GLPBio

PPACK

Catalog No.: GC44671Purity:>98.00%Synonyms: Pebac, D-Phenylalanyl-prolyl-arginyl Chloromethyl Ketone

PPACK هو مشتق ببتيد اصطناعي يثبط بشكل لا رجعة فيه وبشكل خاص تفعيل الصفائح الدموية المسبب من قِبَل الترومبين عن طريق الارتباط بالموقع النشط للترومبين (Ki = 0.24 nM) بأفضلية عالية.

المنتجات مخصصة للاستخدام البحثي فقط، وليست للاستخدام البشري. نحن لا نبيع للمرضى.


PPACK
Cas No.: 71142-71-7
1mgIn Stock
$38.00
1
5mgIn Stock
$160.00
1
10mgIn Stock
$283.00
1
25mgIn Stock
$660.00
1

المراجع (Citations)

3 publicationsمنشورات الباحثين الذين استخدموا هذا المنتج

الوصف (Description)

PPACK is a potent selective and irreversible thrombin inhibitor that inhibits human alpha thrombin with a Ki value of 0.24 nM. PPACK inhibit the binding of rt-PA to plasma protease inhibitors in vitro[1-3]. It forms a covalent bond to the thrombin active site Ser and cross-links with His57 at the active site to form a tetrahedral PPack-thrombin complex. PPACK completely inhibited changes in fibrin degradation products, plasminogen and alpha 2-antiplasmin[4-6].

Coincubation with PPACK(0.2 mM;2h) reduced the increase in endothelial permeability induced by plasmin by 59% in bovine aortic endothelial cells[7]. Heme oxygenase (HO)-1 is a stress-inducible rate-limiting enzyme in heme degradation that confers cytoprotection against oxidative injury. Pretreatment of cells with PPACK(24h; 30 nM) effectively antagonized the potentiating effect of thrombin on HO-1 expression[8].

PPACK(bolus dose of 10-100 μg/kg or infusion of 0.25-1.0 μg/kg/min) pretreatment can inhibit thrombine-induced cerebral thromboembolism in rabbits[9].

References:

[1]. Mohler MA, Refino CJ, et,al. D-Phe-Pro-Arg-chloromethylketone: its potential use in inhibiting the formation of in vitro artifacts in blood collected during tissue-type plasminogen activator thrombolytic therapy. Thromb Haemost. 1986 Oct 21;56(2):160-4. PMID: 2433785.

[2]. Bode W, Mayr I, et,al. The refined 1.9 A crystal structure of human alpha-thrombin: interaction with D-Phe-Pro-Arg chloromethylketone and significance of the Tyr-Pro-Pro-Trp insertion segment. EMBO J. 1989 Nov;8(11):3467-75. doi: 10.1002/j.1460-2075.1989.tb08511.x. PMID: 2583108; PMCID: PMC401503.

[3]. Lyon ME, Fine JS, et,al. D-phenylalanyl-L-prolyl-L-arginine chloromethyl ketone (PPACK): alternative anticoagulant to heparin salts for blood gas and electrolyte specimens. Clin Chem. 1995 Jul;41(7):1038-41. PMID: 7600685.

[4]. Kovach IM, Kelley P, et,al. Proton bridging in the interactions of thrombin with small inhibitors. Biochemistry. 2009 Aug 4;48(30):7296-304. doi: 10.1021/bi900098s. PMID: 19530705; PMCID: PMC2800789.

[5]. Kettner C, Shaw E. D-Phe-Pro-ArgCH2C1-A selective affinity label for thrombin. Thromb Res. 1979;14(6):969-73. doi: 10.1016/0049-3848(79)90014-8. PMID: 473131.

[6]. Nienaber VL, Mersinger LJ, et,al. Structure-based understanding of ligand affinity using human thrombin as a model system. Biochemistry. 1996 Jul 30;35(30):9690-9. doi: 10.1021/bi952164b. PMID: 8703940.

[7]. Rabbani LE, Johnstone MT, et,al. PPACK attenuates plasmin-induced changes in endothelial integrity. Thromb Res. 1993 Jun 15;70(6):425-36. doi: 10.1016/0049-3848(93)90085-3. PMID: 8362368.

[8].Liu JF, Hou SM, et,al. Thrombin induces heme oxygenase-1 expression in human synovial fibroblasts through protease-activated receptor signaling pathways. Arthritis Res Ther. 2012 Apr 27;14(2):R91. doi: 10.1186/ar3815. PMID: 22541814; PMCID: PMC3446465.

[9]. Liu JT, Paul W, et,al. Thrombin inhibitors and anti-coagulants on thrombin-induced embolisation in rabbit cranial vasculature. Eur J Pharmacol. 1994 Oct 24;264(2):183-90. doi: 10.1016/0014-2999(94)00464-1. PMID: 7851481.

البروتوكول (Protocol)

Kinetic Procedures(Inhibition of Thrombin with PPACK) [1]:

Preparation method

The thrombin stock solution was diluted in the appropriate buffer, resulting in a 20 mL solution with a concentration of 3-5×10-10 M. An aliquot of 980 μL was incubated in a cuvette in the temperature controlled cell compartment of the spectrophotometer to reach thermal equilibrium. Thrombin inhibition was initiated by injecting 10 μL of a thermally equilibrated 1.1 × 10-7 to 3.65 × 10-7 M PPACK solution and mixing. The reaction mixture was promptly incubated for a time interval between 15 and 200 s, after which 10 μL of a 3-5×10-3 M solution of substrate in DMSO was quickly added to measure the remaining enzyme activity. Pseudo-first-order rate constants were calculated by fitting the exponential function to the remaining enzyme activity versus time of inhibition for 10 successive incubation times. The thrombin activity remained constant for the duration of the experiment in the 288-308 K temperature range.

Applications

PPACK is a potent selective and irreversible thrombin inhibitor that inhibits human alpha thrombin with a Ki value of 0.24 nM.

Cell experiment [2]:

Cell lines

Bovine aortic endothelial cells

Preparation method

Confluent bovine aortic endothelial cell monolayers were obtained three to five days after plating on the polycarbonate membrane cluster plates. Cells were treated with plasminogen and a plasminogen activator. PPACK were added to the upper compartments. The monolayers were subsequently incubated for two hours in a 5% CO2 / 95% O2 atmosphere.

Reaction Conditions

0.2 mM;2h

Applications

Coincubation with PPACK reduced the increase in endothelial permeability induced by plasmin by 59%.

Cell experiment [3]:

Cell lines

Human osteoarthritis synovial fibroblasts (OASF)

Preparation method

Cell were treated with thrombin (3 U/ml), thrombin plus PPACK (30 nM) for 24 hours.

Reaction Conditions

24h; 30 nM

Applications

Pretreatment of cells with PPACK effectively antagonized the potentiating effect of thrombin on HO-1 expression.

Animal experiment [4]:

Animal models

Male rabbits

Preparation method

PPACK was prepared in saline and administered as a bolus dose of 10-100 μg/kg or as an infusion of 0.25-1.0 μg/kg/min. Rabbits were treated with PPACK bolus 1 min either before or after the administration of thrombin or were infused with PPACK commencing 30 min prior to the administration of thrombin and continued for 1 h at a rate of 0.1 mL/min.

Applications

PPACK pretreatment can inhibit thrombine-induced cerebral thromboembolism in rabbits.

References:

[1]. Kovach IM, Kelley P, et,al. Proton bridging in the interactions of thrombin with small inhibitors. Biochemistry. 2009 Aug 4;48(30):7296-304. doi: 10.1021/bi900098s. PMID: 19530705; PMCID: PMC2800789.

[2]. Rabbani LE, Johnstone MT, et,al. PPACK attenuates plasmin-induced changes in endothelial integrity. Thromb Res. 1993 Jun 15;70(6):425-36. doi: 10.1016/0049-3848(93)90085-3. PMID: 8362368.

[3].Liu JF, Hou SM, et,al. Thrombin induces heme oxygenase-1 expression in human synovial fibroblasts through protease-activated receptor signaling pathways. Arthritis Res Ther. 2012 Apr 27;14(2):R91. doi: 10.1186/ar3815. PMID: 22541814; PMCID: PMC3446465.

[4]. Liu JT, Paul W, et,al. Thrombin inhibitors and anti-coagulants on thrombin-induced embolisation in rabbit cranial vasculature. Eur J Pharmacol. 1994 Oct 24;264(2):183-90. doi: 10.1016/0014-2999(94)00464-1. PMID: 7851481.

وثائق المنتج (Product Documents)

Purity:>98.00%Appearance:A solid

البيانات البيولوجية (Biological Data)

1 / 1

الخصائص الكيميائية (Chemical Properties)

رقم CAS
71142-71-7
المرادفات
Pebac, D-Phenylalanyl-prolyl-arginyl Chloromethyl Ketone
الاسم الكيميائي
D-phenylalanyl-N-[(1S)-4-[(aminoiminomethyl)amino]-1-(2-chloroacetyl)butyl]-L-prolinamide, trifluoroacetate salt
SMILES
O=C([C@H](N)CC1=CC=CC=C1)N2[C@H](C(N[C@H](C(CCl)=O)CCCNC(N)=N)=O)CCC2
الصيغة الجزيئية
C21H31ClN6O3
الوزن الجزيئي
451
الذوبانية
20mg/mL in ethanol, 33mg/mL in DMSO, or in DMF
التخزين
Store at -20°C
إرشادات عامة
اختر مذيبًا مناسبًا وفقًا لبيانات ذوبانية المنتج. بعد التحضير، قسّم المحلول المخزون إلى أجزاء لتجنب دورات التجميد والذوبان المتكررة.
استخدم المحاليل المخزونة خلال 6 أشهر عند حفظها في -80°C، أو خلال شهر واحد عند حفظها في -20°C.
لتحسين الذوبانية، سخّن الأنبوب إلى 37°C وعرّضه للموجات فوق الصوتية لمدة مناسبة.
شروط الشحن
تُشحن عينات التقييم مع عبوات تبريد. وتُشحن الأحجام الأخرى المتاحة في درجة حرارة الغرفة، أو مع عبوات تبريد عند الطلب.

الحاسبات (Calculators)المولارية / التخفيف / الوزن الجزيئي / تحويل الوحدات / تركيبة داخل الجسم الحي / الذوبانية

g/mol

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