QIAN SHI - Academia.edu (original) (raw)

Papers by QIAN SHI

Research paper thumbnail of Anti-AIDS Agents, 4. Tripterifordin, a Novel Anti-HIV Principle from Tripterygium wilfordii: Isolation and Structural Elucidation

Journal of Natural Products, 1992

A new kaurane-type diterpene lactone, tripterifordin [I], has been isolated from the roots of Tri... more A new kaurane-type diterpene lactone, tripterifordin [I], has been isolated from the roots of Tripterygium wilfmdii. The structure of 1 was elucidated by spectroscopic methds, including the concerted application of a number of 2D nmr techniques that involved the 'H-'H COSY, heteronucleus-detected variants of the heteronuclear chemical shift correlation (HETCOR), phase-sensitive NOESY, and long-range HETCOR. Compound 1 shows anti-HIV replication activity in H9 lymphocyte cells with an EC,, of 1 &ml.

Research paper thumbnail of Anti-AIDS Agents, 6. Salaspermic Acid, an Anti-HIV Principle from Tripterycium wilfordii, and the Structureactivity Correlation with its Related Compounds

Journal of Natural Products, 1992

Salaspermic acid [1], an inhibitor of HIV reverse transcriptase and HIV replication in H9 lymphoc... more Salaspermic acid [1], an inhibitor of HIV reverse transcriptase and HIV replication in H9 lymphocyte cells, was isolated from the roots of Tripterygium wilfordii for the first time. The structure of 1 derived from spectral data was established unequivocally by an X-ray analysis of crystals of the monohydrate. A structure-activity correlation of 1 with ten related compounds indicated that the acetal linkage in ring A and the carboxyl group in ring E of 1 may be required for the anti-HIV activity.

Research paper thumbnail of Anti-AIDS Agents, 10. Acacetin7-O-β-D-galactopyranoside, an Anti-HIV Principle from Chrysanthemum morifolium and a StructureActivity Correlation with Some Related Flavonoids

Journal of Natural Products, 1994

Research paper thumbnail of Antitumor Agents, 154. Cytotoxic and Antimitotic Flavonols from Polanisia dodecandra

Journal of Natural Products, 1995

Three flavonols, 5,3'-dihydroxy-3,6,7,8,4'-pentamethoxyflavone [1], 5,4'-... more Three flavonols, 5,3'-dihydroxy-3,6,7,8,4'-pentamethoxyflavone [1], 5,4'-dihydroxy-3,6,7,8,3'-pentamethoxyflavone [2], and quercetin 3-O-beta-D-glucopyranosyl-7-O-alpha-L-rhamnopyranoside [3], were isolated from Polanisia dodecandra. Compound 1 showed remarkable cytotoxicity in vitro against panels of central nervous system cancer (SF-268, SF-539, SNB-75, U-251), non-small cell lung cancer (HOP-62, NCI-H266, NCI-H460, NCI-H522), small cell lung cancer (DMS-114), ovarian cancer (OVCAR-3, SK-OV-3), colon cancer (HCT-116), renal cancer (UO-31), a melanoma cell line (SK-MEL-5), and two leukemia cell lines (HL-60 [TB], SR), with GI50 values in the low micromolar to nanomolar concentration range. This substance also inhibited rubulin polymerization (IC50 = 0.83 +/- 0.2 microM) and the binding of radiolabeled colchicine to tubulin with 59% inhibition when present in equimolar concentrations with colchicine. Compound 2 also showed cytotoxicity against medulloblastoma (TE-671) tumor cells with an ED50 value of 0.98 microgram/ml. Compound 1 appears to be the first example of a flavonol to exhibit potent inhibition of tubulin polymerization and, therefore, warrants further investigation as an antimitotic agent.

Research paper thumbnail of Syntheses and Characterizations of Copper(II) Polymeric Complexes Constructed from 1,2,4,5-Benzenetetracarboxylic Acid

Inorganic Chemistry, 2002

Four polymeric complexes with rectangular grids or channels, [Cu2(btec)(H2O)4*2H2O]n (2), [Cu2(bt... more Four polymeric complexes with rectangular grids or channels, [Cu2(btec)(H2O)4*2H2O]n (2), [Cu2(btec)4/4[Cu(Hbtec)2/2(4,4'-Hbpy)(H2O)2]2*4H2O]n (3), [Cu2(btec)(hmt)(H2O)4*8H2O]n (4), and [Cu3(btec)(OH)2]n (5), were designed and constructed from Cu(II) ion and 1,2,4,5-benzenetetracarboxylic acid along with auxiliary ligands (where H4btec = 1,2,4,5-benzenetetracarboxylic acid, 4,4'-Hbpy = monoprotonated 4,4'-bipyridine, and hmt = hexamethylenetetramine). Complexes 2, 3, and 4 have rectangular pores with the size of 6.5 A x 4.5 A, 6 A x 7 A, and 10.1 A x 11.8 A, respectively, while 5 has a channel of 7.4 A x 9.6 A. The complexes show interesting magnetic properties due to the different coordination modes of the carboxylate groups and the presence of auxiliary ligands. On lowering the temperature, the magnetic interactions in 2 are changed from antiferromagnetic to ferromagnetic. For 3, the antiferromagnetic interactions weaken sharply at low temperature. Complex 4 shows ferromagnetic interactions while 5 is antiferromagnetic.

Research paper thumbnail of Solvothermal syntheses and crystal structures of two metal coordination polymers with double-chain structures

Polyhedron, 2001

Two polymeric complexes, [Cu 2 (btec)(phen) 2 ] n ·(H 2 O) n (1) and [Cd 4 (btec) 2 (phen) 4 (H 2... more Two polymeric complexes, [Cu 2 (btec)(phen) 2 ] n ·(H 2 O) n (1) and [Cd 4 (btec) 2 (phen) 4 (H 2 O) 4 ] n (2) (H 4 btec=1,2,4,5-benzenetetracarboxylic acid; phen =1,10-phenanthroline), were synthesized by solvothermal reactions at 140°C. Both complex 1 and 2 possess infinite double-chain structures, in which each Cu(II) center has a tetrahedral configuration and the Cd(II) centers adopt triangular prismatic and square-based pyramidal configurations simultaneously. The inter-chain face to face p -p interactions among the aromatic rings of phen and the hydrogen bond interactions between aqua molecules and carboxyl O atoms result in 3-D networks in the two complexes. The ESR spectra study of complex 1 shows that there is negligibly small long-range super-exchange interactions between the Cu(II) atoms via benzenecarboxylate bridging.

Research paper thumbnail of Syntheses and Characterizations of Three-Dimensional Channel-like Polymeric Lanthanide Complexes Constructed by 1,2,4,5-Benzenetetracarboxylic Acid

Inorganic Chemistry, 2002

The hydrothermal reaction of YbCl(3) small middle dot6H(2)O with 1,2,4,5-benzenetetracarboxylic d... more The hydrothermal reaction of YbCl(3) small middle dot6H(2)O with 1,2,4,5-benzenetetracarboxylic dianhydride resulted in [[Yb((b)btec)(1/4)((d)btec)(3/6)(H(2)O)(2)](4).6H(2)O](n)() (1) (H(4)btec = 1,2,4,5-benzenetetracarboxylic acid), and the solvothermal reaction of Er(NO(3))(3) small middle dot6H(2)O or TbCl(3).6H(2)O with 1,2,4,5-benzenetetracarboxylic dianhydride in H(2)O/acetic acid gave rise to [[Er(2)((c)btec)(2/4)((e)btec)(2/4)((f)btec)(2/4)(H(2)O)(4)].4H(2)O](n)() (2) and [[Tb(H(2)btec)(2/4)((f)btec)(3/6)(H(2)O)].2H(2)O](n)() (3), respectively. Complex 1 crystallizes in monoclinic space group C2/m with a = 20.8119(5) A, b = 17.6174(1) A, c = 5.7252(2) A, beta = 92.324(1) degrees, and Z = 1. 1 possesses a three-dimensional framework consisting of eight-coordinate ytterbium centers and two kinds of channels along the c axis. Complex 2 crystallizes in triclinic space group P with a = 9.6739(5) A, b = 11.0039(5) A, c = 11.5523 A, alpha = 104.8330(10) degrees, beta = 91.0000(10) degrees, gamma = 114.2570(10) degrees, and Z = 2. 2 has a three-dimensional framework comprising both eight- and nine-coordinate erbium centers and channels along the a axis. Complex 3 crystallizes in monoclinic space group P2(1)/n with a = 10.7246(12) A, b = 7.1693(9) A, c = 17.158(2) A, beta = 97.109(2) degrees, and Z = 4. 3 shows a three-dimensional framework containing nine-coordinate terbium centers and channels along the b axis. Uncoordinated water molecules occupy the channels in the three complexes. TGA and XRPD were determined for the three complexes, and the results illustrate that the framework of 1 is retained upon removal of uncoordinated and coordinated water molecules.

Research paper thumbnail of Identification of interleukin-8 as estrogen receptor-regulated factor involved in breast cancer invasion and angiogenesis by protein arrays

International Journal of Cancer, 2004

With the goal of identifying key factors involved in human breast cancer progression, we applied ... more With the goal of identifying key factors involved in human breast cancer progression, we applied human cytokine antibody arrays we have developed to screen cytokine expression levels in human breast cancer cell lines and identified interleukin (IL)-8 as a key factor involved in breast cancer invasion and angiogenesis. Elevated expression of IL-8 in breast cancer cells was associated with breast cancer invasiveness and angiogenesis. Neutralization of antibody against IL-8 specifically blocked IL-8-mediated tumor cell invasion and angiogenesis. Furthermore, IL-8 levels in human breast cancer cells were closely related to estrogen receptor (ER) status. ER positive cells expressed low levels of IL-8 whereas ER negative cells expressed high levels of IL-8. Expression of exogenous ERα substantially inhibited IL-8 expression. Our findings raise intriguing questions regarding the role of IL-8 in the development and progression of human breast cancer in association with ER status. © 2004 Wiley-Liss, Inc.

Research paper thumbnail of Connexin 43 Suppresses Human Glioblastoma Cell Growth by Down-Regulation of Monocyte Chemotactic Protein 1, as Discovered Using Protein Array Technology1

Previously, we demonstrated that connexin 43 (cx43) suppressed the growth of human glioblastoma c... more Previously, we demonstrated that connexin 43 (cx43) suppressed the growth of human glioblastoma cells. To investigate the molecular mechanisms involved in tumor suppression by cx43, we developed a human cytokine array system, which simultaneously detects the expression of 43 cytokines. By using this new technology, we analyzed the cx43-regulated genes in cx43-transfected cells. The cytokine arrays showed that expression of monocyte chemotactic protein-1 (MCP-1) was profoundly reduced in cx43-transfected cells. RT-PCR, immuno-Western blot, and cDNA microarrays further confirmed this observation. Addition of conditioned medium from control-transfected cells and recombinant MCP-1 to cx43transfected cells significantly enhanced cx43-transfected cell proliferation and colony formation in soft agar. In contrast, addition of neutralization antibody against MCP-1 significantly inhibited cell proliferation in control-transfected cells. Our results suggested that MCP-1 is involved in the suppression of human glioblastoma cell growth by cx43.

Research paper thumbnail of Anti-AIDS Agents, 4. Tripterifordin, a Novel Anti-HIV Principle from Tripterygium wilfordii: Isolation and Structural Elucidation

Journal of Natural Products, 1992

A new kaurane-type diterpene lactone, tripterifordin [I], has been isolated from the roots of Tri... more A new kaurane-type diterpene lactone, tripterifordin [I], has been isolated from the roots of Tripterygium wilfmdii. The structure of 1 was elucidated by spectroscopic methds, including the concerted application of a number of 2D nmr techniques that involved the 'H-'H COSY, heteronucleus-detected variants of the heteronuclear chemical shift correlation (HETCOR), phase-sensitive NOESY, and long-range HETCOR. Compound 1 shows anti-HIV replication activity in H9 lymphocyte cells with an EC,, of 1 &ml.

Research paper thumbnail of Anti-AIDS Agents, 6. Salaspermic Acid, an Anti-HIV Principle from Tripterycium wilfordii, and the Structureactivity Correlation with its Related Compounds

Journal of Natural Products, 1992

Salaspermic acid [1], an inhibitor of HIV reverse transcriptase and HIV replication in H9 lymphoc... more Salaspermic acid [1], an inhibitor of HIV reverse transcriptase and HIV replication in H9 lymphocyte cells, was isolated from the roots of Tripterygium wilfordii for the first time. The structure of 1 derived from spectral data was established unequivocally by an X-ray analysis of crystals of the monohydrate. A structure-activity correlation of 1 with ten related compounds indicated that the acetal linkage in ring A and the carboxyl group in ring E of 1 may be required for the anti-HIV activity.

Research paper thumbnail of Anti-AIDS Agents, 10. Acacetin7-O-β-D-galactopyranoside, an Anti-HIV Principle from Chrysanthemum morifolium and a StructureActivity Correlation with Some Related Flavonoids

Journal of Natural Products, 1994

Research paper thumbnail of Antitumor Agents, 154. Cytotoxic and Antimitotic Flavonols from Polanisia dodecandra

Journal of Natural Products, 1995

Three flavonols, 5,3'-dihydroxy-3,6,7,8,4'-pentamethoxyflavone [1], 5,4'-... more Three flavonols, 5,3'-dihydroxy-3,6,7,8,4'-pentamethoxyflavone [1], 5,4'-dihydroxy-3,6,7,8,3'-pentamethoxyflavone [2], and quercetin 3-O-beta-D-glucopyranosyl-7-O-alpha-L-rhamnopyranoside [3], were isolated from Polanisia dodecandra. Compound 1 showed remarkable cytotoxicity in vitro against panels of central nervous system cancer (SF-268, SF-539, SNB-75, U-251), non-small cell lung cancer (HOP-62, NCI-H266, NCI-H460, NCI-H522), small cell lung cancer (DMS-114), ovarian cancer (OVCAR-3, SK-OV-3), colon cancer (HCT-116), renal cancer (UO-31), a melanoma cell line (SK-MEL-5), and two leukemia cell lines (HL-60 [TB], SR), with GI50 values in the low micromolar to nanomolar concentration range. This substance also inhibited rubulin polymerization (IC50 = 0.83 +/- 0.2 microM) and the binding of radiolabeled colchicine to tubulin with 59% inhibition when present in equimolar concentrations with colchicine. Compound 2 also showed cytotoxicity against medulloblastoma (TE-671) tumor cells with an ED50 value of 0.98 microgram/ml. Compound 1 appears to be the first example of a flavonol to exhibit potent inhibition of tubulin polymerization and, therefore, warrants further investigation as an antimitotic agent.

Research paper thumbnail of Syntheses and Characterizations of Copper(II) Polymeric Complexes Constructed from 1,2,4,5-Benzenetetracarboxylic Acid

Inorganic Chemistry, 2002

Four polymeric complexes with rectangular grids or channels, [Cu2(btec)(H2O)4*2H2O]n (2), [Cu2(bt... more Four polymeric complexes with rectangular grids or channels, [Cu2(btec)(H2O)4*2H2O]n (2), [Cu2(btec)4/4[Cu(Hbtec)2/2(4,4'-Hbpy)(H2O)2]2*4H2O]n (3), [Cu2(btec)(hmt)(H2O)4*8H2O]n (4), and [Cu3(btec)(OH)2]n (5), were designed and constructed from Cu(II) ion and 1,2,4,5-benzenetetracarboxylic acid along with auxiliary ligands (where H4btec = 1,2,4,5-benzenetetracarboxylic acid, 4,4'-Hbpy = monoprotonated 4,4'-bipyridine, and hmt = hexamethylenetetramine). Complexes 2, 3, and 4 have rectangular pores with the size of 6.5 A x 4.5 A, 6 A x 7 A, and 10.1 A x 11.8 A, respectively, while 5 has a channel of 7.4 A x 9.6 A. The complexes show interesting magnetic properties due to the different coordination modes of the carboxylate groups and the presence of auxiliary ligands. On lowering the temperature, the magnetic interactions in 2 are changed from antiferromagnetic to ferromagnetic. For 3, the antiferromagnetic interactions weaken sharply at low temperature. Complex 4 shows ferromagnetic interactions while 5 is antiferromagnetic.

Research paper thumbnail of Solvothermal syntheses and crystal structures of two metal coordination polymers with double-chain structures

Polyhedron, 2001

Two polymeric complexes, [Cu 2 (btec)(phen) 2 ] n ·(H 2 O) n (1) and [Cd 4 (btec) 2 (phen) 4 (H 2... more Two polymeric complexes, [Cu 2 (btec)(phen) 2 ] n ·(H 2 O) n (1) and [Cd 4 (btec) 2 (phen) 4 (H 2 O) 4 ] n (2) (H 4 btec=1,2,4,5-benzenetetracarboxylic acid; phen =1,10-phenanthroline), were synthesized by solvothermal reactions at 140°C. Both complex 1 and 2 possess infinite double-chain structures, in which each Cu(II) center has a tetrahedral configuration and the Cd(II) centers adopt triangular prismatic and square-based pyramidal configurations simultaneously. The inter-chain face to face p -p interactions among the aromatic rings of phen and the hydrogen bond interactions between aqua molecules and carboxyl O atoms result in 3-D networks in the two complexes. The ESR spectra study of complex 1 shows that there is negligibly small long-range super-exchange interactions between the Cu(II) atoms via benzenecarboxylate bridging.

Research paper thumbnail of Syntheses and Characterizations of Three-Dimensional Channel-like Polymeric Lanthanide Complexes Constructed by 1,2,4,5-Benzenetetracarboxylic Acid

Inorganic Chemistry, 2002

The hydrothermal reaction of YbCl(3) small middle dot6H(2)O with 1,2,4,5-benzenetetracarboxylic d... more The hydrothermal reaction of YbCl(3) small middle dot6H(2)O with 1,2,4,5-benzenetetracarboxylic dianhydride resulted in [[Yb((b)btec)(1/4)((d)btec)(3/6)(H(2)O)(2)](4).6H(2)O](n)() (1) (H(4)btec = 1,2,4,5-benzenetetracarboxylic acid), and the solvothermal reaction of Er(NO(3))(3) small middle dot6H(2)O or TbCl(3).6H(2)O with 1,2,4,5-benzenetetracarboxylic dianhydride in H(2)O/acetic acid gave rise to [[Er(2)((c)btec)(2/4)((e)btec)(2/4)((f)btec)(2/4)(H(2)O)(4)].4H(2)O](n)() (2) and [[Tb(H(2)btec)(2/4)((f)btec)(3/6)(H(2)O)].2H(2)O](n)() (3), respectively. Complex 1 crystallizes in monoclinic space group C2/m with a = 20.8119(5) A, b = 17.6174(1) A, c = 5.7252(2) A, beta = 92.324(1) degrees, and Z = 1. 1 possesses a three-dimensional framework consisting of eight-coordinate ytterbium centers and two kinds of channels along the c axis. Complex 2 crystallizes in triclinic space group P with a = 9.6739(5) A, b = 11.0039(5) A, c = 11.5523 A, alpha = 104.8330(10) degrees, beta = 91.0000(10) degrees, gamma = 114.2570(10) degrees, and Z = 2. 2 has a three-dimensional framework comprising both eight- and nine-coordinate erbium centers and channels along the a axis. Complex 3 crystallizes in monoclinic space group P2(1)/n with a = 10.7246(12) A, b = 7.1693(9) A, c = 17.158(2) A, beta = 97.109(2) degrees, and Z = 4. 3 shows a three-dimensional framework containing nine-coordinate terbium centers and channels along the b axis. Uncoordinated water molecules occupy the channels in the three complexes. TGA and XRPD were determined for the three complexes, and the results illustrate that the framework of 1 is retained upon removal of uncoordinated and coordinated water molecules.

Research paper thumbnail of Identification of interleukin-8 as estrogen receptor-regulated factor involved in breast cancer invasion and angiogenesis by protein arrays

International Journal of Cancer, 2004

With the goal of identifying key factors involved in human breast cancer progression, we applied ... more With the goal of identifying key factors involved in human breast cancer progression, we applied human cytokine antibody arrays we have developed to screen cytokine expression levels in human breast cancer cell lines and identified interleukin (IL)-8 as a key factor involved in breast cancer invasion and angiogenesis. Elevated expression of IL-8 in breast cancer cells was associated with breast cancer invasiveness and angiogenesis. Neutralization of antibody against IL-8 specifically blocked IL-8-mediated tumor cell invasion and angiogenesis. Furthermore, IL-8 levels in human breast cancer cells were closely related to estrogen receptor (ER) status. ER positive cells expressed low levels of IL-8 whereas ER negative cells expressed high levels of IL-8. Expression of exogenous ERα substantially inhibited IL-8 expression. Our findings raise intriguing questions regarding the role of IL-8 in the development and progression of human breast cancer in association with ER status. © 2004 Wiley-Liss, Inc.

Research paper thumbnail of Connexin 43 Suppresses Human Glioblastoma Cell Growth by Down-Regulation of Monocyte Chemotactic Protein 1, as Discovered Using Protein Array Technology1

Previously, we demonstrated that connexin 43 (cx43) suppressed the growth of human glioblastoma c... more Previously, we demonstrated that connexin 43 (cx43) suppressed the growth of human glioblastoma cells. To investigate the molecular mechanisms involved in tumor suppression by cx43, we developed a human cytokine array system, which simultaneously detects the expression of 43 cytokines. By using this new technology, we analyzed the cx43-regulated genes in cx43-transfected cells. The cytokine arrays showed that expression of monocyte chemotactic protein-1 (MCP-1) was profoundly reduced in cx43-transfected cells. RT-PCR, immuno-Western blot, and cDNA microarrays further confirmed this observation. Addition of conditioned medium from control-transfected cells and recombinant MCP-1 to cx43transfected cells significantly enhanced cx43-transfected cell proliferation and colony formation in soft agar. In contrast, addition of neutralization antibody against MCP-1 significantly inhibited cell proliferation in control-transfected cells. Our results suggested that MCP-1 is involved in the suppression of human glioblastoma cell growth by cx43.