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Chemical Structure| 6578-06-9 Chemical Structure| 6578-06-9
Chemical Structure| 6578-06-9

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BCIP is an artificial chromogenic substrate used for the sensitive colorimetric detection of alkaline phosphatase activity.

Synonyms: BCIP p-toluidine salt; X-phosphate p-toluidine salt; 5-Bromo-4-chloro-3-indoyl phosphate

4.5 *For Research Use Only! Not for Human Use. We Do Not Sell to Patients.

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Product Citations

Product Citations

Alatawi, Hissah ; Nair, Haritha H ; Ai, Lingbao ; Mahmud, Iqbal ; Gour, Abhishek ; Singh, Amandeep , et al.

Abstract: Triple-negative breast cancer (TNBC) remains a significant clinical challenge due to its aggressive nature and lack of effective targeted therapies. The enzyme ceramide synthase 2 (CerS2), which synthesizes pro-apoptotic very long-chain ceramides (VLCCs), represents a promising therapeutic target. Here, we identify and characterize DH20931, a novel, first-in-class small-molecule agonist of CerS2. We demonstrate that DH20931 directly activates CerS2 with nanomolar potency, leading to significant VLCC accumulation in breast cancer cells. This lipotoxic event induces endoplasmic reticulum (ER) stress and triggers apoptosis via the canonical ATF4/CHOP/PUMA signaling pathway. Mechanistically, we uncover a novel interaction between CerS2 and the ER calcium channel, Inositol 1,4,5-trisphosphate receptor 1 (IP3R1). We demonstrate that DH20931 promotes this interaction, enhancing ER-mitochondria proximity and facilitating a CerS2-dependent flux of calcium (Ca2+) from the ER into mitochondria. This subsequent mitochondrial Ca2+ overload serves as a critical trigger for apoptosis. In preclinical evaluations, DH20931 potently inhibited the growth of TNBC cells in 2D and 3D cultures and significantly suppressed tumor progression in orthotopic and patient-derived xenograft (PDX) models, all while exhibiting a favorable safety profile. Our findings validate CerS2 as a druggable target in TNBC and establish a novel therapeutic strategy that leverages a coordinated attack on cancer cells through ER stress and calciummediated mitochondrial dysfunction.

Keywords: Triple-negative breast cancer (TNBC) ; DH20931 ; ceramide synthase 2 (CerS2) ; very long chain ceramides (VLCC) ; ER stress ; IP3R1 ; calcium signaling ; mitochondria ; apoptosis ; targeted therapy

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Product Details of BCIP

CAS No. :6578-06-9
Formula : C15H15BrClN2O4P
M.W : 433.62
SMILES Code : NC1=CC=C(C)C=C1.O=P(O)(O)OC2=CNC3=C2C(Cl)=C(Br)C=C3
Synonyms :
BCIP p-toluidine salt; X-phosphate p-toluidine salt; 5-Bromo-4-chloro-3-indoyl phosphate
English Name :P-toluidine 5-bromo-4-chloro-1H-indol-3-yl phosphate
MDL No. :MFCD00040636
InChI Key :QEIFSLUFHRCVQL-UHFFFAOYSA-N
Pubchem ID :81059

Safety of BCIP

Application In Synthesis of BCIP

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 6578-06-9 ]

[ 6578-06-9 ] Synthesis Path-Downstream   1~2

YieldReaction ConditionsOperation in experiment
3.e (e) The ester (27) (35 mg) was dissolved in dioxan (15 ml) and water (3 ml) and hydrogenated using 10% palladium/carbon catalyst (18 mg). The mixture was filtered through Kieselguhr, and the filtrate evaporated to dryness, followed by re-evaporation from ethanol, then toluene to give a gum. Trituration with ether gave the p-toluidine salt (28); (24 mg) as a pale yellow solid [α]D22 -11.25° (c 0.32 in DMSO); λmax. (EtOH) 245 (ε 9140) 284 nm (5820); νmax. (KBr) 3400b, 1775, 1715, 1680, 1610 cm-1.
  • 2
  • [ 110-91-8 ]
  • [ 6578-06-9 ]
  • [ 538-75-0 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
99% In 2-methyl-propan-1-ol; water for 15h; Heating;
 

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