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461054-93-3

461054-93-3 Structure

461054-93-3 Structure
IdentificationBack Directory
[Name]

(3S,6S,12aS)-1,2,3,4,6,7,12,12a-Octahydro-9-methoxy-6-(2-methylpropyl)-1,4-dioxopyrazino[1',2':1,6]pyrido[3,4-b]indole-3-propanoic acid 1,1-dimethylethyl ester
[CAS]

461054-93-3
[Synonyms]

Ko 143
12aS)-
4-dioxo-
6]pyrido[3
Ko143 ,99%
Pyrazino[1'
Ko143 hydrate
KO 143;KO-143;KO143
4-b]indole-3-propanoicacid
12a-octahydro-9-Methoxy-6-(2-Methylpropyl)-1
1,6]pyrido[3,4-b]indole-3-propanoic acid 1,1-dimethylethyl ester
tert-Butyl 3-((3S,6S,12aS)-6-isobutyl-9-methoxy-1,4-dioxo-1,2,3,4,6,7,12,12a-octahydropyrazino
(3S,6S,12aS)-1,2,3,4,6,7,12,12a-Octahydro-9-methoxy-6-(2-methylpropyl)-1,4-dioxopyrazino[1',2'
tert-Butyl 3-((3S,6S,12aS)-6-isobutyl-9-methoxy-1,4-dioxo-1,2,3,4,6,7, 12,12a-octahydropyrazino[1
tert-butyl 3-((3S,6S,12aS)-6-isobutyl-9-methoxy-1,4-dioxo-1,2,3,4,6,7,12,12a-octahydropyrazino[1',2':1,6]pyrido[3,4-b]indol-3-yl)propanoate
(3S,6S,12aS)-1,2,3,4,6,7,12,12a-Octahydro-9-methoxy-6-(2-methylpropyl)-1,4-dioxopyrazino[1',2':1,6]pyrido[3,4-b]indole-3-propanoic acid 1,1-dimethylethyl ester
(3S,6S,12aS)-1,2,3,4,6,7,12,12a-Octahydro-9-methoxy-6-( 2-methylpropyl)-1,4-dioxopyrazino[1′,2′:1,6]pyrido[3,4- b]indole-3-propanoic acid 1,1-dimethylethyl ester hydrate
Pyrazino[1',2':1,6]pyrido[3,4-b]indole-3-propanoic acid, 1,2,3,4,6,7,12,12a-octahydro-9-methoxy-6-(2-methylpropyl)-1,4-dioxo-, 1,1-dimethylethyl ester, (3S,6S,12aS)-(Ko143)
[Molecular Formula]

C26H35N3O5
[MDL Number]

MFCD11042273
[MOL File]

461054-93-3.mol
[Molecular Weight]

469.57
Chemical PropertiesBack Directory
[Melting point ]

147 ºC
[Boiling point ]

689.8±55.0 °C(Predicted)
[density ]

1.24
[storage temp. ]

Desiccate at -20°C
[solubility ]

DMSO: >10mg/mL
[form ]

powder
[pka]

13.31±0.60(Predicted)
[color ]

white to off-white
[Stability:]

Stable for 2 years from date of purchase as supplied. Protect from exposure to moisture. Solutions in DMSO or ethanol may be stored at -20°C for up to 3 months.
Safety DataBack Directory
[Hazard Codes ]

Xi
[Risk Statements ]

36/37/38
[Safety Statements ]

26-36
[WGK Germany ]

3
Hazard InformationBack Directory
[Description]

Breast cancer resistance protein (BCRP) is an ATP-binding cassette protein known also as ABCG2. While it normally functions as a high-capacity urate exporter in the renal system, it also acts as a xenobiotic transporter and contributes to multidrug resistance (e.g., to mitoxantrone) in certain types of cancer. BCRP is abundant at the intestinal epithelium and blood-brain barrier, potentially restricting the distribution of certain drugs. Ko 143 is a potent and selective inhibitor of BCRP, preventing the export of mitoxantrone and topotecan in breast cancer cell lines (EC50s = 23 and 26 nM, respectively). It is much less effective at the transporters P-glycoprotein and multidrug resistance-associated protein 1, MRP1. Ko 143 is effective in vivo in mice.
[Uses]

A potent BCRP (breast cancer resistance protein) inhibitor
[Definition]

ChEBI: LSM-6260 is a member of beta-carbolines and a tert-butyl ester.
[Biological Activity]

Potent and selective breast cancer resistance protein multidrug transporter (BCRP) inhibitor (EC 90 = 26 nM). Displays > 200-fold selectivity over P-gp and MRP-1 transporters. Increases intracellular drug accumulation and reverses BCRP-mediated multidrug resistance.
[Biochem/physiol Actions]

Ko143 has been used as a positive control inhibitor on functions of breast cancer resistance protein (BCRP) using a BCRP prototypical substrate mitoxantrone. BCRP, an ABCG2 transporter, plays an important role in disposition of many drugs and environmental toxins. Ko143 displays > 200-fold selectivity over P-gp and MRP-1 transporters and thus is more specific than other known BCRP inhibitors such as fumitremorgin C and GF120918. It increases intracellular drug accumulation and reverses BCRP-mediated multidrug resistance. It blocks topotecan and ABZSO transport in a concentration-dependent manner.
[storage]

Store at -20°C
[References]

1) Allen et al. (2002), Potent and specific inhibition of breast cancer resistance protein multidrug transporter in vitro and in mouse intestine by a novel analogue of fumitremorgin C; Mol. Cancer Ther., 1 417 2) Weidner et al. (2015), The Inhibitor Ko143 Is Not Specific for ABCG2; J. Pharmacol. Exp. Ther., 354 384 3) Palasuberniam et al. (2015), ABCG2 transporter inhibitor restores the sensitivity of triple negative breast cancer cells to aminolevulinic acid-mediated photodynamic therapy; Sci. Rep., 5 13298 4) Moreno-Sanz et al. (2011), The ABC membrane transporter ABCG2 prevents access of FAAH inhibitor URB937 to the central nervous system; Pharmacol. Res., 64 359 5) Sabnis et al. (2017),?The Efflux Transporter ABCG2 Maintains Prostate Stem Cells;? Mol. Cancer Res., 15 128
Spectrum DetailBack Directory
[Spectrum Detail]

Ko 143(461054-93-3)1HNMR
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