1997
DOI: 10.1073/pnas.94.2.652
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Design, synthesis, and in vitro evaluation of cytotoxic analogs of bombesin-like peptides containing doxorubicin or its intensely potent derivative, 2-pyrrolinodoxorubicin

Abstract: Five peptide fragments, based on the Cterminal sequence of bombesin (BN)-(6-14) or BN-(7-14), were selected as carriers for radicals doxorubicin (DOX) and 2-pyrrolino-DOX to create hybrid cytotoxic analogs. All these compounds had a reduced peptide bond (CH 2 -NH or CH 2 -N) between positions 13 (Phe or Leu) and 14 (Phe, Leu, or Tac

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Cited by 92 publications
(100 citation statements)
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“…Targeting of antineoplastic agents to cancer cells by linking them to a ligand with high affinity for tumour cells should improve tumour growth inhibition and decrease peripheral toxicity . The presence of high affinity receptors for bombesin (BN)-like peptides on a wide variety of tumours prompted us to employ some of our powerful BN/gastrin releasing peptide (GRP) antagonists as carrier molecules for targeting cytotoxic agents to tumour cells (Nagy et al, 1997). One of these cytotoxic BN conjugates, AN-215 (Nagy et al, 1997) consists of a potent cytotoxic derivative of doxorubicin (DOX), 2-pyrrolino-DOX (AN-201) (Nagy et al, 1996), covalently linked through a glutaric acid spacer to the amino terminal of Gln-Trp-Ala-Val-Gly-His-Leu-c-Leu-NH 2, a BN-like peptide carrier (Nagy et al, 1997).…”
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confidence: 99%
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“…Targeting of antineoplastic agents to cancer cells by linking them to a ligand with high affinity for tumour cells should improve tumour growth inhibition and decrease peripheral toxicity . The presence of high affinity receptors for bombesin (BN)-like peptides on a wide variety of tumours prompted us to employ some of our powerful BN/gastrin releasing peptide (GRP) antagonists as carrier molecules for targeting cytotoxic agents to tumour cells (Nagy et al, 1997). One of these cytotoxic BN conjugates, AN-215 (Nagy et al, 1997) consists of a potent cytotoxic derivative of doxorubicin (DOX), 2-pyrrolino-DOX (AN-201) (Nagy et al, 1996), covalently linked through a glutaric acid spacer to the amino terminal of Gln-Trp-Ala-Val-Gly-His-Leu-c-Leu-NH 2, a BN-like peptide carrier (Nagy et al, 1997).…”
mentioning
confidence: 99%
“…The presence of high affinity receptors for bombesin (BN)-like peptides on a wide variety of tumours prompted us to employ some of our powerful BN/gastrin releasing peptide (GRP) antagonists as carrier molecules for targeting cytotoxic agents to tumour cells (Nagy et al, 1997). One of these cytotoxic BN conjugates, AN-215 (Nagy et al, 1997) consists of a potent cytotoxic derivative of doxorubicin (DOX), 2-pyrrolino-DOX (AN-201) (Nagy et al, 1996), covalently linked through a glutaric acid spacer to the amino terminal of Gln-Trp-Ala-Val-Gly-His-Leu-c-Leu-NH 2, a BN-like peptide carrier (Nagy et al, 1997). AN-215 displays high affinity to BN receptors on Swiss 3T3 fibroblasts and retains the antiproliferative effect of its cytotoxic moiety (Nagy et al, 1997).…”
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“…13 Cytotoxic hybrids consisting of BN/GRP analogs conjugated to a cytotoxic radical and designed for targeting to prostate cancer and other neoplasms that express high percentage of BN receptors have been synthesized. 14 One of these analogs, AN-215, containing a potent derivative of doxorubicin (AN-201), 15 was made by coupling 2-pyrrolinodoxorubicin through hemiglutaric acid to the amino terminus of BN/GRP carrier analog RC-3095 [Gln-Trp-Ala-Val-GlyHis-Leu-W(CH 2 -NH)-Leu-NH 2 ]. AN-215 displays high affinity binding to BN receptors and retains the antiproliferative activity of its cytotoxic moiety 14,16 and has been shown to inhibit growth of experimental human prostate cancer in nude mice.…”
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confidence: 99%