Leucine-aspartic acid-valine sequence as targeting ligand and drug carrier for doxorubicin delivery to melanoma cells: In vitro cellular uptake and cytotoxicity studies

Pharmaceutical Research

Volumn 26, Issue 12, 2009, Pages 2578-2587

  Zhong, Sha ^a   Bhattacharya, Shiladitya ^a   Chan, William ^a   Jasti, Bhaskara ^a   Li, Xiaoling ^a  

^a UNIVERSITY OF THE PACIFIC   (United States)

Author keywords

Binding specificity; Cellular uptake; LDV; Oligo(LDV); Targeted delivery

Indexed keywords

ALPHA4 INTEGRIN; DOXORUBICIN; DOXORUBICIN POLYLEUCYLASPARTYLVALINE CONJUGATE; DRUG CARRIER; POLYLEUCYLASPARTYLVALINE; UNCLASSIFIED DRUG; VERY LATE ACTIVATION ANTIGEN 4;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG CONJUGATION; DRUG CYTOTOXICITY; DRUG PENETRATION; DRUG SYNTHESIS; DRUG TARGETING; DRUG UPTAKE; GENE OVEREXPRESSION; HUMAN; HUMAN CELL; IC 50; INTERNALIZATION; MELANOMA CELL; MOLECULAR RECOGNITION; PRIORITY JOURNAL;

ANTINEOPLASTIC AGENTS; BLOTTING, WESTERN; CELL LINE, TUMOR; DOXORUBICIN; DRUG CARRIERS; DRUG DELIVERY SYSTEMS; HUMANS; INHIBITORY CONCENTRATION 50; INTEGRIN ALPHA4BETA1; LIGANDS; MELANOMA; MOLECULAR STRUCTURE; OLIGOPEPTIDES; POLYMERASE CHAIN REACTION;

EID: 70449102680     PISSN: 07248741     EISSN: 1573904X     Source Type: Journal    
DOI: 10.1007/s11095-009-9971-6     Document Type: Article

References (47)

1. B Rihova 1998 Receptor-mediated targeted drug or toxin delivery Adv Drug Deliv Rev 29 273 89 10.1016/S0169-409X(97)00084-7 1:CAS:528:DyaK2sXotVOrtr4%3D 10837595 (Pubitemid 28090046)
2. PJ Hudson C Souriau 2003 Engineered antibodies Nat Med 9 129 34 10.1038/nm0103-129 1:CAS:528:DC%2BD3sXivFOi 12514726 (Pubitemid 36098274)
3. CP Leamon JA Reddy 2004 Folate-targeted chemotherapy Adv Drug Deliv Rev 56 1127 41 10.1016/j.addr.2004.01.008 1:CAS:528:DC%2BD2cXjtF2rtLw%3D 15094211 (Pubitemid 38496512)
4. NS Chung KM Wasan 2004 Potential role of the low-density lipoprotein receptor family as mediators of cellular drug uptake Adv Drug Deliv Rev 56 1315 34 10.1016/j.addr.2003.12.003 1:CAS:528:DC%2BD2cXjtl2ktrc%3D 15109771 (Pubitemid 38510476)
5. D Fischer T Kissel 2001 Histochemical characterization of primary capillary endothelial cells from porcine brains using monoclonal antibodies and fluorescein isothiocyanate-labelled lectins: implications for drug delivery Eur J Pharm Biopharm 52 1 11 10.1016/S0939-6411(01)00159-X 1:CAS:528: DC%2BD3MXkvVeksL4%3D 11438418 (Pubitemid 32594784)
6. ZM Qian H Li H Sun K Ho 2002 Targeted drug delivery via the transferrin receptor-mediated endocytosis pathway Pharmacol Rev 54 561 87 10.1124/pr.54.4.561 1:CAS:528:DC%2BD38Xps1Grs7k%3D 12429868 (Pubitemid 35351196)
7. MA Arnaout 2002 Integrin structure: new twists and turns in dynamic cell adhesion Immunol Rev 186 125 40 10.1034/j.1600-065X.2002.18612.x 1:CAS:528:DC%2BD38XotFeht7k%3D 12234368
8. GJ Mizejewski 1999 Role of integrins in cancer: survey of expression patterns Proc Soc Exp Biol Med 222 124 38 10.1046/j.1525-1373.1999.d01-122.x 1:CAS:528:DyaK1MXntFCgtr4%3D 10564536
9. R Makarem MJ Humphries 1991 LDV: a novel cell adhesion motif recognized by the integrin alpha 4 beta 1 Biochem Soc Trans 19 380S 1:CAS:528: DyaK3MXlsFGqtbw%3D 1724433
10. JW Smith DA Cheresh 1990 Integrin (alpha v beta 3)-ligand interaction. Identification of a heterodimeric RGD binding site on the vitronectin receptor J Biol Chem 265 2168 72 1:CAS:528:DyaK3cXhtFCntrY%3D 1688848
11. V Pedchenko R Zent BG Hudson 2004 Alpha(v)beta3 and alpha(v)beta5 integrins bind both the proximal RGD site and non-RGD motifs within noncollagenous (NC1) domain of the alpha3 chain of type IV collagen: implication for the mechanism of endothelia cell adhesion J Biol Chem 279 2772 80 10.1074/jbc.M311901200 1:CAS:528:DC%2BD2cXkslyjtw%3D%3D 14610079 (Pubitemid 38114267)
12. K Suehiro J Mizuguchi K Nishiyama S Iwanaga DH Farrell S Ohtaki 2000 Fibrinogen binds to integrin alpha(5)beta(1) via the carboxyl-terminal RGD site of the Aalpha-chain J Biochem 128 705 10 1:CAS:528:DC%2BD3cXosFOjs7c%3D 11011154
13. MedImmune initiates phase I/II clinical study with Vitaxin. Expert Rev Anticancer Ther. 2001;1:166.
14. DC Bibby JE Talmadge MK Dalal SG Kurz KM Chytil SE Barry, et al. 2005 Pharmacokinetics and biodistribution of RGD-targeted doxorubicin-loaded nanoparticles in tumor-bearing mice Int J Pharm 293 281 90 10.1016/j.ijpharm. 2004.12.021 1:CAS:528:DC%2BD2MXitlSgur4%3D 15778066 (Pubitemid 40381100)
15. M Maeda Y Izuno K Kawasaki Y Kaneda Y Mu Y Tsutsumi, et al. 1997 Amino acids and peptides. XXX. Preparation of Arg-Gly-Asp (RGD) hybrids with poly(ethylene glycol) analogs and their antimetastatic effect Chem Pharm Bull (Tokyo) 45 1788 92 1:CAS:528:DyaK2sXnslWmtLs%3D
16. R Chen S Curran JM Curran JA Hunt 2006 The use of poly(l-lactide) and RGD modified microspheres as cell carriers in a flow intermittency bioreactor for tissue engineering cartilage Biomaterials 27 4453 60 10.1016/j.biomaterials. 2006.04.011 1:CAS:528:DC%2BD28XkvVajtrY%3D 16677706 (Pubitemid 44255660)
17. N Koizumi H Mizuguchi T Hosono A Ishii-Watabe E Uchida N Utoguchi, et al. 2001 Efficient gene transfer by fiber-mutant adenoviral vectors containing RGD peptide Biochim Biophys Acta 1568 13 20 1:CAS:528:DC%2BD3MXos1Kiu7c%3D 11731080
18. JX Niu WJ Zhang LY Ye LQ Wu GJ Zhu ZH Yang, et al. 2007 The role of adhesion molecules, alpha v beta 3, alpha v beta 5 and their ligands in the tumor cell and endothelial cell adhesion Eur J Cancer Prev 16 517 27 10.1097/CEJ.0b013e3280145c00 1:CAS:528:DC%2BD2sXhtlKqs7nJ 18090124 (Pubitemid 350307501)
19. EA Wayner NL Kovach 1992 Activation-dependent recognition by hematopoietic cells of the LDV sequence in the V region of fibronectin J Cell Biol 116 489 97 10.1083/jcb.116.2.489 1:CAS:528:DyaK38Xks1ygsrk%3D 1530947
20. JL Guan RO Hynes 1990 Lymphoid cells recognize an alternatively spliced segment of fibronectin via the integrin receptor alpha 4 beta 1 Cell 60 53 61 10.1016/0092-8674(90)90715-Q 1:CAS:528:DyaK3cXhslKisr8%3D 2295088 (Pubitemid 20033908)
21. A Chigaev GJ Zwartz T Buranda BS Edwards ER Prossnitz LA Sklar 2004 Conformational regulation of alpha 4 beta 1-integrin affinity by reducing agents. :"Inside-out" signaling is independent of and additive to reduction-regulated integrin activation J Biol Chem 279 32435 43 10.1074/jbc.M404387200 1:CAS:528:DC%2BD2cXmtVChsbo%3D 15166232 (Pubitemid 39014698)
22. J Singh S Adams MB Carter H Cuervo WC Lee RR Lobb, et al. 2004 Rational design of potent and selective VLA-4 inhibitors and their utility in the treatment of asthma Curr Top Med Chem 4 1497 507 10.2174/1568026043387520 1:CAS:528:DC%2BD2cXotFakt78%3D 15544540 (Pubitemid 39317605)
23. M Garcia-Gila C Cabanas A Garcia-Pardo 1997 Analysis of the activation state of alpha4beta1 integrin in human B cell lines derived from myeloma, leukemia or lymphoma FEBS Lett 418 337 40 10.1016/S0014-5793(97)01407-5 1:CAS:528:DyaK2sXnsVyjsL8%3D 9428740 (Pubitemid 27515952)
24. Zhong S, Li Y, Chan W, Jasti B, Li X. Integrin a41-dependent Binding of Leucine-Aspartate-Valine (LDV) to A375 Cells: a Rationale for Targeting Drug Delivery. Vienna: Cotrolled Release Society; 2006.
25. M Liu C Xie H Pan J Pan W Lu 2006 Separation of polyethylene glycols and their fluorescein-labeled compounds depending on the hydrophobic interaction by high-performance liquid chromatography J Chromatogr A 1129 61 6 10.1016/j.chroma.2006.06.088 1:CAS:528:DC%2BD28XpsVWktLo%3D 16860330 (Pubitemid 44331862)
26. SJ Hyduk JR Chan ST Duffy M Chen MD Peterson TK Waddell, et al. 2007 Phospholipase C, calcium, and calmodulin are critical for alpha4beta1 integrin affinity up-regulation and monocyte arrest triggered by chemoattractants Blood 109 176 84 10.1182/blood-2006-01-029199 1:CAS:528:DC%2BD2sXivVyrtbk%3D 16960156 (Pubitemid 46053059)
27. AC Luissint PG Lutz DA Calderwood PO Couraud S Bourdoulous 2008 JAM-L-mediated leukocyte adhesion to endothelial cells is regulated in cis by alpha4beta1 integrin activation J Cell Biol 183 1159 73 10.1083/jcb.200805061 1:CAS:528:DC%2BD1cXhsFCqt7jI 19064666
28. EC Andersson JP Christensen O Marker AR Thomsen 1994 Changes in cell adhesion molecule expression on T cells associated with systemic virus infection J Immunol 152 1237 45 1:CAS:528:DyaK2cXhvV2mtL4%3D 7507962
29. J Singh H Van Vlijmen Y Liao WC Lee M Cornebise M Harris, et al. 2002 Identification of potent and novel alpha4beta1 antagonists using in silico screening J Med Chem 45 2988 93 10.1021/jm020054e 1:CAS:528:DC%2BD38XktlCgsLY%3D 12086484 (Pubitemid 34721520)
30. O Stuve JL Bennett 2007 Pharmacological properties, toxicology and scientific rationale for the use of natalizumab (Tysabri) in inflammatory diseases CNS Drug Rev 13 79 95 10.1111/j.1527-3458.2007.00003.x 17461891 (Pubitemid 46697841)
31. DY Jackson C Quan DR Artis T Rawson B Blackburn M Struble, et al. 1997 Potent alpha 4 beta 1 peptide antagonists as potential anti-inflammatory agents J Med Chem 40 3359 68 10.1021/jm970175s 1:CAS:528:DyaK2sXmtlWltL4%3D 9341911 (Pubitemid 27441328)
32. D Haworth A Rees PJ Alcock LJ Wood AS Dutta JJ Gormley, et al. 1999 Anti-inflammatory activity of c(ILDV-NH(CH2)5CO), a novel, selective, cyclic peptide inhibitor of VLA-4-mediated cell adhesion Br J Pharmacol 126 1751 60 10.1038/sj.bjp.0702511 1:CAS:528:DyaK1MXjtVGquro%3D 10372817 (Pubitemid 29213092)
33. AS Dutta JJ Gormley M Coath L Hassall CF Hayward PR Gellert, et al. 2000 Potent cyclic peptide inhibitors of VLA-4 (alpha4beta1 integrin)-mediated cell adhesion. Discovery of compounds like cyclo(MePhe-Leu-Asp-Val-D-Arg-D-Arg) (ZD7349) compatible with depot formulation J Pept Sci 6 398 412 10.1002/1099-1387(200008)6:8<398::AID-PSC270>3.0.CO;2-1 1:CAS:528:DC%2BD3cXmtFylsr0%3D 10969869 (Pubitemid 30702410)
34. AS Dutta M Crowther JJ Gormley L Hassall CF Hayward PR Gellert, et al. 2000 Potent cyclic monomeric and dimeric peptide inhibitors of VLA-4 (alpha4beta1 integrin)-mediated cell adhesion based on the Ile-Leu-Asp-Val tetrapeptide J Pept Sci 6 321 41 10.1002/1099-1387(200007)6:7<321::AID- PSC259>3.0.CO;2-A 1:CAS:528:DC%2BD3cXlsFOksr4%3D 10946997 (Pubitemid 30488741)
35. Y Kaneda Y Yamamoto N Okada Y Tsutsuml S Nakagawa M Kakiuch, et al. 1997 Antimetastatic effect of synthetic Glu-Ile-Leu-Asp-Val peptide derivatives containing D-amino acids Anticancer Drugs 8 702 7 10.1097/00001813-199708000- 00009 1:CAS:528:DyaK2sXmvFSiu7c%3D 9311447 (Pubitemid 27404728)
36. M Momtaz V Rerat S Gharbi E Gerard V Pourcelle J Marchand-Brynaert 2008 A graftable LDV peptidomimetic: design, synthesis and application to a blood filtration membrane Bioorg Med Chem Lett 18 1084 90 10.1016/j.bmcl.2007.12.006 1:CAS:528:DC%2BD1cXhsFWltLw%3D 18155910 (Pubitemid 351179334)
37. A Nori J Kopecek 2005 Intracellular targeting of polymer-bound drugs for cancer chemotherapy Adv Drug Deliv Rev 57 609 36 10.1016/j.addr.2004.10.006 1:CAS:528:DC%2BD2MXhslWnsr0%3D 15722167 (Pubitemid 40267695)
38. G Nowak 1998 Methods and data analyses in radioligand-receptor binding: unnecessary transformations may cause biased results Pol J Pharmacol 50 101 5 1:CAS:528:DyaK1cXktVSrsbk%3D 9798261
39. M Steinitz L Baraz 2000 A rapid method for estimating the binding of ligands to ELISA microwells J Immunol Methods 238 143 50 10.1016/S0022-1759(00) 00160-5 1:CAS:528:DC%2BD3cXitlOls7o%3D 10758244 (Pubitemid 30175994)
40. BN Dardik CD Schwartzkopf DE Stevens RE Chatelain 2000 A quantitative assay for the non-covalent association between apolipoprotein[a] and apolipoprotein B: an alternative measure of Lp[a] assembly J Lipid Res 41 1013 9 1:CAS:528:DC%2BD3cXkt1aktbk%3D 10828094
41. P Sriramarao M Mendler MA Bourdon 1993 Endothelial cell attachment and spreading on human tenascin is mediated by alpha 2 beta 1 and alpha v beta 3 integrins J Cell Sci 105 Pt 4 1001 12 1:CAS:528:DyaK2cXhsF2rt7k%3D 7693733
42. AJ Schraa RJ Kok AD Berendsen HE Moorlag EJ Bos DK Meijer, et al. 2002 Endothelial cells internalize and degrade RGD-modified proteins developed for tumor vasculature targeting J Control Release 83 241 51 10.1016/S0168-3659(02) 00206-7 1:CAS:528:DC%2BD38XntlymtLs%3D 12363450 (Pubitemid 35279469)
43. AP Mould A Komoriya KM Yamada MJ Humphries 1991 The CS5 peptide is a second site in the IIICS region of fibronectin recognized by the integrin alpha 4 beta 1. Inhibition of alpha 4 beta 1 function by RGD peptide homologues J Biol Chem 266 3579 85 1:CAS:528:DyaK3MXitVWqtL4%3D 1750929
44. J Murata I Saiki R Ogawa N Nishi S Tokura I Azuma 1991 Molecular properties of poly(RGD) and its binding capacities to metastatic melanoma cells Int J Pept Protein Res 38 212 7 1:CAS:528:DyaK3MXmt1akurg%3D 1761368
45. I Saiki J Murata K Matsuno R Ogawa N Nishi S Tokura, et al. 1990 Anti-metastatic and anti-invasive effects of polymeric Arg-Gly-Asp (RGD) peptide, poly(RGD), and its analogues Jpn J Cancer Res 81 660 7 1:CAS:528:DyaK3cXlvVCgsrc%3D 2119367
46. I Saiki J Iida J Murata R Ogawa N Nishi K Sugimura, et al. 1989 Inhibition of the metastasis of murine malignant melanoma by synthetic polymeric peptides containing core sequences of cell-adhesive molecules Cancer Res 49 3815 22 1:CAS:528:DyaL1MXltVynu70%3D 2736523
47. RJ Tressler PN Belloni GL Nicolson 1989 Correlation of inhibition of adhesion of large cell lymphoma and hepatic sinusoidal endothelial cells by RGD-containing peptide polymers with metastatic potential: role of integrin-dependent and -independent adhesion mechanisms Cancer Commun 1 55 63 1:CAS:528:DyaK3MXmsVOlsr4%3D 2640156