rgd peptides product brochure

1-800-777-4779 E-mail: [email protected]

Phone: 502-266-8787 Fax: 502-267-1329

P.O. Box 99703Louisville, KY 40269-0703 USA

Peptides International, Inc.

1. M Kantlehner, P. Schaffner, D. Finsinger, J. Meyer, A. Jonczyk, B. Diefenbach, B. Nies, G. Hozemann, S.L. Goodman, and H. Kessler, Chembiochem., 1, 107 (2000). 2. P.K. Dubey, V. Mishra, S. Jain, S. Mahor, and S.P. Vyas, J. Drug Targeting, 12, 257 (2004). 3. P. Holig, M. Bach, T. Volkel, T. Nahde, S. Hoffmann, R. Muller, and R.E. Kontermann, Protein Engin. Design Selection, 17, 433 (2004). 4. C. Dolce, A. Vakani, L. Archer, J.A. Morris-Wiman, and L.S. Holliday, J. Dent. Res., 82, 682 (2003). 5. R.J. Kok, A.J. Schraa, E.J. Bos, H.E. Moorlag, S.A. Asgeirsdottir, M. Everts, D.K.F. Meijer, and G. Molema, Bioconjug. Chem., 13, 28 (2002). 6. R.M. Schiffelers, G.A. Koning,, T.L.M. ten Hagen, M.H.A.M. Fens, A.J. Schraa, A.P.C.A. Janssen, R.J. Kok, G. Molema, and G. Storm, J. of Controlled Release, 91, 115 (2003). 7. M.L. Janssen, W.J. Oyen, I. Dijkgraaf, L.F. Massuger, C. Frielink, D.S. Edwards, M. Rajopadhye, H. Boonstra, F.H. Corstens, and O.C. Boerman, Cancer. Res., 62, 6146 (2002). 8. X. Chen, S. Liu, Y. Hou, M. Tohme, R. Park, J.R. Bading, and P.S. Conti, Mol. Imaging Biol., 6, 350 (2004). 9. R. Haubner, H.J. Wester, F. Burkhart, R. Senekowitsch-Schmidtky, W. Weber, S.L. Goodman, H. Kessler, and M. Schwaiger, J. Nuclear Med., 42, 326 (2001). 10. X. Chen, R. Park. A.H. Shahinian, M. Tohme, V. Khankaldyyan, M.H. Bozorgzdeh, J.R. Bading, R. Moats, W.E. Laug, and P.S. Conti, Nucl. Med. Biol., 31, 179 (2004). 11. X. Chen, C. Plasencia, Y. Hou, and N. Neamati, J. Med. Chem., 48, 1098 (2005). 12. X. Chen, M. Tohme, R. Park, Y. Hou, J.R. Bading, and P.S. Conti, Mol. Imaging, 3, 96 (2004).

RGD Peptides

Integrins are heterodimeric cell surface receptors that were found in early studies to mediate adhesion between cells and the extracellular matrix (ECM), by binding to ligands with an exposed arginine-glycine-aspartate (RGD) sequence. These receptors also stimulate intracellular signaling and gene expression involved in cell growth, migration, and survival. These same processes, if not properly regulated, can lead to thrombosis, inflammation, and cancer. In fact, integrins have been demonstrated to be participants in these diseases and can also act as disease markers. Because of this, research has focused on developing RGD peptides that could mimic cell adhesion proteins and bind to integrins. The diverse applications for these peptides include inhibiting apoptosis, angiogenesis, and tumor formation, coating surfaces for use as biomaterials, enhancing drug delivery systems, and imaging for diagnostic purposes.

Peptides International offers a variety of cyclic RGD peptides and peptide templates which confer greater stability and selectivity over linear peptides. cyclo (Arg-Gly-Asp-D-Phe-Lys) (PCI-3661-PI) can be functionalized with various linker molecules through the amino group on the lysine residue. These linkers can act as spacers or anchors for diverse surfaces. For example, linkage of this peptide with an acrylamide group allowed attachment to poly(methyl methacrylate) surfaces and led to improved binding to osteoblast cells and increased circulation time in the body.1 Others have functionalized this peptide with polyethylene glycol for enhanced binding to lysosomes for targeted drug delivery, resulting in effective tumor regression.2 Alanine replacement of glycine yields a negative control variant for this cyclic peptide, cyclo (Arg-Ala-Asp-D-Phe-Lys). Functionalized versions of cyclo (RGDfK) such as cyclo [Arg-Gly-Asp-D-Phe-Lys(PEG-PEG)] are also available.

This analog contains two mini-PEGTM derivatives (FXX-5521-PI) or 8-amino-3,6-dioxaoctanoic acids that act as spacers between ligand and lipid head groups, to allow for more efficient binding to lipid surfaces.3 cyclo [Arg-Gly-Asp-D-Phe-Lys(Biotin-PEG-PEG)] (PCI-3697-PI) analog contains 2 PEG spacers and is biotinylated for use as a reporting tag. Previous studies have used biotinylated peptides for histological staining of RGD peptides in tissue sections.4 The cyclo [Arg-Gly-Asp-D-Phe-Lys(Ac-SCH2CO)] (PCI-3699-PI) analog contains an S-acetylthioacetyl group, which following deprotection, can allow coupling to liposomes via a thioether bond.5,6

A bicyclic RGD peptide, H-Glu[cyclo(Arg-Gly-Asp-D-Phe-Lys)]2, was recently reported

to possess high affinity for v3 integrin. Conjugation of E-[c(RGDfK)2] with a DOTA chelator allowed for radiolabeling, and this radiolabeled peptide was demonstrated to significantly delay tumor growth in mice and have high, specific tumor uptake in human cancer xenograft, suggesting a

possible role in imaging as well as potential therapy. 7,8 In addition, cyclo (Arg-Gly-

Asp-D-Phe-Glu) and cyclo (Arg-Gly-Asp-D-Tyr-Lys) are also available for potential imaging.

The latter can be radiolabeled through the tyrosine residue or a linker, which can be attached via the

side chain amino group of lysine.9,10 A bicyclic form of this peptide, H-E[c(RGDyK)]2 (PCI-3899-PI), has been recently modified with labels via the glutamine residue, allowing for enhanced imaging and tumor targeting.11,12

RGD peptides are proving to be promising new tools for drug therapy and imaging of tumors, thrombosis, and inflammatory-related diseases. Peptides International provides the proper tools for further exploration and manipulation of this intriguing group of peptides for research applications.

Molecular Glue? A Cell Adhesion Motif

NH2

NH

O

ONH

HN

O

O

HO2C

O

NH

NHNH

NH

ICA-4304


Phone: 502-266-8787 Fax: 502-267-1329



CODE RGD PEPTIDEs QTY

PCI-3686-PI cyclo (Arg-Gly-Asp-d-Phe-Cys)* c(RGDfC)(M.W. 578.65) C24H34N8O7S RGD Tumor Targeting Peptide (linker additions via Cys)C. Pattillo, F. Sari-Sarraf, R. Nallamothu, B. Moore, G. Wood, and M. Kiani, Pharm. Res., 22, 1117, (2005). R. Nallamothu, G.C. Wood, C.B. Pattillo, R.c. Scott, M.F. Kiani, B.M. Moore, and L.A. Thoma, AAPS PharmSciTech, 7, E1 (2006).

1 mg 5 mg

PCI-3960-PI cyclo (Arg-Ala-Asp-d-Phe-Cys)c(RADfC)(M.W. 592.68) C25H36N8O7SControl for PCI-3686-PI

1 mg 5 mg

25 mg

PCI-3687-PI cyclo (Arg-Gly-Asp-d-Phe-Glu)* c(RGDfE)(M.W. 604.63) C26H36N8O9 RGD Peptide for Radiolabeling and ImagingG. Thumshirn, U. Hersel, S.L. Goodman, and H. Kessler, Chem. Eur. J., 9, 2717 (2003).T. Poethko, M. Schottelius, G. Thumshirn, U. Hersel, M. Herz, G. Henriksen, H. Kessler, M. Schwaiger, and H.J. Wester, J. Nucl. Med., 45, 892 (2004).

1 mg 5 mg

25 mg

PCI-3661-PI cyclo (Arg-Gly-Asp-d-Phe-Lys)*c(RGDfK)(M.W. 603.68) C27H41N9O7 RGD Tumor Targeting Peptide, v 3 Integrin Binding RGD PeptideM. Kantlehner, P. Schaffner, D. Finsinger, J. Meyer, A. Jonczyk, B. Diefenbach, B. Nies, G. Hozemann, S.L. Goodman, and H. Kessler. Chembiochem., 1, 107 (2000).R.J. Kok, A.J. Schraa, E.J. Bos, H.E. Moorlag, S.A. sgeirsdttir, M. Everts, DK. Meijer, and G. Molema, Bioconjug. Chem., 13, 128 (2002). J. Schraa, R.J. Kok, S.M. Botter, S. Withoff, D.K. Meijer, L.F. de Leij, and G. Molema, Int. J. Cancer, 112, 279 (2004).

1 mg 5 mg

25 mg

PCI-3919-PI cyclo (Arg-Gly-Asp-d-Phe-Lys)c(RGDfK) Trifluoroacetate Salt(M.W. 603.68) C27H41N9O7

1 mg 5 mg

25 mg

PCI-3883-PI cyclo (Arg-Ala-Asp-d-Phe-Lys)c(RADfK) (M.W. 617.71) C28H43N9O7 Negative Control RGD Peptide for PCI-3661-PIP.K. Dubey, V. Mishra, S. Jain, S. Mahor, and S.P. Vyas, J. Drug Targeting, 12, 257 (2004).

1 mg5 mg

25 mg

RGD-3795-PI

NEW!

cyclo [Arg-Gly-Asp-d-Phe-Lys(mal)](M.W. 754.81) C34H46N10O10 RGD peptide with 3-maleimide propionic acid functional group

1 mg5 mg

25 mg

RGD-3736-PI Galactosyl-cyclo (Arg-Gly-Asp-d-Phe-Lys) C(-RDGFK(SAA)(M.W. 792.85) C34H52N10O12 [922175-70-0] Glycosylated RGD for radiolabellingHabner, et al., Bioconjugate Chem., 15, 1, (2004).

1 mg 5 mg

PCI-3696-PI cyclo [Arg-Gly-Asp-d-Phe-Lys(PEG-PEG)]* c(RGDfK(PEG-PEG))where PEG = 8-Amino-3,6-Dioxaoctanoic Acid(M.W. 894.0) C39H63N11O13RGD Peptide equipped with PEG spacers for more efficient binding to lipid surfaces P.K. Dubey, V. Mishra, S. Jain, S. Mahor, and S.P. Vyas, J. Drug Targeting, 12, 257 (2004).R.M. Schiffelers, G.A. Koning, T.L. ten Hagen, M.H., Fens, A.J. Schraa, A.P. Janssen, R.J. Kok, G. Molema, and G. Storm, J. Controlled Release, 91, 115 (2003).

1 mg 5 mg

H

NH

NH2

NH

O

ONH

HN

O

O

HO2C

NO

NH

NHNH

NH

C

O

OO C

OO

ONH2

Arg

AspD-Phe

Lys PEG PEG

Gly

CYCLO[RGDfK (PEG-PEG)]

* May require further derivatization before use + Requires deprotection before use

NH2

NH

O

ONH

HN

O

O

HO2C

NH2

O

NH

NHNH

NHArg

Lys

D-PheAsp

Gly

CYCLO(RGDfK)

NH2

NH

O

ONH

HN

O

O

HO2C

O

NH

NHNH

NH

SH

AspD-Phe

Cys

Arg

Gly

CYCLO(RGDfC)


Phone: 502-266-8787 Fax: 502-267-1329




RGD-3782-PI

NEW!

Galacto-RGD2(Trifluoroacetate Form) (M.W. 2149.24) C91H137N29O32 Tumor-imaging RGD peptide

1 mg 5 mg

PCI-3954-PI cyclo [Arg-Ala-Asp-d-Phe-Lys(PEG-PEG)] RADfK(PEG-PEG)](M.W. 908.03) C40H65N11O13 Negative Control for PCI-3696-PI

1 mg5 mg

25 mg

RGD-3759-PI cyclo [Arg-Gly-Asp-d-Phe-Lys (PEG-PEG-Azide)] one of The Clickables(Trilfuoroacetate salt) (M.W. 921.01) C39H62N13O13Clickable RGD for Dendrimer Constructs

1 mg5 mg

PCI-3697-PI cyclo [Arg-Gly-Asp-d-Phe-Lys(Biotin-PEG-PEG)]* c[RGDfK(Biotin-PEG-PEG)]where PEG = 8-Amino-3,6-Dioxaoctanoic Acid(M.W. 1120.30) C49H77N13O15SRGD Peptide equipped with a biotin reporting tag andPEG spacers for more efficient binding to lipid surfaces W.G. Lesniak, M.S. Kariapper, B.M. Nair, W. Tan, A. Hutson, L.P. Balogh, and M.K. Khan, Bioconjug. Chem.,18, 4 (2007)D. Boturyn, J.-L. Coll, E. Garanger, M.-C. Favrot, and P. Dumy, J. Am. Chem. Soc., 126, 5730 (2004).D. Boturyn and P. Dumy, Tetrahedron Lett., 42, 2787 (2001).

NHC

O

OO

H

NH2

NH

O

ONH

HN

O

O

HO2C

NO

NH

NHNH

NH

CO

OO

NH Biotin

Arg

D-Phe

PEG PEG

Asp

Gly

Lys

CYCLO[RGDfK (Biotin-PEG-PEG)]

1 mg 5 mg

PCI-3895-PI cyclo [Arg-Gly-Asp-d-Phe-Lys(Biotin)] c[RGDfK(Biotin)] (M.W. 829.98) C37H55N11O9SNegative Control RGD Peptide for PCI-3697-PID. Boturyn, J.-L. Coll, E. Garanger, M.-C. Favrot, and P. Dumy, J. Am. Chem. Soc., 126, 5730 (2004).D. Boturyn and P. Dumy, Tetrahedron Lett., 42, 2787 (2001).

1 mg 5 mg

PCI-3699-PI cyclo [Arg-Gly-Asp-d-Phe-Lys(Ac-sCH2CO)]*+ c[RGDfK (Ac-SCH2CO)](M.W. 719.82) C31H45N9O9S RGD Peptide equipped with thioacetyl group for linking to liposomesR.J. Kok, A.J. Schraa, E.J. Bos, H.E. Moorlag, S.A. Asgeirsdottir, M. Everts, D.K.F. Meijer, and G. Molema, Bioconjug. Chem., 13, 128 (2002).R.M. Schiffelers, G.A. Koning,, T.L.M. ten Hagen, M.H.A.M. Fens, A.J. Schraa, A.P.C.A. Janssen, R.J. Kok, G. Molema, and G. Storm, J. of Controlled Release, 91, 115 (2003).K. Darlak, R.B. Miller, M.S. Stack, A.F. Spatola, and R.D. Gray, J. Biol. Chem., 265, 5199 (1990).

1 mg5 mg

H

NH2

NH

O

ONH

HN

O

O

HO2C

NO

NH

NHNH

NH

C

O

CH2S-COCH3Acetyl group

Arg

Lys

D-PheAsp

Gly

CYCLO[RGDfK (Ac-SCH2CO)]

PCI-3959-PI cyclo [Arg-Ala-Asp-d-Phe-Lys(Ac-sCH2CO)]c[RADfK(Ac-SCH2CO)](M.W. 733.85) C32H47N9O9SControl for PCI-3699-PI

1 mg5 mg

25 mg


H

NH2

NH

O

ONH

HN

O

O

HO2C

NO

NH

NHNH

NH

Biotin

Arg

Lys

D-PheAsp

Gly

CYCLO[RGDfK (Biotin)]


Phone: 502-266-8787 Fax: 502-267-1329




PCI-3898-PI cyclo [Arg-Gly-Asp-d-Phe-Lys(H-ser)] c[RGDfK(H-Ser)] (M.W. 690.76) C30H46N10O9RGD Peptide equipped with H-Ser

1 mg5 mg

PCI-3651-PI

H-Glu[cyclo (Arg-Gly-Asp-d-Phe-Lys)]2*E-[c(RGDfK)2] Acetate Salt(M.W. 1318.47) C59H87N19O16 RGD Tumor Targeting and Tumor Imaging PeptideC. Ryppa, et al., Bioconjugate Chem., 19, 7 (2008). M.L. Janssen, W.J. Oyen, I. Dijkgraaf, L.F. Massuger, C. Frielink, D.S. Edwards, M. Rajopadhye, H. Boonstra, F.H. Corstens, and O.C. Boerman, Cancer. Res., 62, 6146 (2002).M. Janssen, C. Frielink, I. Dijkgraaf, W. Oyen, D.S. Edwards, S. Liu, M. Rajopadhye, L. Massuger, F. Corstens, and O. Boerman, Cancer Biother. Radiopharm, 19, 399 (2004).M. Janssen, W.J. Oyen, L.F. Massuger, C. Frielink, I. Dijkgraaf, D.S. Edwards, M. Radjopadhye, F.H. Corstens, and O.C. Boerman, Cancer Biother. Radiopharm., 17, 641 (2002).

1 mg5 mg

25 mg

OO O O

NH

OC

OO

NH

O

NH

NH2 N OH

NH

OC

O O

NH

O

NH

NH2NO H

2HN

HN

HO

O

HN

NHNH

D-PheLys

ArgGly

Asp

HN

HO

O

HN

NHNHD-Phe

Lys

Asp

Gly

Arg

Glu

H-E[c(RGDfK)]2

PCI-3979-PI

H-Glu[cyclo (Arg-Ala-Asp-d-Phe-Lys)]2*Trifluroacetate Salt Negative Control Peptides for PCI-3651-PI

1 mg5 mg

25 mg

PCI-3904-PI H-Glu[cyclo (Arg-Gly-Asp-d-Phe-Lys)]2*E-[c(RGDfK)2] Trifluoroacetate Salt(M.W. 1318.47) C59H87N19O16RGD Tumor Targeting and Tumor Imaging Peptide

1 mg5 mg

25 mg

PCI-3975-PI H-Glu{Glu[cyclo (Arg-Gly-Asp-d-Phe-Lys)]2}2*H-E{E[cRGDfK]2}2 Trifluoroacetate Salt(M.W. 2748.04) C123H179N39O34Tetrameric RGD Peptide

1 mg5 mg

25 mg

PCI-3903-PI DOTA-Glu-[cyclo (Arg-Gly-Asp-d-Phe-Lys)]2* DOTA-E-[c(RGDfK)2](M.W. 1704.88) C75H113N23O23RGD Tumor Targeting and Tumor Targeting Peptide equipped with DOTA chelatorM.L. Janssen, W.J. Oyen, I. Dijkgraaf, L.F. Massuger, C. Frielink, D.S. Edwards, M. Rajopadhye, H. Boonstra, F.H. Corstens, and O.C. Boerman, Cancer Res., 62, 6146 (2002). M. Janssen, C. Frielink, I. Dijkgraaf, W. Oyen, D.S. Edwards, S. Liu, M. Rajopadhye, L. Massuger, F. Corstens, and O. Boerman, Cancer Biother. Radiopharm, 19, 399 (2004).X. Chen, S. Liu, Y. Hou, M. Tohme, R. Park, J.R. Bading, and P.S. Conti, Mol. Imaging Biol., 6, 350 (2004).

1 mg5 mg

OO O O

NH

OC

OO

NH

O

NH

NH2 N OH

NH

OC

O O

NH

O

NH

NH2NO H

NH

NO N

NN

CO2H

CO2HHO2C

DOTA-E[c(RGDfK)]2

Asp

Glu

HN

HO

O

HN

NHNH

D-PheLys

ArgGly

HN

HO

O

HN

NHNHD-Phe

Lys

Asp

Gly

Arg

DOTA

DOTA = 1,4,7,10-TETRAAZACYCLODODECANE- N,N',N'',N'''-TETRAACETIC ACID



Phone: 502-266-8787 Fax: 502-267-1329




ICA-4304 cyclo (Arg-Gly-Asp-d-Phe-Val)c(RGDfV) (M.W. 574.63) C26H38N8O7Angiogenesis InhibitorP.C. Brooks, A.M.P. Montgomery, M. Rosenfeld, R.A. Reisfeld, T. Hu, G. Klier, and D.A. Cheresh, Cell, 79, 1157 (1994). M. Aumailley, M. Gurrath, G. Muller, J. Calvete, R. Timpl, and H. Kessler, FEBS Lett., 291, 50 (1991).M. Friedlander, C.L. Theesfeld, M. Sugita, M. Fruttiger, M.A. Thomas, S. Chang, and D.A. Cheresh, PNAS, 93, 9764 (1996).

25 mg

NH2

NH

O

ONH

HN

O

O

HO2C

O

NH

NHNH

NH

CYCLO(RGDfV)

Gly

Arg

Val

D-PheAsp

PCA-3618-PI cyclo (Arg-Ala-Asp-d-Phe-Val)c(RADfV) (M.W. 588.67) C27H40N8O7Negative Control RGD Peptide for ICA-4304-PIM. Friedlander, C.L. Theesfeld, M. Sugita, M. Fruttiger, M.A. Thomas, S. Chang, and D.A. Cheresh, PNAS, 93, 9764 (1996).

1mg5 mg

25 mg

PCI-3912-PI cyclo (Arg-Gly-Asp-D-Tyr-Cys)* c(RGDyC)(M.W. 594.65) C24H34N8O8S

1 mg 5 mg

PCI-3917-PI cyclo (Arg-Ala-Asp-d-Tyr-Cys)*c(RADyC)C25H36N8O8S (M.W. 608.68) C25H36N8O8SNegative Control for PCI-3912-PI

1 mg5 mg

PCI-3688-PI cyclo (Arg-Gly-Asp-D-Tyr-Glu)* c(RGDyE)(M.W. 620.62) C26H36N8O10 RGD Peptide for Radiolabeling

1 mg 5 mg

25 mg

PCI-3662-PI cyclo (Arg-Gly-Asp-d-Tyr-Lys)*c(RGDyK) (M.W. 619.68) C27H41N9O7 RGD Tumor Targeting and Tumor Imaging Peptide, v 3 Integrin Binding RGD PeptideR. Haubner, H.J. Wester, F. Burkhart, R. Senekowitsch-Schmidtky, W. Weber, S.L. Goodman, H. Kessler, and M. Schwaiger, J. Nuclear Med., 42, 326 (2001).X. Chen, R. Park. A.H. Shahinian, M. Tohme, V. Khankaldyyan, M.H. Bozorgzdeh, J.R. Bading, R. Moats, W.E. Laug, and P.S. Conti, Nucl. Med. Biol., 31, 179 (2004).X. Chen, P.S. Conti, and R.A. Moats, Cancer Res., 641, 8009 (2004).

1 mg 5 mg

25 mg

O

NH

OHO

O

O NH2HN

NH2C

O O

NH

c(RGDyK)

D-TyrLys

Asp GlyArg

HN

HO

O

HN

NH

NH

PCI-3894-PI cyclo (Arg-Ala-Asp-d-Tyr-Lys) c(RADyK) (M.W. 633.71) C28H43N9O8Negative control RGD Peptide for PCI-3662-PI

1 mg 5 mg

25 mg



Phone: 502-266-8787 Fax: 502-267-1329




PCI-3899-PI H-Glu[cyclo (Arg-Gly-Asp-d-Tyr-Lys)]2*H-E[c(RGDyK)]2(M.W. 1350.47) C59H87N19O18RGD Tumor Targeting and Tumor Imaging Peptide X. Chen, S. Liu, Y. Hou, M. Tohme, R. Park, J.R. Bading, and P.S. Conti, Mol. Imaging Biol., 6, 350 (2004).X. Chen, C. Plasencia, Y. Hou, and N. Neamati, J. Med. Chem., 48, 1098 (2005).X. Chen, M. Tohme, R. Park, Y. Hou, J.R. Bading, and P.S. Conti, Mol. Imaging, 3, 96 (2004).

OO O O

NH

OC

OO

NH

HO

O

NH

NH2 N OH

NH

OC

O O

NH

HO

O

NH

NH2NO H

2HN

HN

HO

O

HN

NHNH

D-TyrLys

Asp

Gly

Arg

H-E[c(RGDyK)]2

HN

HO

O

HN

NHNH

D-TyrLys

Glu

ArgGly

Asp

1 mg 5 mg

25 mg

RGD-3766-PI H-AEEEA-Glu[cyclo (Arg-Gly-Asp-D-Tyr-Lys)]2PEG3-c(RGDyk)2(Trifluoroacetate Form) (M.W. 1539.68) C67H102N20O22 Byclic RGD peptide for imaging E. Chang, S. Liu, G. Gowrishankar, S. Yaghoubi, J.P. Wedgeworth, F. Chin, D. Berndorff, V. Gekeler, S.S. Gambhir and Z. Cheng, European Journal of Nuclear Medicine and Molecular Imaging, 38, 722 (2010). F.T. Chin, B. Shen, S. Liu, R.A. Berganos, E. Chang, E. Mittra, X. Chen and S.S. Gambhir, Molecular Imaging and Biology, 14, 88 (2011)..

1 mg5 mg

PCI-3953-PI cyclo (Arg-Gly-Glu-d-Phe-Lys) c(RGEfK)(M.W. 617.71) C28H43N9O7

1 mg5 mg

25 mg

RGD for Cell Adhesion of Biomaterials

Integrins, such as fibronectin, are involved in mediating cell to cell interactions and cell to extracellular matrix interactions. They play a central roll in cell adhesion, chemotaxis, cell growth, tissue repair, and tumor development among others. A peptide containing the fibronectin active fragment or cell binding domain was first developed to increase cell attachment to biomaterial or plastic surfaces.1 Ac-GrGDSPASSKGGGGSrLLLLLLr-NH2 also contains a hydrophobic region, SPASSK which acts as a spacer between the cell attachment and biomaterial domains for improved cell attachment to nonbiological surfaces. Additional leucine residues were incorporated to obtain saturated binding. D-arginines were introduced and the N- and C- termini were protected to prevent degradation by endoproteases and exopeptidases respectively.

Ac-GrGDSPASSKGGGGSrLLLLLLr-NH2 has been used as a research application for studying mechanochemical transduction and contractile forces by coating the peptide to magnetic microbeads. This has allowed for the study of contractile forces of airway smooth muscle cells and their role with asthma and mechanical study of the elasticity of alveolar epithelial cells.2,3 Besides its role in understanding cytoskeletal remodeling, the peptide has also been employed to block C. albicans adherence by binding to a fibronectin-like receptor on the yeast cells, reducing the number of pathogens in vitro and in vivo.4 This peptide could also prove useful in cell attachment to nonbiological surfaces for tissue regeneration and implantation associated with therapeutic applications.

1. W.S. Craig, S. Cheng, D.G. Mullen, J. Blevitt, and M.D. Pierschbacher, Biopolymers Peptide Science, 37, 157 (1995). 2. S.S. An, B. Fabry, X. Trepat, N. Wang, and J.J. Fredberg, Am. J. Resp. Cell and Molec. Biol., 35, 55 (2006). 3. X. Trepat, M. Grabulosa, F. Puig, G.N. Maksym, D. Navajas, and R. Farre, Am. J. Physiol. Lung Cell Mol. Physiol., 287, L1025 (2004).4. S.A. Klotz, R.L. Smith, and B.W. Stewart, Antimicrob. Agents and Chemother., 36, 132 (1992).

PFA-3924-PI Ac-Gly-d-Arg-Gly-Asp-ser-Pro-Ala-ser-ser-Lys-(Gly)4-ser-d-Arg-(Leu)6-d-Arg-NH2Ac-GrGDSPASSKGGGGSrLLLLLLr-NH2(M.W. 2308.69) C98H174N34O30Hydrophobic Fibronectin PeptideW.S. Craig, S. Cheng, D.G. Mullen, J. Blevitt, and M.D. Pierschbacher, Biopolymers (Peptide Sci.), 37, 157 (1995).

1 mg 5 mg


Phone: 502-266-8787 Fax: 502-267-1329




PCI-3929-PI H-Arg-Gly-Asp-ser-Lys-OH RGDSK(M.W. 561.60) C21H39N9O9 RGD Tumor Targeting PeptideS. S. Jasseron, C. Contino-Pepin, J.C. Maurizis, M. Rapp, B. Pucci, Bioorganic & Medicinal Chemistry Letters, 12, 7, (2002).S. Jasseron, C. Contino-Pepin, J.C. Maurizis, M. Rapp, B. Pucci, Eur J Med Chem, 38, 9, (2003).

1 mg 5 mg

PCI-3930-PI H-Arg-Ala-Asp-ser-Lys-OH RADSK(M.W. 575.63) C22H41N9O9 Negative Control for PCI-3929-PI

1 mg 5 mg

RGD-3762-PI H-[Cys-Arg-Gly-Asp-Arg-Gly-Pro-Asp-Cys]-NH2(Trifluoroacetate Form) (M.W. 975.08) C35H58N16O13S2 (Disulfide bond between Cys1-Cys9) RGD Tumor Targeting PeptideK Sugahara, et al., Science, 328, 1031 (2010).Y. Ye, et al., Bioorg Med Chem Lett., 21, 1146 (2011).

1 mg 5 mg

PFA-4171-v Fibronectin Active Fragment (RGDs)RGDSArg-Gly-Asp-Ser(M.W. 433.42 ) C15H27N7O8M.D. Piershbacher and E. Ruoslahti, Nature, 309, 30 (1984). (Original) D.M. Haverstick, J.F. Cowan, K.M. Yamada, and S.A. Santoro, Blood, 66, 946 (1985). (Pharmacol.)

0.5 mgvial

PFA-4171 Fibronectin Active Fragment (RGDs) RGDSArg-Gly-Asp-Ser(M.W. 433.42 30.03 36.03) C15H27N7O8 1/2CH3COOH 2H2O

25 mg100 mg

PFA-4189-v Fibronectin Active Fragment (GRGDs)(M.W. 490.47 ) C17H30N8O9S.K. Akiyama and K.M. Yamada, J. Biol. Chem., 260, 10402 (1985). (Original) K. Olden, S. Mohla, S.A. Newton, S.L. White, and M.J. Humphries, Ann. N. Y. Acad. Sci., 551, 421 (1988). (Review)

0.5 mgvial

FAP-3758-PI Fibronectin Adhesion-Promoting PeptideH-Trp-Gln-Pro-Pro-Arg-Ala-Arg-Ile-OH(M.W. 1023.22) C47H74N16O10 [125720-21-0]D.L.Mooradian, et al., Invest. Ophthalmol. Vis. Sci., 34, 153 (1993).A.Woods, et al., Mol. Biol. Cell, 4, 605 (1993).K.L.Hines, et al., Proc. Natl. Acad. Sci. USA, 91, 5187 (1994).

1 mg 5 mg

PCI-3790-PI

NEW!

cyclo (Arg-Gly-Asp-d-Phe-Lys)(dPEGTm4)](Trifluoroacetate Form) (M.W. 2060.35) C92H150N22O31 RGD Tumor Targeting and Tumor Imaging Peptide

1 mg 5 mg

25 mg

PFA-3907-PI

H-Gly-Arg-Gly-Glu-ser-OH GRGES(M.W. 504.50) C18H32N8O9Negative Control for PFA-4189-v

5 mg 25 mg

PCI-3909-PI

H-Gly-Arg-Gly-Asp-Asn-Pro-OH GRGDNP Inhibitor of Cell Adhesion to Fibronectin

5 mg 25 mg

PCI-3910-PI H-Gly-Arg-Ala-Asp-ser-Pro-OH GRADSP Negative Control for Fibronectin Inhibitor

1 mg 5 mg

PCI-3965-PI H-Gly-Gly-Gly-Gly-Arg-Gly-Asp-ser-Pro-OHH-Gly-Gly-Gly-Gly-Arg-Gly-Asp-Ser-Pro-OHGGGGRGDSP(M.W. 758.75) C28H46N12O13

5 mg25 mg



Phone: 502-266-8787 Fax: 502-267-1329



CODE iRGD PEPTIDE QTY

RGD-3761-PI H-[Cys-Arg-Gly-Asp-Lys-Gly-Pro-Asp-Cys]-NH2(M.W. 947.07) C35H58N14O13S2 K Sugahara, et al., Science, 328, 1031 (2010). Y. Ye, et al., Bioorg Med Chem Lett., 21, 1146 (2011).

1 mg 5 mg

RGD CLICk CHEmIsTRY TOOLs

RGD-3749-PI cyclo[Arg-Gly-Asp-d-Phe-Lys(Azide)] one of The Clickables(Trifluoroacetate Form) (M.W. 629.68) C27H39N11O7 Clickable RGD for Dendrimer Constructs

1 mg 5 mg

Please contact Peptides International for bulk quantities or for custom synthesis services available for RGD related products.

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