Communication
Organic & Biomolecular Chemistry
J. A. O’Meara, R. Plante, B. Simoneau, B. Thavonekham,
M. Bos and M. G. Cordingley, Bioorg. Med. Chem. Lett.,
2004, 14, 739–742.
Notes and references
‡At physiological pH and 25 °C, H2S dissociates into an equilibrium between
H2S and HS−, with pKa(H2S/HS−) = 6.97 (the second pKa(HS−/S2−) is well above
14). In this paper “H2S” refers to the mixture of the two forms obtained by dis-
solving the salt NaSH in a buffer solution, their respective proportions being
fixed by the pH of the buffer.
17 R. Romagnoli, P. G. Baraldi, C. L. Cara, E. Hamel, G. Basso,
R. Bortolozzi and G. Viola, Eur. J. Med. Chem., 2010, 45,
5781–5791.
§During the writing of this paper, Akaike et al. nicely showed that 8-SH-cGMP 18 Y. Saito, H. Taguchi, S. Fujii, T. Sawa, E. Kida, C. Kabuto,
(up to 3 µM after 3 hours in Tris buffer pH 7.4, 37 °C) is formed when 8-NO2-
T. Akaike and H. Arimoto, Chem. Commun., 2008,
5984–5986.
19 M. N. Hughes, M. N. Centelles and K. P. Moore, Free
Radical Biol. Med., 2009, 47, 1346–1353.
cGMP (1 mM) is reacted with a thiol (GSH, 100 µM), H2S (100 µM) and a NO
donor (P-NONOate, 100 µM). They proposed the implication of persulfides/poly-
sulfides in this transformation.36
20 G. W. Luther 3rd, A. J. Findlay, D. J. Macdonald,
S. M. Owings, T. E. Hanson, R. A. Beinart and P. R. Girguis,
Front. Microbiol., 2011, 2, 62.
1 Special issue of Antioxid. Redox Signaling, 2012, 17, 1–186.
2 G. K. Kolluru, X. Shen, S. C. Bir and C. G. Kevil, Nitric
Oxide, 2013, 35C, 5–20.
21 J. A. Squella, S. Bollo and L. J. Nunez-Vergara, Curr. Org.
Chem., 2005, 9, 565–581.
3 G. K. Kolluru, X. Shen and C. G. Kevil, Redox Biol., 2013, 1,
313–318.
22 T. Sawa, T. Akaike, K. Ichimori, T. Akuta, K. Kaneko,
H. Nakayama, D. J. Stuehr and H. Maeda, Biochem. Biophys.
Res. Commun., 2003, 311, 300–306.
4 A. K. Mustafa, M. M. Gadalla, N. Sen, S. Kim, W. Mu,
S. K. Gazi, R. K. Barrow, G. Yang, R. Wang and
S. H. Snyder, Sci. Signal., 2009, 2, ra72.
23 K. Stolze, N. Udilova and H. Nohl, Free Radical Biol. Med.,
2000, 29, 1005–1014.
5 B. D. Paul and S. H. Snyder, Nat. Rev. Mol. Cell Biol., 2012,
13, 499–507.
24 K. Asada and S. Kanematsu, Agric. Biol. Chem., 1976, 40,
1891–1892.
25 D. G. Searcy, J. P. Whitehead and M. J. Maroney, Arch.
Biochem. Biophys., 1995, 318, 251–263.
26 A. Rockenbauer and L. Korecz, Appl. Magn. Reson., 1996,
10, 29–43.
27 S. Carballal, M. Trujillo, E. Cuevasanta, S. Bartesaghi,
M. N. Moller, L. K. Folkes, M. A. Garcia-Bereguiain,
C. Gutierrez-Merino, P. Wardman, A. Denicola, R. Radi and
B. Alvarez, Free Radical Biol. Med., 2011, 50, 196–205.
28 D. I. Edwards, Biochem. Pharmacol., 1986, 35, 53–58.
29 S. K. Maity, N. C. Pradhan and A. V. Patwardhan, Chem.
Eng. J., 2008, 141, 187–193.
30 M. Hojo, Y. Takagi and Y. Ogata, J. Am. Chem. Soc., 1960,
82, 2459–2462.
31 P. Wardman, Environ. Health Perspect., 1985, 64, 309–320.
32 M. Hoffman, A. Rajapakse, X. Shen and K. S. Gates, Chem.
Res. Toxicol., 2012, 25, 1609–1615.
6 M. M. Cortese-Krott, B. O. Fernandez, J. L. Santos,
E. Mergia, M. Grman, P. Nagy, M. Kelm, A. Butler and
M. Feelisch, Redox Biol., 2014, 2, 234–244.
7 M. R. Filipovic, J. L. Miljkovic, T. Nauser, M. Royzen,
K. Klos, T. Shubina, W. H. Koppenol, S. J. Lippard and
I. Ivanovic-Burmazovic, J. Am. Chem. Soc., 2012, 134,
12016–12027.
8 M. Nishida, T. Sawa, N. Kitajima, K. Ono, H. Inoue,
H. Ihara, H. Motohashi, M. Yamamoto, M. Suematsu,
H. Kurose, A. van der Vliet, B. A. Freeman, T. Shibata,
K. Uchida, Y. Kumagai and T. Akaike, Nat. Chem. Biol.,
2012, 8, 714–724.
9 T. Sawa, M. H. Zaki, T. Okamoto, T. Akuta, Y. Tokutomi,
S. Kim-Mitsuyama, H. Ihara, A. Kobayashi, M. Yamamoto,
S. Fujii, H. Arimoto and T. Akaike, Nat. Chem. Biol., 2007, 3,
727–735.
10 S. Fujii and T. Akaike, Antioxid. Redox Signaling, 2013, 19,
1236–1246.
33 Y. Saito, T. Sawa, J. Yoshitake, C. Ito, S. Fujii, T. Akaike and
H. Arimoto, Mol. BioSyst., 2012, 8, 2909–2915.
34 J. I. Toohey, Anal. Biochem., 2011, 413, 1–7.
35 R. Greiner, Z. Palinkas, K. Basell, D. Becher, H. Antelmann,
P. Nagy and T. P. Dick, Antioxid. Redox Signaling, 2013, 19,
1749–1765.
36 T. Ida, T. Sawa, H. Ihara, Y. Tsuchiya, Y. Watanabe,
Y. Kumagai, M. Suematsu, H. Motohashi, S. Fujii,
T. Matsunaga, M. Yamamoto, K. Ono, N. O. Devarie-Baez,
M. Xian, J. M. Fukuto and T. Akaike, Proc. Natl. Acad.
Sci. U. S. A., 2014, DOI: 10.1073/pnas.1321232111.
37 Y. Kimura, Y. Mikami, K. Osumi, M. Tsugane, J. Oka and
H. Kimura, FASEB J., 2013, 27, 2451–2457.
11 H. K. Porter, Org. React., 1973, 20.
12 L. A. Montoya and M. D. Pluth, Chem. Commun., 2012, 48,
4767–4769.
13 M. Y. Wu, K. Li, J. T. Hou, Z. Huang and X. Q. Yu, Org.
Biomol. Chem., 2012, 10, 8342–8347.
14 N. Kornblum, S. C. Carlson and R. G. Smith, J. Am. Chem.
Soc., 1978, 100, 289–290.
15 T. C. Kuhler, M. Swanson, B. Christenson, A. C. Klintenberg,
B. Lamm, J. Fagerhag, R. Gatti, M. Olwegard-Halvarsson,
V. Shcherbuchin, T. Elebring and J. E. Sjostrom, J. Med.
Chem., 2002, 45, 4282–4299.
16 C. Yoakim, P. R. Bonneau, R. Deziel, L. Doyon, J. Duan,
I. Guse, S. Landry, E. Malenfant, J. Naud, W. W. Ogilvie,
5364 | Org. Biomol. Chem., 2014, 12, 5360–5364
This journal is © The Royal Society of Chemistry 2014