Department of Chemistry

Ming Xian Research Group


Publications from independent research (WSU)

79.           Ida, T.; Sawa, T.; Ihara, H.; Tsuchiya, Y.; Watanabe, Y.; Kumagai, Y.; Suematsu, M.; Motohashi, H.; Fujii, S.; Matsunaga, T.; Yamamoto, M.; Ono, K.; Devarie-Baez, N. O.; Xian, M.; Fukuto, J. M.; Akaike, T. “Reactive cysteine persulfides and S-polythiolation regulate oxidative stress and redox signaling”. Proc. Natl. Acad. Sci. USA2014, in press.

78.          Zhang, D.; Chen, W.; Miao, Z.; Ye, Y.; Zhao, Y.; King, S. B.; Xian, M. “A reductive ligation based fluorescent probe for S-nitrosothiols”. Chem. Commun2014, in press, DOI: 10.1039/C4CC01288G.

77.          Li, Y.-J.; Chen, J.; Xian, M.; Zhou, L.-G.; Han, F. X.; Gan, L.-J.; Shi, Z.-Q. “In site bioimaging of hydrogen sulfide uncovers its pivotal role in regulating nitric oxide-induced lateral root formation.” PLOS One20149, e90340.

76.          Zhang, D.; Macinkovic, I.; Devarie-Baez, N. O.; Pan, J.; Park, C.-M.; Carroll, K. S.; Filipovic, M. R.; Xian, M. “Detection of Protein S-Sulfhydration by a Tag-Switch Technique.” Angew. Chem. Int. Ed. 2014, 53, 575 –581. (selected as a hot paper for the months, January/February, of European Network on Gasotransmitters)

75.          Peng, B.; Chen, W.; Liu, C.; Rosser, E. W., Pacheco, A.; Zhao, Y.; Aguilar, H. C.; Xian, M. “Fluorescent probes on nucleophilic substitution-cyclization for hydrogen sulfide detection and bioimaging.” Chem. Eur. J. 2014, 20, 1010 – 1016.

74.          Park, C.-M.; Zhao, Y.; Zhu, Z.; Pacheco, A.; Peng, B. Devarie-Baez, N.; Bagdon, P.; Zhang, H.; Xian, M. “Synthesis and evaluation of phosphorodithioate-based hydrogen sulfide donors” Mol. BioSys. 2013, 9, 2430-2434

73.          Devarie-Baez, N.; Bagdon, P.; Peng, B.; Zhao, Y.; Park, C.-M., Xian, M. “Light-induced hydrogen sulfide release from “Caged” gem-dithiols” Org. Lett2013, 15, 2786-2789.

72.          Chen, W.; Liu, C.; Peng, B.; Zhao, Y.; Pacheco, A.; Xian, M. “New fluorescent probe for sulfane sulfurs and the application in bioimaging” Chemical Science 2013, 4, 2892-2896.  (highlighted in ChemistryWorld).

71.          Devarie, N. O.; Zhang, D.; Li, S.; Whorton, A. R. Xian, M. “Direct methods for the detection of protein S-nitrosation”. Methods 2013, 62, 171-176.

70           Zhao, Y.; Bhushan, S.; Yang, C.; Otsuka, H.; Stein, J. D.; Pacheco, A.; Peng, B.; Devarie, N. O.; Aguilar, H. C.; Lefer, D. J.; Xian, M. “Controllable hydrogen sulfide donors and the activity against myocardial ischemia-reperfusion injury” ACS Chem. Biol. 2013, 8, 1283-1290. (highlighted in C&EN)

69.          Markand, S.; Tawfik, A.; Ha, Y.; Gnana-Prakasam, J.; Sonne, S.; Ganapathy, V.; Sen, N.; Xian, M.; Smith, S. B. “Cystathionine beta synthase expression in mouse retina”. Curr. Eye. Res. 2013, 38, 597-604.

68.          Talipov, M. R.; Khomyakov, D. G.; Xian, M.; Timerghazin, Q. K. “Computational design of S-nitrosothiol ‘Click’ reactions”. J. Comput. Chem. 2013. 34, 1527-1530.

67.          Zhang, D.; Devarie-Baez, N. O.; Li, Q.; Lancaster, J. R. Jr.; Xian, M. “Methylsulfonyl benzothiozole (MSBT): a selective protein thiol blocking reagent”. Org. Lett. 2012, 14, 3396.

66.          Park, C. –M.; Niu, W.; Liu, C.; Biggs, T. D.; Guo, J.; Xian, M. “A proline based phosphine template for Staudinger ligation”. Org. Lett. 2012, 14, 4697.

65.          Liu, C.; Peng, B.; Li, S.; Park, C. –M.; Whorton, A. R.; Xian, M. “Reaction based fluorescent probes for hydrogen sulfide”. Org. Lett. 2012, 14, 2184.

64.          Li, S.; Wang, H.; Xian, M.; Whorton, A. R. “Identification of protein nitrosothiols using phosphine-mediated selective reduction”. Nitric Oxide 2012, 26, 20.

63.          Liu, C.; Pan, J.; Li, S.; Zhao, Y.; Wu, L. Y.; Berkman, C. E.; Whorton, A. R.; Xian, M. “Capture and visualization of hydrogen sulfide by a fluorescent probe”. Angew. Chem. Int. Ed. 2011, 50, 10327.

62.          Pan, J.; Devarie, N. O.; Xian, M. “Facile amide formation via S-nitrosothioacids”. Org. Lett. 2011, 13, 1092.

61.          Liu, X.; Wang, Y.; Cao, Y.; Yadama, V.; Xian, M.; Zhang, J. “Study of dextrin-derived curing agent for waterborne epoxy adhesive. Carbohyd. Polym. 2011, 83, 1180.

60.          Zhao, Y.; Wang, H.; Xian, M. “Cysteine activated hydrogen sulfide (H2S) donors”. J. Am. Chem. Soc. 2011, 133, 15.

59.          Wang, H.; Xian, M. “Chemical methods to detect S-nitrosation”. Curr. Opin. Chem. Biol. 2011, 15, 32.

58.          Pan, J.; Xian, M. “Disulfide formation via sulfenamides”. Chem. Commun. 2011, 352. (Emerging Investigators Issue).

57.          Zhang, D. H.; Davarie-Baez, N. O.; Pan, J.; Wang, H.; Xian, M. “One-pot thioether formation from S-nitrosothiols“. Org. Lett. 2010. 12, 5674.

56.          Zhang, J.; Li, S.; Zhang, D.; Wang, H.; Whorton, R.; Xian, M. “Reductive ligation mediated one-step disulfide formation of S-nitrosothiols“. Org. Lett. 2010, 12, 4208.

55.          Devarie, N.; Xian, M. “Facile preparation of 3-substituted benzisothiazoles from o-mercapto-acylphenones”. Org. Lett. 2010, 12, 752.

54.          Wang, H.; Zhang, J.; Xian, M. “Facile formation of dehydroalanine from S-nitrosocysteines”. J. Am. Chem. Soc. 2009, 131, 13238.

53.          Wang, H.; Liu, X.; Liu, B.; Zhang, J.; Xian, M. “Synthesis of rosin-based flexible anhydride type curing agents and properties of the cured epoxy”. Polym. Int. 2009, 58, 1435.

52.          Zhang, J.; Wang, H.; Xian, M. “An unexpected bis-ligation of S-nitrosothiols”. J. Am. Chem. Soc. 2009, 131, 3854. (this work is featured by Chemical & Engineering News 2009, March 16, Vol 87).

51.          Devarie, N.; Kim, W.; Smith, A. B. III, Xian, M. “Multicomponent type II anion relay chemistry (ARC): one-pot syntheses of 2,3-disubstituted furans and thiophenes exploiting 2-trialkylsilyl-3-formyl bifunctional linchpins”. Org. Lett. 2009, 11, 1861.

50.          Pan, J.; Downing, J. A.; McHale, J. L.; Xian, M. “A fluorogenic dye activated by S-nitrosothiols”. Mol. BioSyst. 2009, 5, 918. (Emerging Investigators Issue)

49.          Zhang, J.; Wang, H.; Xian, M. “Exploration of the traceless reductive ligation of S-nitrosothiols”. Org. Lett. 2009, 11, 477.

48.          Wang, H.; Liu, B.; Liu, X.; Zhang, J.; Xian, M. “Synthesis of biobased epoxy and curing agents using rosin and study of cure reactions”. Green Chem. 2008, 10, 1190.

47.          Wang, H.; Shuhler, B. J.; Xian, M. “Total synthesis of diospongins A and B”. Synlett 2008, 2651.

46.          Wang, H.; Xian, M. “Fast reductive ligation of S-nitrosothiols”. Angew Chem. Int. Ed. 2008, 47, 6598.

45.          Xian, M.; Zhu, C-J. “2-[Bis-(3,5-bistrifluoromethyl)-phenyl]-[(trimethylsilyl)oxy]-methyl]-pyrrolidine. Encyclo. Reagents for Org. Syn. 2008.

44.          Devarie, N.; Shuhler, B. J.; Wang, H.; Xian, M. “Solvent controlled C(sp2)O silyl migration: the one-pot synthesis of 2,3-disubstituted thiophenes”  Org. Lett. 2007, 9, 4655.

43.          Wang, H.; Shuhler, B. J. Xian, M. “A versatile strategy for the synthesis of 2,6-disubstituted dihydropyranones” J. Org. Chem. 2007, 72, 4280.

42.          Xian, M.; Shuhler, B. J. “Study of the synthesis of poecillanosine” Tetrahedron Lett. 2007, 48, 1209.


Publications from postdoctoral research (UPenn)

41.          Shaw, S. J.; Menzella, H. G.; Myles, D. C.; Xian, M.; Smith, A. B., III. “Coumarin-derived discodermolide analogues possessing equivalent antiproliferative activity as the natural product-a further simplification of the lactone region” Org. Biomol. Chem., 2007, 5, 2753.

40.          Smith, A. B., III; Kim, D.-S.; Xian, M. “Anion relay chemistry extended.  Synthesis of a gorgonian sesquiterpene” Org. Lett. 2007, 9, 3307.

39.          Smith, A. B., III; Xian, M.; Kim, W. –S.; Kim, D.-S. “The 1,5-Brook rearrangement: an initial application in anion relay chemistry” J. Am. Chem. Soc. 2006, 128, 12368.

38.          Smith, A. B., III; Xian, M. “Anion relay chemistry: an effective tactic for diversity oriented synthesis” J. Am. Chem. Soc. 2006, 128, 66. (This work is featured by Chemical & Engineering News 2006, January 2, Vol 84).

37.          Smith, A. B., III; Xian, M. “Design, synthesis and biological evaluation of simplified analogues of discodermolide, additional insights on the importance of the diene, the C(7) hydroxyl, and the lactone” Org. Lett. 2005, 7, 5229.

36.          Smith, A. B., III; Xian, M.; Liu, F. “Design, total synthesis and evaluation of C13,C14 cyclopropane analogues of discodermolide” Org. Lett. 2005, 7, 4613.

35.          Shaw, S. J.; Sundermann, K. F.; Burlingame, M. A.; Myles, D. C.; Freeze, B. S.; Xian, M.; Brouard, I.; Smith, A. B., III. “Toward understanding how the lactone moiety of discodermolide affects activity” J. Am. Chem. Soc. 2005, 127, 6532.

34.          Smith, A. B., III; Freeze, B. S.; Xian, M.; Hirose, T. “Total synthesis of (+)-Discodermolide: A highly convergent fourth-generation approach” Org. Lett. 2005, 7. 1825.

33.          Smith, A. B., III; Freeze, B. S.; LaMarche, M. J.; Hirose, T.; Brouard, I.; Xian, M.; Myles, D. C.; Sundermann, K. F.; Shaw, S. J.; Burlingame, M. A. “Design, synthesis and evaluation of analogues of (+)-14-normethyldiscodermolide” Org. Lett. 2005, 7, 315.

32.          Smith, A. B. III; Freeze, B. S.; LaMarche, M. J.; Hirose, T.; Brouard, I.; Rucker, P. V.; Xian, M.; Myles, D. C.; Sundermann, K. F.; Shaw, S. J.; Burlingame, M. A. “Carbamate-substituted analogues of (+)-discodermolide” Org. Lett. 2005, 7, 311.


Publications from graduate research (Nankai & Wayne State)

31.          Zhu, L.; Kedenburg, J.; Xian, M.; Wang, P. G. “A systematic strategy for preparation of uncommon sugars through enzymatic resolution and ring closing metathesis” Tetrahedron Lett., 2005, 46, 811-813.

30.          Cheng, H.; Xian, M.; Wu, J.; Tunac, J. B.; Sun, D.; Wang, P. G. “Synthesis and enzyme-specific activation of carbohydrate-geldanamycin conjugates with potent anticancer activity” J. Med. Chem. 2005, 48, 645-652.

29.          Xian, M.; Fatima, Z.; Zhang, W.; Fang, J.; Pei, D.; Loo, J.; Stevenson, T.; Wang, P. G. “Identification of alpha-Gal epitope mimetics through rapid generation and screening of C-linked glycopeptide library” J. Comb. Chem. 2004, 6, 126-134.

28.          Jia, Q.; Cai, T.; Huang, M. Li, H.; Xian, M.; Poulos, T. L.; Wang, P. G. “Isoform-selective substrates of nitric oxide synthases” J. Med. Chem., 2003, 46, 2271.

27.          Li, H.; Shimizu, H.; Flinspach, M.; Jamal, J.; Yang, W.; Xian, M.; Cai, T.; Wen, Z.; Jia, Q.; Wang, P. G.; Poulos, T. L. “The novel binding mode of N-alkyl-N’-hydroxyguanidine to nNOS provide mechanistic insights into NO biosynthesis” Biochemistry 2002, 41, 13868.

26.          Jia, Q.; Janczuk, A.; Cai, T.; Xian, M.; Wen, Z.; Wang, P. G. “NO donors with anticancer activity” Expt. Opin. Therap. Pat. 2002. 12, 819.

25.          Cai, T. W.; Xian, M.; Wang, P. G. “Electrochemical and peroxidase oxidation study of N-hydroxyguanidine derivatives as NO donors” Bioorg. Med. Chem. Lett. 2002, 12, 1507.

24.          Wu, X.; Tang, X.; Xian, M.; Brauschweiger, P. G.; Wang, P. G. “Synthesis and cytotoxicities of mannose conjugated SNAP” Bioorg. Med. Chem. 2002, 10, 2303.

23.          Xian, M.; Fujiwara, N.; Cai, T.; Wen, Z.; Kazuma, S.; Janczuk, A.; Tang, X.; Telyatnikov, V.; Miyamoto, Y.; Taniguchi, N.; Wang, P. G. “Novel substrates for nitric oxide synthases” Bioorg. Med. Chem. 2002, 10, 3049-3055.

22.          Wang, P. G.; Xian, M.; Tang, X. -P.; Wu, X. –J; Wen, Z.; Cai, T. –W. “Nitric oxide donors: chemical activities and biological applications” Chem. Rev. 2002, 102, 1091.

21.          Chen, X. C.; Wen, Z.; Xian, M.; Wang, K.; Ramachandran, N.; Schlegel, H. B.; Mutus, B.; Wang, P. G.  “Fluorophore-labeled S-nitrosothiols”  J. Org. Chem., 2001, 66, 6064.

20.          Xian, M.; Li, X. P.; Tang, X. P.; Chen, X. C.; Zheng, X. L.; Galligan, J. J.; Kreulen, D. L.; Wang, P. G.  “N-hydroxyl derivatives of guanidine based drugs as enzymatic NO donors”  Bioorg. Med. Chem. Lett. 2001, 11, 2377-2380.

19.          Wu, X. J.; Tang, X. P.; Xian, M.; Wang, P. G.  “Glycosylated diazeniumdiolates: a novel class of enzyme-activated nitric oxide donors”  Tetrahedron Lett. 2001, 42, 3779.

18.          Tang, X. P.; Xian, M.; Trikha, M.; Honn, K. V.; Wang, P. G. “Synthesis of peptide-diazeniumdiolate conjugates: towards enzyme activated antitumor agents”  Tetrahedron Lett. 2001, 42, 2625.

17.          Wang, K.; Wen, Z.; Zhang, W.; Xian, M.; Cheng, J. P.; Wang, P. G.  “Equilibrium and kinetics studies of transnitrosation between S-nitrosothiols and thiols”  Bioorg. Med. Chem. Lett. 2001, 11, 433.

16.          Guo, Z.-M.; Xian, M.; Zhang, W.; McGill, A.; Wang, P. G.  “N-Nitrosoanilines: A new class of caspase-3 inhibitors”  Bioorg. Med. Chem. 2001, 9, 99.

15.          Zhu, X.-Q.; He, J.; Li, Q.; Xian, M.; Lu, J. M.; Cheng, J.-P. “N-NO bond dissociation energies of N-nitroso diphenylamine derivatives (or analogues) and their radical anions: Implications for the effect of reductive electron transfer on N-NO bond activation and for the mechanisms of NO transfer to nitranions” J. Org. Chem. 2000, 65, 6729.

14.          Lu, J.; Zhu, X.; Li, Q.; He, J.; Xian, M.; Cheng, J.-P. “Determination of heterolytic and homolytic S-NO bond dissociation energies in acetonitrile” Chem. J. Chin. Univ. 2000, 21, 570.

13.          Xian, M.; Wang, M.; Chen, X.-C.; Wang, K.; Wang, P. G. “S-Nitrosothiols as novel, reversible inhibitors of human rhinovirus 3C protease” Bioorg. Med. Chem. Lett. 2000, 10, 2097-2100.

12.          Xian, M.; Chen, X. -C.; Liu, Z.; Wang, K.; Wang, P. G.  “Inhibition of papain by S-nitrosothiols: formation of mixed disulfides”  J. Biol. Chem. 2000, 275, 20467-20473.

11.          Wang, K.; Zhang, W.; Xian, M.; Chen, X. –C.; Cheng, J. –P.; Wang, P. G. “New chemical and biological aspects of S-nitrosothiols” Curr. Med. Chem. 2000. 7, 821.

10.          Xian, M.; Zhu, X. –Q.; Lu, J. –M.; Wen, Z.; Cheng, J. –P. “The first O-NO bond energy scale in solution: heterolytic and homolytic cleavage enthalpies of O-nitrosyl carboxylate compounds”. Org. Lett. 2000, 2, 265-268.

9.            Xian, M.; Wang, K.; Chen, X. –C.; McGill, A.; Zhang, Z. –Y.; Cheng, J. –P.; Wang, P. G. “Inhibition of protein tyrosine phosphatases by low-molecular-weight S-nitrosothiols and S-nitrosylated human serum albumin”.  Biochem. Biophys. Res. Commun. 2000, 268, 310-314.

8.            Wang, K.; Hou, Y. C.; Zhang, W.; Ksebati, M. B.; Xian, M.; Cheng, J. –P.; Wang, P. G. “N15 NMR and electronic properties of S-nitrosothiols”.  Bioorg. Med. Chem. Lett.  1999, 9, 2897.

7.            Zhu, X. –Q.; Xian, M.; Wang, K.; Cheng, J. –P. “Is NO (nitric oxide) an electron acceptor or an electrophile? A detailed thermodynamic investigation on the mechanisms of NO-initiated reactions with 3,6-dibromocarbazolide anion and related carbanion”. J. Org. Chem. 1999, 64, 4187-4190.

6.            Xian, M.; Zhu, X. –Q.; Li, Q.; Cheng, J. –P. “A high-yielding and facile preparation of N-substituted thioureas by substitution of nitrosothioureas with alkylamines”.  Tetrahedron. Lett. 1999, 40, 1957.

5.            Cheng, J. -P.; Xian, M.; Wang, K.; Zhu, X. –Q.; Yin, Z.; Wang, P. G. “Heterolytic and homolytic Y-NO bond energy scales of nitroso-containing compounds: Chemical origin of NO release and NO capture”  J. Am. Chem. Soc. 1998, 120, 10266-10267.

4.            Xian, M.; Lu, J. –M.; Zhu, X. –Q.; Mu, L. –J.; Cheng, J. –P. “ A facile and high-yielding preparation of 1-aryl-3,3-dialkylureas”. J. Chem. Res. (S). 1998, 442.

3.            Lu, Y.; Xian, M.; Zhu, X. –Q.; Mu, L. -J.; Cheng, J. P. “Studies on structure-reactivity relationship for NAD(P)H model compounds: Electronic effect of the 3-acyls”. Chem. J. Chinese. U. 1999, 20, 59.

2.            Lu, Y.; Xian, M.; Cheng, J. –P.; Xia, C. –Z. “Investigation on the reduction of carbocations by BNAH – Kinetics, thermodynamics, and reaction mechanisms”.  Acta. Chim. Sinica. 1997, 55, 1145.

1.            Lu, Y.; Xian, M.; Cheng, J. –P. “Studies on the Mg2+-catalyzed reductions of N-arylfluorenimines by NAD(P)H models”.  Chem. J. Chinese. U. 1997, 18, 1484.

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