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Volumn 55, Issue 23, 2012, Pages 10460-10474

Synthesis and biological evaluation (in Vitro and in Vivo) of cyclic arginine-glycine-aspartate (RGD) peptidomimetic-paclitaxel conjugates targeting integrin αvβ3

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; ARGINYLGLYCYLASPARTIC ACID; CISPLATIN; CPD 11; CYCLO[DIKETOPIPERAZINE F2 ARGINYLGLYCYLASPARTIC ACID]PACLITAXEL; CYCLO[DIKETOPIPERAZINE F3 ARGINYLGLYCYLASPARTIC ACID]; CYCLO[DIKETOPIPERAZINE F3 ARGINYLGLYCYLASPARTIC ACID]PACLITAXEL; CYCLO[DIKETOPIPERAZINE F4 ARGINYLGLYCYLASPARTIC ACID]PACLITAXEL; CYCLO[DIKETOPIPERAZINE F6 ARGINYLGLYCYLASPARTIC ACID]PACLITAXEL; PACLITAXEL; PEPTIDOMIMETIC AGENT; UNCLASSIFIED DRUG; VITRONECTIN RECEPTOR;

EID: 84870974922     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm301058f     Document Type: Article
Times cited : (69)

References (65)
  • 1
    • 0038713666 scopus 로고    scopus 로고
    • Resistance to cytotoxic and anti-angiogenic anticancer agents: Similarities and differences
    • Broxterman, H. J.; Lankelma, J.; Hoekman, K. Resistance to cytotoxic and anti-angiogenic anticancer agents: similarities and differences Drug Resist. Updates 2003, 6, 111-127
    • (2003) Drug Resist. Updates , vol.6 , pp. 111-127
    • Broxterman, H.J.1    Lankelma, J.2    Hoekman, K.3
  • 3
    • 84862698355 scopus 로고    scopus 로고
    • Drug targeting to tumors: Principles, pitfalls and (pre-) clinical progress
    • Lammers, T.; Kiessling, F.; Hennink, W. E.; Storm, G. Drug targeting to tumors: principles, pitfalls and (pre-) clinical progress J. Controlled Release 2012, 161, 175-187
    • (2012) J. Controlled Release , vol.161 , pp. 175-187
    • Lammers, T.1    Kiessling, F.2    Hennink, W.E.3    Storm, G.4
  • 5
    • 35548987921 scopus 로고    scopus 로고
    • The optimal strategy for drug targeting
    • Low, P. S. The optimal strategy for drug targeting Mol. Pharmacol. 2007, 4, 629-630
    • (2007) Mol. Pharmacol. , vol.4 , pp. 629-630
    • Low, P.S.1
  • 7
    • 77949762340 scopus 로고    scopus 로고
    • Targeting of drugs and nanoparticles to tumors
    • Ruoslahti, E.; Bhatia, S. N.; Sailor, M. J. Targeting of drugs and nanoparticles to tumors J. Cell Biol. 2010, 188, 759-768
    • (2010) J. Cell Biol. , vol.188 , pp. 759-768
    • Ruoslahti, E.1    Bhatia, S.N.2    Sailor, M.J.3
  • 8
    • 79959972712 scopus 로고    scopus 로고
    • Prodrugs for improving tumor targetability and efficiency
    • Mahato, R.; Tai, W.; Cheng, K. Prodrugs for improving tumor targetability and efficiency Adv. Drug Delivery Rev. 2011, 63, 659-670
    • (2011) Adv. Drug Delivery Rev. , vol.63 , pp. 659-670
    • Mahato, R.1    Tai, W.2    Cheng, K.3
  • 9
    • 77649342167 scopus 로고    scopus 로고
    • The role of integrins in cancer and the development of anti-integrin therapeutic agents for cancer therapy
    • Lu, X.; Lu, D.; Scully, M.; Kakkar, V. The role of integrins in cancer and the development of anti-integrin therapeutic agents for cancer therapy Perspect. Med. Chem. 2008, 2, 57-73
    • (2008) Perspect. Med. Chem. , vol.2 , pp. 57-73
    • Lu, X.1    Lu, D.2    Scully, M.3    Kakkar, V.4
  • 11
    • 0037145037 scopus 로고    scopus 로고
    • Integrins: Bidirectional, allosteric signaling machines
    • Hynes, R. O. Integrins: bidirectional, allosteric signaling machines Cell 2002, 110, 673-687
    • (2002) Cell , vol.110 , pp. 673-687
    • Hynes, R.O.1
  • 12
    • 0142026204 scopus 로고    scopus 로고
    • Therapeutic antagonists and conformational regulation of integrin function
    • Shimaoka, M.; Springer, T. A. Therapeutic antagonists and conformational regulation of integrin function Nat. Rev. Drug Discovery 2003, 2, 703-716
    • (2003) Nat. Rev. Drug Discovery , vol.2 , pp. 703-716
    • Shimaoka, M.1    Springer, T.A.2
  • 13
    • 77349113764 scopus 로고    scopus 로고
    • Important role of integrins in the cancer biology
    • Rathinam, R.; Alahari, S. K. Important role of integrins in the cancer biology Cancer Metastasis Rev. 2010, 29, 223-237
    • (2010) Cancer Metastasis Rev. , vol.29 , pp. 223-237
    • Rathinam, R.1    Alahari, S.K.2
  • 16
    • 0037131442 scopus 로고    scopus 로고
    • The structures of integrins and integrin-ligand complexes: Implications for drug design and signal transduction
    • Gottschalk, K. E.; Kessler, H. The structures of integrins and integrin-ligand complexes: implications for drug design and signal transduction Angew. Chem., Int. Ed. 2002, 41, 3967-3774
    • (2002) Angew. Chem., Int. Ed. , vol.41 , pp. 3967-3774
    • Gottschalk, K.E.1    Kessler, H.2
  • 17
    • 79952741178 scopus 로고    scopus 로고
    • Cilengitide: The first anti-angiogenic small molecule drug candidate design, synthesis and clinical evaluation
    • Mas-Moruno, C.; Rechenmacher, F.; Kessler, H. Cilengitide: the first anti-angiogenic small molecule drug candidate design, synthesis and clinical evaluation Anti-Cancer Agents Med. Chem. 2010, 10, 753-768
    • (2010) Anti-Cancer Agents Med. Chem. , vol.10 , pp. 753-768
    • Mas-Moruno, C.1    Rechenmacher, F.2    Kessler, H.3
  • 24
    • 78249280319 scopus 로고    scopus 로고
    • An inhibitor of a cell adhesion receptor stimulates cell migration
    • Shabbir, S. H.; Eisenberg, J. L.; Mrksich, M. An inhibitor of a cell adhesion receptor stimulates cell migration Angew. Chem., Int. Ed. 2010, 49, 7706-7709
    • (2010) Angew. Chem., Int. Ed. , vol.49 , pp. 7706-7709
    • Shabbir, S.H.1    Eisenberg, J.L.2    Mrksich, M.3
  • 25
    • 80053374576 scopus 로고    scopus 로고
    • The role of β3-integrins in tumor angiogenesis: Context is everything
    • Robinson, S. D.; Hodivala-Dilke, K. M. The role of β3-integrins in tumor angiogenesis: context is everything Curr. Opin. Cell Biol. 2011, 23, 630-637
    • (2011) Curr. Opin. Cell Biol. , vol.23 , pp. 630-637
    • Robinson, S.D.1    Hodivala-Dilke, K.M.2
  • 26
    • 81555224647 scopus 로고    scopus 로고
    • Integrin targeted delivery of chemotherapeutics
    • Chen, K.; Chen, X. Integrin targeted delivery of chemotherapeutics Theranostics 2011, 1, 189-200
    • (2011) Theranostics , vol.1 , pp. 189-200
    • Chen, K.1    Chen, X.2
  • 27
    • 0032535999 scopus 로고    scopus 로고
    • Cancer treatment by targeted drug delivery to tumor vasculature in a mouse model
    • Arap, W.; Pasqualini, R.; Ruoslahti, E. Cancer treatment by targeted drug delivery to tumor vasculature in a mouse model Science 1998, 279, 377-80
    • (1998) Science , vol.279 , pp. 377-80
    • Arap, W.1    Pasqualini, R.2    Ruoslahti, E.3
  • 28
    • 16644385119 scopus 로고    scopus 로고
    • Tumor targeting by doxorubicin-RGD-4C peptide conjugate in an orthotopic mouse hepatoma model
    • Kim, J. W.; Lee, H. S. Tumor targeting by doxorubicin-RGD-4C peptide conjugate in an orthotopic mouse hepatoma model Int. J. Mol. Med. 2004, 14, 529-535
    • (2004) Int. J. Mol. Med. , vol.14 , pp. 529-535
    • Kim, J.W.1    Lee, H.S.2
  • 34
    • 13944278751 scopus 로고    scopus 로고
    • Synthesis and biological evaluation of dimeric RGD peptide-paclitaxel conjugate as a model for integrin-targeted drug delivery
    • Chen, X.; Plasencia, C.; Hou, Y.; Neamati, N. Synthesis and biological evaluation of dimeric RGD peptide-paclitaxel conjugate as a model for integrin-targeted drug delivery J. Med. Chem. 2005, 48, 1098-106 (corrigendum
    • (2005) J. Med. Chem. , vol.48 , pp. 1098-106
    • Chen, X.1    Plasencia, C.2    Hou, Y.3    Neamati, N.4
  • 35
    • 24744440559 scopus 로고    scopus 로고
    • J. Med. Chem. 2005, 48, 5874
    • (2005) J. Med. Chem. , vol.48 , pp. 5874
  • 36
    • 48149102140 scopus 로고    scopus 로고
    • Evaluation of biodistribution and anti-tumor effect of a dimeric RGD peptide-paclitaxel conjugate in mice with breast cancer
    • Cao, Q.; Li, Z.-B.; Chen, K.; Wu, Z.; He, L.; Neamati, N.; Chen, X. Evaluation of biodistribution and anti-tumor effect of a dimeric RGD peptide-paclitaxel conjugate in mice with breast cancer Eur. J. Nucl. Med. Mol. Imaging 2008, 35, 1489-98
    • (2008) Eur. J. Nucl. Med. Mol. Imaging , vol.35 , pp. 1489-98
    • Cao, Q.1    Li, Z.-B.2    Chen, K.3    Wu, Z.4    He, L.5    Neamati, N.6    Chen, X.7
  • 38
    • 78149469144 scopus 로고    scopus 로고
    • Selective O -acylation of unprotected N -benzylserine methyl ester and O, N -acyl transfer in the formation of cyclo[Asp-Ser] diketopiperazines
    • Marchini, M.; Mingozzi, M.; Colombo, R.; Gennari, C.; Durini, M.; Piarulli, U. Selective O -acylation of unprotected N -benzylserine methyl ester and O, N -acyl transfer in the formation of cyclo[Asp-Ser] diketopiperazines Tetrahedron 2010, 66, 9528-9531
    • (2010) Tetrahedron , vol.66 , pp. 9528-9531
    • Marchini, M.1    Mingozzi, M.2    Colombo, R.3    Gennari, C.4    Durini, M.5    Piarulli, U.6
  • 39
    • 0027280854 scopus 로고
    • Comparison of methods for the Fmoc solid-phase synthesis and cleavage of a peptide containing both tryptophan and arginine
    • Choi, H.; Aldrich, J. V. Comparison of methods for the Fmoc solid-phase synthesis and cleavage of a peptide containing both tryptophan and arginine Int. J. Pept. Protein Res. 1993, 42, 58-63
    • (1993) Int. J. Pept. Protein Res. , vol.42 , pp. 58-63
    • Choi, H.1    Aldrich, J.V.2
  • 42
    • 79851507720 scopus 로고    scopus 로고
    • Synthesis and evaluation of new iRGD peptide analogs for tumor optical imaging
    • Ye, Y.; Zhu, L.; Ma, Y.; Niu, G.; Chen, X. Synthesis and evaluation of new iRGD peptide analogs for tumor optical imaging Bioorg. Med. Chem. Lett. 2011, 21, 1146-1150
    • (2011) Bioorg. Med. Chem. Lett. , vol.21 , pp. 1146-1150
    • Ye, Y.1    Zhu, L.2    Ma, Y.3    Niu, G.4    Chen, X.5
  • 53
    • 79955679067 scopus 로고    scopus 로고
    • Spindle poisons and cell fate: A tale of two pathways
    • Matson, D. R.; Stukenberg, P. T. Spindle poisons and cell fate: a tale of two pathways Mol. Interventions 2011, 11, 141-150
    • (2011) Mol. Interventions , vol.11 , pp. 141-150
    • Matson, D.R.1    Stukenberg, P.T.2
  • 54
    • 77949450557 scopus 로고    scopus 로고
    • Mechanisms of drug-induced mitotic catastrophe in cancer cells
    • Portugal, J.; Mandilla, S.; Bataller, M. Mechanisms of drug-induced mitotic catastrophe in cancer cells Curr. Pharm. Des. 2010, 16, 69-78
    • (2010) Curr. Pharm. Des. , vol.16 , pp. 69-78
    • Portugal, J.1    Mandilla, S.2    Bataller, M.3
  • 55
    • 0035736138 scopus 로고    scopus 로고
    • If not apoptosis, then what? Treatment-induced senescence and mitotic catastrophe in tumor cells
    • Roninson, I. B.; Broude, E. V.; Chang, B. D. If not apoptosis, then what? Treatment-induced senescence and mitotic catastrophe in tumor cells Drug Resist. Updates 2001, 4, 303-313
    • (2001) Drug Resist. Updates , vol.4 , pp. 303-313
    • Roninson, I.B.1    Broude, E.V.2    Chang, B.D.3
  • 56
    • 0031054288 scopus 로고    scopus 로고
    • The efficient, enantioselective synthesis of aza sugars from amino acids. 1. The polyhydroxylated pyrrolidines
    • Huang, Y.; Dalton, D. R.; Carroll, P. J. The efficient, enantioselective synthesis of aza sugars from amino acids. 1. The polyhydroxylated pyrrolidines J. Org. Chem. 1997, 62, 372-376
    • (1997) J. Org. Chem. , vol.62 , pp. 372-376
    • Huang, Y.1    Dalton, D.R.2    Carroll, P.J.3
  • 57
    • 0034742736 scopus 로고    scopus 로고
    • Design and preparation of serine-threonine protein phosphatase inhibitors based upon the nodularin and microcystin toxin structures. Part 3
    • Webster, K. L.; Maude, A. B.; O'Donnell, M. E.; Mehrotra, A. P.; Gani, D. Design and preparation of serine-threonine protein phosphatase inhibitors based upon the nodularin and microcystin toxin structures. Part 3 J. Chem. Soc., Perkin Trans. 1 2001, 1673-1695
    • (2001) J. Chem. Soc., Perkin Trans. 1 , pp. 1673-1695
    • Webster, K.L.1    Maude, A.B.2    O'Donnell, M.E.3    Mehrotra, A.P.4    Gani, D.5
  • 58
    • 33751158037 scopus 로고
    • Photoremovable protecting groups for phosphorylation of chiral alcohols. Asymmetric synthesis of phosphotriesters of (-)-3′,5′- dimethoxybenzoin
    • Pirrung, M. C.; Shuey, S. W. Photoremovable protecting groups for phosphorylation of chiral alcohols. Asymmetric synthesis of phosphotriesters of (-)-3′,5′-dimethoxybenzoin J. Org. Chem. 1994, 59, 3890-3897
    • (1994) J. Org. Chem. , vol.59 , pp. 3890-3897
    • Pirrung, M.C.1    Shuey, S.W.2
  • 60
    • 34249736342 scopus 로고    scopus 로고
    • Toward the development of chemoprevention agents. Part 1: Design, synthesis, and anti-inflammatory activities of a new class of 2,5-disubstituted-dioxacycloalkanes
    • Gu, K.; Bi, L.; Zhao, M.; Wang, C.; Ju, J.; Peng, S. Toward the development of chemoprevention agents. Part 1: Design, synthesis, and anti-inflammatory activities of a new class of 2,5-disubstituted- dioxacycloalkanes Bioorg. Med. Chem. 2007, 15, 6273-6290
    • (2007) Bioorg. Med. Chem. , vol.15 , pp. 6273-6290
    • Gu, K.1    Bi, L.2    Zhao, M.3    Wang, C.4    Ju, J.5    Peng, S.6
  • 61
    • 0028200030 scopus 로고
    • 2,3-Pyrrolidinedicarboxylates as neurotransmitter conformer mimics: Enantioselective synthesis via chelation-controlled enolate alkylation
    • Humphrey, J. M.; Bridges, R. J.; Hart, J. A.; Chamberlin, A. R. 2,3-Pyrrolidinedicarboxylates as neurotransmitter conformer mimics: enantioselective synthesis via chelation-controlled enolate alkylation J. Org. Chem. 1994, 59, 2467-2472
    • (1994) J. Org. Chem. , vol.59 , pp. 2467-2472
    • Humphrey, J.M.1    Bridges, R.J.2    Hart, J.A.3    Chamberlin, A.R.4
  • 62
    • 0026756882 scopus 로고
    • Synthesis of optically active β-lactams by the photolytic reaction of imines with optically active chromium carbene complexes. 2. Synthesis of 1-carbacephalothin and 3-ANA relays
    • Narukawa, Y.; Juneau, K. N.; Snustad, D.; Miller, D. B.; Hegedus, L. S. Synthesis of optically active β-lactams by the photolytic reaction of imines with optically active chromium carbene complexes. 2. Synthesis of 1-carbacephalothin and 3-ANA relays J. Org. Chem. 1992, 57, 5453-5462
    • (1992) J. Org. Chem. , vol.57 , pp. 5453-5462
    • Narukawa, Y.1    Juneau, K.N.2    Snustad, D.3    Miller, D.B.4    Hegedus, L.S.5
  • 63
    • 0002714675 scopus 로고
    • Rapid chromatographic techniques for preparative separation with moderate resolution
    • Still, W. C.; Kahn, M.; Mitra, A. Rapid chromatographic techniques for preparative separation with moderate resolution J. Org. Chem. 1978, 43, 2923-2925
    • (1978) J. Org. Chem. , vol.43 , pp. 2923-2925
    • Still, W.C.1    Kahn, M.2    Mitra, A.3


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