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SML2154

Sigma-Aldrich

Deltarasin trihydrochloride

≥98% (HPLC)

Synonym(s):

(S)-1-Benzyl-2-(4-(2-(2-phenyl-1H-benzo[d]imidazol-1-yl)-2-(piperidin-4-yl)ethoxy)phenyl)-1H-benzo[d]imidazole trihydrochloride, 2-[4-[(2S)-2-(2-Phenyl-1H-benzimidazol-1-yl)-2-(4-piperidinyl)ethoxy]phenyl]-1-(phenylmethyl)-1H-benzimidazole trihydrochloride

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About This Item

Empirical Formula (Hill Notation):
C40H37N5O · 3HCl
CAS Number:
1440898-61-2
Molecular Weight:
713.14
UNSPSC Code:
12352200
NACRES:
NA.77

Assay

≥98% (HPLC)

form

powder

storage condition

desiccated

color

white to beige

solubility

H2O: 2 mg/mL, clear

storage temp.

2-8°C

InChI

1S/C40H37N5O/c1-3-11-29(12-4-1)27-44-36-17-9-7-15-34(36)42-39(44)32-19-21-33(22-20-32)46-28-38(30-23-25-41-26-24-30)45-37-18-10-8-16-35(37)43-40(45)31-13-5-2-6-14-31/h1-22,30,38,41H,23-28H2/t38-/m1/s1

InChI key

LTZKEDSUXKTTTC-KXQOOQHDSA-N

Biochem/physiol Actions

Deltarasin is a membrane-permeable benzimidazole derivative that effectively abolishes cellular KRas plasma membrane localization (5 μM for 1 hr) by blocking KRas-PDEδ interaction via high affinity interaction with PDEδ prenyl-binding pocket (KD = 38 nM). Deltarasin inhibits oncogenic KRas-dependent proliferation (by ~50% of Panc-Tu-I cells; 5μM for 70 hrs) and survival (52% and 46% death induction of Panc-Tu-I and Capan-1 cells, respectively; 5μM for 24 hrs) in human pancreatic ductal adenocarcinoma (PDAC) cultures and is efficacious against Panc-Tu-I xenograft-derived tumor growth in mice in vivo (60% and 80% retardation on day 9, respectively, with 15 mg/kg q.d. or 10 mg/kg b.i.d. via i.p.).

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Certificates of Analysis (COA)

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Pablo Martín-Gago et al.
Angewandte Chemie (International ed. in English), 56(9), 2423-2428 (2017-01-21)
Small-molecule inhibition of the interaction between the KRas oncoprotein and the chaperone PDE6δ impairs KRas spatial organization and signaling in cells. However, despite potent binding in vitro (K
Malte Schmick et al.
Cell, 157(2), 459-471 (2014-04-15)
KRas is a major proto-oncogene product whose signaling activity depends on its level of enrichment on the plasma membrane (PM). This PM localization relies on posttranslational prenylation for membrane affinity, while PM specificity has been attributed to electrostatic interactions between
Philipp Küchler et al.
Bioorganic & medicinal chemistry, 26(8), 1426-1434 (2017-09-25)
Prenylation is a post-translational modification that increases the affinity of proteins for membranes and mediates protein-protein interactions. The retinal rod rhodopsin-sensitive cGMP 3',5'-cyclic phosphodiesterase subunit delta (PDEδ) is a prenyl binding protein that is essential for the shuttling of small
Sandip Murarka et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 23(25), 6083-6093 (2016-11-04)
The K-Ras GTPase is a major target in anticancer drug discovery. However, direct interference with signaling by K-Ras has not led to clinically useful drugs yet. Correct localization and signaling by farnesylated K-Ras is regulated by the prenyl binding protein
Jianman Guo et al.
American journal of cancer research, 7(4), 923-934 (2017-05-05)
Patients with Neurofibromatosis type 1 (NF1) and Neurofibromatosis type 2 (NF2) are predisposed to tumors of the nervous system. NF1 patients predominantly develop neurofibromas, and Malignant Peripheral Nerve Sheath Tumors (MPNST) while NF2 patients develop schwannomas and meningiomas. Here we
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