Ki-Ras-overexpressing transformed adrenocortical cells. FEBS Lett. 1999 Oct 29;460(2):235-40. PubMed PMID: 10544242.

5: Coxon FP, Helfrich MH, Van't Hof R, Sebti S, Ralston SH, Hamilton A, Rogers MJ. Protein geranylgeranylation is required for osteoclast formation, function, and survival: inhibition by bisphosphonates and GGTI-298. J Bone Miner Res. 2000 Aug;15(8):1467-76. PubMed PMID: 10934645.

6: Edwards DC, McKinnon KM, Fenizia C, Jung KJ, Brady JN, Pise-Masison CA. Inhibition of geranylgeranyl transferase-I decreases cell viability of HTLV-1-transformed cells. Viruses. 2011 Oct;3(10):1815-35. doi: 10.3390/v3101815. PubMed PMID: 22069517; PubMed Central PMCID: PMC3205383.

7: Adnane J, Bizouarn FA, Qian Y, Hamilton AD, Sebti SM. p21(WAF1/CIP1) is upregulated by the geranylgeranyltransferase I inhibitor GGTI-298 through a transforming growth factor beta- and Sp1-responsive element: involvement of the small GTPase rhoA. Mol Cell Biol. 1998 Dec;18(12):6962-70. PubMed PMID: 9819384; PubMed Central PMCID: PMC109279.

8: Sun J, Qian Y, Chen Z, Marfurt J, Hamilton AD, Sebti SM. The geranylgeranyltransferase I inhibitor GGTI-298 induces hypophosphorylation of retinoblastoma and partner switching of cyclin-dependent kinase inhibitors. A potential mechanism for GGTI-298 antitumor activity. J Biol Chem. 1999 Mar 12;274(11):6930-4. PubMed PMID: 10066746.

9: Vogt A, Sun J, Qian Y, Hamilton AD, Sebti SM. The geranylgeranyltransferase-I inhibitor GGTI-298 arrests human tumor cells in G0/G1 and induces p21(WAF1/CIP1/SDI1) in a p53-independent manner. J Biol Chem. 1997 Oct 24;272(43):27224-9. PubMed PMID: 9341167.

10: Duque G, Vidal C, Rivas D. Protein isoprenylation regulates osteogenic differentiation of mesenchymal stem cells: effect of alendronate, and farnesyl and geranylgeranyl transferase inhibitors. Br J Pharmacol. 2011 Mar;162(5):1109-18. doi: 10.1111/j.1476-5381.2010.01111.x. PubMed PMID: 21077849; PubMed Central PMCID: PMC3051383.

11: Lau CP, Huang L, Tsui SK, Ng PK, Leung PY, Kumta SM. Pamidronate, farnesyl transferase, and geranylgeranyl transferase-I inhibitors affects cell proliferation, apoptosis, and OPG/RANKL mRNA expression in stromal cells of giant cell tumor of bone. J Orthop Res. 2011 Mar;29(3):403-13. doi: 10.1002/jor.21249. PubMed PMID: 20886653.

12: Virtanen SS, Sandholm J, Yegutkin G, Kalervo Väänänen H, Härkönen PL. Inhibition of GGTase-I and FTase disrupts cytoskeletal organization of human PC-3 prostate cancer cells. Cell Biol Int. 2010 Aug;34(8):815-26. doi: 10.1042/CBI20090288. PubMed PMID: 20446922.

13: Miquel K, Pradines A, Sun J, Qian Y, Hamilton AD, Sebti SM, Favre G. GGTI-298 induces G0-G1 block and apoptosis whereas FTI-277 causes G2-M enrichment in A549 cells. Cancer Res. 1997 May 15;57(10):1846-50. PubMed PMID: 9157972.

14: Sarrabayrouse G, Pich C, Moriez R, Armand-Labit V, Rochaix P, Favre G, Tilkin-Mariamé AF. Melanoma cells treated with GGTI and IFN-gamma allow murine vaccination and enhance cytotoxic response against human melanoma cells. PLoS One. 2010 Feb 3;5(2):e9043. doi: 10.1371/journal.pone.0009043. PubMed PMID: 20140259; PubMed Central PMCID: PMC2815789.

15: Chen S, Fu L, Raja SM, Yue P, Khuri FR, Sun SY. Dissecting the roles of DR4, DR5 and c-FLIP in the regulation of geranylgeranyltransferase I inhibition-mediated augmentation of TRAIL-induced apoptosis. Mol Cancer. 2010 Jan 29;9:23. doi: 10.1186/1476-4598-9-23. PubMed PMID: 20113484; PubMed Central PMCID: PMC2824632.

16: Kagami S, Owada T, Kanari H, Saito Y, Suto A, Ikeda K, Hirose K, Watanabe N, Iwamoto I, Nakajima H. Protein geranylgeranylation regulates the balance between Th17 cells and Foxp3+ regulatory T cells. Int Immunol. 2009 Jun;21(6):679-89. doi: 10.1093/intimm/dxp037. PubMed PMID: 19380384.

17: Lee DH, Lee HR, Shin HK, Park SY, Hong KW, Kim EK, Bae SS, Lee WS, Rhim BY, Kim CD. Cilostazol enhances integrin-dependent homing of progenitor cells by activation of cAMP-dependent protein kinase in synergy with Epac1. J Neurosci Res. 2011 May;89(5):650-60. doi: 10.1002/jnr.22558. PubMed PMID: 21337364.

18: Ageberg M, Rydström K, Lindén O, Linderoth J, Jerkeman M, Drott K. Inhibition of geranylgeranylation mediates sensitivity to CHOP-induced cell death of DLBCL cell lines. Exp Cell Res. 2011 May 1;317(8):1179-91. doi: 10.1016/j.yexcr.2011.02.006. PubMed PMID: 21324313.

19: Abeles AM, Marjanovic N, Park J, Attur M, Chan ES, Al-Mussawir HE, Dave M, Fisher MC, Stuchin SA, Abramson SB, Pillinger MH. Protein isoprenylation regulates secretion of matrix metalloproteinase 1 from rheumatoid synovial fibroblasts: effects of statins and farnesyl and geranylgeranyl transferase inhibitors. Arthritis Rheum. 2007 Sep;56(9):2840-53. Erratum in: Arthritis Rheum. 2007 Oct;56(10):3510. Al-Mussawir, Hayfez [corrected to Al-Mussawir, Hayf E]. PubMed PMID: 17763406.

20: Alarcon VB, Marikawa Y. Statins inhibit blastocyst formation by preventing geranylgeranylation. Mol Hum Reprod. 2016 May;22(5):350-63. doi: 10.1093/molehr/gaw011. PubMed PMID: 26908642; PubMed Central PMCID: PMC4847613.