LYP, a novel bestatin derivative, inhibits cell growth and suppresses APN/CD13 activity in human ovarian carcinoma cells more potently than bestatin

Investigational New Drugs

Volumn 29, Issue 4, 2011, Pages 574-582

  Gao, Jian Jun ^a   Gao, Zu Hua ^b   Zhao, Cui Rong ^a   Yuan, Yi ^a   Cui, Shu Xiang ^c   Zhang, Xiao Fan ^a   Cheng, Yan Na ^a   Xu, Wen Fang ^a   Tang, Wei ^a   Qu, Xian Jun ^a  

^a SHANDONG UNIVERSITY   (China)

^b UNIVERSITY OF CALGARY   (Canada)

^c SHANDONG PROVINCIAL HOSPITAL AFFILIATED TO SHANDONG FIRST MEDICAL UNIVERSITY   (China)

Author keywords

Aminopeptidase N (APN CD13); Bestatin; Growth inhibition; LYP; Ovarian carcinoma (OVCA)

Indexed keywords

BESTATIN; BESTATIN DERIVATIVE; BESTATIN DIMETHYLAMINOETHYL ESTER; MICROSOMAL AMINOPEPTIDASE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; CANCER INHIBITION; CARCINOMA CELL; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG EFFECT; DRUG EFFICACY; DRUG POTENCY; DRUG SENSITIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; DRUG TOLERABILITY; ENZYME INHIBITION; FEMALE; HUMAN; HUMAN CELL; IN VIVO STUDY; MOUSE; NONHUMAN; OVARY CARCINOMA; PRIORITY JOURNAL; PROTEIN EXPRESSION;

ANIMALS; ANTIGENS, CD13; CELL LINE, TUMOR; CELL MEMBRANE; CELL PROLIFERATION; ESTERS; FEMALE; HUMANS; LEUCINE; MICE; OVARIAN NEOPLASMS; XENOGRAFT MODEL ANTITUMOR ASSAYS;

EID: 79959698334     PISSN: 01676997     EISSN: 15730646     Source Type: Journal    
DOI: 10.1007/s10637-010-9391-9     Document Type: Article

References (30)

1. Mou J, Fang H, Jing F, Wang Q, Liu Y, Zhu H, Shang L, Wang X, Xu W (2009) Design, synthesis and primary activity evaluation of L-arginine derivatives as amino-peptidase N/CD13 inhibitors. Bioorg Med Chem 17:4666-4673. doi:10.1016/j.bmc.2009.04.056
2. Pérez I, Varona A, Blanco L, Gil J, Santaolalla F, Zabala A, Ibarguen AM, Irazusta J, Larrinaga G (2009) Increased APN/CD13 and acid aminopeptidase activities in head and neck squamous cell carcinoma. Head Neck 31:1335-1340. doi:10.1002/hed.21099
3. Kehlen A, Lendeckel U, Dralle H, Langner J, Hoang-Vu C (2003) Biological significance of aminopeptidase N/CD13 in thyroid carcinomas. Cancer Res 63:8500-8506 (Pubitemid 37549507)
4. Bank U, Bohr UR, Reinhold D, Lendeckel U, Ansorge S, Malfertheiner P, Tager M (2008) Inflammatory bowel diseases: multiple benefits from therapy with dipeptidyl and alanylaminopeptidase inhibitors. Front Biosci 13:3699-3713. doi:org/10.2741/2960
5. Reinhold D, Bank U, Täger M, Ansorge S, Wrenger S, Thielitz A, Lendeckel U, Faust J, Neubert K, Brocke S (2008) DP IV/CD26, APN/CD13 and related enzymes as regulators of T cell immunity: implications for experimental encephalomyelitis. Front Biosci 13:2356-2363. doi:org/10.2741/2849
6. Bhagwat SV, Lahdenranta J, Giordano R, Arap W, Pasqualini R, Shapiro LH (2001) CD13/APN is activated by angiogenic signals and is essential for capillary tube formation. Blood 97:652-659. doi:10.1182/blood.V97.3.652 (Pubitemid 32113397)
7. Terauchi M, Kajiyama H, Shibata K, Ino K, Nawa A, Mizutani S, Kikkawa F (2007) Inhibition of APN/CD13 leads to suppressed progressive potential in ovarian carcinoma cells. BMC Cancer 7:140. doi:10.1186/1471-2407-7-140
8. Wulfaenger J, Niedling S, Riemann D, Seliger B (2008) Aminopeptidase N (APN)/CD13-dependent CXCR4 downregulation is associated with diminished cell migration, proliferation and invasion. Mol Membr Biol 25:72-82. doi:10.1080/09687680701551855
9. Wang C, Fan G, Lin M, Chen Y, Zhao W, Wu Y (2007) Development of a liquid chromatography/tandem mass spectrometry assay for the determination of bestatin in rat plasma and its application to a pharmacokinetic study. J Chromatogr B Analyt Technol Biomed Life Sci 850:101-108. doi:10.1016/j.jchromb.2006.11.015
10. Yamashita M, Kajiyama H, Terauchi M, Shibata K, Ino K, Nawa A, Mizutani S, Kikkawa F (2007) Involvement of aminopeptidase N in enhanced chemosensitivity to paclitaxel in ovarian carcinoma in vitro and in vivo. Int J Cancer 120:2243-2250. doi:10.1002/ijc.22528 (Pubitemid 46555865)
11. Xu Y, Lai LT, Gabrilove JL, Scheinberg DA (1998) Antitumor activity of actinonin in vitro and in vivo. Clin Cancer Res 4:171-176 (Pubitemid 28062892)
12. Urabe A, Mutoh Y, Mizoguchi H, Takaku F, Ogawa N (1993) Ubenimex in the treatment of acute nonlymphocytic leukemia in adults. Ann Hematol 67:63-66 (Pubitemid 23246571)
13. Luan YP, Wang XJ, Zhu HW, Qu XJ, Fang H, Xu WF (2009) The synthesis and activity evaluation of a bestatin derivative (LYP) as an aminopeptidase N inhibitor. Lett Drug Des Discov 6:420-423
14. Chandrappa S, Benaka Prasad SB, Vinaya K, Ananda Kumar CS, Thimmegowda NR, Rangappa KS (2008) Synthesis and in vitro antiproliferative activity against human cancer cell lines of novel 5-(4-methyl-benzylidene)-thiazolidine-2, 4-diones. Invest New Drugs 26:437-444. doi:10.1007/s10637-008-9130-7
15. Shahabuddin MS, Nambiar M, Choudhary B, Advirao GM, Raghavan SC (2010) A novel DNA intercalator, butylaminopyrimido[ 4′, 5′:4, 5]selenolo(2, 3-b)quinoline, induces cell cycle arrest and apoptosis in leukemic cells. Invest New Drugs 28:35-48. doi:10.1007/s10637-008-9212-6
16. Bauvois B, Puiffe ML, Bongui JB, Paillat S, Monneret C, Dauzonne D (2003) Synthesis and biological evaluation of novel flavone-8-acetic acid derivatives as reversible inhibitors of aminopeptidase N/CD13. J Med Chem 46:3900-3913. doi:10.1021/jm021109f (Pubitemid 37034139)
17. Qu XJ, Yang JL, Russell PJ, Goldstein D (2004) Changes in epidermal growth factor receptor expression in human bladder cancer cell lines following interferon-alpha treatment. J Urol 172:733-738. doi:10.1097/01.ju.0000130751. 83953.55 (Pubitemid 38900251)
18. Xiong X, Fu L, Wang L, Cai H, Li L, Jiang H, Duan W, Mei C (2009) Antitumor activity of a novel EGFR tyrosine kinase inhibitor against human lung carcinoma in vitro and in vivo. Invest New Drugs 27:1-11. doi:10.1007/s10637- 008-9132-5
19. Liu J, Li X, Cheng YN, Cui SX, Chen MH, Xu WF, Tian ZG, Makuuchi M, Tang W, Qu XJ (2007) Inhibition of human gastric carcinoma cell growth by treatment of N(3)-o-toluyl-fluorouracil as a precursor of 5-fluorouracil. Eur J Pharmacol 574:1-7. doi:10.1016/j.ejphar.2007.06.064 (Pubitemid 47503158)
20. Okutucu B, Dincer A, Habib O, Zihnioglu F (2007) Comparison of five methods for determination of total plasma protein concentration. J Biochem Biophys Methods 70:709-711. doi:10.1016/j.jbbm.2007.05.009 (Pubitemid 47021223)
21. Wang SB, Cheng YN, Cui SX, Zhong JL, Ward SG, Sun LR, Chen MH, Kokudo N, Tang W, Qu XJ (2009) Des-gamma-carboxy prothrombin stimulates human vascular endothelial cell growth and migration. Clin Exp Metastasis 26:469-477. doi:10.1007/s10585-009-9246-y
22. Fortin JP, Gera L, Bouthillier J, Stewart JM, Adam A, Marceau F (2005) Endogenous aminopeptidase N decreases the potency of peptide agonists and antagonists of the kinin B1 receptors in the rabbit aorta. J Pharmacol Exp Ther 314:1169-1176. doi:10.1124/jpet.105.088799 (Pubitemid 41205981)
23. Bauvois B, Dauzonne D (2006) Aminopeptidase-N/CD13 (EC 3.4.11.2) inhibitors: chemistry, biological evaluations, and therapeutic prospects. Med Res Rev 26:88-130. doi:10.1002/med.20044 (Pubitemid 43986471)
24. Zhang X, Xu W (2008) Aminopeptidase N (APN/CD13) as a target for anti-cancer agent design. Curr Med Chem 15:2850-2865
25. Jope RS, Jenden DJ (1979) Dimethylaminoethanol (deanol) metabolism in rat brain and its effect on acetylcholine synthesis. J Pharmacol Exp Ther 211:472-479 (Pubitemid 10128315)
26. Haubrich DR, Gerber NH, Pflueger AB (1981) Deanol affects choline metabolism in peripheral tissues of mice. J Neurochem 37:476-482 (Pubitemid 11059466)
27. Sekine K, Fujii H, Abe F (1999) Induction of apoptosis by bestatin (ubenimex) in human leukemic cell lines. Leukemia 13:729-734 (Pubitemid 29243624)
28. Ito K, Nakajima Y, Onohara Y, Takeo M, Nakashima K, Matsubara F, Ito T, Yoshimoto T (2006) Crystal structure of aminopeptidase N (proteobacteria alanyl aminopeptidase) from Escherichia coli and conformational change of methionine 260 involved in substrate recognition. J Biol Chem 281:33664-33676. doi:10.1074/jbc.M605203200 (Pubitemid 46036745)
29. Xu W, Li Q (2005) Progress in the development of aminopeptidase N (APN/CD13) inhibitors. Curr Med Chem Anticancer Agents 5:281-301 (Pubitemid 40645595)
30. Luan Y, Xu W (2007) The structure and main functions of aminopeptidase N. Curr Med Chem 14:639-647 (Pubitemid 46477717)