RGD Peptides

Molecular Glue? A Cell Adhesion Motif

I
ntegrins are heterodimeric cell surface receptors that This analog contains two mini-PEGTM derivatives (FXX-
were found in early studies to mediate adhesion 5521-PI) or 8-amino-3,6-dioxaoctanoic acids that act as
between cells and the extracellular matrix (ECM), by spacers between ligand and lipid head groups, to allow
binding to ligands with an exposed arginine-glycine- for more efficient binding to lipid surfaces.3 cyclo
aspartate (RGD) sequence. These receptors also stimulate [Arg-Gly-Asp-D-Phe-Lys(Biotin-PEG-PEG)] (PCI-3697-
intracellular signaling and gene expression involved in cell PI) analog contains 2 PEG spacers and is biotinylated
growth, migration, and survival. These same processes, for use as a reporting tag. Previous studies have used
if not properly regulated, can lead to thrombosis, biotinylated peptides for histological staining of RGD
inflammation, and cancer. In fact, integrins have been peptides in tissue sections.4 The cyclo [Arg-Gly-Asp-D-
demonstrated to be participants in these diseases and can Phe-Lys(Ac-SCH2CO)] (PCI-3699-PI) analog contains an
also act as disease markers. Because of this, research has S-acetylthioacetyl group, which following deprotection,
focused on developing RGD peptides that could mimic can allow coupling to liposomes via a thioether bond.5,6
cell adhesion proteins and bind to integrins. The diverse
applications for these peptides include inhibiting A bicyclic RGD peptide, H-Glu[cyclo(Arg-Gly-
apoptosis, angiogenesis, and tumor formation, Asp-D-Phe-Lys)]2, was recently reported
coating surfaces for use as biomaterials, NH NH2
to possess high affinity for αvβ3 integrin.
enhancing drug delivery systems, and Conjugation of E-[c(RGDfK)2] with a DOTA
imaging for diagnostic purposes. O NH chelator allowed for radiolabeling, and this
NH
radiolabeled peptide was demonstrated to
NH
Peptides International offers a variety O O NH significantly delay tumor growth in mice
of cyclic RGD peptides and peptide HN O and have high, specific tumor uptake in
templates which confer greater stability HO2C NH human cancer xenograft, suggesting a
O
and selectivity over linear peptides. cyclo possible role in imaging as well as potential
(Arg-Gly-Asp-D-Phe-Lys) (PCI-3661-PI) can therapy. 7,8 In addition, cyclo (Arg-Gly-
be functionalized with various linker molecules Asp-D-Phe-Glu) and cyclo (Arg-Gly-Asp-D-
through the amino group on the lysine residue. ICA-4304 Tyr-Lys) are also available for potential imaging.
These linkers can act as spacers or anchors for diverse The latter can be radiolabeled through the tyrosine
surfaces. For example, linkage of this peptide with residue or a linker, which can be attached via the
an acrylamide group allowed attachment to poly(methyl side chain amino group of lysine.9,10 A bicyclic form of this
methacrylate) surfaces and led to improved binding to peptide, H-E[c(RGDyK)]2 (PCI-3899-PI), has been recently
osteoblast cells and increased circulation time in the body.1 modified with labels via the glutamine residue, allowing
Others have functionalized this peptide with polyethylene for enhanced imaging and tumor targeting.11,12
glycol for enhanced binding to lysosomes for targeted drug
delivery, resulting in effective tumor regression.2 Alanine RGD peptides are proving to be promising new tools for
replacement of glycine yields a negative control variant drug therapy and imaging of tumors, thrombosis, and
for this cyclic peptide, cyclo (Arg-Ala-Asp-D-Phe-Lys). inflammatory-related diseases. Peptides International
Functionalized versions of cyclo (RGDfK) such as cyclo provides the proper tools for further exploration and
[Arg-Gly-Asp-D-Phe-Lys(PEG-PEG)] are also available. manipulation of this intriguing group of peptides for
research applications.
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).

Peptides International, Inc. P.O. Box 99703 Phone: 502-266-8787 1-800-777-4779

Louisville, KY 40269-0703 USA Fax: 502-267-1329 E-mail: peptides@pepnet.com
 CYCLO(RGDfC)

* May require further derivatization before use

+ Requires deprotection before use

CODE RGD PEPTIDES QTY

PCI-3686-PI cyclo (Arg-Gly-Asp-d-Phe-Cys)* Arg 1 mg
c(RGDfC) NH NH2 5 mg
(M.W. 578.65) C24H34N8O7S O NH
Gly
RGD Tumor Targeting Peptide (linker additions via Cys) NH
NH SH
C. Pattillo, F. Sari-Sarraf, R. Nallamothu, B. Moore, G. Wood, and M. Kiani, O O NH Cys
Pharm. Res., 22, 1117, (2005). HN O
R. Nallamothu, G.C. Wood, C.B. Pattillo, R.c. Scott, M.F. Kiani, B.M. Moore, HO2C NH
and L.A. Thoma, AAPS PharmSciTech, 7, E1 (2006). O
D-Phe
Asp

PCI-3960-PI cyclo (Arg-Ala-Asp-d-Phe-Cys) 1 mg

c(RADfC) 5 mg
(M.W. 592.68) C25H36N8O7S 25 mg
Control for PCI-3686-PI
PCI-3687-PI cyclo (Arg-Gly-Asp-d-Phe-Glu)* 1 mg
c(RGDfE) 5 mg
(M.W. 604.63) C26H36N8O9 25 mg
RGD Peptide for Radiolabeling and Imaging
CYCLO(RGDfK)
G. 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).

PCI-3661-PI cyclo (Arg-Gly-Asp-d-Phe-Lys)* Arg 1 mg

c(RGDfK) NH NH2 5 mg
(M.W. 603.68) C27H41N9O7 NH
25 mg
O
RGD Tumor Targeting Peptide, αv β3 Integrin Binding RGD Peptide Gly NH NH2
NH
M. Kantlehner, P. Schaffner, D. Finsinger, J. Meyer, A. Jonczyk, B. Diefenbach, B. Nies, O O NH
Lys
G. Hozemann, S.L. Goodman, and H. Kessler. Chembiochem., 1, 107 (2000). HN O
R.J. Kok, A.J. Schraa, E.J. Bos, H.E. Moorlag, S.A. Ásgeirsdóttir, HO2C NH
M. Everts, DK. Meijer, and G. Molema, Bioconjug. Chem., 13, 128 (2002). O

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). Asp D-Phe

PCI-3919-PI cyclo (Arg-Gly-Asp-d-Phe-Lys) 1 mg

c(RGDfK) 5 mg
Trifluoroacetate Salt 25 mg
(M.W. 603.68) C27H41N9O7
PCI-3883-PI cyclo (Arg-Ala-Asp-d-Phe-Lys) 1 mg
c(RADfK) 5 mg
(M.W. 617.71) C28H43N9O7 25 mg
Negative Control RGD Peptide for PCI-3661-PI
P.K. Dubey, V. Mishra, S. Jain, S. Mahor, and S.P. Vyas, J. Drug Targeting, 12, 257 (2004).

PCI-3823-PI cyclo [Arg-Ala-Asp-d-Phe-LysPEG-PEG-Cys)] 1 mg

c[RGDfK(PEG-PEG-Cys)] 5 mg
NEW!
Trifluoroacetate Salt
(M.W. 997.15) C42H68N12O14S

RGD-3795-PI cyclo [Arg-Gly-Asp-d-Phe-Lys(Mal)] 1 mg

(M.W. 754.81) C34H46N10O10 5 mg
NEW!
RGD peptide with 3-maleimide propionic acid functional group 25 mg

RGD-3736-PI Galactosyl-cyclo (Arg-Gly-Asp-d-Phe-Lys) 1 mg

c(-RDGFK(SAA) 5 mg
(M.W. 792.85) C34H52N10O12 [922175-70-0]
Glycosylated RGD for radiolabelling CYCLO[RGDfK (PEG-PEG)]

Habner, et al., Bioconjugate Chem., 15, 1, (2004).

PCI-3696-PI cyclo [Arg-Gly-Asp-d-Phe-Lys(PEG-PEG)]* 1 mg

c(RGDfK(PEG-PEG)) 5 mg
where PEG = 8-Amino-3,6-Dioxaoctanoic Acid Arg
NH NH2
(M.W. 894.0) C39H63N11O13 Gly
RGD Peptide equipped with PEG spacers O NH
H O
NH
for more efficient binding to lipid surfaces NH
N
C O
O
N
C O
O
NH2
O O NH H
P.K. Dubey, V. Mishra, S. Jain, S. Mahor, and S.P. Vyas, Lys O PEG PEG
HN O
J. Drug Targeting, 12, 257 (2004). HO2C NH
R.M. Schiffelers, G.A. Koning, T.L. ten Hagen, M.H., Fens, A.J. Schraa, O
A.P. Janssen, R.J. Kok, G. Molema, and G. Storm, Asp
D-Phe

J. Controlled Release, 91, 115 (2003).

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

CODE RGD PEPTIDES QTY

RGD-3782-PI Galacto-RGD2 1 mg
(Trifluoroacetate Form) 5 mg
NEW!
(M.W. 2149.24) C91H137N29O32
Tumor-imaging RGD peptide

PCI-3954-PI cyclo [Arg-Ala-Asp-d-Phe-Lys(PEG-PEG)] 1 mg

RADfK(PEG-PEG)] 5 mg
(M.W. 908.03) C40H65N11O13 25 mg
Negative Control for PCI-3696-PI
RGD-3759-PI cyclo [Arg-Gly-Asp-d-Phe-Lys (PEG-PEG-Azide)] one of The Clickables 1 mg
(Trilfuoroacetate salt) 5 mg
(M.W. 921.01) C39H62N13O13
Clickable RGD for Dendrimer Constructs

PCI-3697-PI cyclo [Arg-Gly-Asp-d-Phe-Lys(Biotin-PEG-PEG)]* 1 mg

c[RGDfK(Biotin-PEG-PEG)] 5 mg
where PEG = 8-Amino-3,6-Dioxaoctanoic Acid
(M.W. 1120.30) C49H77N13O15S
RGD Peptide equipped with a biotin reporting tag and
PEG 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).
CYCLO[RGDfK (Biotin-PEG-PEG)]
D. Boturyn and P. Dumy, Tetrahedron Lett., 42, 2787 (2001).
Arg
NH NH2

Gly NH
O H O
NH N O C O N Biotin
NH C O N O H
O H
O NH Lys O
HN O
PEG PEG
HO2C NH
O
Asp

D-Phe

PCI-3808-PI cyclo [Arg-Ala-Asp-d-Phe-Lys(Biotin-PEG-PEG)] 1 mg

c(RADfK(Biotin-PEG-PEG)] CYCLO[RGDfK (Biotin)] 5 mg
NEW!
(M.W. 1134.33 C50H79N13O15S
Negative control peptide for PCI-3697-PI
PCI-3895-PI cyclo [Arg-Gly-Asp-d-Phe-Lys(Biotin)] Arg 1 mg
c[RGDfK(Biotin)] NH NH2 5 mg
(M.W. 829.98) C37H55N11O9S NH
O
Negative Control RGD Peptide for PCI-3697-PI Gly NH H
N Biotin
D. Boturyn, J.-L. Coll, E. Garanger, M.-C. Favrot, and P. Dumy, NH
O O NH
J. Am. Chem. Soc., 126, 5730 (2004). Lys
D. Boturyn and P. Dumy, Tetrahedron Lett., 42, 2787 (2001). HN O
HO2C NH
O
D-Phe
Asp
CYCLO[RGDfK (Ac-SCH2CO)]

PCI-3699-PI cyclo [Arg-Gly-Asp-d-Phe-Lys(Ac-SCH2CO)]*+ 1 mg

c[RGDfK (Ac-SCH2CO)] 5 mg
(M.W. 719.82) C31H45N9O9S Arg
RGD Peptide equipped with thioacetyl group for linking to liposomes NH NH2

R.J. Kok, A.J. Schraa, E.J. Bos, H.E. Moorlag, S.A. Asgeirsdottir, M. Everts, D.K.F. Meijer, O
O NH
and G. Molema, Bioconjug. Chem., 13, 128 (2002). NH H
R.M. Schiffelers, G.A. Koning,, T.L.M. ten Hagen, M.H.A.M. Fens, A.J. Schraa, Gly N C CH2S-COCH3
NH Acetyl group
A.P.C.A. Janssen, R.J. Kok, G. Molema, and G. Storm, O O NH
J. of Controlled Release, 91, 115 (2003). Lys
K. Darlak, R.B. Miller, M.S. Stack, A.F. Spatola, and R.D. Gray, HN O
J. Biol. Chem., 265, 5199 (1990). HO2C NH
O
D-Phe
Asp

PCI-3959-PI cyclo [Arg-Ala-Asp-d-Phe-Lys(Ac-SCH2CO)] 1 mg

c[RADfK(Ac-SCH2CO)] 5 mg
(M.W. 733.85) C32H47N9O9S 25 mg
Control for PCI-3699-PI
* May require further derivatization before use
+ Requires deprotection before use
CODE RGD PEPTIDES QTY
PCI-3898-PI cyclo [Arg-Gly-Asp-d-Phe-Lys(H-Ser)] 1 mg
c[RGDfK(H-Ser)] 5 mg
(M.W. 690.76) C30H46N10O9
RGD Peptide equipped with H-Ser

PCI-3651-PI H-Glu[cyclo (Arg-Gly-Asp-D-Phe-Lys)]2* H-E[c(RGDfK)]2 1 mg

E-[c(RGDfK)2] 5 mg
Acetate Salt 25 mg
(M.W. 1318.47) C59H87N19O16
RGD Tumor Targeting and Tumor Imaging Peptide Gly Gly
O O
NH Arg Asp
Asp Arg
C. Ryppa, et al., Bioconjugate Chem., 19, 7 (2008). NH NH NH
M.L. Janssen, W.J. Oyen, I. Dijkgraaf, L.F. Massuger, C. Frielink, HO NH
N NH2 H2N N
NH HO
O H H O
D.S. Edwards, M. Rajopadhye, H. Boonstra, F.H. Corstens, and O.C. Boerman, O O
HN HN
O O
O O
Cancer. Res., 62, 6146 (2002). HN O O O O
HN
CO NH OC
M. Janssen, C. Frielink, I. Dijkgraaf, W. Oyen, D.S. Edwards, S. Liu, N N
NH

M. Rajopadhye, L. Massuger, F. Corstens, and O. Boerman, D-Phe H H

D-Phe
2HN Lys
Cancer Biother. Radiopharm, 19, 399 (2004). Lys
M. Janssen, W.J. Oyen, L.F. Massuger, C. Frielink, I. Dijkgraaf, D.S. Edwards, Glu
M. Radjopadhye, F.H. Corstens, and O.C. Boerman,
Cancer Biother. Radiopharm., 17, 641 (2002).

PCI-3979-PI H-Glu[cyclo (Arg-Ala-Asp-D-Phe-Lys)]2* 1 mg

Trifluroacetate Salt 5 mg
Negative Control Peptides for PCI-3651-PI 25 mg
PCI-3904-PI H-Glu[cyclo (Arg-Gly-Asp-d-Phe-Lys)]2* 1 mg
E-[c(RGDfK)2] 5 mg
Trifluoroacetate Salt 25 mg
(M.W. 1318.47) C59H87N19O16
RGD Tumor Targeting and Tumor Imaging Peptide
PCI-3975-PI H-Glu{Glu[cyclo (Arg-Gly-Asp-d-Phe-Lys)]2}2* 1 mg
H-E{E[cRGDfK]2}2 5 mg
Trifluoroacetate Salt 25 mg
(M.W. 2748.04) C123H179N39O34
Tetrameric RGD Peptide
DOTA-E[c(RGDfK)]2
PCI-3903-PI DOTA-Glu-[cyclo (Arg-Gly-Asp-d-Phe-Lys)]2* 1 mg
DOTA-E-[c(RGDfK)2] 5 mg
(M.W. 1704.88) C75H113N23O23
RGD Tumor Targeting and Tumor Targeting Peptide equipped Gly Gly
O
O Asp
with DOTA chelator Asp NH Arg NH
NH Arg
NH
HO NH NH HO
M.L. Janssen, W.J. Oyen, I. Dijkgraaf, L.F. Massuger, C. Frielink, O O
N
H
NH2 H2N N
H O O
O O
HN HN
D.S. Edwards, M. Rajopadhye, H. Boonstra, F.H. Corstens, HN O
O O O O
O HN
and O.C. Boerman, Cancer Res., 62, 6146 (2002). CO NH NH OC
N
M. Janssen, C. Frielink, I. Dijkgraaf, W. Oyen, D.S. Edwards, S. Liu, D-Phe
N
H H
NH D-Phe
M. Rajopadhye, L. Massuger, F. Corstens, and O. Boerman, Lys Glu Lys
Cancer Biother. Radiopharm, 19, 399 (2004). CO2H
X. Chen, S. Liu, Y. Hou, M. Tohme, R. Park, J.R. Bading, and P.S. Conti, O N
N
Mol. Imaging Biol., 6, 350 (2004).
CYCLO(RGDfV)
N N
HO2C CO2H

DOTA
ICA-4304 cyclo (Arg-Gly-Asp-d-Phe-Val) 25 mg
DOTA = 1,4,7,10-TETRAAZACYCLODODECANE-
c(RGDfV) Arg
N,N',N'',N'''-TETRAACETIC ACID
(M.W. 574.63) C26H38N8O7 NH NH2
Angiogenesis Inhibitor Gly
O NH
P.C. Brooks, A.M.P. Montgomery, M. Rosenfeld, R.A. Reisfeld, NH
T. Hu, G. Klier, and D.A. Cheresh, Cell, 79, 1157 (1994). NH
M. Aumailley, M. Gurrath, G. Muller, J. Calvete, R. Timpl, O O NH Val
and H. Kessler, FEBS Lett., 291, 50 (1991). HN O
M. Friedlander, C.L. Theesfeld, M. Sugita, M. Fruttiger, M.A. Thomas, HO2C NH
S. Chang, and D.A. Cheresh, PNAS, 93, 9764 (1996). O D-Phe
Asp
* May require further derivatization before use
+ Requires deprotection before use
CODE RGD PEPTIDES QTY
PCA-3618-PI cyclo (Arg-Ala-Asp-d-Phe-Val) 1mg
c(RADfV) 5 mg
(M.W. 588.67) C27H40N8O7 25 mg
Negative Control RGD Peptide for ICA-4304-PI
M. Friedlander, C.L. Theesfeld, M. Sugita, M. Fruttiger, M.A. Thomas, S. Chang, and D.A. Cheresh,
PNAS, 93, 9764 (1996).

PCI-3912-PI cyclo (Arg-Gly-Asp-D-Tyr-Cys)* 1 mg

c(RGDyC) 5 mg
(M.W. 594.65) C24H34N8O8S

PCI-3917-PI cyclo (Arg-Ala-Asp-d-Tyr-Cys)* 1 mg

c(RADyC) 5 mg
C25H36N8O8S
(M.W. 608.68) C25H36N8O8S
Negative Control for PCI-3912-PI
PCI-3688-PI cyclo (Arg-Gly-Asp-D-Tyr-Glu)* 1 mg
c(RGDyE) 5 mg
(M.W. 620.62) C26H36N8O10 25 mg
RGD Peptide for Radiolabeling
c(RGDyK)
PCI-3662-PI cyclo (Arg-Gly-Asp-d-Tyr-Lys)* 1 mg
c(RGDyK) 5 mg
(M.W. 619.68) C27H41N9O7 25 mg
RGD Tumor Targeting and Tumor Imaging Peptide, αv β3 Integrin Binding D-Tyr
RGD Peptide Lys

R. Haubner, H.J. Wester, F. Burkhart, R. Senekowitsch-Schmidtky, W. Weber, S.L. Goodman, H. Kessler, HO NH2
CO NH
and M. Schwaiger, J. Nuclear Med., 42, 326 (2001). O
HN
X. Chen, R. Park. A.H. Shahinian, M. Tohme, V. Khankaldyyan, M.H. Bozorgzdeh, J.R. Bading, R. Moats, O
HN
W.E. Laug, and P.S. Conti, Nucl. Med. Biol., 31, 179 (2004). O O
O H
N NH2
HO
X. Chen, P.S. Conti, and R.A. Moats, Cancer Res., 641, 8009 (2004). NH
NH
O Arg NH
Asp Gly

PCI-3894-PI cyclo (Arg-Ala-Asp-d-Tyr-Lys) 1 mg

c(RADyK) 5 mg
(M.W. 633.71) C28H43N9O8 25 mg
Negative control RGD Peptide for PCI-3662-PI
PCI-3899-PI H-Glu[cyclo (Arg-Gly-Asp-d-Tyr-Lys)]2* 1 mg
H-E[c(RGDyK)]2 5 mg
(M.W. 1350.47) C59H87N19O18 25 mg
RGD Tumor Targeting and Tumor Imaging Peptide H-E[c(RGDyK)]2

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).
Gly Gly
O O
NH Arg Asp
Asp NH Arg NH NH
HO NH NH HO
N NH2 H2N N
O O H H O O
O O
HN HN
HN O O O O HN
O O
CO NH NH OC
HO N N
OH
H H
HN
Lys
2 Lys
D-Tyr
D-Tyr
Glu

RGD-3766-PI H-AEEEA-Glu[cyclo (Arg-Gly-Asp-D-Tyr-Lys)]2 1 mg

PEG3-c(RGDyK)2 5 mg
(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)..
 CODE RGD PEPTIDES QTY
PCI-3953-PI cyclo (Arg-Gly-Glu-d-Phe-Lys) 1 mg
c(RGEfK) 5 mg
(M.W. 617.71) C28H43N9O7 25 mg

RGD for Cell Adhesion of Biomaterials

I
ntegrins, 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-NH2 1 mg
Ac-GrGDSPASSKGGGGSrLLLLLLr-NH2 5 mg
(M.W. 2308.69) C98H174N34O30
Hydrophobic Fibronectin Peptide
W.S. Craig, S. Cheng, D.G. Mullen, J. Blevitt, and M.D. Pierschbacher, Biopolymers (Peptide Sci.), 37, 157 (1995).

PCI-3929-PI H-Arg-Gly-Asp-Ser-Lys-OH 1 mg
RGDSK 5 mg
(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).

PCI-3930-PI H-Arg-Ala-Asp-Ser-Lys-OH 1 mg
RADSK 5 mg
(M.W. 575.63) C22H41N9O9
Negative Control for PCI-3929-PI
RGD-3762-PI H-[Cys-Arg-Gly-Asp-Arg-Gly-Pro-Asp-Cys]-NH2 1 mg
(Trifluoroacetate Form) 5 mg
(M.W. 975.08) C35H58N16O13S2
(Disulfide bond between Cys1-Cys9)
RGD Tumor Targeting Peptide
K Sugahara, et al., Science, 328, 1031 (2010).
Y. Ye, et al., Bioorg Med Chem Lett., 21, 1146 (2011).

PFA-4171-v Fibronectin Active Fragment (RGDS) 0.5 mg

RGDS vial
Arg-Gly-Asp-Ser
(M.W. 433.42 ) C15H27N7O8
M.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.)

PFA-4171 Fibronectin Active Fragment (RGDS) 25 mg

RGDS 100 mg
Arg-Gly-Asp-Ser
(M.W. 433.42 ⋅ 30.03 ⋅ 36.03) C15H27N7O8 ⋅ 1/2CH3COOH ⋅ 2H2O
* May require further derivatization before use
+ Requires deprotection before use

CODE RGD PEPTIDES QTY

PFA-4189-v Fibronectin Active Fragment (GRGDS) 0.5 mg
(M.W. 490.47 ) C17H30N8O9 vial
S.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)

FAP-3758-PI Fibronectin Adhesion-Promoting Peptide 1 mg

H-Trp-Gln-Pro-Pro-Arg-Ala-Arg-Ile-OH 5 mg
(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).

PCI-3790-PI cyclo (Arg-Gly-Asp-d-Phe-Lys)(dPEGTM4)] 1 mg

(Trifluoroacetate Form) 5 mg
NEW! (M.W. 2060.35) C92H150N22O31 25 mg
RGD Tumor Targeting and Tumor Imaging Peptide

PFA-3907-PI H-Gly-Arg-Gly-Glu-Ser-OH 5 mg
GRGES 25 mg
(M.W. 504.50) C18H32N8O9
Negative Control for PFA-4189-v
PCI-3909-PI H-Gly-Arg-Gly-Asp-Asn-Pro-OH 5 mg
GRGDNP 25 mg
Inhibitor of Cell Adhesion to Fibronectin
PCI-3910-PI H-Gly-Arg-Ala-Asp-Ser-Pro-OH 1 mg
GRADSP 5 mg
Negative Control for Fibronectin Inhibitor
PCI-3965-PI H-Gly-Gly-Gly-Gly-Arg-Gly-Asp-Ser-Pro-OH 5 mg
H-Gly-Gly-Gly-Gly-Arg-Gly-Asp-Ser-Pro-OH 25 mg
GGGGRGDSP
(M.W. 758.75) C28H46N12O13
CODE iRGD PEPTIDE QTY
RGD-3761-PI H-[Cys-Arg-Gly-Asp-Lys-Gly-Pro-Asp-Cys]-NH2 1 mg
(M.W. 947.07) C35H58N14O13S2 5 mg
K Sugahara, et al., Science, 328, 1031 (2010).
Y. Ye, et al., Bioorg Med Chem Lett., 21, 1146 (2011).

RGD Click Chemistry Tools

RGD-3749-PI cyclo[Arg-Gly-Asp-d-Phe-Lys(Azide)] 1 mg
→ one of The Clickables 5 mg
(Trifluoroacetate Form)
(M.W. 629.68) C27H39N11O7
Clickable RGD for Dendrimer Constructs
 Please contact Peptides International for bulk quantities
or for custom synthesis services available for RGD related products.

Peptides International, Inc. P.O. Box 99703 Phone: 502-266-8787 1-800-777-4779

Louisville, KY 40269-0703 USA Fax: 502-267-1329 E-mail: peptides@pepnet.com