Kendarimide A, a novel peptide reversing P-glycoprotein-mediated multidrug resistance in tumor cells, from a marine sponge of Haliclona sp.

被引：50

作者：

Aoki, S

Cao, LW

Matsui, K

Rachmat, R

Akiyama, S

Kobayashi, M

机构：

[1] Osaka Univ, Grad Sch Pharmaceut Sci, Suita, Osaka 5650871, Japan

[2] LIPI, Res & Dev Ctr Oceanol, Jakarta 11048, Indonesia

[3] Kagoshima Univ, Fac Med, Inst Canc Res, Dept Canc Chemotherapy, Kagoshima 8908520, Japan

来源：

TETRAHEDRON | 2004年 / 60卷 / 33期

关键词：

multidrug resistance; marine sponge; Haliclona sp; kendarimide A; N-methyl amino acid;

D O I：

10.1016/j.tet.2003.07.020

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel modulator of multidrug resistance (MDR) in tumor cells, kendarimide A (1), was isolated from an Indonesian marine sponge of Haliclona sp. Compound 1 reversed MDR in KB-C2 cells mediated by P-glycoprotein (P-gp) at a 6 muM concentration, and the chemical structure of 1 was characterized to be a linear peptide composed of N-methylpyroglutamic acid (pyroMeGlu), N-methylated eight-membered cysteinyl-cysteine (ox-[MeCys-MeCys]) together with many N-methyl amino acid residues. The amino acid sequence of 1 was determined by 2D NMR and FAB MS analysis. The absolute configuration of the amino acid residues in 1 except for the MeCys part was determined to be L-form respectively, based on interpretation of the HPLC analysis of Marfey's derivatives of the hydrolysates of 1 and the synthetic method for the pyroMeGlu residue. (C) 2004 Elsevier Ltd. All rights reserved.

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页码：7053 / 7059

页数：7

相关论文

共 17 条

[1] ISOLATION AND GENETIC-CHARACTERIZATION OF HUMAN KB-CELL LINES RESISTANT TO MULTIPLE-DRUGS [J].

AKIYAMA, SI ;

FOJO, A ;

HANOVER, JA ;

PASTAN, I ;

GOTTESMAN, MM .

SOMATIC CELL AND MOLECULAR GENETICS, 1985, 11 (02) :117-126

[2] Agosterol A, a novel polyhydroxylated sterol acetate reversing multidrug resistance from a marine sponge of Spongia sp. [J].

Aoki, S ;

Yoshioka, Y ;

Miyamoto, Y ;

Higuchi, K ;

Setiawan, A ;

Murakami, N ;

Chen, ZS ;

Sumizawa, T ;

Akiyama, S ;

Kobayashi, M .

TETRAHEDRON LETTERS, 1998, 39 (35) :6303-6306

[3] Brianthein A, a novel briarane-type diterpene reversing multidrug resistance in human carcinoma cell line, from the gorgonian Briareum excavatum [J].

Aoki, S ;

Okano, M ;

Matsui, K ;

Itoh, T ;

Satari, R ;

Akiyama, S ;

Kobayashi, M .

TETRAHEDRON, 2001, 57 (43) :8951-8957

[4] Reversing effect of agosterol A, a spongean sterol acetate, on multidrug resistance in human carcinoma cells [J].

Aoki, S ;

Chen, ZS ;

Higasiyama, K ;

Setiawan, A ;

Akiyama, S ;

Kobayashi, M .

JAPANESE JOURNAL OF CANCER RESEARCH, 2001, 92 (08) :886-895

[5] Reversal of multidrug resistance in human carcinoma cell line by agosterols, marine spongean sterols. [J].

Aoki, S ;

Setiawan, A ;

Yoshioka, Y ;

Higuchi, K ;

Fudetani, R ;

Chen, ZS ;

Sumizawa, T ;

Akiyama, S ;

Kobayashi, M .

TETRAHEDRON, 1999, 55 (49) :13965-13972

[6]

BOCCHI V, 1979, SYNTHESIS-STUTTGART, P961

[7] STRUCTURE AND SYNTHESIS OF MALFORMIN-A [J].

BODANSZK.M ;

STAHL, GL .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1974, 71 (07) :2791-2794

[8] THE COMPLETE SPECTRAL ASSIGNMENT OF DIDEMNIN-H, NEW CONSTITUENT OF THE TUNICATE TRIDIDEMNUM-CYANOPHORUM [J].

BOULANGER, A ;

ABOUMANSOUR, E ;

BADRE, A ;

BANAIGS, B ;

COMBAUT, G ;

FRANCISCO, C .

TETRAHEDRON LETTERS, 1994, 35 (25) :4345-4348

[9] Conformational analysis of the eight-membered ring of the oxidized cysteinyl-cysteine unit implicated in nicotinic acetylcholine receptor ligand recognition [J].

Creighton, CJ ;

Reynolds, CH ;

Lee, DHS ;

Leo, GC ;

Reitz, AB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (50) :12664-12669

[10] A nonempirical method using LC/MS for determination of the absolute configuration of constituent amino acids in a peptide: Combination of Marfey's method with mass spectrometry and its practical application [J].

Fujii, K ;

Ikai, Y ;

Oka, H ;

Suzuki, M ;

Harada, K .

ANALYTICAL CHEMISTRY, 1997, 69 (24) :5146-5151