Tumor-specific cytotoxic activity of 1,2,3,4-tetrahydroisoquinoline derivatives against human oral squamous cell carcinoma cell lines

Anticancer Research

Volumn 29, Issue 8, 2009, Pages 3079-3086

  Hatano, Hajime ^a   Takekawa, Fumihiro ^a   Hashimoto, Ken ^a   Ishihara, Mariko ^a   Kawase, Masami ^b   Qing, Chu ^a,c   Wang, Qin Tao ^c   Sakagami, Hiroshi ^a  

^a MEIKAI UNIVERSITY SCHOOL OF DENTISTRY   (Japan)

^b MATSUYAMA UNIVERSITY   (Japan)

^c FOURTH MILITARY MEDICAL UNIVERSITY   (China)

Author keywords

Autophagy; Cytotoxicity; Tetrahydroisoquinolines; Tumor specificity

Indexed keywords

[6,7 DIMETHOXY 3,4 DIHYDROISOQUINOLIN 2(1H) YL](3,4 DIMETHOXYPHENYL)METHANONE; ACRIDINE ORANGE; CASPASE 3; ETHYL 2 BENZYLOXYCARBONYL 1,2,3,4 TETRAHYDROISOQUINOLINE 1 CARBOXYLATE; TETRAHYDROISOQUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; AUTOPHAGY; CANCER CELL CULTURE; CELL DEATH; CELL ORGANELLE; CELL STRAIN HL 60; CONTROLLED STUDY; CYTOTOXICITY; DNA FRAGMENTATION; DRUG MECHANISM; DRUG SPECIFICITY; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; MOLECULAR SIZE; MOUTH CANCER; NUCLEOSOME; PRIORITY JOURNAL; SQUAMOUS CELL CARCINOMA;

APOPTOSIS; AUTOPHAGY; CARCINOMA, SQUAMOUS CELL; CASPASE 3; ENZYME ACTIVATION; HUMANS; MOUTH NEOPLASMS; ORGANELLES; TETRAHYDROISOQUINOLINES; TUMOR CELLS, CULTURED;

EID: 68549083510     PISSN: 02507005     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (40)

1. Abe K, Saitoh T, Horiguchi Y, Utsunomiya I and Taguchi K: Review. Synthesis and neurotoxicity of tetrahydroisoquinoline derivatives for studying Parkinson's disease. Biol Pharm Bull 28: 1355-1362, 2005.
2. Page D, Nguyen N, Bernard S, Coupal M, Gosselin M, Lepage J, Adam L and Brown W: New scaffolds in the development of mu opioid-receptor ligands. Bioorg Med Chem Lett 13: 1585-1589, 2003. (Pubitemid 36428566)
3. Mohler ML, Kang G-S, Hong S-S, Patil R, Kirichenko OV, Li W, Rakov IM, Geisert EE and Miller DD: Discovery of antiglioma activity of biaryl 1,2,3,4-tetrahydroisoquinoline derivatives and conformationally flexible analogues. J Med Chem 49: 5845-5848, 2006.
4. Lin H-R, Safo MK and Abraham DJ: Identification of a series of tetrahydroisoquinoline derivatives as potential therapeutic agents for breast cancer. Bioorg Med Chem Lett 17: 2581-2589, 2007.
5. Seo JW, Srisook E, Son HJ, Hwang O, Cha Y-N and Chi DY: Syntheses of tetrahydroisoquinoline derivatives that inhibit NO production in activated BV-2 microglial cells. Eur J Med Chem 43: 1160-1170, 2008. (Pubitemid 351734560)
6. 3 antagonists and serotonin reuptake inhibitors. Bioorg Med Chem Lett 17: 1047-1051, 2007. (Pubitemid 46177610)
7. Gitto R, Ficarra R, Stancanelli R, Guardo M, De Luca L, Barreca ML, Pagano B, Rotondo A, Bruno G, Russo E, De Sarro G and Chimirri A: Synthesis, resolution, stereochemistry, and molecular modeling of (R)- and (S)-2-acetyl-1-(4′-chlorophenyl)-6,7-dimethoxy-1,2,3,4- tetrahydroisoquinoline AMPAR antagonists. Bioorg Med Chem 15: 5417-5423, 2007.
8. Kubota H, Watanabe T, Kakefuda A, Masuda N, Wada K, Ishii N, Sakamoto S and Tsukamoto S: Synthesis and pharmacological evaluation of piperidinoalkanoyl-1,2,3,4-tetrahydroisoquinoline derivatives as novel specific bradycardic agents. Bioorg Med Chem Lett 14: 3049-3052, 2004.
9. Hirose M, Egashira S, Goto Y, Hashihayata T, Ohtake N, Iwaasa H, Hata M, Fukami T, Kanatani A and Yamada K: N-Acyl 6,7-dimethoxy-1,2,3,4- tetrahydroisoquinoline: the first orexin-2 receptor selective non-peptidic antagonist. Bioorg Med Chem Lett 13: 4497-4499, 2003.
10. Fang W, Li Y, Cai Y, Kang K, Yan F, Liu G and Huang W: Substituted tetrahydroisoquinoline compounds B3 inhibited P-glycoprotein-mediated multidrug resistance in vitro and in vivo. J Pharm Pharmacol 59: 1649-1655, 2007. (Pubitemid 350221809)
11. Yan F, Jiang Y, Li Y-M, Zhen X, Cen J and Fang W-R: Reversal of P-glycoprotein and multidrug resistance-associated protein 1-mediated multidrug resistance in cancer cells by HZ08 isomers, tetraisohydroquinoline derivatives. Biol Pharm Bull 31: 1258-1264, 2008. (Pubitemid 351871172)
12. Li Y, Zhang H-B, Huang W-L and Li Y-M: Design and synthesis of tetrahydroisoquinoline derivatives as potential multidrug resistance reversal agents in cancer. Bioorg Med Chem Lett 18: 3652-3655, 2008. (Pubitemid 351787549)
13. Hu M-K, Liao Y-F, Chen J-F, Wang B-J, Tung Y-T, Lin H-C and Lee K-P: New 1,2,3,4-tetrahydroisoquinoline derivatives as modulators of proteolytic cleavage of amyloid precursor proteins. Bioorg Med Chem 16: 1957-1965, 2008.
14. Choquette D, Teffera Y, Polverino A and Harmange J-C: Discovery of novel 1,2,3,4-tetrahydroisoquinolines and 3,4-dihydroisoquinoline-1(2H)-ones as potent and selective inhibitors of KDR: synthesis, SAR, and pharmacokinetic properties. Bioorg Med Chem Lett 18: 4054-4058, 2008.
15. Azukizawa S, Kasai M, Takahashi K, Mike T, Kunishiro K, Kanda M, Mukai C and Shirahase H: Synthesis and biological evaluation of (S)-1,2,3,4- tetrahydroisoquinoline-3-carboxylic acids: a novel series of PPARγ agonists. Chem Pharm Bull 56: 335-345, 2008.
16. Scott JD and Williams RM: Chemistry and biology of the tetrahydroisoquinoline antitumor antibiotics. Chem Rev 102: 1669-1730, 2002. (Pubitemid 35377652)
17. Ruchirawat S, Chaisupakitsin M, Patranuwatana N, Cashaw JL and Davis VE: A convenient synthesis of simple tetrahydroisoquinolines. Synth Commun 14: 1221-1228, 1984.
18. Stephen S Jr, Veradaraj E and Maurice S: Conversion of tetrahydroisoquinolinium salts into benzazepines. J Org Chem 49: 581-586, 1984.
19. Kawase M, Motohashi N, Niwa M and Nozaki M: Use of the triflamide group for Friedel-Crafts acylation of N-(β-phenethyl) amino acids to 3-benzazepine derivatives. Heterocycles 45: 1121-1129, 1997. (Pubitemid 127689229)
20. Shah RJ, Vaghani DD and Merchant JR: Heterocyclic compounds. I. Synthesis of some isoquinoline derivatives. J Org Chem 26: 3533-3534, 1961.
21. Kawase M, Niwa M, Nozaki M and Motohashi N: Synthesis of 2-trifluoromethyl-2,3,4,5-tetrahydro-1H-3-benzazepine derivatives. Heterocycles 48: 555-560, 1998.
22. Rehse K, Fredrich D and Kehr W: Neuropsychotropic activity of dopamine-analogous piperidine and piperazine derivatives. Archiv der Pharmazie (Weinheim, Germany) 312: 670-681, 1979.
23. Aissaoui H, Cappi M, Clozel M, Fischli W and Koberstein R: Preparation of 1,2,3,4-tetrahydroisoquinolines as orexin receptor antagonists. PCT Int Appl (2001), 158 pp. CODEN: PIXXD2 WO 2001068609 A1 20010920 CAN 135:257167 AN 2001:693286.
24. Kawase M, Okada Y and Miyamae H: The Dakin-West reaction of N-acyl-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acids using trifluoroacetic anhydride: structural revision for the unexpected product. Heterocycles 48: 285-294, 1998.
25. Craig PN, Nabenhauer FP, Williams PM, Macko E and Toner J: Tetrahydroisoquinolines. I. 1-Alkyl-6,7-dihydroxy-1,2,3,4- tetrahydroisoquinolines. J Am Chem Soc 74: 1316-1317, 1952.
26. Kawase M: Autoxidation of intermediary mesoionic 1,3-oxazolium-5-olates generated from cyclic N-acyl α-amino acids. Chem Pharm Bull 45: 1248-1253, 1997.
27. Popp FD, Blount W and Soto A: Reissert compound studies: Generality of a new procedure. Chem Ind 1022, 1962.
28. Brossi A: Mammalian alkaloids: conversions of tetrahydroisoquinoline-1- carboxylic acids derived from dopamine. Planta Medica 57: S93-S100, 1991.
29. Gensler WJ and Bluhm AL: Cinnamic acids from tetrahydroisoquinolinecarboxylic acids. J Org Chem 21: 336-339, 1956.
30. Narasaka K and Kohno Y: Oxidative generation of N-acyliminium ions from N-1-(tributylstannyl)alkyl carboxamides and carbamates and their reactions with carbon nucleophiles. Bull Chem Soc Japan 66: 3456-3463, 1993.
31. Satoh R, Kishino K, Morshed SRM, Takayama F, Otsuki S, Suzuki F, Hashimoto K, Kikuchi H, Nishikawa H, Yasui T and Sakagami H: Changes in fluoride sensitivity during in vitro senescence of human normal oral cells. Anticancer Res 25: 2085-2090, 2005. (Pubitemid 40904608)
32. Sekine T, Takahashi J, Nishishiro M, Arai A, Wakabayashi H, Kurihara T, Kobayashi M, Hashimoto K, Kikuchi H, Katayama T, Kanda Y, Kunii S, Motohashi N and Sakagami H: Tumor-specificity and type of cell death induced by trihaloacetylazulenes in human tumor cell lines. Anticancer Res 27: 133-144, 2007. (Pubitemid 46363325)
33. Yanagisawa-Shiota F, Sakagami H, Kuribayashi N, Iida M, Sakagami T and Takeda M: Endonuclease activity and induction of DNA fragmentation in human myelogenous leukemic cell lines. Anticancer Res 15: 259-266, 1995.
34. Byfield MP, Murray JT and Backer JM: hVps34 is a nutrient-regulated lipid kinase required for activation of p70 S6 kinase. J Biol Chem 280: 33076-33082, 2005.
35. Saitoh T, Abe K, Ishikawa M, Nakatani M, Shimazu S, Satoh N, Yoneda F, Taguchi K and Horiguchi Y: Synthesis and in vitro cytotoxicity of 1,2,3,4-tetrahydroisoquinoline derivatives. Eur J Med Chem 41: 241-253, 2006.
36. Ishihara M, Hatano H, Kawase M and Sakagami H: Estimation of relationship between structure of 1,2,3,4-tetrahydroisoquinoline derivatives determined by a semiempirical molecular-orbital method and their cytotoxicity. Anticancer Res 29: in press, 2009.
37. Kang JH: Salsolinol, a tetrahydroisoquinoline catechol neurotoxin, induces human Cu,Zn-superoxide dismutase modification. J Biochem Mol Biol 40: 684-689, 2007.
38. Maruyama W, Naoi M, Kasamatsu T, Hashizume Y, Takahashi T, Kohda K and Dostert P: An endogenous dopaminergic neurotoxin, N-methyl-(R)-salsolinol, induces DNA damage in human dopaminergic neuroblastoma SH-SY5Y cells. J Neurochem 69: 322-329, 1997. (Pubitemid 27274188)
39. Deng Y, Luan Y, Qing H, Xie H, Lu J and Zhou J: The formation of catechol isoquinolines in PC12 cells exposed to manganese. Neurosci Lett 444: 122-126, 2008.
40. Kang GS, Wang XD, Mohler ML, Kirichendo OV, Patil R, Orr WE, Miller DD and Geisert EE: Effects, in an in vivo model system, of 1,2,3,4- tetrahydroisoquinoline on glioma. Anticancer Drugs 19: 859-870, 2008.