| Identification | Back Directory | [Name]
HA-15 | [CAS]
1609402-14-3 | [Synonyms]
HA-15
CS-2893
HA15;HA 15
HA15 >=98% (HPLC)
Acetamide, N-[4-[3-[[[5-(dimethylamino)-1-naphthalenyl]sulfonyl]amino]phenyl]-2-thiazolyl]- | [EINECS(EC#)]
604-604-1 | [Molecular Formula]
C23H22N4O3S2 | [MDL Number]
MFCD30377202 | [MOL File]
1609402-14-3.mol | [Molecular Weight]
466.58 |
| Chemical Properties | Back Directory | [density ]
1.406±0.06 g/cm3(Predicted) | [storage temp. ]
Store at -20°C | [solubility ]
DMSO:71.5(Max Conc. mg/mL);153.24(Max Conc. mM)
Ethanol:45.0(Max Conc. mg/mL);96.45(Max Conc. mM) | [form ]
A solid | [pka]
7.32±0.50(Predicted) | [color ]
Light yellow to green yellow | [InChI]
1S/C23H22N4O3S2/c1-15(28)24-23-25-20(14-31-23)16-7-4-8-17(13-16)26-32(29,30)22-12-6-9-18-19(22)10-5-11-21(18)27(2)3/h4-14,26H,1-3H3,(H,24,25,28) | [InChIKey]
LBSMEKVVMYSTIH-UHFFFAOYSA-N | [SMILES]
CC(NC1=NC(C2=CC=CC(NS(C3=C(C=CC=C4N(C)C)C4=CC=C3)(=O)=O)=C2)=CS1)=O |
| Hazard Information | Back Directory | [Definition]
ChEBI: HA15 is a sulfonamide resulting from the formal condensation of the sulfonic acid group of 5-(dimethylamino)naphthalene-1-sulfonic acid with the aniline nitrogen of 3-(2-acetamido-1,3-thiazol-4-yl)aniline. It has been reported that by triggering an endoplasmic reticulum (ER) stress response, HA15 can reduce the viability of melanoma cells without being toxic to normal cells. It has a role as an antineoplastic agent. It is a sulfonamide, a member of 1,3-thiazoles, a member of acetamides, a tertiary amino compound, an aminonaphthalene and a biaryl. | [Biological Activity]
HA15 is a small molecule that specifically targets HSPA5 (Heat shock 70kDa protein 5), also known as BiP (Immunoglobulin heavy-chain-binding protein) or Grp78 (glucose-regulated protein 78). Antitumor activity in melanoma cells tested, including cells isolated from patients and cells resistant to BRAF inhibitors. | [in vitro]
HA15 induces endoplasmic reticulum stress in cells in vitro, leading to cancer cell death; in melanoma cells, it overcomes its resistance to BRAF inhibitors. | [in vivo]
In xenograft mouse models (bearing melanoma cells sensitive or resistant to BRAF inhibitors), HA15 was able to induce endoplasmic reticulum stress leading to cancer cell death. | [target]
| Target | Value | BiP/GRP78/HSPA5
() |
|
|
|