Cytotoxic peptides: Naphthoquinonyl derivatives of luteinizing hormone-releasing hormone

Shai Rahimipour; Lev Weiner; Prativa Bade Shrestha-Dawadi; Shmuel Bittner; Yitzhak Koch; Mati Fridkin

doi:10.1007/BF02443499

Cytotoxic peptides: Naphthoquinonyl derivatives of luteinizing hormone-releasing hormone

Shai Rahimipour, Lev Weiner, Prativa Bade Shrestha-Dawadi, Shmuel Bittner, Yitzhak Koch, Mati Fridkin

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

1 Scopus citations

Abstract

In an attempt to produce efficient cytotoxic derivatives of luteinizing hormone-releasing hormone (LH-RH), two novel 1,4-naphthoquinone derivatives of [D-Lys⁶]-LH-RH were synthesized primarily by solid-phase peptide synthesis, in good yield and high purity. The ability of each analog to produce reactive oxygen species using enzymatic reduction, i.e. NADPH-cytochrome P-450 reductase, was evaluated employing electron spin resonance (ESR) spectroscopy and spin-trapping techniques. The ESR results suggest that the novel cytotoxic analogs are extremely effective in generating oxygen radicals.

Original language	English
Pages (from-to)	421-427
Number of pages	7
Journal	International Journal of Peptide Research and Therapeutics
Volume	5
Issue number	5-6
DOIs	https://doi.org/10.1007/BF02443499
State	Published - 1 Jan 1998

Keywords

ESR
LH-RH
Quinones
Solid phase synthesis
Targeted chemotherapy

ASJC Scopus subject areas

Analytical Chemistry
Bioengineering
Biochemistry
Molecular Medicine
Drug Discovery

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10.1007/BF02443499

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title = "Cytotoxic peptides: Naphthoquinonyl derivatives of luteinizing hormone-releasing hormone",

abstract = "In an attempt to produce efficient cytotoxic derivatives of luteinizing hormone-releasing hormone (LH-RH), two novel 1,4-naphthoquinone derivatives of [D-Lys6]-LH-RH were synthesized primarily by solid-phase peptide synthesis, in good yield and high purity. The ability of each analog to produce reactive oxygen species using enzymatic reduction, i.e. NADPH-cytochrome P-450 reductase, was evaluated employing electron spin resonance (ESR) spectroscopy and spin-trapping techniques. The ESR results suggest that the novel cytotoxic analogs are extremely effective in generating oxygen radicals.",

keywords = "ESR, LH-RH, Quinones, Solid phase synthesis, Targeted chemotherapy",

author = "Shai Rahimipour and Lev Weiner and Shrestha-Dawadi, {Prativa Bade} and Shmuel Bittner and Yitzhak Koch and Mati Fridkin",

year = "1998",

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T1 - Cytotoxic peptides

T2 - Naphthoquinonyl derivatives of luteinizing hormone-releasing hormone

AU - Rahimipour, Shai

AU - Weiner, Lev

AU - Shrestha-Dawadi, Prativa Bade

AU - Bittner, Shmuel

AU - Koch, Yitzhak

AU - Fridkin, Mati

PY - 1998/1/1

Y1 - 1998/1/1

N2 - In an attempt to produce efficient cytotoxic derivatives of luteinizing hormone-releasing hormone (LH-RH), two novel 1,4-naphthoquinone derivatives of [D-Lys6]-LH-RH were synthesized primarily by solid-phase peptide synthesis, in good yield and high purity. The ability of each analog to produce reactive oxygen species using enzymatic reduction, i.e. NADPH-cytochrome P-450 reductase, was evaluated employing electron spin resonance (ESR) spectroscopy and spin-trapping techniques. The ESR results suggest that the novel cytotoxic analogs are extremely effective in generating oxygen radicals.

AB - In an attempt to produce efficient cytotoxic derivatives of luteinizing hormone-releasing hormone (LH-RH), two novel 1,4-naphthoquinone derivatives of [D-Lys6]-LH-RH were synthesized primarily by solid-phase peptide synthesis, in good yield and high purity. The ability of each analog to produce reactive oxygen species using enzymatic reduction, i.e. NADPH-cytochrome P-450 reductase, was evaluated employing electron spin resonance (ESR) spectroscopy and spin-trapping techniques. The ESR results suggest that the novel cytotoxic analogs are extremely effective in generating oxygen radicals.

KW - ESR

KW - LH-RH

KW - Quinones

KW - Solid phase synthesis

KW - Targeted chemotherapy

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JO - International Journal of Peptide Research and Therapeutics

JF - International Journal of Peptide Research and Therapeutics

IS - 5-6

ER -

Cytotoxic peptides: Naphthoquinonyl derivatives of luteinizing hormone-releasing hormone

Abstract

Keywords

ASJC Scopus subject areas

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