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722544-51-6 (AZD1152-HQPA)

1

Identification

AZD1152-HQPA AZD1152-HQPA
Name AZD1152-HQPA
Formula C26H30FN7O3
MW 507.56
CAS No. 722544-51-6
EINECS
Smiles O=C(CC1=NNC(NC2=C3C=CC(OCCCN(CCO)CC)=CC3=NC=N2)=C1)NC4=CC=CC(F)=C4
Synonyms Barasertib; AZD1152; AZD 1152; 2-(5-((7-(3-(ethyl(2-hydroxyethyl)amino)propoxy)quinazolin-4-yl)amino)-1H-pyrazol-3-yl)-N-(3-fluorophenyl)acetamide
InChI InChI=1S/C26H30FN7O3/c1-2-34(10-11-35)9-4-12-37-21-7-8-22-23(16-21)28-17-29-26(22)31-24-14-20(32-33-24)15-25(36)30-19-6-3-5-18(27)13-19/h3,5-8,13-14,16-17,35H,2,4,9-12,15H2,1H3,(H,30,36)(H2,28,29,31,32,33)
2

Introduction

AZD1152-HQPA is the active metabolite of AZD-1152, AZD1152-HQPA (Barasertib) is a highly selective Aurora B inhibitor with IC50 of 0.37 nM, ~100 fold more selective for Aurora B over Aurora A. IC50 Value: 0.37 nM Target: Aurora B in vitro: AZD1152 displays >3000-fold selectivity for Aurora B as compared with Aurora A which has an IC50 of 1.368 μM.

Background Information

A potent, highly selective Aurora Kinase B inhibitor ......by AOBIOUS INC
AZD1152-HQPA (Barasertib) is a highly potent and selective inhibitor of Aurora with Ki values of 0.36 and 1369 nM  for Aurora B and Aurora A respectively.Consistent with inhibition of Aurora B kinase, addition of AZD1152-HQPA to tumor cells in vitro induces chromosome misalignment, prevents cell division, and consequently reduces cell viability and induces apoptosis. ......by AbMole BioScience
AZD 1152-HQPA is a highly potent and selective inhibitor of Aurora B, with Ki values to be 0.36 (Aurora B) and 1369 nM (Aurora A) respectively and has a high specificity versus a panel of 50 other kinases. ......by AdooQ BioScience, LLC
Description ......by Apexbio Technology LLC
AZD-1152HQPA is an active metabolite of Barasertib (AZD-1152), which is a novel acetanilide-substituted pyrazole-aminoquinazoline prodrug that is converted rapidly to the active drug AZD-1152 hydroxy-QPA (AZD1152-HQPA) in human plasma. AZD1152-HQPA is a ......by BOC Sciences
A potent and specific Aurora kinase B inhibitor. It is 1000-fold more selective for aurora kinase B than for aurora kinase A ( Ki values of 1300 nM and 0.36 nM for aurora kinase A and B, respectively). At concentrations as low as 0.01 µM, AZD 1152 produced a significant (p<0.05) decrease in the ability of NB4 cells to proliferate by 48 hours. ......by BioVision, Inc.,
AZD1152-HQPA is a highly selective Aurora B inhibitor with IC50 of 0.37 nM in a cell-free assay, and appr 3700 fold more selective for Aurora B over Aurora A. ......by MedChemexpress Co., Ltd.
AZD-1152 HQPA is a potent and selective Aurora B inhibitor (IC50 of 0.37 nM versus 1368 nM for Aurora B and A kinases, respectively) and is also an active metabolite of Barasertib ( AZD-1152). Barasertib is a prodrug and will be converted rapidly to the active drug AZD1152-HQPA in human plasma. Preliminary studies showed that AZD-1152 was active against a variety of solid tumors including colon, breast, and lung cancers. IMPORTANT NOTE: AZD-1152HQPA IS NOT AZD-1152 or Barasertib. Many vendors is selling Barasertib with wrong structure ......by MedKoo Biosciences, Inc.
The active product of AZD1152, a potent, selective inhibitor of Aurora B kinase with IC50 of 0.37 nM; displays >3,700-fol selectivity for Aurora B over Aurora A; potently inhibits the growth of human colon, lung, and hematologic tumor xenografts. ......by ProbeChem
Barasertib (AZD1152-HQPA) is a highly selective Aurora B inhibitor with IC50 of 0.37 nM in a cell-free assay, ~3700 fold more selective for Aurora B over Aurora A. Phase 1. ......by Selleck Chemicals LLC
Barasertib (AZD1152-HQPA) is a highly selective Aurora B inhibitor with IC50 of 0.37 nM in a cell-free assay, ~3700 fold more selective for Aurora B over Aurora A. Phase 1. ......by Target Molecule Corp.
3

Protocol(Only for Reference)

Cell Experiment

Cell lines HL-60 cells
Conditions 25 nM, 72 hours
Method The cells exhibited increased DNA contents of 4N and 8N, indicative of polyploidy, within 24–48 h of treatment. After 48–72 h, barasertib-HQPA induced apoptotic cell death, as detected by an increased sub-G1 population compared for that of untreated cells. The induction of polyploidy was obvious at 24–48 h, and thereafter, the nuclei showed morphology typical of apoptosis, such as nuclear fragmentation and condensation. These observations were in accordance with the findings of the flow cytometric analysis.
Source Apexbio Technology LLC
Cell lines HL-60, NB4, MOLM13, PALL-2, MV4-11, EOL-1, and K562 cells
Conditions Dissolved in DMSO, final concentrations ~100 nM; 24 or 48 hours
Method Cells are exposed to various concentrations of AZD1152 for 24 or 48 hours. Cell proliferation is measured by 3H-thymidine uptake (isotope added 6 hours before harvest), and the concentration that induced 50% growth inhibition (IC50) is calculated from dose-response curves. Cell cycle analysis is performed by flow cytometry. Cell apoptosis is measured by annexin V–FITC apoptosis detection kit.
Source Selleck Chemicals LLC

Animal Experiment

Animal Models Female nude mice injected with SW620, Colo205 or HCT116 cells
Dosage Form Subcutaneous injection, 150 mg/kg/day, minipump infusion over 48 h
Applications In SW620, HCT116 and Colo205 xenografts significant tumor growth inhibitions of 79% (P<0.001, day 23), 60% (P<0.001, day 25) and 81% (P<0.05, day 21) were observed, respectively. Colo205 xenografts appeared the most sensitive to treatment with a mean tumor volume (± SEM) on day 21 after cell implantation, of 0.42±0.19 cm3 for the barasertib group compared to 2.24±0.75 cm3 (P<0.05) for the vehicle control animals.
Source Apexbio Technology LLC
Animal Models Female immune-deficient BALB/c nude mice subcutaneously injected with MOLM13 cells
Dosage 5 or 25 mg/kg
Formulation Dissolved in 3M Tris, pH 9.0, at a concentration of 2.5 mg/mL
Administration Intraperitoneal injection 4 times a week or every another day
Source Selleck Chemicals LLC
4

Physical and Chemical Properties

Appearance:White to off-white Solid EBNumber:EB000029003

Storage condition

Store at -20°C by Apexbio Technology LLC

Solubility

Soluble in DMSO > 10 mM by Apexbio Technology LLC
DMSO ≥100mg/mL Water ≥100mg/mL Ethanol ≥2.8mg/mL by MedChemexpress Co., Ltd.
(25°C) * In vitro DMSO 102 mg/mL (200.96 mM); Ethanol3 mg/mL (5.91 mM); Water<1 mg/mL (<1 mM); In vivo 30% PEG 400+0.5% Tween 80+5% Propylene glycol30mg/mL by Selleck Chemicals LLC
5

Mechanism and Indication

6

Clinical Information

Product Name Sponsor & Collaborators Indications Start Date End Date Phase
AZD1152-HQPA AstraZeneca plc Acute myelogenous leukemia 2009/7/31 2015/6/30 Phase 3 Clinical
AZD1152-HQPA University of Oxford Diffuse large B-cell lymphoma 2011/9/30 2014/9/30 Phase 2 Clinical
AZD1152-HQPA AstraZeneca plc Acute myelogenous leukemia 2006/5/31 2010/4/30 Phase 2 Clinical
AZD1152-HQPA AstraZeneca plc Acute myelogenous leukemia 2009/11/30 2010/6/1 Phase 1 Clinical
AZD1152-HQPA AstraZeneca plc Acute myelogenous leukemia 2009/6/30 2011/5/31 Phase 1 Clinical
AZD1152-HQPA - Phase 3
7

Safety Data of AZD1152-HQPA

8

Spectral Information

9

Suppliers List

Company Price and Availability Country/Region
AOBIOUS INC 1mg/USD11() USA
AbMole BioScience USA
AdooQ BioScience, LLC USA
Apexbio Technology LLC USA
Ark Pharm, Inc. USA
BOC Sciences
BioVision, Inc., USA
Biochempartner Co., Ltd China
CHEMSCENE, LLC 5mg/USD50();10mg/USD70() USA
Cayman Chemical Company USA
MedChemexpress Co., Ltd. 5mg/USD50();10mg/USD70() USA
MedKoo Biosciences, Inc. USA
ProbeChem
Selleck Chemicals LLC 5mg/USD120(In stock);10mM/1mLIn DMSO/USD168(In stock);10mg/USD210(In stock);50mg/USD670(In stock) USA
Shanghai Haoyuan Chemexpress Co., Ltd. 5mg/USD50();10mg/USD70() China
Target Molecule Corp. 1mg/USD51();5mg/USD98();10mg/USD148();25mg/USD258();50mg/USD458() USA
10

Related Products

Other Forms of 722544-51-6

Name CAS No Formula MW
ATPA 140158-50-5 C10H16N2O4 228.25
CHMFL-KIT-110 1902961-57-2 C26H24F3N3O3 0.0
CHMFL-ABL-053 1808287-83-3 C28H26F3N7O2 0.0
CHMFL-BMX-078 1808288-51-8 C33H35N7O6 0.0
Milademetan 1398568-47-2 C30H34Cl2FN5O4 618.53
S1p receptor agonist 1 1514888-56-2 C23H24FN3O3 0.0
AZD2423 1380100-86-6 C17H25FN2O2 0.0
2-thio-PAF 96801-55-7 C26H54NO6PS 0.0
SB234551 188257-69-4 C34H34N2O9 0.0
DORA-22 1088991-95-0 C23H22F2N4O2 0.0

Recommended Compounds in Aurora Kinase

Name CAS No Formula MW
TAK-632 1228591-30-7 C27H18F4N4O3S 554.52
XL228 898280-07-4 C22H31N9O 437.54
MK-8745 885325-71-3 C20H19ClFN5OS 431.9142
ENMD-2076 934353-76-1 C21H25N7 375.47
ABT-348 1227939-82-3 C25H21FN6O2S 488.54
Reversine 656820-32-5 C21H27N7O 393.49
PF-03814735 942487-16-3 C23H25F3N6O2 474.48
MK-5108 1010085-13-8 C22H21ClFN3O3S 461.94
CCT 137690 1095382-05-0 C26H31BrN8O 551.48
SCH-1473759 (hydrochloride) 1094067-13-6 C20H27ClN8OS 462.9994
SCH-1473759 1094069-99-4 C20H26N8OS 426.54
AZD1152 722543-31-9 C26H31FN7O6P 587.54
AMG 900 945595-80-2 C28H21N7OS 503.58
TAK-901 934541-31-8 C28H32N4O3S 504.64
Hesperadin 422513-13-1 C29H32N4O3S 516.65
ENMD-2076 (Tartrate) 1291074-87-7 C25H31N7O6 525.56
CCT129202 942947-93-5 C23H25ClN8OS 497.02
PHA-680632 398493-79-3 C28H35N7O2 501.62
JNJ-7706621 443797-96-4 C15H12F2N6O3S 394.36
Danusertib 827318-97-8 C26H30N6O3 474.55

Recommended Compounds in Same Indication

Name CAS No Formula MW
AZD1152 722543-31-9 C26H31FN7O6P 587.54
Mocetinostat 726169-73-9 C23H20N6O 396.44
Volasertib 755038-65-4 C34H50N8O3 618.81
KX2-391 897016-82-9 C26H29N3O3 431.53
MLN4924 905579-51-3 C21H25N5O4S 443.52
Crenolanib 670220-88-9 C26H29N5O2 443.54
ARRY-520 (R enantiomer) 885060-08-2 C20H22F2N4O2S 420.48
ARRY-520 885060-09-3 C20H22F2N4O2S 420.48
LY2090314 603288-22-8 C28H25FN6O3 512.53
Posaconazole 171228-49-2 C37H42F2N8O4 700.78
Decitabine 2353-33-5 C8H12N4O4 228.21
5-Azacytidine 320-67-2 C8H12N4O5 244.2
2-(2-chlorophenyl)-5,7-dihydroxy-8-((3R,4S)-3-hydroxy-1-methylpiperidin-4-yl)-4H-chromen-4-one C21H20ClNO5 401.8402
Lenalidomide 191732-72-6 C13H13N3O3 259.26
Tipifarnib 192185-72-1 C27H22Cl2N4O 489.4
Daunorubicin (Hydrochloride) 23541-50-6 C27H30ClNO10 563.98
Eltrombopag (Olamine) 496775-62-3 C29H36N6O6 564.63
Entinostat 209783-80-2 C21H20N4O3 376.41
Romidepsin 128517-07-7 C24H36N4O6S2 540.7
Vorinostat 149647-78-9 C14H20N2O3 264.32
11

Route of Synthesis

12

References

[1]. Oke, Adedayo; Pearce, Daniel; Wilkinson, Robert W.; AZD1152 Rapidly and Negatively Affects the Growth and Survival of Human Acute Myeloid Leukemia Cells In vitro and In vivo. Cancer Research (2009), 69(10), 4150-4158.

[2]. Yang, Jing; Ikezoe, Takayuki; Nishioka, Chie; Tasaka, Taizo; Taniguchi, Ayuko; AZD1152, a novel and selective aurora B kinase inhibitor, induces growth arrest, apoptosis, and sensitization for tubulin depolymerizing agent or topoisomerase II inhibitor in human acute leukemia cells in vitro and in vivo. Blood (2007), 110(6), 2034-2040.

Protocol Reference

[1] Yamauchi T, Uzui K, Shigemi H, et al. Aurora B inhibitor barasertib and cytarabine exert a greater-than-additive cytotoxicity in acute myeloid leukemia cells. Cancer science, 2013, 104(7): 926-933.

[2] Alferez D G, Goodlad R A, Odedra R, et al. Inhibition of Aurora-B kinase activity confers antitumor efficacy in preclinical mouse models of early and advanced gastrointestinal neoplasia. International journal of oncology, 2012, 41(4): 1475-1485.

......by Apexbio Technology LLC
13

More Information

AZD1152-HQPA

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