Cilengitide trifluoroacetate

For research use only.

Catalog No.S7077 Synonyms: EMD 121974, NSC 707544

36 publications

Cilengitide trifluoroacetate Chemical Structure

CAS No. 199807-35-7

Cilengitide (EMD 121974, NSC 707544) is a potent integrin inhibitor for αvβ3 receptor and αvβ5 receptor with IC50 of 4.1 nM and 79 nM in cell-free assays, respectively; ~10-fold selectivity against gpIIbIIIa. Phase 2.

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Selleck's Cilengitide trifluoroacetate has been cited by 36 publications

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Choose Selective Integrin Inhibitors

Biological Activity

Description Cilengitide (EMD 121974, NSC 707544) is a potent integrin inhibitor for αvβ3 receptor and αvβ5 receptor with IC50 of 4.1 nM and 79 nM in cell-free assays, respectively; ~10-fold selectivity against gpIIbIIIa. Phase 2.
Targets
αvβ3 receptor [1]
(Cell-free assay)
αvβ5 receptor [2]
(Cell-free assay)
4.1 nM 79 nM
In vitro

Cilengitide is a cyclized pentapeptide peptidomimetic designed to compete for the arginine-glycine-aspartic acid (RGD) peptide sequence that regulates integrin-ligand binding. Cilengitide selectively and potently blocks the ligation of theαvβ3 andαvβ5 integrins to provisional matrix proteins such as vitronectin, fibronectin, fibrinogen, von Willebrand factor, osteopontin, and others. [1] Cilegitide inhibits angiogenesis in vitro. 10 μM Cilengitide completely inhibits attachment of BAE, BME and HUVE cells on vitronectin and fibronectin. Cilengitide inhibits in vitro angiogenesis of BAE cells on three-dimensional collagen and fibrin gels pretreated with FGF-2(or VEGF-A) with IC50 of 15 μM and 8 μM, 4 μM and 3 μM, respectively. [2] Cilengitide blocks proliferation and induces apoptosis of endothelial cells as well as differentiation of human endothelial precursor cells (EPCs). 50 μg/mL Cilengitide completely inhibits the proliferation of human microvascular endothelial cell line HMEC-1 and leads to apoptosis in ~30% cells. [3] 1.0 μM Cilengitide treating for 9 days inhibits the proliferation of EPCs by nearly 40%. 1 μM Cilengitide inhibits the differentiation of EPCs by more than 80% at 14 days. [4] Cilengitide inhibits adhesion and induces apoptosis of tumor cells. 25 μg/mL Cilengitide causes detachment of DAOY cells (medulloblastoma) and U87MG cells (glioblastoma) from vitronectin and tenascin by more than 60%. 25 μg/mL Cilengitide induces a nearly 50% apoptosis rate of these cells. [5]

Cell Data
Cell Lines Assay Type Concentration Incubation Time Formulation Activity Description PMID
LN-308  NIiwN2lHfW6ldHnvckBCe3OjeR?= NIXuboQyNzFyL{GwNQKBkc7:bR?= M{X5fVI1KGh? NUfuTZhoTE2VT9Mg M{LCcpJm\HWlZYOgSHJGKHKncH;yeIVzKGGldHn2bZR6KGmwIHGgZ49v[2WwdILheIlwdi2mZYDlcoRmdnRibXHucoVz MYCyOlUxODB3Nh?=
ZH-161 Mlv4SpVv[3Srb36gRZN{[Xl? MWCxM|Ex6oDLzszt NH\MZoszPCCq M2fPWmROW00EoB?= NF\yZWpz\WS3Y3XzJGRTTSC{ZYDvdpRmeiCjY4Tpeol1gQ>? NEHvVIczPjVyMEC1Oi=>
S-24 MoTBSpVv[3Srb36gRZN{[Xl? MknFNU8yOOLCid88cS=> MkT3NlQhcA>? M{[3XGROW00EoB?= NY\LXGlXemWmdXPld{BFWkVicnXwc5J1\XJiYXP0bZZqfHl? NXzwOIo3OjZ3MECwOVY>
HaCaT  M{ezTWZ2dmO2aX;uJGF{e2G7 NIi5ZVcyOOLCid88cS=> M4HYTlQ5KGh? NXnMNZc1TE2VT9Mg M1LkdJJm\HWlZYOgWGdHNc7{MtMgcXJPSSCneIDy[ZN{cW:w NHf4S4szPjVyMEC1Oi=>
LN-308  MUfGeY5kfGmxbjDBd5NigQ>? M1vZNFEx6oDLzszt M4PNUVI1KGh? MnzLSG1UV8Li M1;hTZJm\HWlZYOgRYhTKHC{b4TlbY4hdGW4ZXzzJIFv\CCGUlWgdoVxd3K2ZYKgZYN1cX[rdIm= NIjnU3QzPjVyMEC1Oi=>
REN NWjENZczS2WubDDWbYFjcWyrdImgRZN{[Xl? NGj2PXAyKG6PLUKwNEDPxE1? NF3he2Q4OiCq MkDG[IVkemWjc3XzJINmdGxidnnhZoltcXS7IHnuJIEh\G:|ZTDk[ZBmdmSnboSgcYFvdmW{ MV2yOFU6PTJ5NB?=
MSTO-211H MnnRR4VtdCCYaXHibYxqfHliQYPzZZk> M1v1fFEhdk1vMkCwJO69VQ>? M{PmUVczKGh? MULk[YNz\WG|ZYOgZ4VtdCC4aXHibYxqfHliaX6gZUBld3OnIHTldIVv\GWwdDDtZY5v\XJ? MVSyOFU6PTJ5NB?=
MM05 NHLTSXBE\WyuIG\pZYJqdGm2eTDBd5NigQ>? MWexJI5ONTJyMDFOwG0> MWG3NkBp NWjxXZly\GWlcnXhd4V{KGOnbHygeoli[mmuaYT5JIlvKGFiZH;z[UBl\XCnbnTlcpQhdWGwbnXy NIDSOWozPDV7NUK3OC=>
H28 MVPD[YxtKF[rYXLpcIl1gSCDc4PhfS=> NFHtXVIyKG6PLUKwNEDPxE1? MVS3NkBp M3HrN4Rm[3KnYYPld{Bk\WyuII\pZYJqdGm2eTDpckBiKGSxc3Wg[IVx\W6mZX70JI1idm6nch?= MVyyOFU6PTJ5NB?=
SCC25 Ml7zS5Jwf3SqIFnubIljcXSrb36gRZN{[Xl? M3Tpc|YvOjYkgKOyNFDDqML3TR?= NFvhWVc4OiCq NIfkXVJz\XO3bITzJI1w\GW{YYTlMEBld3OnLXTldIVv\GWwdDDndo94fGhiaX7obYJqfGmxbh?= NHmxOoczPDV3N{C1Oi=>
CAL27 M4f6U2dzd3e2aDDJcohq[mm2aX;uJGF{e2G7 NGrhVlA3NjJ34pETNlAxyqEEtV2= M1;GelczKGh? M3;rWZJme3WudIOgcY9l\XKjdHWsJIRwe2VvZHXw[Y5l\W62IHfyc5d1cCCrbnjpZol1cW:w NWSwUG1VOjR3NUewOVY>
FaDu  M1nrXGdzd3e2aDDJcohq[mm2aX;uJGF{e2G7 NF7wN2Q3NjJ34pETNlAxyqEEtV2= NEPGbVg4OiCq MWry[ZN2dHS|IH3v[IVz[XSnLDDkc5NmNWSncHXu[IVvfCCpcn;3eIghcW6qaXLpeIlwdg>? NW[4PWROOjR3NUewOVY>
SCC25 NX7LU|N1SXCxcITvd4l{KEG|c3H5 NIXqT|UzPcLiwsXNxsA> M{[wVVQ5yqCqwrC= M1\wcolv\HWlZYOgZZBweHSxc3nz NYPudmkyOjR3NUewOVY>
CAL27 MYPBdI9xfG:|aYOgRZN{[Xl? NGHDRXkzPcLiwsXNxsA> NH3vbIs1QMLiaNMg Mk\GbY5lfWOnczDhdI9xfG:|aYO= M2S2dFI1PTV5MEW2
FaDu  MWfBdI9xfG:|aYOgRZN{[Xl? NGrWcVEzPcLiwsXNxsA> M2rPU|Q5yqCqwrC= MnXqbY5lfWOnczDhdI9xfG:|aYO= NYn3UlJmOjR3NUewOVY>
T-47D M3PYOGdzd3e2aDDJcohq[mm2aX;uJGF{e2G7 MUSwMVIxKM7:TR?= MV[5OkBp NXrGU2J{cW6qaXLpeJMh[2WubDDndo94fGhiaX6gZUBld3OnIHTldIVv\GWwdDDtZY5v\XJ? NEntd3gzPDF3M{GwNi=>
MCF-7  NWS3eZVMT3Kxd4ToJGlvcGmkaYTpc44hSXO|YYm= NWP4T5FJOC1{MDFOwG0> MUm5OkBp MW\pcohq[mm2czDj[YxtKGe{b4f0bEBqdiCjIHTvd4Uh\GWyZX7k[Y51KG2jbn7ldi=> MmnJNlQyPTNzMEK=
T-47D MkDlRZBweHSxc3nzJGF{e2G7 M4fvSVAuOjBizszN MUG0PEBp NHvGZoJqdmS3Y3XzJIFxd3C2b4Ppdy=> NE\iXIEzPDF3M{GwNi=>
MCF-7  MXnBdI9xfG:|aYOgRZN{[Xl? NV7BO5NwOC1{MDFOwG0> NEnaUZQ1QCCq M1v0V4lv\HWlZYOgZZBweHSxc3nz NILCVpYzPDF3M{GwNi=>
U87MG NF22c4pIem:5dHigTY5pcWKrdHnvckBCe3OjeR?= MnLsNE0zPSEQvF2= Mn3RNlQwPDhiaB?= M1vlTIlvcGmkaYTzJINmdGxiZ4Lve5RpKGmwIHTvd4Uh[W6mIITpcYUh\GWyZX7k[Y51KG2jbn7ldi=> MV:yN|M2PDhyNx?=
U251MG MlnLS5Jwf3SqIFnubIljcXSrb36gRZN{[Xl? MUewMVI2KM7:TR?= M3LWRVI1NzR6IHi= MVPpcohq[mm2czDj[YxtKGe{b4f0bEBqdiCmb4PlJIFv\CC2aX3lJIRmeGWwZHXueEBu[W6wZYK= MYGyN|M2PDhyNx?=
U87MG MXTBdI9xfG:|aYOgRZN{[Xl? MWixJOK2VQ>? NWrLR2V2PDhiaB?= NIW0fIJqdmS3Y3XzJIFxd3C2b4Ppdy=> NVjzZm1LOjN|NUS4NFc>
U251MG MVvBdI9xfG:|aYOgRZN{[Xl? MnjHNUDDvU1? M1fWRVQ5KGh? M13FRYlv\HWlZYOgZZBweHSxc3nz MU[yN|M2PDhyNx?=
U251 NGDiPXlIem:5dHigTY5pcWKrdHnvckBCe3OjeR?= MX:wMVI2KM7:Zz;tUC=> NXPjeJo{OC12ODDo M2XOU4lvcGmkaYTzJINmdGxiZ4Lve5RpKGmwIHTvd4Uh[W6mIITpcYUh\GWyZX7k[Y51KG2jbn7ldi=> Mn;xNlE4QDh|NEO=
U87  MXrHdo94fGhiSX7obYJqfGmxbjDBd5NigQ>? MWiwMVI2KM7:Zz;tUC=> M3zHelAuPDhiaB?= NWnk[JBLcW6qaXLpeJMh[2WubDDndo94fGhiaX6g[I9{\SCjbnSgeIlu\SCmZYDlcoRmdnRibXHucoVz NGrJZm4zOTd6OEO0Ny=>
U251 M3vFU2Fxd3C2b4Ppd{BCe3OjeR?= NFqwTpUzPSEQvHevcWw> NVfWTo5EOjRxNEigbC=> M2PnOYlv\HWlZYOgZZBweHSxc3nzJIF1KDR6IHigd4lodmmoaXPhcpRtgQ>? M3XpTVIyPzh6M{Sz
U87  M1mwcmFxd3C2b4Ppd{BCe3OjeR?= Mk\XNlUh|rypL33M M1\mfVI1NzR6IHi= NEm5VGxqdmS3Y3XzJIFxd3C2b4Ppd{BifCB2ODDoJJNq\26rZnnjZY51dHl? NGDuVY8zOTd6OEO0Ny=>
U251 Mke0SpVv[3Srb36gRZN{[Xl? MVqwMVI2KM7:Zz;tUC=> MmGxNVIhcMLi M1HJeIlv\HWlZYOgZZV1d3CqYXf5JIRwe2ViZHXw[Y5l\W62bIm= NEPJe48zOTd6OEO0Ny=>
U87  NHXaVYJHfW6ldHnvckBCe3OjeR?= M{\DR|AuOjVizsznM41N NEPK[GcyOiCqwrC= MWHpcoR2[2W|IHH1eI9xcGGpeTDkc5NmKGSncHXu[IVvfGy7 MVmyNVc5QDN2Mx?=
U87MG M3vhbGZ2dmO2aX;uJGF{e2G7 NFrzdncxNjFxMT:xNEDPxE1? MX2yOEBp NVjRUnp2cW2yYXnyd{B1cGViYXTo[ZNqd25ib3[gZ4VtdHNidH:geol1em:wZXP0bY4hcW5iYTDkc5NmKGSncHXu[IVvfCCvYX7u[ZI> NFmzWZcyQTJ{MUG3NS=>
LN-308 MVHGeY5kfGmxbjDBd5NigQ>? NWfK[mpbOC5zL{GvNVAh|ryP MoHmNlQhcA>? M3nHVIlueGGrcoOgeIhmKGGmaHXzbY9vKG:oIHPlcIx{KHSxII\peJJwdmWldHnuJIlvKGFiZH;z[UBl\XCnbnTlcpQhdWGwbnXy MXqxPVIzOTF5MR?=
LN-18 M4rMTGZ2dmO2aX;uJGF{e2G7 M4\NXVAvOS9zL{GwJO69VQ>? NIiyWmczPCCq NX\6b|F{cW2yYXnyd{B1cGViYXTo[ZNqd25ib3[gZ4VtdHNidH:geol1em:wZXP0bY4hcW5iYTDkc5NmKGSncHXu[IVvfCCvYX7u[ZI> NGrZb2wyQTJ{MUG3NS=>
T98G MlfzSpVv[3Srb36gRZN{[Xl? Mke1NE4yNzFxMUCg{txO M2S4[VI1KGh? NHjqVI1qdXCjaYLzJJRp\SCjZHjld4lwdiCxZjDj[YxteyC2bzD2bZRzd26nY4TpckBqdiCjIHTvd4Uh\GWyZX7k[Y51KG2jbn7ldi=> NWnoe3BxOTl{MkGxO|E>
LNT-229  MkfpSpVv[3Srb36gRZN{[Xl? NHyxTVUxNjFxMT:xNEDPxE1? Mo\HNlQhcA>? MkPIbY1x[Wm{czD0bIUh[WSqZYPpc44hd2ZiY3XscJMhfG9idnn0do9v\WO2aX6gbY4h[SCmb4PlJIRmeGWwZHXueEBu[W6wZYK= NILGO40yQTJ{MUG3NS=>
HMEC-1  NHvpRWlHfW6ldHnvckBCe3OjeR?= M3uyV|EwPS93MDFOwIcwdWx? NES4O3AzPCCq M{XTSYlv\HWlZYOgZUBld3OnIHTldIVv\GWwdDDk[ZRi[2ivZX70xsA> MlvTNVkyOTRyMEW=
HMEC-1  NFzh[YJRem:uaX\ldoF1cW:wIFHzd4F6 NYK3b25DOS93L{WwJO69\y:vbB?= NV3ncXFWOjRxNEivO|IhcA>? MoDKbY5pcWKrdIOgdJJwdGmoZYLheIlwdiCrbjDhJIRwe2ViZHXw[Y5l\W62IH3hco5meg>? MU[xPVEyPDByNR?=
HMEC-1  NG\tcGFCeG:ydH;zbZMhSXO|YYm= NIrE[pcyNzVxNUCg{txoN22u M{T1fFI1KGh? NUjwN4hEcW6mdXPld{BieG:ydH;zbZM> MX:xPVEyPDByNR?=
G28 NH7McJVRem:uaX\ldoF1cW:wIFHzd4F6 NID6OYsyNzVxNUCg{txoN22u MnzVNlQwPDhxN{KgbC=> NWW5W2YxcW6qaXLpeJMheHKxbHnm[ZJifGmxbjDpckBiKGSxc3Wg[IVx\W6mZX70JI1idm6nch?= NUK3UJU4OTlzMUSwNFU>
G44 MoLPVJJwdGmoZYLheIlwdiCDc4PhfS=> M3vOT|EwPS93MDFOwIcwdWx? MXmyOE81QC95MjDo MV\pcohq[mm2czDwdo9tcW[ncnH0bY9vKGmwIHGg[I9{\SCmZYDlcoRmdnRibXHucoVz M3XZfFE6OTF2MEC1
G28 Mnz0RZBweHSxc3nzJGF{e2G7 MWOxM|UwPTBizsznM41t NF;FTWUzPCCq M4TMNolv\HWlZYOgZZBweHSxc3nz NUTrXnhsOTlzMUSwNFU>
G44 M1vRNmFxd3C2b4Ppd{BCe3OjeR?= NH\aZZIyNzVxNUCg{txoN22u NIrsS24zPCCq NIHr[4tqdmS3Y3XzJIFxd3C2b4Ppdy=> MnPzNVkyOTRyMEW=
HMEC-1  MWfGeY5kfGmxbjDBd5NigQ>? MlnJNlAwPDBxNkCg{txoN22u MoDRbY5pcWKrdIOgSmFMKGGwZDDTdoPDqA>? MnnCNVkyOTRyMEW=
G28 M4TYb2Z2dmO2aX;uJGF{e2G7 NUDie4JvPTBizsznM41t NH;5dIE{OC94MD:xNlAhdWmw NHfnWGRqdmirYnn0d{BxcG:|cHjvdplt[XSrb36gc4YhTkGNLDDTdoMh[W6mIFHreC=> NITGVGoyQTFzNECwOS=>

... Click to View More Cell Line Experimental Data

Assay
Methods Test Index PMID
Western blot
pFAK / p-AKT ; 

PubMed: 19114005     


G28 cells were treated with 50 μg/ml cilengitide for 30, 60 and 120 minutes at 37°C. Cell lysates containing similar amounts of protein were separated by SDS-PAGE, transferred to a nitrocellulose membrane and probed with specific antibodies for detection of β-actin and phosphorylated FAK and Akt.

GLI1; 

PubMed: 31366904     


Western blottingting showing downregulated GLI1 with Integrin αvβ3 inhibitor Cilengitide and upregulated GLI1 with co-stimulator ligand RGD compared to the blank control in SGC7901 MCAs and BGC823 MCAs. 

19114005 31366904
Immunofluorescence
VE-cadherin / β3 integrin ; 

PubMed: 19212436     


Confluent HUVEC plated on fibronectin or collagen I were exposed to cilengitide (10 µM each) for the indicated time and double stained for VE-cadherin and β3 integrin. Cilengitide disrupted VE-cadherin staining and promoted appearance of β3 at VE-cadherin-depleted cell-cell borders. Higher magnification of HUVEC cultures demonstrate rare co-localization of VE-cadherin and β3 integrin at cellular junctions upon cilengitide stimulation (arrowheads). Bars: 10 µm.

19212436
Growth inhibition assay
Cell number ; 

PubMed: 24153102     


Cell detachment following 1 hr Cilengitide treatment. Cells were treated with cilengitide for 1 hr, washed with PBS, and remaining attached cells were trypsinized and counted. A) T-47D cells showed a strong dose response, with almost complete cell detachment at 20 uM cilengitide treatment. B) MCF-7 cells showed moderate cell detachment similar to C) MDA-MB-231 cells. D) MDA-MB-468 cells showed little to no cell detachment following this short exposure to cilengitide. Figures show Mean ± SEM and represent the average of three experiments. * = ≤ 0.05.

24153102
In vivo Cilengitide is activity against tumor growth and angiogenesis as single-agent. 100 μg Cilengitide induces a significant decrease in the number of CD 31+ vessels seen in tumors (2/high-power field) compared with control tumors (56/high-power field). 100 μg Cilengitide increases cellular apoptosis in the brain tumors of animals (2.2% apoptotic cells/high-power field) compared with those receiving the inactive peptide (1.7% cells/high-power field). Cilengitide treatment results in prolonged survival of the mice bearing melanoma xenografts M21 compared with control treatment group. (36.5 vs 17.3 days). [5] Cilengitide can augment the therapeutic benefit associated with cytotoxic agents including chemotherapy and radiation therapy in tumor models. Cilengitide (250 mg/dose) alone does not alter tumor growth of breast cancer xenografts when compared with untreated mice, but combined modality RIT (CMRIT) using RIT and six doses of Cilengitide (250 mg/dose) increases efficacy of treatment, with the cure rate for mice that receives only RIT increasing from 15 to 53%. CMRIT significantly increases apoptosis of tumor and endothelial cells 5 days, and decreases tumor proliferation. [6]

Protocol

Kinase Assay:[2]
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Integrin-binding competition assay:

Recombinant soluble integrins are immobilized, and peptides, which are serially diluted in Tris-buffered saline (TBS++) (0.1% (w/v) BSA, 150 mM NaCl, 1 mM CaCl2, 1 mM MgCl2 10 μM MnCl2, 20 mM Tris-HCl; pH 7.4), are added in parallel with biotinylated vitronectin (to 1μg/mL). After a 3-h incubation at 37℃ and washing with Tris–buffered saline, bound ligand is detected by incubation with an antibiotin alkaline phosphatase-conjugated antibody (BioRad) followed by development with p-nitrophenyl phosphatase substrate. The reaction is stopped by the addition of NaOH and the color intensity read at 405 nm.
Cell Research:[3]
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  • Cell lines: Human microvascular endothelial cell line HMEC-1
  • Concentrations: 1-50 μg/mL
  • Incubation Time: 3 days
  • Method: HMEC-1 (1×104 per well) are seeded on uncoated 48 well plates and incubated in medium containing 4% FCS with Cilengitide. After incubation for 72 hours at 37℃, cells are trypsinized and counted.
    (Only for Reference)
Animal Research:[5]
- Collapse
  • Animal Models: Human glioblastoma xenografts U87 MG
  • Dosages: 100μg
  • Administration: Daily i.p.
    (Only for Reference)

Solubility (25°C)

In vitro DMSO 100 mg/mL (142.31 mM)
Water 8 mg/mL (11.38 mM)
Ethanol Insoluble

* Please note that Selleck tests the solubility of all compounds in-house, and the actual solubility may differ slightly from published values. This is normal and is due to slight batch-to-batch variations.

Chemical Information

Molecular Weight 702.68
Formula

C29H41F3N8O9

CAS No. 199807-35-7
Storage powder
in solvent
Synonyms EMD 121974, NSC 707544
Smiles CC(C)C1C(=O)NC(C(=O)NCC(=O)NC(C(=O)NC(C(=O)N1C)CC2=CC=CC=C2)CC(=O)O)CCCN=C(N)N.C(=O)(C(F)(F)F)O

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Clinical Trial Information

NCT Number Recruitment interventions Conditions Sponsor/Collaborators Start Date Phases
NCT01517776 Terminated Drug: Cilengitide|Drug: Temozolomide Gliomas Martin-Luther-Universität Halle-Wittenberg|Merck KGaA Darmstadt Germany January 2012 Phase 2
NCT01118676 Completed Drug: cilengitide radiochemotherapy Locally Advanced Non Small Cell Lung Cancer (NSCLC)* Institut Claudius Regaud|Merck KGaA Darmstadt Germany March 2010 Phase 1

Tech Support

Answers to questions you may have can be found in the inhibitor handling instructions. Topics include how to prepare stock solutions, how to store inhibitors, and issues that need special attention for cell-based assays and animal experiments.

Handling Instructions

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Frequently Asked Questions

  • Question 1:

    The recommend vehicle is 30% propylene glycol, 5% Tween 80, 65% D5W at 30mg/ml, can you let me know if this is a suspension or clear solution?

  • Answer:

    S7077 Cilengitide can be dissolved in 30% propylene glycol/5% Tween 80/65% D5W at 10 mg/ml as a clear solution.

  • Question 2:

    Is Cilengitide a TFA salt?

  • Answer:

    S7077 Cilengitide is actually a TFA salt, and the ratio between Cilengitide and TFA is 1:1.

Integrin Signaling Pathway Map

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Cell Lines Assay Type Concentration Incubation Time Formulation Activity Description PMID