899
Views
11
CrossRef citations to date
0
Altmetric
Research Article

Synthesis of new N,N′-bis[1-aryl-3-(piperidine-1-yl)propylidene]hydrazine dihydrochlorides and evaluation of their cytotoxicity against human hepatoma and breast cancer cells

, , , , , , & show all
Pages 420-426 | Received 05 Mar 2013, Accepted 10 Apr 2013, Published online: 16 Jul 2013

References

  • Bosch FX, Ribes J, Diaz M, Cleries R. Primary liver cancer: worldwide incidence and trends. Gastroenterology 2004;127:S5–16
  • El-Serag HB, Rudolph KL. Hepatocellular carcinoma: epidemiology and molecular carcinogenesis. Gastroenterology 2007;132:2557–76
  • Bruix J, Sherman M. Management of hepatocellular carcinoma. Hepatology 2005;42:1208–36
  • Bruix J, Sherman M. Management of hepatocellular carcinoma: an update. Hepatology 2011;53:1020–2
  • Schwartz M, Roayaie S, Konstadoulakis M. Strategies for the management of hepatocellular carcinoma. Nat Clin Pract Oncol 2007;4:424–32
  • Parkin DM, Bray F, Ferlay J, Pisani P. Global cancer statistics, 2002. CA Cancer J Clin 2005;55:74–108
  • Bange J, Zwick E, Ullrich A. Molecular targets for breast cancer therapy and prevention. Nat Med 2001;7:548–52
  • Dimmock JR, Kumar P. Anticancer and cytotoxic properties of Mannich bases. Curr Med Chem 1997;4:1–22
  • Bilginer S, Gul HI, Mete E, et al. 1-(3-Aminomethyl-4-hydroxyphenyl)-3-pyridinyl-2-propen-1-ones: a novel group of tumour-selective cytotoxins. J Enzyme Inhib Med Chem 2012, doi: 10.3109/14756366.2012.700927
  • Gul HI, Das U, Pandit B, Li PK. Evaluation of the cytotoxicity of some mono-Mannich bases and their corresponding azine derivatives against androgen-independent prostate cancer cells. Arzneimittel-Forsch 2006;56:850–5
  • Gul HI, Gul M, Erciyas E. Toxicity of some bis Mannich bases and corresponding piperidinols in the brine shrimp (Artemia salina) bioassay. J Appl Toxicol 2003;23:53–7
  • Gul HI, Yerdelen KO, Gul M, et al. Synthesis of 4′-hydroxy-3′-piperidinomethylchalcone derivatives and their cytotoxicity against PC-3 cell lines. Arch Pharm 2007;340:195–201
  • Gul M, Mete E, Atalay M, et al. Cytotoxicity of 1-Aryl-3-buthylamino-1-propanone hydrochlorides against Jurkat and L6 cells. Arzneimittel-Forsch 2009;59:364–9
  • Gul HI, Suleyman H, Gul M. Evaluation of the anti-inflammatory activity of N,N′-bis(3-dimethylamino-1-phenyl-propylidene) hydrazine dihydrochloride. Pharm Biol 2009;47:968–72
  • Gul HI, Calis U, Ozturk Z, et al. Evaluation of anticonvulsant activities of bis(3-aryl-3-oxo-propyl)ethylamine hydrochlorides and 4-aryl-3-arylcarbonyl-1-ethyl-4-piperidinol hydrochlorides. Arzneimittel-Forsch 2007;57:133–6
  • Gul HI, Sahin F, Gul M, et al. Evaluation of antimicrobial activities of several Mannich bases and their derivatives. Arch Pharm 2005;338:335–8
  • Mete E, Ozelgul C, Kazaz C, et al. Synthesis and antifungal activity of 1-aryl-3-phenethylamino-1-propanone hydrochlorides and 3-aroyl-4-aryl-1-phenethyl-4-piperidinols. Arch Pharm 2010;343:291–300
  • Gul M, Atalay M, Gul HI, et al. The effects of some Mannich bases on heat shock proteins HSC70 and GRP75, and thioredoxin and glutaredoxin levels in Jurkat cells. Toxicol In Vitro 2005;19:573–80
  • Gul M, Gul HI, Hanninen O. Effects of Mannich bases on cellular glutathione and related enzymes of Jurkat cells in culture conditions. Toxicol In Vitro 2002;16:107–12
  • Gul M, Gul HI, Vepsalainen J, et al. Effect of acetophenone derived Mannich bases on cellular glutathione level in jurkat cells - A possible mechanism of action. Arzneimittel-Forsch 2001;51:679–82
  • Dimmock JR, Shyam K, Hamon NW, et al. bis-Mannich bases of styryl ketones as antileukemic agents. Neoplasma 1985;32:85–91
  • Hamon NW, Bassendowski DL, Wright DE, et al. Effect of antineoplastic and cytotoxic Mannich Bases derived from conjugated styryl ketones on mitochondrial respiration in rat liver cells. J Pharm Sci 1978;67:1539–42
  • Warburg O, Wind F, Neglers E. On the metabolism of tumours in the body. In: Warburg O, ed. Metabolism of tumors. London: Arnold Constable; 1930:254–70
  • Newell K, Franchi A, Pouyssegur J, Tannock I. Studies with glycolysis-deficient cells suggest that production of lactic acid is not the only cause of tumor acidity. Proc Natl Acad Sci USA 1993;90:1127–31
  • Yamagata M, Hasuda K, Stamato T, Tannock IF. The contribution of lactic acid to acidification of tumours: studies of variant cells lacking lactate dehydrogenase. Br J Cancer 1998;77:1726–31
  • Stubbs M, McSheehy PM, Griffiths JR. Causes and consequences of acidic pH in tumors: a magnetic resonance study. Adv Enzyme Regul 1999;39:13–30
  • Gatenby RA. The potential role of transformation-induced metabolic changes in tumor-host interaction. Cancer Res 1995;55:4151–6
  • Griffiths L, Dachs GU, Bicknell R, et al. The influence of oxygen tension and pH on the expression of platelet-derived endothelial cell growth factor/thymidine phosphorylase in human breast tumor cells grown in vitro and in vivo. Cancer Res 1997;57:570–2
  • Martinez-Zaguilan R, Seftor EA, Seftor RE, et al. Acidic pH enhances the invasive behavior of human melanoma cells. Clin Exp Metastasis 1996;14:176–86
  • Stubbs M, Rodrigues L, Howe FA, et al. Metabolic consequences of a reversed pH gradient in rat tumors. Cancer Res 1994;54:4011–16
  • Gerweck LE, Seetharaman K. Cellular pH gradient in tumor versus normal tissue: potential exploitation for the treatment of cancer. Cancer Res 1996;56:1194–8
  • McSheehy PM, Seymour MT, Ojugo AS, et al. A pharmacokinetic and pharmacodynamic study in vivo of human HT29 tumours using 19F and 31P magnetic resonance spectroscopy. Eur J Cancer 1997;33:2418–27
  • Ojugo AS, McSheehy PM, Stubbs M, et al. Influence of pH on the uptake of 5-fluorouracil into isolated tumour cells. Br J Cancer 1998;77:873–9
  • Vukovic V, Tannock IF. Influence of low pH on cytotoxicity of paclitaxel, mitoxantrone and topotecan. Br J Cancer 1997;75:1167–72
  • Kozin SV, Gerweck LE. Cytotoxicity of weak electrolytes after the adaptation of cells to low pH: role of the transmembrane pH gradient. Br J Cancer 1998;77:1580–5
  • Volk T, Jahde E, Fortmeyer HP, et al. pH in human tumour xenografts: effect of intravenous administration of glucose. Br J Cancer 1993;68:492–500
  • Rollas S, Kucukguzel SG. Biological activities of hydrazone derivatives. Molecules 2007;12:1910–39
  • Hruby M, Konak C, Ulbrich K. Polymeric micellar pH-sensitive drug delivery system for doxorubicin. J Control Release 2005;103:137–48
  • Bae Y, Nishiyama N, Fukushima S, et al. Preparation and biological characterization of polymeric micelle drug carriers with intracellular pH-triggered drug release property: tumor permeability, controlled subcellular drug distribution, and enhanced in vivo antitumor efficacy. Bioconjug Chem 2005;16:122–30
  • Jain RK. Delivery of molecular and cellular medicine to solid tumors. Adv Drug Deliv Rev 2001;46:149–68
  • Bae Y, Fukushima S, Harada A, Kataoka K. Design of environment-sensitive supramolecular assemblies for intracellular drug delivery: polymeric micelles that are responsive to intracellular pH change. Angew Chem Int Ed Engl 2003;42:4640–3
  • Denton JJ, Turner RJ, Neier WB, et al. Antispasmodics. I. Substituted β-amino ketones. J Am Chem Soc 1949;71:2048–50
  • Fry EM. Observations on the Mannich reaction. J Org Chem 1945;10:259–62
  • Okuda T. Alkylation with Mannich bases. II. Exchange reaction of p-substituted β-dimethylaminopropiophenone with piperidine. Yakugaku Zasshi 1956;76:4–6
  • Pathak VN, Singh RP. Studies in fluorinated Mannich bases. Part 2: synthesis and biological activity of some new 3-alkylaminopropiophenones. Die Pharmazie 1980;35:434
  • Shoemaker RH. The NCI60 human tumour cell line anticancer drug screen. Nat Rev Cancer 2006;6:813–23
  • Mete E, Gul HI, Cetin-Atalay R, et al. The design and cytotoxic evaluation of some 1-aryl-3-isopropylamino-1-propanone hydrochlorides towards human Huh-7 hepatoma Cells. Arch Der Pharm 2011;344:333–9
  • Vichai V, Kirtikara K. Sulforhodamine B colorimetric assay for cytotoxicity screening. Nat Protoc 2006;1:1112–16
  • Bradford MM. A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal Biochem 1976;72:248–54
  • Charles AL, Guilbert AS, Bouitbir J, et al. Effect of postconditioning on mitochondrial dysfunction in experimental aortic cross-clamping. Br J Surg 2011;98:511–16
  • Dimmock JR, Erciyas E, Kirkpatrick DL, King KM. Evaluation of some azines of aminomethylacetophenones and related quaternary ammonium compounds versus the EMT6 tumour. Die Pharmazie 1988;43:614–16
  • Gul HI, Gul M, Vepsalainen J, et al. Cytotoxicity of some azines of acetophenone derived mono-Mannich bases against Jurkat cells. Biol Pharm Bull 2003;26:631–7
  • Thaveau F, Zoll J, Rouyer O, et al. Ischemic preconditioning specifically restores complexes I and II activities of the mitochondrial respiratory chain in ischemic skeletal muscle. J Vasc Surg 2007;46:541–7; discussion 547

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.