Design, synthesis, and preliminary cardioprotective effect evaluation of danshensu derivatives

Chemical Biology and Drug Design

Volumn 84, Issue 3, 2014, Pages 282-291

  Cui, Qingbin ^a   Chen, Yonghong ^a   Zhang, Mingjuan ^a   Shan, Luchen ^a   Sun, Yewei ^a   Yu, Pei ^a   Zhang, Gaoxiao ^a   Wang, Dingyuan ^a   Zhao, Zengchao ^a   Xu, Qian ^a   Xu, Benhong ^a   Wang, Yuqiang ^a  

^a JINAN UNIVERSITY   (China)

Author keywords

biological screening; chemical synthesis; Danshensu derivatives; drug design; myocardial ischemia

Indexed keywords

(3,5,6-TRIMETHYLPYRAZINYL)METHYL 2-ACETOXY-3-(3,4-DIACETOXYPHENYL)PROPANOATE; 3,4-DIHYDROXYPHENYLLACTIC ACID; CARDIOTONIC AGENT; CREATINE KINASE; GLYCOGEN SYNTHASE KINASE 3; GLYCOGEN SYNTHASE KINASE 3 BETA; HEME OXYGENASE 1; LACTATE DEHYDROGENASE; LACTIC ACID DERIVATIVE; MALONALDEHYDE; PHENYLPROPIONIC ACID DERIVATIVE; PHOSPHATIDYLINOSITOL 3 KINASE; PROTEIN BINDING; PROTEIN KINASE B; PYRAZINE DERIVATIVE; TRANSCRIPTION FACTOR NRF2;

ANIMAL; BLOOD; CHEMISTRY; DISEASE MODEL; DRUG DESIGN; DRUG EFFECTS; ISCHEMIA; METABOLISM; RAT; SIGNAL TRANSDUCTION; STEREOISOMERISM; SYNTHESIS; TUMOR CELL LINE;

ANIMALS; CARDIOTONIC AGENTS; CELL LINE, TUMOR; CREATINE KINASE; DISEASE MODELS, ANIMAL; DRUG DESIGN; GLYCOGEN SYNTHASE KINASE 3; HEME OXYGENASE-1; ISCHEMIA; L-LACTATE DEHYDROGENASE; LACTATES; MALONDIALDEHYDE; NF-E2-RELATED FACTOR 2; PHENYLPROPIONATES; PHOSPHATIDYLINOSITOL 3-KINASES; PROTEIN BINDING; PROTO-ONCOGENE PROTEINS C-AKT; PYRAZINES; RATS; SIGNAL TRANSDUCTION; STEREOISOMERISM;

EID: 84905827583     PISSN: 17470277     EISSN: 17470285     Source Type: Journal    
DOI: 10.1111/cbdd.12312     Document Type: Article

References (52)

1. Choi D., Hwang K., Lee K., Kim Y., (2009) Ischemic heart diseases: current treatments and future. J Controlled Release; 140: 194-202.
2. Radke P., (2011) Acute myocardial infarction: diagnosis and treatment. Med Monatsschr Pharm; 34: 78-84.
3. Han J., Fan J., Yoshinori H., Soichiro M., Cui D., Hiromasa I., Toshifumi H., Hiroshi T., Ikuko K., (2008) Ameliorating effects of compounds derived from Salvia miltiorrhiza root extract on microcirculatory disturbance and target organ injury by ischemia and reperfusion. Pharmacol Thera; 117: 280-295.
4. Chang J.Y., Kuo C.C., Chen L.T., Wein Y.S., Kuo Y.H., (2004) Salvinal, a novel microtubule inhibitor isolated from Salvia miltiorrhizae Bunge (Danshen), with antimitotic activity in multidrug-sensitive and resistant human tumor cells. Mol Pharmacol; 65: 77-84.
5. Wang X.B., Morris-Natschke S.L., Lee K.H., (2007) New developments in the chemistry and biology of the bioactive constituents of Tanshen. Med Res Rev; 27: 133-148.
6. Lu Y.Q., (2007) Chemical composition and clinical application of Salvia. China Pharm; 18: 947-948.
7. Wu L., Qiao H., Li Y., Li L., (2007) Protective roles of puerarin and Danshensu on acute ischemic myocardial injury in rats. Phytomedicine; 14: 652-658.
8. Chen L.N., Zhu X.X., (2005) Advances in study of the pharmacological effects of danshen on hemorheology. J Chin Materia Medica; 30: 630-633.
9. Husna B., On T., Zhu Y.Z., (2007) Effects of purified Salvia miltiorrhiza extract on cardiac vascular smooth muscle hypoxic cells. J Pharmacol Sci; 104: 202-211.
10. Zhou X., Han D.W., Yin L., Zhao H.Z., (2006) Effects of Danshensu protection on the liver injury and its mechanism. Shanxi Med J; 35: 108-110.
11. Zhang J., Zeng X.Y., Yang Y., Liu Z.F., (2005) Effect of Danshensu on calcium-activated potassium channel in cultured porcine coronary artery smooth muscle cells. Basic Clin Med; 25: 1054-1057.
12. Guo Z.Q., Niu F.L., Zhu L.Q., Wang W., (2000) Effects of Danshensu on Angiotension II-induced cardiac hypertrophy. J Beijing Univ TCM; 23: 30-31.
13. Zhao Y.W., Xie W.L., Sun W.J., Liu B., (2005) Effects of Danshensu on sodium current in isolated ventricular cells in guinea pig. Acta Acad Med CPAPF; 24: 256-263.
14. Cao C.M., Xia Q., Zhang X., Xu W.H., Jiang H.D., Chen J.Z., (2003) Salvia miltiorrhiza attenuates the changes in contraction and intracellular calcium induced by anoxia and reoxygenation in rat cardiomyocytes. Life Sci; 72: 2451-2463.
15. Zhao G.R., Zhang H.M., Ye T.X., Xiang Z.J., Yuan Y.J., Guo Z.X., Zhao L.B., (2008) Characterization of the radical scavenging and antioxidant activities of danshensu and salvianolic acid B. Food Chem Toxcol; 46: 73-81.
16. Jin X., Chen B., Wu W., Gu Z., Jiang M., Zhang Z., Dong J., (2000) Effects of eight Danshensu's derivatives on rabbit platelet aggregation. J Shanghai Med Univ; 27: 181-184.
17. Han M., Zhao C.Q., Wang Y.Y., (2009) β-(3,4-dihydroxyphenyl)-2- hydroxy-propanoate and its application in pharmaceutics. CN patent 101475483A.
18. Zhu Y.Z., Wang Y., Dong C., (2009) Preparation of a serial of danshensu derivatives and their application in pharmaceutics. CN patent 101607954.
19. Dong C., Wang Y., Zhu Y.Z., (2009) Asymmetric synthesis and biological evaluation of Danshensu derivates as anti-myocardial ischemia drug candidates. Bioorg Med Chem; 17: 3499-3507.
20. Xiang Z., Jing L., Liu W., Wang P., Gao F., Sun X., (2009) Protective effect of acetyl Danshen acid isosorbide monoitrate on myocardial ischemia/reperfusion injury in rats. J Fourth Mil Med Univ; 14: 1257-1261.
21. Cui G., Shan L., Hung M., Lei S., Choi I., Zhang Z., Yu P., Hoi M.P., Wang Y., Lee S.M., (2013) A novel Danshensu derivative confers cardioprotection via PI3K/Akt and Nrf2 pathways. Int J Cardiol; 168: 1349-1359.
22. Han S.Y., Li H.X., Ma X., Zhang K., Ma Z.Z., Tu P.F., (2009) Protective effects of purified safflower extract on myocardial ischemia in vivo and in vitro. Phytomedicine; 16: 694-702.
23. Valentine W.J., Kiss G.N., Liu J., Shu-yu E., Gotoh M., Murakami-Murofushi K., Pham T.C., Baker D.L., Parrill A.L., Lu X., Sun C., Bittman R., Pyne N.J., Tigyi G., (2010) (S)-FTY720-vinylphosphonate, an analogue of the immunosuppressive agent FTY720, is a pan-antagonist of sphingosine 1-phosphate GPCR signaling and inhibits autotaxin activity. Cell Signal; 22: 1543-1553.
24. Lu T.M., Kuo D.H., Ko H.H., Ng L.T., (2010) Synthesis and structure-activity relationship study of deoxybenzoins on relaxing effects of porcine coronary artery. J Agric Food Chem; 58: 10027-10032.
25. Shyu K.G., Wang M.T., Wang B.W., Chang C.C., Leu J.G., Kuan P., Chang H., (2002) Intramyocardial injection of naked DNA encoding HIF-1a/VP16 hybrid to enhance angiogenesis in an acute myocardial infarction model in the rat. Cardiovasc Res; 54: 576-583.
26. Vivaldi M.T., Kloner R.A., Schoen F.J., (1985) Triphenyltetrazolium staining of irreversible ischemic injury following coronary artery occlusion in rats. Am J Pathol; 121: 522-530.
27. Thomas C., Ohlweiler D., Carr A., Nieduzak T., Hay D., Adams G., Vaz R., Bernotas R., (1996) Characterization of the radical trapping activity of a novel series of cyclic nitrone spin traps. J Bio Chem; 271: 3097-3104.
28. Han S., Zhu J., Wang Y., (2009) Measurement of the antioxidant activity by pyrogallol autooxidation. Chin Brewing; 6: 155-157.
29. Van D., McConnell P., Marquardt L., (2000) Green tea extract and its polyphenols markedly inhibit luminol-dependent chemiluminescence activated by peroxynitrite or SIN-1. Luminescence; 15: 37-43.
30. Hong X., Wang N.S., (2000) The kinetics of Danshensu in Danshen dropping pill drug. Tradit Chin Med Clin Pharm; 11: 286-288.
31. Lee J.C., Oh Y.S., Cho S.H., Lee J.I., (1996) Efficient in situ esterification of carboxylic acids using cesium carbonate. Org Prep Proced Int; 28: 480-483.
32. 7 receptor. J Med Chem; 50: 3706-3715.
33. Ma Y., Chen Y., (2008) Effect of tetramethylpyrazine on cerebral ischemia-reperfusion injury in rats. Nerv Dis Mental Heal; 8: 438-442.
34. Lu Y.G., Lu L.L., Wu W.L., (2008) Salvia Ligustrazine injection in treating acute cerebral infarction. Chin Prac Med; 3: 88-89.
35. Yin L., Yin X.J., (2008) Clinical study of salviae miltiorrhizae and ligustrazine on treatment of acute cerebral infarction. China Hosp Pharm J; 28: 1703-1704.
36. Cui L., Wang S.X., Liu X.Y., (2008) The effective mechanism of tetramethylpyrazine in anti-atherosclerosis. Med Recap; 14: 3491-3493.
37. Zhang Q., Li B.H., (2008) Mobilization of Danshensu and Ligustrazine on peripheral blood hematopoietic stem cells in mice. Prac Clin Med; 9: 7-10.
38. Zhou Y.P., Liu Q., (2010) Protective effects of ligustrazine on hypoxia/reoxygenation injury in cardiomyocytes. Prac Clin Med; 12: 5-8.
39. Sun Y., Jiang J., Zhang Z., Yu P., Wang L., Xu C., Liu W., Wang Y., (2008) Antioxidative and thrombolytic TMP nitrone for treatment of ischemic stroke. Bioorg Med Chem; 16: 8868-8874.
40. Sherman C.L., Brodbelt J.S., (2005) Electrospray ionization mass spectrometric detection of self-assembly of a crown ether complex directed by stacking interactions. J Am Soc Mass Spect; 16: 1162-1171.
41. Hori M., Nishida K., (2009) Oxidative stress and left ventricular remodelling after myocardial infarction. Cardiovasc Res; 81: 457-464.
42. Werns S.W., Shea M.J., Lucchesi B.R., (1985) Free radicals in ischemic myocardial injury. J Free Radic Biol Med; 2: 103-110.
43. Zweier J., Talukder M., (2006) The role of oxidants and free radicals in reperfusion injury. Cardiovasc Res; 70: 181-190.
44. Chambers D.E., Parks D.A., Patterson G., Roy R., McCord J.M., Yoshida S., Parmley L.F., Downey J.M., (1985) Xanthine oxidase as a source of free radical damage in myocardial ischemia. J Mol Cell Cardiol; 2: 145-152.
45. Du L., Miao X., Jiang Y., Jia H., Tian Q., Shen J., Liu Y., (2013) An effective strategy for the synthesis of biocompatible gold nanoparticles using danshensu antioxidant: prevention of cytotoxicity via attenuation of free radical formation. Nanotoxicology; 7: 294-300.
46. Bian X., Chen X., Liu Y., Pan Q., (2003) Scavenging action to hydroxyl free radical of ligustrazine and its derivatives. Chin Hosp Pharm J; 23: 678-679.
47. Werns S.W., Shea M.J., Driscoll E.M., Cohen C., Abrams G.D., Pitt B., Lucchesi B.R., (1985) The independent effects of oxygen radical scavengers on canine infarct size. Reduction by superoxide dismutase but not catalase. Circ Res; 6: 895-898.
48. 2+ overload during postischemic reperfusion. Am J Physiol; 266: H2174-H2181.
49. Mergner G.W., Weglicki W.B., Kramer J.H., (1991) Postischemic free radical production in the venous blood of the regionally ischemic swine heart. Effect of deferoxamine. Circulation; 84: 2079-2090.
50. Zhao B.L., Jiang W., Zhao Y., Hou J.W., Xin W.J., (1996) Scavenging effects of salvia miltiorrhiza on free radicals and its protection for myocardial mitochondrial membranes from ischemia-reperfusion injury. Biochem Mol Biol Int; 6: 1171-1182.
51. Pachori A.S., Smith A., McDonald P., Zhang L., Dzau V.J., Melo L.G., (2007) Heme-oxygenase-1-induced protection against hypoxia/reoxygenation is dependent on biliverdin reductase and its interaction with PI3K/Akt pathway. J Mol Cell Cardiol; 43: 580-592.
52. Kaspar J., Niture S., Jaiswal A., (2009) Nrf 2: INrf2 (keap1) signalling in oxidative stress. Free Radic Biol Med; 47: 1304-1309.