Sonodynamic and photodynamic mechanisms of action of the novel hypocrellin sonosensitizer, SL017: Mitochondrial cell death is attenuated by 11, 12-epoxyeicosatrienoic acid

Investigational New Drugs

Volumn 29, Issue 6, 2011, Pages 1328-1336

  El Sikhry, Haitham E ^a   Miller, Gerald G ^b   Madiyalakan, Madi R ^b   Seubert, John M ^a  

^a UNIVERSITY OF ALBERTA   (Canada)

^b Quest PharmaTech Inc   (Canada)

Author keywords

Cancer; EET; Hypocrellin; Mitochondria; Photodynamic therapy; SL017; Sonodynamic therapy

Indexed keywords

2 (N,N DIMETHYLAMINOPROPYL)AMINO 15 ACETYL 3,10 DIHYDROXY 6,7,11 TRIMETHOXY 14 METHYL 15 H CYCLOHEPTA(GHI)PERYLENE 4,9 DIONE; PHOTOSENSITIZING AGENT; REACTIVE OXYGEN METABOLITE; SL 017; UNCLASSIFIED DRUG; 11,12 EPOXY 5,8,14 EICOSATRIENOIC ACID; 11,12-EPOXY-5,8,14-EICOSATRIENOIC ACID; 2-(N,N-DIMETHYLAMINOPROPYL)AMINO-15-ACETYL-3,10-DIHYDROXY-6,7,11-TRIMETHOXY-14-METHYL-15-H-CYCLOHEPTA(GHI)PERYLENE-4,9-DIONE; DIHOMO GAMMA LINOLENIC ACID; DRUG DERIVATIVE; HYPOCRELLIN B; PERYLENE; QUINONE DERIVATIVE;

APOPTOSIS; ARTICLE; CELLULAR DISTRIBUTION; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG MECHANISM; DRUG UPTAKE; HUMAN; HUMAN CELL; INTRACELLULAR TRANSPORT; MITOCHONDRIAL MEMBRANE POTENTIAL; PHOTODYNAMIC THERAPY; PRIORITY JOURNAL; ULTRASOUND THERAPY; CELL CULTURE; CELL DEATH; DOSE RESPONSE; DRUG EFFECT; FIBROBLAST; METABOLISM; METHODOLOGY; MITOCHONDRION; PHOTOCHEMOTHERAPY;

8,11,14-EICOSATRIENOIC ACID; CELL DEATH; CELLS, CULTURED; DOSE-RESPONSE RELATIONSHIP, DRUG; FIBROBLASTS; HUMANS; MEMBRANE POTENTIAL, MITOCHONDRIAL; MITOCHONDRIA; PERYLENE; PHOTOCHEMOTHERAPY; PHOTOSENSITIZING AGENTS; QUINONES; REACTIVE OXYGEN SPECIES; ULTRASONIC THERAPY;

EID: 84856049851     PISSN: 01676997     EISSN: 15730646     Source Type: Journal    
DOI: 10.1007/s10637-010-9495-2     Document Type: Article

References (34)

1. Rockson SG, Lorenz DP, Cheong WF, Woodburn KW (2000) Photoangioplasty: an emerging clinical cardiovascular role for photodynamic therapy. Circulation 102(5):591-596 (Pubitemid 30639979)
2. Tachibana K, Feril LB Jr, Ikeda-Dantsuji Y (2008) Sonodynamic therapy. Ultrasonics 48(4):253-259. doi:10.1016/j.ultras.2008.02.003
3. Tang W, Liu Q, Wang X, Wang P, Zhang J, Cao B (2009) Potential mechanism in sonodynamic therapy and focused ultrasound induced apoptosis in sarcoma 180 cells in vitro. Ultrasonics 49(8):786-793. doi:10.1016/j.ultras.2009.06.002
4. Hiraoka W, Honda H, Feril LB Jr, Kudo N, Kondo T (2006) Comparison between sonodynamic effect and photodynamic effect with photosensitizers on free radical formation and cell killing. Ultrason Sonochem 13(6):535-542. doi:10.1016/j. ultsonch.2005.10.001 (Pubitemid 44051962)
5. Rosenthal I, Sostaric JZ, Riesz P (2004) Sonodynamic therapy-a review of the synergistic effects of drugs and ultrasound. Ultrason Sonochem 11(6):349-363. doi:10.1016/j.ultsonch.2004.03.004 (Pubitemid 39070478)
6. Ali SM, Chee SK, Yuen GY, Olivo M (2001) Hypericin and hypocrellin induced apoptosis in human mucosal carcinoma cells. J Photochem Photobiol B 65(1):59-73 (Pubitemid 34145092)
7. Miller GG, Brown K, Ballangrud AM, Barajas O, Xiao Z, Tulip J, Lown JW, Leithoff JM, Allalunis-Turner MJ, Mehta RD, Moore RB (1997) Preclinical assessment of hypocrellin b and hypocrellin b derivatives as sensitizers for photodynamic therapy of cancer: progress update. Photochem Photobiol 65(4):714-722 (Pubitemid 27210658)
8. Roman RJ (2002) P-450 metabolites of arachidonic acid in the control of cardiovascular function. Physiol Rev 82(1):131-185. doi:10.1152/physrev. 00021.2001 (Pubitemid 34654217)
9. Seubert JM, Sinal CJ, Graves J, DeGraff LM, Bradbury JA, Lee CR, Goralski K, Carey MA, Luria A, Newman JW, Hammock BD, Falck JR, Roberts H, Rockman HA, Murphy E, Zeldin DC (2006) Role of soluble epoxide hydrolase in postischemic recovery of heart contractile function. Circ Res 99(4):442-450. doi:10.1161/01. RES.0000237390.92932.37 (Pubitemid 44253701)
10. Dhanasekaran A, Gruenloh SK, Buonaccorsi JN, Zhang R, Gross GJ, Falck JR, Patel PK, Jacobs ER, Medhora M (2008) Multiple antiapoptotic targets of the pi3k/akt survival pathway are activated by epoxyeicosatrienoic acids to protect cardiomyocytes from hypoxia/anoxia. Am J Physiol Heart Circ Physiol 294 (2): H724-H735. doi:10.1152/ajpheart.00979.2007 (Pubitemid 351253284)
11. Gauthier KM, Yang W, Gross GJ, Campbell WB (2007) Roles of epoxyeicosatrienoic acids in vascular regulation and cardiac preconditioning. J Cardiovasc Pharmacol 50(6):601-608. doi:10.1097/FJC.0b013e318159cbe3 (Pubitemid 350307028)
12. Gross GJ, Hsu A, Falck JR, Nithipatikom K (2007) Mechanisms by which epoxyeicosatrienoic acids (eets) elicit cardioprotection in rat hearts. J Mol Cell Cardiol 42(3):687-691. doi:10.1016/j. yjmcc.2006.11.020 (Pubitemid 46349123)
13. Zhang Y, El-Sikhry H, Chaudhary KR, Batchu SN, Shayeganpour A, Jukar TO, Bradbury JA, Graves JP, DeGraff LM, Myers P, Rouse DC, Foley J, Nyska A, Zeldin DC, Seubert JM (2009) Overexpression of cyp2j2 provides protection against doxorubicininduced cardiotoxicity. Am J Physiol Heart Circ Physiol 297 (1): H37-H46. doi:10.1152/ajpheart.00983.2008
14. Katragadda D, Batchu SN, Cho WJ, Chaudhary KR, Falck JR, Seubert JM (2009) Epoxyeicosatrienoic acids limit damage to mitochondrial function following stress in cardiac cells. J Mol Cell Cardiol 46(6):867-875. doi:10.1016/j.yjmcc.2009.02.028
15. Jiang JG, Chen CL, Card JW, Yang S, Chen JX, Fu XN, Ning YG, Xiao X, Zeldin DC, Wang DW (2005) Cytochrome p450 2j2 promotes the neoplastic phenotype of carcinoma cells and is upregulated in human tumors. Cancer Res 65(11):4707-4715. doi:10.1158/0008-5472. CAN-04-4173 (Pubitemid 40740807)
16. Jiang JG, Ning YG, Chen C, Ma D, Liu ZJ, Yang S, Zhou J, Xiao X, Zhang XA, Edin ML, Card JW, Wang J, Zeldin DC, Wang DW (2007) Cytochrome p450 epoxygenase promotes human cancer metastasis. Cancer Res 67(14):6665-6674. doi:10.1158/0008-5472. CAN-06-3643 (Pubitemid 47105512)
17. Jakus J, Farkas O (2005) Photosensitizers and antioxidants: a way to new drugs? Photochem Photobiol Sci 4(9):694-698. doi:10.1039/b417254j (Pubitemid 41367019)
18. Estey EP, Brown K, Diwu ZJ, Lin JX, Lown JW, Miller GG, Moore RB, Tulip J, McPhee MS (1996) Hypocrellins as photosensitizers for photodynamic therapy: a screening evaluation and pharmacokinetic study. Cancer Chemother Pharmacol 37(4):343-350 (Pubitemid 26031012)
19. Yumita N, Umemura S, Magario N, Umemura K, Nishigaki R (1996) Membrane lipid peroxidation as a mechanism of sonodynamically induced erythrocyte lysis. Int J Radiat Biol 69:397-404 (Pubitemid 26153276)
20. Yumita N, Nishigaki R, Umemura K, Morse PD, Swartz HM, Cain CA, Umemura S (1994) Sonochemical activation of hematoporphyrin: an esr study. Radiat Res 138:171-176 (Pubitemid 24151443)
21. Yumita N, Nishigaki R, Umemura K, Umemura S (1989) Hematoporphyrin as a sensitizer of cell-damaging effect of ultrasound. Jpn J Cancer Res 80:219-222 (Pubitemid 20027211)
22. El Maalouf J, Bera JC, Alberti L, Cathignol D, Mestas JL (2009) In vitro sonodynamic cytotoxicity in regulated cavitation conditions. Ultrasonics 49(2):238-243. doi:10.1016/j.ultras.2008.09.001
23. Chan DC (2006) Mitochondria: dynamic organelles in disease, aging, and development. Cell 125(7):1241-1252. doi:10.1016/j. cell.2006.06.010 (Pubitemid 43929096)
24. Furt F, Moreau P (2009) Importance of lipid metabolism for intracellular and mitochondrial membrane fusion/fission processes. Int J Biochem Cell Biol 41(10):1828-1836. doi:10.1016/j. biocel.2009.02.005
25. Maack C, O'Rourke B (2007) Excitation-contraction coupling and mitochondrial energetics. Basic Res Cardiol 102(5):369-392. doi:10.1007/s00395- 007-0666-z (Pubitemid 47278811)
26. Stanley WC, Morgan EE, Huang H, McElfresh TA, Sterk JP, Okere IC, Chandler MP, Cheng J, Dyck JR, Lopaschuk GD (2005) Malonyl-coa decarboxylase inhibition suppresses fatty acid oxidation and reduces lactate production during demand-induced ischemia. Am J Physiol Heart Circ Physiol 289 (6): H2304-H2309. doi:10.1152/ajpheart.00599.2005 (Pubitemid 41698536)
27. Ussher JR, Lopaschuk GD (2008) The malonyl coa axis as a potential target for treating ischaemic heart disease. Cardiovasc Res 79(2):259-268. doi:10.1093/cvr/cvn130 (Pubitemid 351951618)
28. Wang W, Fang H, Groom L, Cheng A, Zhang W, Liu J, Wang X, Li K, Han P, Zheng M, Yin J, Wang W, Mattson MP, Kao JPY, Lakatta EG, Sheu S-s, Ouyang K, Chen J, Dirksen RT, Cheng H (2008) Superoxide flashes in single mitochondria. Cell 279-290 (Pubitemid 352010332)
29. Hanley PJ, Daut J (2005) K (atp) channels and preconditioning: a re-examination of the role of mitochondrial k (atp) channels and an overview of alternative mechanisms. J Mol Cell Cardiol 39(1):17-50. doi:10.1016/j.yjmcc. 2005.04.002 (Pubitemid 40836043)
30. Hausenloy DJ, Yellon DM (2004) New directions for protecting the heart against ischaemia-reperfusion injury: targeting the reperfusion injury salvage kinase (risk)-pathway. Cardiovasc Res 61(3):448-460. doi:10.1016/j.cardiores. 2003.09.024 (Pubitemid 38210151)
31. Hom J, (2009) Morphological dynamics of mitochondria-a special emphasis on cardiac muscle cells. J Mol Cell Cardiol 46:811-820
32. Benard G, Bellance N, James D, Parrone P, Fernandez H, Letellier T, Rossignol R (2007) Mitochondrial bioenergetics and structural network organization. J Cell Sci 120(Pt 5):838-848. doi:10.1242/jcs.03381 (Pubitemid 46523485)
33. Davies VJ, Hollins AJ, Piechota MJ, Yip W, Davies JR, White KE, Nicols PP, Boulton ME, Votruba M (2007) Opa1 deficiency in a mouse model of autosomal dominant optic atrophy impairs mitochondrial morphology, optic nerve structure and visual function. Hum Mol Genet 16:1307-1318 (Pubitemid 47055126)
34. Spector AA, Norris AW (2007) Action of epoxyeicosatrienoic acids on cellular function. Am J Physiol Cell Physiol 292 (3): C996-C1012. doi:10.1152/ajpcell.00402.2006 (Pubitemid 46442641)