Synonym
RN-18; RN 18; RN18;
IUPAC/Chemical Name
N-(2-methoxyphenyl)-2-[(4-nitrophenyl)thio]-benzamide
InChi Key
JKNUDHUHXMELIJ-UHFFFAOYSA-N
InChi Code
InChI=1S/C20H16N2O4S/c1-26-18-8-4-3-7-17(18)21-20(23)16-6-2-5-9-19(16)27-15-12-10-14(11-13-15)22(24)25/h2-13H,1H3,(H,21,23)
SMILES Code
O=C(NC1=CC=CC=C1OC)C2=CC=CC=C2SC3=CC=C([N+]([O-])=O)C=C3
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 and DMF
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO and DMF
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
More Info
The HIV-1 protein Vif, essential for in vivo viral replication, targets the human DNA-editing enzyme, APOBEC3G (A3G), which inhibits replication of retroviruses and hepatitis B virus. As Vif has no known cellular homologs, it is an attractive, yet unrealized, target for antiviral intervention. HIV-1 Vif-A3G axis is a valid target for developing small molecule-based new therapies for HIV infection or for enhancing innate immunity against viruses.
Biological target:
RN-18 inhibits Vif-mediated degradation of the DNA editing enzyme APOBEC3G with IC50 values of 10-30 µM in a high-throughput fluorescence screen. It inhibits viral replication of HIV-1 with IC50 values of 4.5 and 10 µM for nonpermissive CEM and H9 cells, respectively, and >100 µM for permissive cells.
In vitro activity:
RN-18 increases cellular A3G levels in a Vif-dependent manner and increases A3G incorporation into virions without inhibiting general proteasome-mediated protein degradation. RN-18 enhances Vif degradation only in the presence of A3G, reduces viral infectivity by increasing A3G incorporation into virions, and enhances cytidine deamination of the HIV genome.
Reference: Nat Biotechnol. 2008 Oct;26(10):1187-92. https://pubmed.ncbi.nlm.nih.gov/18806783/
In vivo activity:
To be determined
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMSO |
30.0 |
78.86 |
| DMF |
30.0 |
78.86 |
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
380.42
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. Nathans R, Cao H, Sharova N, Ali A, Sharkey M, Stranska R, Stevenson M, Rana TM. Small-molecule inhibition of HIV-1 Vif. Nat Biotechnol. 2008 Oct;26(10):1187-92. doi: 10.1038/nbt.1496. Epub 2008 Sep 21. PMID: 18806783; PMCID: PMC2693000.
2. Sinha C, Nischal A, Pant KK, Bandaru S, Nayarisseri A, Khattri S. Molecular docking analysis of RN18 and VEC5 in A3G-Vif inhibition. Bioinformation. 2014 Oct 30;10(10):611-6. doi: 10.6026/97320630010611. PMID: 25489169; PMCID: PMC4248342.
In vitro protocol:
1. Nathans R, Cao H, Sharova N, Ali A, Sharkey M, Stranska R, Stevenson M, Rana TM. Small-molecule inhibition of HIV-1 Vif. Nat Biotechnol. 2008 Oct;26(10):1187-92. doi: 10.1038/nbt.1496. Epub 2008 Sep 21. PMID: 18806783; PMCID: PMC2693000.
2. Sinha C, Nischal A, Pant KK, Bandaru S, Nayarisseri A, Khattri S. Molecular docking analysis of RN18 and VEC5 in A3G-Vif inhibition. Bioinformation. 2014 Oct 30;10(10):611-6. doi: 10.6026/97320630010611. PMID: 25489169; PMCID: PMC4248342.
In vivo protocol:
To be determined
Tavares Junior JMDC, da Silva CDG, Dos Santos BF, Souza NS, de Oliveira AR, Kupfer VL, Rinaldi AW, Domingues NLC. Cerium catalyst promoted C-S cross-coupling: synthesis of thioethers, dapsone and RN-18 precursors. Org Biomol Chem. 2019 Dec 4;17(47):10103-10108. doi: 10.1039/c9ob02171j. PMID: 31755516.
Zhou M, Luo RH, Hou XY, Wang RR, Yan GY, Chen H, Zhang RH, Shi JY, Zheng YT, Li R, Wei YQ. Synthesis, biological evaluation and molecular docking study of N-(2-methoxyphenyl)-6-((4-nitrophenyl)sulfonyl)benzamide derivatives as potent HIV-1 Vif antagonists. Eur J Med Chem. 2017 Mar 31;129:310-324. doi: 10.1016/j.ejmech.2017.01.010. Epub 2017 Jan 12. PMID: 28235704.
Mohammed I, Kummetha IR, Singh G, Sharova N, Lichinchi G, Dang J, Stevenson M, Rana TM. 1,2,3-Triazoles as Amide Bioisosteres: Discovery of a New Class of Potent HIV-1 Vif Antagonists. J Med Chem. 2016 Aug 25;59(16):7677-82. doi: 10.1021/acs.jmedchem.6b00247. Epub 2016 Aug 10. PMID: 27509004; PMCID: PMC5534211.
Sinha C, Nischal A, Pant KK, Bandaru S, Nayarisseri A, Khattri S. Molecular docking analysis of RN18 and VEC5 in A3G-Vif inhibition. Bioinformation. 2014 Oct 30;10(10):611-6. doi: 10.6026/97320630010611. PMID: 25489169; PMCID: PMC4248342.
