RI-1

Details

Stereochemistry	ACHIRAL
Molecular Formula	C14H11Cl3N2O3
Molecular Weight	361.608
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

ClC1=C(N2CCOCC2)C(=O)N(C1=O)C3=CC=C(Cl)C(Cl)=C3

InChI

InChIKey=MWSUIZKGNWELRF-UHFFFAOYSA-N

InChI=1S/C14H11Cl3N2O3/c15-9-2-1-8(7-10(9)16)19-13(20)11(17)12(14(19)21)18-3-5-22-6-4-18/h1-2,7H,3-6H2

HIDE SMILES / InChI

Molecular Formula	C14H11Cl3N2O3
Molecular Weight	361.608
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22573178
Curator's Comment: description was created based on several sources, including: https://www.ncbi.nlm.nih.gov/pubmed/27474153 | https://www.ncbi.nlm.nih.gov/pubmed/23231413

RI-1 is a cell-permeable RAD51 inhibitor that binds covalently to the protein surface at Cysteine 319. RI-1 disrupts homologous recombination in human cells. Also, it is an inhibitor of Bfl-1 protein. RI-1 represents a powerful tool for future investigations on mechanisms of DNA repair. RI-1 holds promise as an oncologic drug. In a glioma xenograft model, the Rad51 inhibitor RI-1 clearly enhanced the effect of lomustine on tumor growth.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Bcl-2-related protein A1 2 Target ID: CHEMBL6044 Sources: https://www.google.com/patents/US20090069324	Inhibitor 8504		1.14 µM [IC50]
DNA repair protein RAD51 homolog 1 1 Target ID: CHEMBL2034807 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22573178	Inhibitor 8504		5.0 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Cancer 609 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22573178	Primary		Basic research	Unknown Approved Use Unknown
Glioblastoma 66 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27474153 https://www.ncbi.nlm.nih.gov/pubmed/28076755 https://www.ncbi.nlm.nih.gov/pubmed/27495836	Primary		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
RAD51 Is a Selective DNA Repair Target to Radiosensitize Glioma Stem Cells.	2017-01-10	28076755
Targeting Homologous Recombination by Pharmacological Inhibitors Enhances the Killing Response of Glioblastoma Cells Treated with Alkylating Drugs.	2016-11	27474153
A radiosensitizing effect of RAD51 inhibition in glioblastoma stem-like cells.	2016-08-05	27495836
An optimized RAD51 inhibitor that disrupts homologous recombination without requiring Michael acceptor reactivity.	2013-01-10	23231413
RI-1: a chemical inhibitor of RAD51 that disrupts homologous recombination in human cells.	2012-08	22573178

Patents

Sample Use Guides

In Vivo Use Guide

50 mg/kg

Route of Administration: Intraperitoneal

In Vitro Use Guide

Immortalized human fibroblasts (SH2038 ± RAD51C) were incubated for 8 h in media containing 150 nM mitomycin C (MMC) and/or 20 uM RI-1. Cells were subsequently harvested and indirectly immunostained. Incubation of RI-1 with RAD51C-complemented cells inhibited MMC-induced RAD51 focus formation (P < 0.001), while not significantly affecting RPA focus formation (P= 0.53).

Substance Class	Chemical Created by `admin` on `Wed Apr 02 11:39:59 GMT 2025` Edited by `admin` on `Wed Apr 02 11:39:59 GMT 2025`
Record UNII	S8WG8ZRQ99
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

RI-1 (CHEMICAL)

Preferred Name

English

RI-1

Code

English

3-CHLORO-1-(3,4-DICHLOROPHENYL)-4-(4-MORPHOLINYL)-1H-PYRROLE-2,5-DIONE

Systematic Name

English

3-CHLORO-1-(3,4-DICHLOROPHENYL)-4-MORPHOLINO-1H-PYRROLE-2,5-DIONE

Systematic Name

English

3-CHLORO-1-(3,4-DICHLOROPHENYL)-4-MORPHOLIN-4-YLPYRROLE-2,5-DIONE

Systematic Name

English

1H-PYRROLE-2,5-DIONE, 3-CHLORO-1-(3,4-DICHLOROPHENYL)-4-(4-MORPHOLINYL)-

Systematic Name

English

Code System Code Type Description

EPA CompTox

DTXSID30360083