Synonym
RG 14620; RG14620; RG-14620; TYRPHOSTIN RG 14620.
IUPAC/Chemical Name
(E)-3-(3,5-dichlorophenyl)-2-(pyridin-3-yl)acrylonitrile
InChi Key
TYXIVBJQPBWBHO-QCDXTXTGSA-N
InChi Code
InChI=1S/C14H8Cl2N2/c15-13-5-10(6-14(16)7-13)4-12(8-17)11-2-1-3-18-9-11/h1-7,9H/b12-4-
SMILES Code
N#C/C(C1=CC=CN=C1)=C/C2=CC(Cl)=CC(Cl)=C2
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
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
Biological target:
RG-14620 is an inhibitor of epidermal growth factor (EGF) receptor kinase with an IC50 value of 3 µM in HT-22 cells.
In vitro activity:
RG-14620 enhances drug-induced apoptosis and restores chemosensitivity to ABCG2-overexpressing multidrug-resistant cancer cells. It also stimulates ATP hydrolysis and inhibits photoaffinity labeling of ABCG2 with IAAP. RG-14620 may be useful to overcome chemoresistance in patients with drug-resistant tumors.
Reference: Cancer Lett. 2017 Nov 28;409:56-65. https://pubmed.ncbi.nlm.nih.gov/28893612/
In vivo activity:
RG-14620 suppressed tumor growth in nude mice.
Reference: Cancer Res. 1991 Aug 15;51(16):4430-5. https://pubmed.ncbi.nlm.nih.gov/1651159/
|
Solvent |
mg/mL |
mM |
comments |
| Solubility |
| DMF |
20.0 |
72.69 |
|
| DMSO |
20.0 |
72.69 |
|
| Ethanol |
1.0 |
3.63 |
|
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
275.13
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. Wu CP, Hsiao SH, Murakami M, Lu MJ, Li YQ, Hsieh CH, Ambudkar SV, Wu YS. Tyrphostin RG14620 selectively reverses ABCG2-mediated multidrug resistance in cancer cell lines. Cancer Lett. 2017 Nov 28;409:56-65. doi: 10.1016/j.canlet.2017.08.035. Epub 2017 Sep 8. PMID: 28893612; PMCID: PMC5634936.
2. Grunt TW. Tyrphostins and retinoids cooperate during inhibition of in vitro growth of ovarian cancer cells. Cancer Lett. 2003 Jan 28;189(2):147-56. doi: 10.1016/s0304-3835(02)00512-8. PMID: 12490307.
3. Yoneda T, Lyall RM, Alsina MM, Persons PE, Spada AP, Levitzki A, Zilberstein A, Mundy GR. The antiproliferative effects of tyrosine kinase inhibitors tyrphostins on a human squamous cell carcinoma in vitro and in nude mice. Cancer Res. 1991 Aug 15;51(16):4430-5. PMID: 1651159.
In vitro protocol:
1. Wu CP, Hsiao SH, Murakami M, Lu MJ, Li YQ, Hsieh CH, Ambudkar SV, Wu YS. Tyrphostin RG14620 selectively reverses ABCG2-mediated multidrug resistance in cancer cell lines. Cancer Lett. 2017 Nov 28;409:56-65. doi: 10.1016/j.canlet.2017.08.035. Epub 2017 Sep 8. PMID: 28893612; PMCID: PMC5634936.
2. Grunt TW. Tyrphostins and retinoids cooperate during inhibition of in vitro growth of ovarian cancer cells. Cancer Lett. 2003 Jan 28;189(2):147-56. doi: 10.1016/s0304-3835(02)00512-8. PMID: 12490307.
In vivo protocol:
1. Yoneda T, Lyall RM, Alsina MM, Persons PE, Spada AP, Levitzki A, Zilberstein A, Mundy GR. The antiproliferative effects of tyrosine kinase inhibitors tyrphostins on a human squamous cell carcinoma in vitro and in nude mice. Cancer Res. 1991 Aug 15;51(16):4430-5. PMID: 1651159.
1: Wu CP, Hsiao SH, Murakami M, Lu MJ, Li YQ, Hsieh CH, Ambudkar SV, Wu YS. Tyrphostin RG14620 selectively reverses ABCG2-mediated multidrug resistance in cancer cell lines. Cancer Lett. 2017 Nov 28;409:56-65. doi: 10.1016/j.canlet.2017.08.035. Epub 2017 Sep 8. PMID: 28893612; PMCID: PMC5634936.
2: Li T, Yang Y, Li X, Xu C, Meng L. EGFR- and AKT-mediated reduction in PTEN expression contributes to tyrphostin resistance and is reversed by mTOR inhibition in endometrial cancer cells. Mol Cell Biochem. 2012 Feb;361(1-2):19-29. doi: 10.1007/s11010-011-1082-0. Epub 2011 Sep 28. PMID: 21952748.
3: Xiao L, Yang YB, Shen HM, Xu CF, Wang XY, Li XM. [Effect of signal transduction inhibitors on human endometrial carcinoma cells with differential PTEN gene expression]. Zhonghua Fu Chan Ke Za Zhi. 2009 Sep;44(9):681-5. Chinese. PMID: 20079181.
4: Grunt TW, Tomek K, Wagner R, Puckmair K, Kainz B, Rünzler D, Gaiger A, Köhler G, Zielinski CC. Upregulation of retinoic acid receptor-beta by the epidermal growth factor-receptor inhibitor PD153035 is not mediated by blockade of ErbB pathways. J Cell Physiol. 2007 Jun;211(3):803-15. doi: 10.1002/jcp.20990. PMID: 17286282.
5: Grunt TW. Tyrphostins and retinoids cooperate during inhibition of in vitro growth of ovarian cancer cells. Cancer Lett. 2003 Jan 28;189(2):147-56. doi: 10.1016/s0304-3835(02)00512-8. PMID: 12490307.
6: Sion-Vardy N, Vardy D, Rodeck U, Kari C, Levin RM, Malkowicz SB. Antiproliferative effects of tyrosine kinase inhibitors (tyrphostins) on human bladder and renal carcinoma cells. J Surg Res. 1995 Dec;59(6):675-80. doi: 10.1006/jsre.1995.1222. PMID: 8538164.
7: Kumar N, Windisch V, Ammon HL. Photoinstability of some tyrphostin drugs: chemical consequences of crystallinity. Pharm Res. 1995 Nov;12(11):1708-15. doi: 10.1023/a:1016213721861. PMID: 8592674.
8: Khetarpal VK, Markham PM, Ziemniak JA. Dispositional characteristics of a tyrosine kinase inhibitor (RG 14620) in rats and rabbits following intravenous administration or dermal application. Drug Metab Dispos. 1994 Mar- Apr;22(2):216-23. PMID: 8013277.
9: Piontek M, Hengels KJ, Porschen R, Strohmeyer G. Antiproliferative effect of tyrosine kinase inhibitors in epidermal growth factor-stimulated growth of human gastric cancer cells. Anticancer Res. 1993 Nov-Dec;13(6A):2119-23. PMID: 8297123.
10: Yoneda T, Lyall RM, Alsina MM, Persons PE, Spada AP, Levitzki A, Zilberstein A, Mundy GR. The antiproliferative effects of tyrosine kinase inhibitors tyrphostins on a human squamous cell carcinoma in vitro and in nude mice. Cancer Res. 1991 Aug 15;51(16):4430-5. PMID: 1651159.
