QSAR studies of aminopeptidase N/CD13 (APN) inhibitors with the scaffold 3-phenylpropane-1,2-diamine and molecular docking

Medicinal Chemistry Research

Volumn 21, Issue 7, 2012, Pages 1000-1015

  Xu, Yingying ^a   Zhang, Lei ^a   Li, Minyong ^a   Xu, Wenfang ^a   Fang, Hao ^a   Shang, Luqing ^a  

^a SHANDONG UNIVERSITY   (China)

Author keywords

Antitumor 3 D QSAR; APN inhibitor; CoMFA; CoMSIA; Docking

Indexed keywords

ANTINEOPLASTIC AGENT; MICROSOMAL AMINOPEPTIDASE INHIBITOR; UNCLASSIFIED DRUG;

ARTICLE; BINDING KINETICS; CHEMICAL MODIFICATION; COMPARATIVE MOLECULAR FIELD ANALYSIS; COMPARATIVE MOLECULAR SIMILARITY INDICES ANALYSIS; DRUG DESIGN; MOLECULAR DOCKING; MOLECULAR MODEL; PROCESS OPTIMIZATION; QUANTITATIVE STRUCTURE ACTIVITY RELATION;

EID: 84861855744     PISSN: 10542523     EISSN: 15548120     Source Type: Journal    
DOI: 10.1007/s00044-011-9597-1     Document Type: Article

References (44)

1. Abe T, Yamamoto Y, Hazato T (1998) Changes in aminopeptidase N located on neutrophils derived from patients with chronic pain. Masui 47(2):151-155
2. Antczak C, De Meester I, Bauvois B (2001a) Ectopeptidases in pathophysiology. Bioessays 23(3):251-260
3. Antczak C, De Meester I, Bauvois B (2001b) Transmembrane proteases as disease markers and targets for therapy. J Biol Regul Homeost Agents 15(2):130-139
4. Bauvois B, Dauzonne D (2006) Aminopeptidase-N/CD13 (EC 3.4.11.2) inhibitors: chemistry, biological evaluations, and therapeutic prospects. Med Res Rev 26(1):88-130
5. Boldt DH, Kopecky KJ, Head D, Gehly G, Radich JP, Appelbaum FR (1994) Expression of myeloid antigens by blast cells in acute lymphoblastic leukemia of adults. The Southwest Oncology Group experience. Leukemia 8(12):2118-2126
6. Bush BL, Nachbar RB (1993) Sample-distance partial least squares: PLS optimized for many variables, with application to CoMFA. J Comput Aid Mol Des 7:587-619
7. Carl-McGrath S, Lendeckel U, Ebert M, Wolter AB, Roessner A, Rocken C (2004) The ectopeptidases CD10, CD13, CD26, and CD143 are upregulated in gastric cancer. Int J Oncol 25(5): 1223-1232
8. Dan H, Tani K, Hase K, Shimizu T, Tamiya H, Biraa Y, Huang L, Yanagawa H, Sone S (2003) CD 13/aminopeptidase N in collagen vascular diseases. Rheumatol Int 23(6):271-276
9. Dixon J, Kaklamanis L, Turley H, Hickson ID, Leek RD, Harris AL, Gatter KC (1994) Expression of aminopeptidase-n (CD 13) in normal tissues and malignant neoplasms of epithelial and lymphoid origin. J Clin Pathol 47:43-47
10. Dunphy CH, Gardner LJ, Manes JL, Bee CS, Taysi K (2000) CD30: anaplastic large-cell lymphoma with aberrant expression of CD13: Case report and review of the literature. J Clin Lab Anal 14(6):299-304
11. Elizabeth RC, Li X, Paula CM, William JW, Salvatore P (1999) Comparative molecular field analysis as a tool to evaluate mode of action of chemical hybridization agents. J Agric Food Chem 47:5245-5251
12. Fujii H, Nakajima M, Saiki I, Yoneda J, Azuma I, Tsuruo T (1995)Human melanoma invasion and metastasis enhancement by high expression of aminopeptidase N/CD13. Clin Exp Metastasis 13(5):337-344
13. Golbraikh A, Tropsha A (2002) Beware of q2!. J Mol Graph Model 20:269-276
14. Golbraikh A, Shen M, Xiao Z, Xiao YD, Lee KH, Tropsha A (2003) Rational selection of training and test sets for the development of validated QSAR models. J Comput Aid Mol Des 17:241-253
15. Hafler DA, Hemler ME, Christenson L, Williams JM, Shapiro HM,Strom TB, Strominger JL, Weiner HL (1985) Investigation of in vivo activated T cells in multiple sclerosis and inflammatory central nervous system diseases. Clin Immunol Immunopathol 37(2):163-171
16. Hashida H, Takabayashi A, Kanai M, Adachi M, Kondo K, Kohno N, Yamaoka Y, Miyake M (2002) Aminopeptidase N is involved in cell motility and angiogenesis: its clinical significance in human colon cancer. Gastroenterology 122(2):376-386
17. Hensbergen YV, Broxterman HJ, Hanemaaijer R, Jorna AS, van Lent NA, Verheul HM, Pinedo HM, Hoekman K (2002) Soluble aminopeptidase N/CD 13 in malignant and nonmalignant effusions and intratumoral fluid. Clin Cancer Res 8(12):3747-3754
18. Ikeda N, Nakajima Y, Tokuhara T, Hattori N, Sho M, Kanehiro H, Miyake M (2003) Clinical significance of aminopeptidase N/CD13 expression in human pancreatic carcinoma. Clin Cancer Res 9(4):1503-1508
19. Ishii K, Usui S, Sugimura Y, Yamamoto H, Yoshikawa K, Hirano K (2001) Inhibition of aminopeptidase N (AP-N) and urokinasetype plasminogen activator (uPA) by zinc suppresses the invasion activity in human urological cancer cells. Biol Pharm Bull 24(3):226-230
20. L-arginine as amino-peptidase N/CD13 inhibitors. Bioorg Med Chem 18:887-895
21. Kehlen A, Lendeckel U, Dralle H, Langner J, Hoang-Vu C (2003) Biological significance of aminopeptidase N/CD13 in thyroid carcinomas. Cancer Res 63(23):8500-8506
22. Kitamura Y, Watanabe M, Komatsubara S, Sakata Y (1990) Urinary excretion of glycine.prolile dipeptidile aminopeptidase, N-acetylbeta-D-glucosaminidase, alanine aminopeptidase, and low molecular protein in patients with renal cell carcinoma. Hinyokika Kiyo 36(5):535-539
23. Kiyoshi I, Yoshitaka N, Yuko O, Masahide T, Kanako N, Futoshi M, Takashi I, Tadashi Y (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
24. Li S, Wenfang X (2009) Peptidomimetics and metalloprotease inhibitors as anticancer drugs. Sci Chin Ser B Chem 52:535-548
25. Luciani N, Marie-Claire C, Ruffet E, Beaumont A, Roques BP, Fournie-Zaluski MC (1998) Characterization of Glu350 as a critical residue involved in the N-terminal amine binding site of aminopeptidase N (EC 3.4.11.2): insights into its mechanism of action. Biochemistry 37:686-692
26. Luqing S, Qiang W, Hao F, Jiajia M, Xuejian W, Yumei Y, Binghe W, Wenfang X (2008) Novel 3-phenylpropane-1,2-diamine derivates as inhibitors of aminopeptidase N (APN). Bioorg Med Chem 16:9984-9990
27. Luqing S, Hao F, Huawei Z, Xuejian W, Qiang W, Jiajia M, Wang B, Shiroh K, Wenfang X (2009) Design, synthesis and SAR studies of tripeptide analogs with the scaffold 3-phenylpropane-1,2-diamine as aminopeptidase N/CD13 inhibitors. Bioorg Med Chem 17:2775-2784
28. Menrad A, Speicher D, Wacker J, Herlyn M (1993) Biochemical and functional characterization of aminopeptidase N expressed by human melanoma cells. Cancer Res 53(6):1450-1455
29. Nack-Do S, Young-Kwon C, Byoung-Mog K, Kwan HH, Chan KK (2004) 3D QSAR studies on cinnamaldehyde analogues as farnesyl protein transferase inhibitors. Arch Pharm Res 27:1001-1008
30. Popnikolov NK, Payne DA, Hudnall SD, Hawkins HK, Kumar M, Norris BA, Elghetany MT (2000) CD 13-positive anaplastic large cell lymphoma of T-cell origin-a diagnostic and histogenetic problem. Arch Pathol Lab Med 124(12):1804-1808
31. Puntambekar DS, Giridhar R, Yadav MR (2006) Understanding the antitumor activity of novel tricyclicpiperazinyl derivatives as farnesyl transferase inhibitors using CoMFA and CoMSIA. Eur J Med Chem 41:1279-1292
32. Qianbin L, Wenfang X (2005) Novel anticancer targets and drugdiscovery in post genomic age. Curr Med Chem Anti-Cancer Agents 5:53-63
33. Qiang W, Maoying C, Huawei Z, Jian Z, Hao F, Binghe W, Wenfang X (2008) Design, synthesis, and QSAR studies of novel lysine derives as amino-peptidase N/CD13 inhibitors. Bioorg Med Chem 16:5473-5481
34. Riemann D, Schwachula A, Hentschel M, Langner J (1993) Demonstration of CD13/aminopeptidase N on synovial fluid T cells from patients with different forms of joint effusions. Immunobiology 187(1-2):24-35
35. Riemann D, Gohring B, Langner J (1994a) Expression of aminopeptidase N/CD13 in tumour-infiltrating lymphocytes from human renal cell carcinoma. Immunol Lett 42(1-2):19-23
36. Riemann D, Wollert HG, Menschikowski J, Mittenzwei S, Langner J (1994b) Immunophenotype of lymphocytes in pericardial fluid from patients with different forms of heart disease. Int Arch Allergy Immunol 104(1):48-56
37. Riemann D, Kehlen A, Langner J (1999) CD13-not just a marker in leukemia typing. Immunol Today 20(2):83-88
38. Scornik OA, Botbol V (2001) Bestatin as an experimental tool in mammals. Curr Drug Metab 2(1):67-85
39. Shao Z, Chen G, Lin Z, Zhang Y, Hao Y, Chu Y, Zheng Y, Qian L, Yang T, Yang C, Feng B (1998) Immunophenotype of myeloid cells in myelodysplastic syndromes and its clinical implications. Chin Med J (Engl) 111(1):28-31
40. Shimizu T, Tani K, Hase K, Ogawa H, Huang L, Shinomiya F, Sone S (2002) CD13/aminopeptidase N-induced lymphocyte involvement in inflamed joints of patients with rheumatoid arthritis. Arthritis Rheum 46(9):2330-2338
41. Tani K, Ogushi F, Huang L, Kawano T, Tada H, Hariguchi N, Sone S (2000) CD13/aminopeptidase N, a novel chemoattractant for T lymphocytes in pulmonary sarcoidosis. Am J Respir Crit Care Med 161(5):1636-1642
42. Tatsumi E (2002) A mini-review of CD13 antigen in AML: Easy induction or enhancement of expression in in vitro culture and necessary consideration for assessment. Southeast Asian J Trop Med Public Health 33(Suppl 2):155-157
43. Umezawa H, Aoyagi T, Suda H, Hamada M, Takeuchi T (1976) Bestatin, an inhibitor of aminopeptidase B produced by actinomycetes. J Antibiot (Tokyo) 29:97
44. Ziaber J, Baj Z, Pasnik J, Chmielewski H, Tchorzewski H (2000) Expression of aminopeptidase N (APN) on peripheral blood mononuclear cells' surface as a marker of these cells' transendothelial migration properties in the course of multiple sclerosis. Mediat Inflamm 9(1):45-48