Delcasertib Free Base | CAS# 949100-39-4 (free base) | δ-protein kinase C (δPKC) inhibitor

MedKoo Cat#: 413502 | Name: Delcasertib Free Base

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Delcasertib Free Base is a potent and selective δ-protein kinase C (δPKC) inhibitor. Delcasertib (KAI-9803) could ameliorate injury associated with ischemia and reperfusion in animal models of acute myocardial infarction (MI)

Chemical Structure

Delcasertib Free Base

CAS#949100-39-4 (free base)

Theoretical Analysis

MedKoo Cat#: 413502

Name: Delcasertib Free Base

CAS#: 949100-39-4 (free base)

Chemical Formula: C120H199N45O34S2

Exact Mass: 2878.4668

Molecular Weight: 2880.31

Elemental Analysis: C, 50.04; H, 6.96; N, 21.88; O, 18.89; S, 2.23

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Related CAS #

949100-40-7 (acetate) 949100-39-4 (free base)

Synonym

Delcasertib Free Base; KAI9803; KAI 9803; KAI-9803; BMS-875944; BMS875944; BMS 875944;

IUPAC/Chemical Name

L-Arginine, L-cysteinyl-L-tyrosylglycyl-L-arginyl-L-lysyl-L-lysyl-L-arginyl-L-arginyl-L- glutaminyl-L-arginyl-L-arginyl-, (1->1')-disulfide with L-cysteinyl-L-seryl-L-phenylalanyl-L- asparaginyl-L-seryl-L-tyrosyl-L-alpha-glutamyl-L-leucylglycyl-L-seryl-L-leucine

InChi Key

XPXZTVWPRKJTAA-PJKOMPQUSA-N

InChi Code

InChI=1S/C120H199N45O34S2/c1-61(2)48-80(96(179)145-55-92(174)148-86(56-166)110(193)163-85(114(198)199)49-62(3)4)159-106(189)78(37-39-93(175)176)156-107(190)83(52-65-30-34-67(170)35-31-65)161-112(195)88(58-168)165-109(192)84(53-90(126)172)162-108(191)82(50-63-18-6-5-7-19-63)160-111(194)87(57-167)164-95(178)69(124)60-201-200-59-68(123)94(177)158-81(51-64-28-32-66(169)33-29-64)97(180)146-54-91(173)147-70(22-12-42-139-115(127)128)98(181)149-71(20-8-10-40-121)99(182)150-72(21-9-11-41-122)100(183)151-73(23-13-43-140-116(129)130)101(184)152-75(25-15-45-142-118(133)134)103(186)155-77(36-38-89(125)171)105(188)154-74(24-14-44-141-117(131)132)102(185)153-76(26-16-46-143-119(135)136)104(187)157-79(113(196)197)27-17-47-144-120(137)138/h5-7,18-19,28-35,61-62,68-88,166-170H,8-17,20-27,36-60,121-124H2,1-4H3,(H2,125,171)(H2,126,172)(H,145,179)(H,146,180)(H,147,173)(H,148,174)(H,149,181)(H,150,182)(H,151,183)(H,152,184)(H,153,185)(H,154,188)(H,155,186)(H,156,190)(H,157,187)(H,158,177)(H,159,189)(H,160,194)(H,161,195)(H,162,191)(H,163,193)(H,164,178)(H,165,192)(H,175,176)(H,196,197)(H,198,199)(H4,127,128,139)(H4,129,130,140)(H4,131,132,141)(H4,133,134,142)(H4,135,136,143)(H4,137,138,144)/t68-,69-,70-,71-,72-,73-,74-,75-,76-,77-,78-,79-,80-,81-,82-,83-,84-,85-,86-,87-,88-/m0/s1

SMILES Code

CC(C[C@H](NC([C@@H](NC([C@@H](NC([C@@H](NC([C@@H](NC([C@@H](NC([C@@H](NC([C@@H](N)CSSC[C@H](N)C(N[C@H](C(NCC(N[C@H](C(N[C@H](C(N[C@H](C(N[C@H](C(N[C@H](C(N[C@H](C(N[C@H](C(N[C@H](C(N[C@H](C(O)=O)CCCNC(N)=N)=O)CCCNC(N)=N)=O)CCCNC(N)=N)=O)CCC(N)=O)=O)CCCNC(N)=N)=O)CCCNC(N)=N)=O)CCCCN)=O)CCCCN)=O)CCCNC(N)=N)=O)=O)CC1=CC=C(O)C=C1)=O)=O)CO)=O)CC2=CC=CC=C2)=O)CC(N)=O)=O)CO)=O)CC3=CC=C(O)C=C3)=O)CCC(O)=O)=O)C(NCC(N[C@H](C(N[C@H](C(O)=O)CC(C)C)=O)CO)=O)=O)C

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

To be determined

Shelf Life

>2 years if stored properly

Drug Formulation

To be determined

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Delcasertib (KAI-9803) is a potent and selective δ-protein kinase C (δPKC) inhibitor.

In vitro activity:

Internalization of KAI-9803 was examined more closely in cell culture using primary rat cardiomyocytes. Figure 8 shows a time course of internalization of the 125I-KAI-9803 and 125I-cargo peptides. To determine cellular uptake, cells were incubated with 125Icargo peptide or 125I-KAI-9803 and then treated with very high doses of heparin to compete with any cell-surface-bound material. As would be expected with a TAT47–57-dependent process, the internalization of 125I-KAI-9803 at 37°C was much higher than at 4°C. The internalization of 125I-cargo peptide at 37°C was minimal and did not increase over time. These results indicated that 125I-KAI9803 was internalized into the cardiomyocytes in a process that was dependent on TAT47–57. Reference: Drug Metab Dispos. 2011 Oct;39(10):1946-53. https://pubmed.ncbi.nlm.nih.gov/21712433/

In vivo activity:

In the study presented here, the TAT₄₇₋₅₇-mediated distribution of KAI-9803 was examined in rats after a single intravenous bolus administration (1 mg/kg). ¹⁴C-KAI-9803 was rapidly delivered to many tissues, including the heart (1.21 μg eq/g tissue), while being quickly cleared from the systemic circulation. The tissue distribution of ¹²⁵I-labeled KAI-9803 was compared to that of ¹²⁵I-labeled cargo peptide; this comparison demonstrated that the distribution of KAI-9803 to tissues such as the liver, kidney, and heart was facilitated by the reversible conjugation to TAT₄₇₋₅₇. The studies demonstrated that after a single intravenous administration, KAI9803 can be delivered into the target cells in the liver, kidney, and heart by a TAT₄₇₋₅₇-mediated mechanism. Reference: Drug Metab Dispos. 2011 Oct;39(10):1946-53. https://pubmed.ncbi.nlm.nih.gov/21712433/

	Solvent	mg/mL	mM
Solubility
	DMSO	100.0	34.72

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 2,880.31 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Miyaji Y, Walter S, Chen L, Kurihara A, Ishizuka T, Saito M, Kawai K, Okazaki O. Distribution of KAI-9803, a novel δ-protein kinase C inhibitor, after intravenous administration to rats. Drug Metab Dispos. 2011 Oct;39(10):1946-53. doi: 10.1124/dmd.111.040725. Epub 2011 Jun 28. PMID: 21712433.

In vitro protocol:

In vivo protocol:

1: Lincoff AM, Roe M, Aylward P, Galla J, Rynkiewicz A, Guetta V, Zelizko M, Kleiman N, White H, McErlean E, Erlinge D, Laine M, Dos Santos Ferreira JM, Goodman S, Mehta S, Atar D, Suryapranata H, Jensen SE, Forster T, Fernandez- Ortiz A, Schoors D, Radke P, Belli G, Brennan D, Bell G, Krucoff M; PROTECTION AMI Investigators. Inhibition of delta-protein kinase C by delcasertib as an adjunct to primary percutaneous coronary intervention for acute anterior ST- segment elevation myocardial infarction: results of the PROTECTION AMI Randomized Controlled Trial. Eur Heart J. 2014 Oct 1;35(37):2516-23. doi: 10.1093/eurheartj/ehu177. Epub 2014 May 5. PMID: 24796339. 2: Bøtker HE, Cabrera-Fuentes HA, Ruiz-Meana M, Heusch G, Ovize M. Translational issues for mitoprotective agents as adjunct to reperfusion therapy in patients with ST-segment elevation myocardial infarction. J Cell Mol Med. 2020 Mar;24(5):2717-2729. doi: 10.1111/jcmm.14953. Epub 2020 Jan 22. PMID: 31967733; PMCID: PMC7077531. 3: Bainey KR, Armstrong PW. Ameliorating reperfusion injury in STEMI: dead or alive? Eur Heart J. 2014 Oct 1;35(37):2504-6. doi: 10.1093/eurheartj/ehu200. Epub 2014 May 29. PMID: 24875796. 4: Bayés M, Rabasseda X, Prous JR. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2007 Jul-Aug;29(6):427-37. PMID: 17922073. 5: Yonezawa T, Kurata R, Kimura M, Inoko H. PKC delta and epsilon in drug targeting and therapeutics. Recent Pat DNA Gene Seq. 2009;3(2):96-101. doi: 10.2174/187221509788654205. PMID: 19519579. 6: Qin X, Byrne M, Mori T, Zou P, Williams DR, McHaourab H, Johnson CH. Intermolecular associations determine the dynamics of the circadian KaiABC oscillator. Proc Natl Acad Sci U S A. 2010 Aug 17;107(33):14805-10. doi: 10.1073/pnas.1002119107. Epub 2010 Aug 2. PMID: 20679240; PMCID: PMC2930409. 7: Miyaji Y, Walter S, Chen L, Kurihara A, Ishizuka T, Saito M, Kawai K, Okazaki O. Distribution of KAI-9803, a novel δ-protein kinase C inhibitor, after intravenous administration to rats. Drug Metab Dispos. 2011 Oct;39(10):1946-53. doi: 10.1124/dmd.111.040725. Epub 2011 Jun 28. PMID: 21712433. 8: Liu G, Ji QC, Jemal M, Tymiak AA, Arnold ME. Approach to evaluating dried blood spot sample stability during drying process and discovery of a treated card to maintain analyte stability by rapid on-card pH modification. Anal Chem. 2011 Dec 1;83(23):9033-8. doi: 10.1021/ac2023876. Epub 2011 Nov 1. PMID: 21995953. 9: Metzler B, Xu Q, Mayr M. Letter by Metzler et al regarding article, "Intracoronary KAI-9803 as an adjunct to primary coronary intervention for acute ST-segment elevation myocardial infarction". Circulation. 2008 Jul 22;118(4):e80. doi: 10.1161/CIRCULATIONAHA.108.772772. PMID: 18645062. 10: Direct Inhibition of delta-Protein Kinase C Enzyme to Limit Total Infarct Size in Acute Myocardial Infarction (DELTA MI) Investigators, Bates E, Bode C, Costa M, Gibson CM, Granger C, Green C, Grimes K, Harrington R, Huber K, Kleiman N, Mochly-Rosen D, Roe M, Sadowski Z, Solomon S, Widimsky P. Intracoronary KAI-9803 as an adjunct to primary percutaneous coronary intervention for acute ST-segment elevation myocardial infarction. Circulation. 2008 Feb 19;117(7):886-96. doi: 10.1161/CIRCULATIONAHA.107.759167. Epub 2008 Feb 4. PMID: 18250271.

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