Abstract
Carbon monoxide (CO), like nitric oxide (NO), is an essential signalling molecule in humans. It is active in the cardiovascular system as a vasodilator. In addition, CO possesses anti-inflammatory, anti-apoptotic and anti-proliferative properties and protects tissues from hypoxia and reperfusion injury. Some of its applications in animal models include suppression of organ graft rejection and safeguarding the heart during reperfusion after cardiopulmonary bypass surgery. CO also suppresses arteriosclerotic lesions following angioplasty, reverses established pulmonary hypertension and mitigates the development of post-operative ileus in the murine small intestine and the development of cerebral malaria in mice as well as graft-induced intimal hyperplasia in pigs. There have been several clinical trials using air–CO mixtures for the treatment of lung-, heart-, kidney- and abdominal-related diseases. This review examines the research involving the development of classes of compounds (with particular emphasis on metal carbonyls) that release CO, which could be used in clinically relevant conditions. The review is drawn not only from published papers in the chemical literature but also from the extensive biological literature and patents on CO-releasing molecules (CO-RMs).
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- AEGL3:
-
Acute exposure guideline level 3 – life-threatening health effects or death
- AMP:
-
Adenosine monophosphate
- ANG:
-
Angiotensin
- ASMC:
-
Airway smooth muscle cells
- BAY:
-
41-2272 5-cyclopropyl-2[1-(2-fluorobenzyl)-1H-pyrazolo [3,4-b] pyridine-3-yl] pyrimidin-4-ylamine
- cGC:
-
Guanylyl cyclase
- cGMP:
-
5′-cyclic guanylyl phosphate
- CORM-1:
-
[Mn2(CO)10]
- CORM-2:
-
[RuCl2(CO)3]2
- CORM-3:
-
[RuCl(glycinate)(CO)3]
- CORM-A1:
-
Na[H3BCO2H]
- CO-RMs:
-
CO-releasing molecules
- COX-2:
-
Cyclooxygenase-2
- DC:
-
Dendritic cell
- DMSO:
-
Dimethylsulfoxide
- EC:
-
Endothelial cells
- ERK1/2:
-
Extracellular signal-regulated kinase-1 and -2
- ICAM-1:
-
Intercellular adhesion molecule-1
- IL:
-
Interleukin
- iNOS:
-
Inducible NO synthase
- LPS:
-
Lipopolysaccharide
- Mb:
-
Myoglobin
- MbCO:
-
Carboxymyoglobin
- MMP:
-
Matrix metalloproteinase
- mRNA:
-
messenger Ribonucleic acid
- mTALH:
-
Medullary thick ascending limb
- NAD(P)H:
-
Nicotinamide adenine dinucleotide phosphate
- NANC:
-
Non-adrenergic/non-cholinergic
- NF-κB:
-
Eukaryotic transcription factor
- Nox4:
-
Gene that encodes the enzyme NADPH oxidase 4
- PC-12:
-
A cancer cell line
- PMN:
-
Human neutrophils
- PPAR-gamma:
-
Peroxisome proliferator-activated receptor-gamma
- PTEN:
-
Phosphatase and tensin homolog
- ROS:
-
Reactive oxygen species
- sFlt-1:
-
Soluble fms-like tyrosine kinase-1
- STZ:
-
Streptozotocin
- THF:
-
Tetrahydrofuran
- TLR:
-
Toll-like receptors
- TNF-α:
-
Tumour necrosis factor-alpha
- VEGFR-2:
-
Vascular endothelial growth factor-2
- YC-1:
-
1-benzyl-3-(5′-hydroxymethyl-2-furyl)indazole
References
Vreman HJ, Wong RJ, Stevenson DK (2002) Carbon monoxide and cardiovascular functions. CRC Press, Boca Raton, p 273
Marks GS, Brien JF, Nakatsu K, McLaughlin BE (1991) Trends Pharmacol Sci 12:185
Stocker R, Yamamoto Y, McDonagh AF, Glazer AN, Ames BN (1987) Science 235:1043
McDonagh AF (1990) Clin Perinatol 17:359
Zayasu K, Sekizawa K, Okinaga S, Yamaya M, Ohrui T, Sasaki H (1997) Am J Respir Crit Care Med 156:1140
Horvath I, Donnelly LE, Kiss A, Paredi P, Kharitonov SA, Barnes PJ (1998) Thorax 53:668
Horvath I, Loukides S, Wodehouse T, Kharitonov SA, Cole PJ, Barnes PJ (1998) Thorax 53:867
Antuni JD, Kharitonov SA, Hughes D, Hodson ME, Barnes PJ (2000) Thorax 55:138
Paredi P, Kharitonov SA, Leak D, Shah PL, Cramer D, Hodson ME, Barnes PJ (2000) Am J Respir Crit Care Med 161:1247
Paredi P, Biernacki W, Invernizzi G, Kharitonov SA, Barnes PJ (1999) Chest 116:1007
Monma M, Yamaya M, Sekizawa K, Ikeda K, Suzuki N, Kikuchi T, Takasaka T, Sasaki H (1999) Clin Exp Allergy 29:1537
Abraham NG, Kappas A (2008) Pharm Rev 60:79
Mann BE, Motterlini R (2007) Chem Commun 4197
Foresti R, Bani-Hani MG, Motterlini R (2008) Int Care Med 34:649
Alberto R, Motterlini R (2007) Dalton Trans 1651
Sato K, Balla J, Otterbein L, Smith RN, Brouard S, Lin Y, Csizmadia E, Sevigny J, Robson SC, Vercellotti G, Choi AM, Bach FH, Soares MP (2001) J Immunol 166:4185
Lavitrano M, Smolenski RT, Musumeci A, Maccherini M, Slominska E, di Florio E, Bracco A, Mancini A, Stassi G, Patti M, Giovannoni R, Froio A, Simeone F, Forni M, Bacci ML, D’Alise G, Cozzi E, Otterbein LE, Yacoub MH, Bach FH, Calise F (2004) Faseb J 18:U709
Otterbein LE, Zuckerbraun BS, Haga M, Liu F, Song RP, Usheva A, Stachulak C, Bodyak N, Smith RN, Csizmadia E, Tyagi S, Akamatsu Y, Flavell RJ, Billiar TR, Tzeng E, Bach FH, Choi AMK, Soares MP (2003) Nat Med 9:183
Zuckerbraun BS, Chin BY, Wegiel B, Billiar TR, Czsimadia E, Rao J, Shimoda L, Ifedigbo E, Kanno S, Otterbein LE (2006) J Exp Med 203:2109
Moore BA, Otterbein LE, Turler A, Choi AMK, Bauer AJ (2003) Gastroenterology 124:377
Pamplona A, Ferreira A, Balla J, Jeney V, Balla G, Epiphanio S, Chora ÂA, Rodrigues CD, Gregoire IP, Cunha-Rodrigues M, Portugal S, Soares MP, Mota MM (2007) Nat Med 13:703
Ramlawi B, Scott JR, Feng J, Mieno S, Raman KG, Gallo D, Csizmadia E, Chin BY, Bach FH, Otterbein LE, Sellke FW (2007) J Surg Res 138:121
Mayr FB, Spiel A, Leitner J, Marsik C, Germann P, Ullrich R, Wagner O, Jilma B (2005) Am J Respir Crit Care Med 171:354
Bathoorn E, Slebos DJ, Postma DS, Koeter GH, van Oosterhout AJM, van der Toorn M, Boezen HM, Kerstjens HAM (2007) Eur Respir J 30:1131
Carbon Monoxide to Prevent Lung Inflammation http://www.clinicaltrials.gov/ct2/show/NCT00094406. Accessed 21 Feb 2010
Safety and Tolerability Study of Inhaled Carbon Monoxide in Kidney Transplant Patients http://www.clinicaltrials.gov/ct2/show/NCT00531856. Accessed 16 Feb 2010
Effects of Heme Arginate in Healthy Male Subjects http://www.clinicaltrials.gov/ct2/show/NCT00682370. Accessed 7 Jan 2009
Does Heme Oxygenase-1 Induction Ameliorate Cardiac Injury After Myocardial Infarction? http://www.clinicaltrials.gov/ct2/show/NCT00483587. Accessed 21 Feb 2010
Study of Inhaling Carbon Monoxide to Treat Patients With Intestinal Paralysis After Colon Surgery http://www.clinicaltrials.gov/ct2/show/NCT01050712. Accessed 16 Feb 2010
Mims MP, Porras AG, Olson JS, Noble RW, Peterson JA (1983) J Biol Chem 258:14219
Alonso J-R, Cardellach F, Lopez S, Casademont J, Miro O (2003) Pharmacol Toxicol 93:142
Zuckerbraun BS, Chin BY, Bilban M, de Costa d’Avila J, Rao J, Billiar TR, Otterbein LE (2007) FASEB J 21:1099
Borisov VB (2008) Biochemistry (Moscow) 73:14
Abu-Soud HM, Wu C, Ghosh DK, Stuehr DJ (1998) Biochemistry 37:3777
Martin E, Berka V, Bogatenkova E, Murad F, Tsai AL (2006) J Biol Chem 281:27836
Goldbaum LR, Ramirez RG, Absolam KB (1975) Aviat Space Environ Med 1289
Noble RW, Gibson QH, Brunori M, Antonini E, Wyman J (1969) J Biol Chem 244:3905
O’Brien HR, Parker WL (1922) J Biol Chem 50:289
Ma XL, Sayed N, Beuve A, van den Akker F (2007) EMBO J 26:578
Friebe A, Schultz G, Koesling D (1996) EMBO J 15:6863
Martin E, Sharina I, Kots A, Murad F (2003) Proc Natl Acad Sci USA 100:9208
Martin E, Czarnecki K, Jayaraman V, Murad F, Kincaid J (2005) J Am Chem Soc 127:4625
Bloch KD, Ichinose F, Zapol WM, Evgenov OV (2005) Enhancing the effectiveness of an inhaled therapeutic gas. Patent WO 2005/077005
Williams SEJ, Wootton P, Mason HS, Bould J, Iles DE, Riccardi D, Peers C, Kemp PJ (2004) Science 306:2093
Williams SE, Brazier SP, Baban N, Telezhkin V, Muller CT, Riccardi D, Kemp PJ (2008) Pflugers Arch 456:561
Wang S, Publicover S, Gu Y (2009) Proc Natl Acad Sci 106:2957
Brazier SP, Telezhkin V, Mears R, Muller CT, Riccardi D, Kemp PJ (2009) Adv Exp Med Biol 648:49
Shititani T, Iwabuchi T, Soga T, Kato Y, Yamamoto T, Takano N, Hishiki T, Ueno Y, Ikeda S, Sakuragawa T, Ishikawa K, Goda N, Kitagawa Y, Kajjimura M, Matsumoto K, Suematsu M (2009) Hepatology 49:141
Schubert MP (1933) J Am Chem Soc 55:4563
Ferrier F, Terzian G, Mossoyan J, Benlian D (1995) J Mol Struct 344:189
Oppenheimer NJ, Rodriguez LO, Hecht SM (1979) Proc Natl Acad Sci 76:5616
Sugiura Y, Kuwahara J, Suzuki T (1985) FEBS Lett 182:39
Ragsdale SW (2006) Chem Rev 106:3317
Bayston JH, Winfield ME (1967) J Catal 9:217
Lee L-P, Schrauzer GN (1968) J Am Chem Soc 90:5274
Schrauzer GN, Lee L-P (1970) Arch Biochem Biophys 138:16
Friedrich W (1970) Z Naturforsch B 25:1431
Motterlini RA, Mann BE (2002) Preparation of metal complexes for therapeutic delivery of carbon monoxide as vasodilator. Patent WO 2002/092075
Motterlini R, Clark JE, Foresti R, Sarathchandra P, Mann BE, Green CJ (2002) Circ Res 90:E17
Alessio E, Milani B, Bolle M, Mestroni G, Faleschini P, Todone F, Geremia S, Calligaris M (1995) Inorg Chem 34:4722
Obirai JC, Hamadi S, Ithurbide A, Wartelle C, Nyokong T, Zagal J, Top S, Bedioui F (2006) Electroanalysis 18:1689
Sawle P, Foresti R, Mann BE, Johnson TR, Green CJ, Motterlini R (2005) Br J Pharmacol 145:800
Kwak HJ, Song JS, No ZS, Song JH, Yang SD, Cheon HG (2005) Inflamm Res 54:508
Srisook K, Han SS, Choi HS, Li MH, Ueda H, Kim C, Cha YN (2006) Biochem Pharmacol 71:307
Tsoyi K, Ha Y-M, Kim Y-M, Lee Y-S, Kim H-J, Kim H-J, Seo H-G, Lee J-H, Chang K-C (2009) Inflammation 32:364
Yang NC, Lu LH, Kao YH, Chau LY (2004) J Biomed Sci 11:799
Li MH, Jang JH, Na HK, Cha YN, Surh YJ (2007) J Biol Chem 282:28577
Li MH, Cha YN, Surh YJ (2006) Biochem Biophys Res Commun 342:984
Botros FT, Navar LG (2006) Am J Physiol 291:H2772
De Backer O, Lefebvre RA (2007) Eur J Pharmacol 572:197
De Backer O, Elinck E, Sips P, Buys E, Brouckaert P, Lefebvre RA (2008) Naunyn-Schmiedeberg’s Arch Pharmacol 378:493
Rattan S, Haj RA, De Godoy MAF (2004) Am J Physiol Gastroint Liver Physiol 287:G605
Stanford SJ, Walters MJ, Hislop AA, Haworth SG, Evans TW, Mann BE, Motterlini R, Mitchell JA (2003) Eur J Pharmacol 473:135
Taille C, El-Benna J, Lanone S, Boczkowski J, Motterlini R (2005) J Biol Chem 280:25350
Cudmore M, Ahmad S, Al-Ani B, Fujisawa T, Coxall H, Chudasama K, Devey LR, Wigmore SJ, Abbas A, Hewett PW, Ahmed A (2007) Circulation 115:1789
Kooli A, Kermorvant-Duchemin E, Sennlaub F, Bossolasco M, Hou X, Honore JC, Dennery PA, Sapieha P, Varma D, Lachapelle P, Zhu T, Tremblay S, Hardy P, Jain K, Balazy M, Chemtob S (2008) Free Rad Biol Méd 44:815
Choi HC, Kim HS, Lee KY, Chang KC, Kang YJ (2008) Biochem Biophys Res Commun 376:753
Hasan RN, Schafer AI (2008) Circ Res 102:42
Megias J, Busserolles J, Alcaraz MJ (2007) Br J Pharmacol 150:977
Sun B, Sun H, Liu C, Shen J, Chen Z, Chen X (2007) J Surg Res 139:128
Sun B-W, Chen X, Chen Z-Y, Katada K, Cepinskas G (2007) Zhonghua Yi Xue Za Zhi 87:3148
Sun B-W, Chen X, Chen Z-Y, Kazuhiro K, Gediminas C (2007) Zhonghua Shao Shang Za Zhi 23:179
Cepinskas G, Katada K, Bihari A, Potter RF (2008) Am J Physiol Gastrointest Liver Physiol 294:G184
Van Landeghem L, Laleman W, Vander Elst I, Zeegers M, van Pelt J, Cassiman D, Nevens F (2009) Liver Int 29:650
Guillen MI, Megias J, Clerigues V, Gomar F, Alcaraz MJ (2008) Rheumatology (Oxford) 47:1323
Liu DM, Sun BW, Sun ZW, Jin Q, Sun Y, Chen X (2008) Acta Pharmacol Sin 29:838
Megias J, Guillen MI, Bru A, Gomar F, Alcaraz MJ (2008) J Pharmacol Exp Ther 325:56
Sun BW, Sun Y, Sun ZW, Chen X (2008) World J Gastroenterol 14:547
Chen P, Wang G, Sun B, Pan S-h, Jiang H-c (2009) Zhonghua Yixianbing Zazhi 9:181
Chen P, Sun B, Chen H, Wang G, Pan SH, Kong R, Bai XW, Wang SJ (2010) Cytokine 49:15
Heo JM, Kim HJ, Ha YM, Park MK, Kang YJ, Lee YS, Seo HG, Lee JH, Yun-Choi HS, Chang KC (2007) Biochem Pharmacol 74:1361
Kim Y-M, Choi B-M, Kim Y-S, Kwon Y-G, Kibbe MR, Billiar TR, Tzeng E (2008) BMB Rep 41:164
Scragg JL, Dallas ML, Wilkinson JA, Varadi G, Peers C (2008) J Biol Chem 283:24412
Scragg JL, Dallas ML, Peers C (2008) Heart 94:e22
Hou SW, Xu R, Heinemann SH, Hoshi T (2008) Proc Nat Acad Sci 105:4039
Dong D-L, Chen C, Huang W, Chen Y, Zhang X-L, Li Z, Li Y, Yang B-F (2008) Eur J Pharmacol 590:99
Dallas ML, Scragg JL, Peers C (2009) Adv Exp Med Biol 648:89
Wilkinson WJ, Gadeberg HC, Harrison AWJ, Allen ND, Riccardi D, Kemp PJ (2009) British J Pharmacol 158:862
Sun B-W, Jin Q, Sun Y, Sun Z-W, Chen X, Chen Z-Y, Cepinskas G (2007) World J Gastroenterol 13:6183
Sun B, Sun Z, Jin Q, Chen X (2008) Int J Biol Sci 4:176
Sun BW, Chen ZY, Chen X, Liu C (2007) J Burn Care Res 28:173
Lee TS, Tsai HL, Chau LY (2003) J Biol Chem 278:19325
Yuan J-F, Zhang Y-Y, Chen S-C, Tang W-F, Shao D-H (2009) Jiefangjun Yaoxue Xuebao 25:21
Chen B, Guo LL, Fan CL, Bolisetty S, Joseph R, Wright MM, Agarwal A, George JF (2009) Am J Pathol 175:422
Nielsen Vance G, Kirklin James K, George James F (2009) Blood Coagul Fibrinolysis 20:377
Nielsen VG, Kirklin JK, George JF (2010) Blood Coagul Fibrinolysis 21:41
Nielsen VG, Kirklin JK, George JF (2009) Blood Coagul Fibrinolysis 20:448
Nielsen VG, Kirklin JK, George JF, Messinger JD (2010) Blood Coagul Fibrinolysis 21:101
Pae HO, Choi BM, Oh GS, Lee MS, Ryu DG, Rhew HY, Kim YM, Chung HT (2004) Mol Pharmacol 66:122
Vera T, Henegar JR, Drummond HA, Rimoldi JM, Stec DE (2005) J Am Soc Nephrol 16:950
Mei D-s, Du Y-a, Wang Y (2007) Zhejiang Da Xue Xue Bao Yi Xue Ban 36:291
Burger D, Xiang FL, Hammoud L, Lu XR, Feng QP (2009) Am J Physiol Heart Circ Physiol 296:H84
Czibik G, Sagave J, Martinov V, Ishaq B, Sohl M, Sefland I, Carlsen H, Farnebo F, Blomhoff R, Valen G (2009) Cardiovasc Res 82:107
Lee BS, Heo J, Kim YM, Shim SM, Pae HO, Kim YM, Chung HT (2006) Biochem Biophys Res Commun 343:965
Allanson M, Reeve VE (2007) Cancer Immunol Immunother 56:1807
Vannacci A, Di Felice A, Giannini L, Marzocca C, Pierpaoli S, Zagli G, Masini E, Mannaioni PF (2004) Inflamm Res 53:S9
Vannacci A, Failli P, Giannini L, Fabrizi F, Uliva C, Mazzetti L, Franchi-Micheli S, Masini E, Motterlini R, Mannaioni PF (2007) Cellular and molecular targets in allergy and clinical immunology. Proc Symp Collegium Int Allergol, 26th:172
Kang KS, Ra JC, Park JR (2007) Multipotent stem cells derived from human adipose tissue and cellular therapeutic agents comprising the same. Patent US 2007/110729
Oh GS, Pae HO, Moon MK, Choi BM, Yun YG, Rim JS, Chung HT (2003) Biochem Biophys Res Commun 302:109
Desmard M, Amara N, Lanone S, Motterlini R, Boczkowski J (2005) Cell Mol Biol 51:403
Zhou J-l, Li G, Hai Y, Guan L, Huang X-l, Sun P (2009) Chin J Traumatol 12:71, English Edition
Uc A, Husted RF, Giriyappa RL, Britigan BE, Stokes JB (2005) Am J Physiol Gastroint Liver Physiol 289:G202
Shiohira S, Yoshida T, Shirota S, Tsuchiya K, Nitta K (2007) Am J Nephrol 27:441
Davies AL, Kramer JLK, Hayes KC (2008) Neuroscience 151:1104
Knipp S, Bicker G (2009) Development 136:85
Hidaka A, Azuma Y-T, Nakajima H, Takeuchi T (2010) J Pharmacol Sci 112:231
Volti GL, Sacerdoti D, Sangras B, Vanella A, Mezentsev A, Scapagnini G, Falck JR, Abraham NG (2005) Antioxid Redox Signal 7:704
Sun B, Zou X, Chen Y, Zhang P, Shi G (2008) Int J Biol Sci 4:270
Zabalgoitia M, Colston JT, Reddy SV, Holt JW, Regan RF, Stec DE, Rimoldi JM, Valente AJ, Chandrasekar B (2008) Free Radic Biol Méd 44:284
Nizamutdinova IT, Kim Y-M, Kim H-J, Seo H-G, Lee J-H, Chang K-C (2009) Atheroscler (Amst) 207:405
Remy S, Blancou P, Tesson L, Tardif V, Brion R, Royer PJ, Motterlini R, Foresti R, Painchaut M, Pogu S, Gregoire M, Bach JM, Anegon I, Chauveau C (2009) J Immunol 182:1877
Orozco-Ibarra M, Estrada-Sanchez AM, Massieu L, Pedraza-Chaverri J (2009) Int J Biochem Cell Biol 41:1304
Nobre LS, Seixas JD, Romão CC, Saraiva LM (2007) Antimicrob Agents Chemother 51:4303
Nobre LS, Seixas JD, Romão CC, Saraiva LM (2008) Treatment of infections by carbon monoxide. Patent WO 2008130261
Nobre LS, Al-Shahrour F, Dopazo J, Saraiva LM (2009) Microbiology-Sgm 155:813
Chung SW, Liu X, Macias AA, Baron RM, Perrella MA (2008) J Clin Invest 118:239
Tsoyi K, Lee TY, Lee YS, Kim HJ, Seo HG, Lee JH, Chang KC (2009) Mol Pharmacol 76:173
Sun B, Chen X, Katada K, Potter F, Cepinskas G (2008) Jiangsu Daxue Xuebao Yixueban 18:369
Sun B, Shi G, Zhang P, Zou X, Chen X (2009) Zhonghua Shaoshang Zazhi 25:111
Sun B, Liu D, Chen X (2009) Application of carbon monoxide-releasing molecules in the treatment of pyohemia in early stage. Patent CN 2008-10038045; 101590228
Han W, Wu L, Chen S, Yu KN (2010) Carcinogenesis 31:275
Clark JE, Naughton P, Shurey S, Green CJ, Johnson TR, Mann BE, Foresti R, Motterlini R (2003) Circ Res 93:E2
Johnson TR, Mann BE, Teasdale IP, Adams H, Foresti R, Green CJ, Motterlini R (2007) Dalton Trans 1500
Seveso M, Vadori M, Bosio E, Boldrin M, Baldan N, Besenzon F, Dedja A, Calabrese F, Busetto R, Ravarotto L, Johnson TR, Mann BE, Motterlini R, Cozzi E, Ancona E (2004) Transplantation 78:222
Seveso M, Vadori M, Bosio E, Fante F, Besenzon F, Ravarotto L, Bedendo S, Johnson TR, Mann BE, Motterlini R, Cozzi E, Ancona E (2005) Am J Transplant 5:306
Vadori M, Seveso M, Besenzon F, Bosio E, Tognato E, Fante F, Boldrin M, Gavasso S, Ravarotto L, Mann Brian E, Simioni P, Ancona E, Motterlini R, Cozzi E (2009) Xenotransplantation 16:99
Foresti R, Hammad J, Clark JE, Johnson TR, Mann BE, Friebe A, Green CJ, Motterlini R (2004) Br J Pharmacol 142:453
Dombkowski RA, Whitfield NL, Motterlini R, Yan G, Olson KR (2009) Am J Physiol 296:R141
Lamon BD, Zhang FF, Puri N, Brodsky SV, Goligorsky MS, Nasjletti A (2009) Circ Res 105:775
Guo YR, Stein AB, Wu WJ, Tan W, Zhu XP, Li QH, Dawn B, Motterlini R, Bolli R (2004) Am J Physiol Heart Circul Physiol 286:H1649
Stein AB, Guo YR, Tan W, Wu WJ, Zhu XP, Li QH, Luo C, Dawn B, Johnson TR, Motterlini R, Bolli R (2005) J Mol Cell Cardiol 38:127
Varadi J, Lekli I, Juhasz B, Bacskay I, Szabo G, Gesztelyi R, Szendrei L, Varga E, Bak I, Foresti R, Motterlini R, Tosaki A (2007) Life Sci 80:1619
Musameh MD, Green CJ, Mann BE, Motterlini R, Fuller BJ (2010) J Cardiovasc Pharmacol 55:168
Li Volti G, Sacerdoti D, Sangras B, Vanella A, Mezentsev A, Scapagnini G, Falck JR, Abraham NG (2005) Antioxid Redox Signal 7:704
Song H, Bergstrasser C, Rafat N, Hoger S, Schmidt M, Endres N, Goebeler M, Hillebrands JL, Brigelius-Flohe R, Banning A, Beck G, Loesel R, Yard BA (2009) Br J Pharmacol 157:769
Musameh MD, Fuller BJ, Mann BE, Green CJ, Motterlini R (2006) Br J Pharmacol 149:1104
Clark JE, Kottam A, Motterlini R, Marber MS (2009) J Pharmacol Toxicol Meth 59:94
Chlopicki S, Olszanecki R, Marcinkiewicz E, Lomnicka M, Motterlini R (2006) Cardiovasc Res 71:393
Musameh MD, Green CJ, Mann BE, Fuller BJ, Motterlini R (2007) J Heart Lung Transplant 26:1192
De Backer O, Elinck E, Blanckaert B, Leybaert L, Motterlini R, Lefebvre RA (2009) Gut 58:347
Di Pascoli M, Rodella L, Sacerdoti D, Bolognesi M, Turkseven S, Abraham NG (2006) Biochem Biophys Res Commun 340:935
Rodella LF, Vanella L, Peterson SJ, Drummond G, Rezzani R, Falck JR, Abraham NG (2008) Drug Metab Lett 2:290
Piepoli AL, de Salvatore G, Lemoli M, de Benedictis L, Mitolo-Chieppa D, de Salvia MA (2008) Neurogastroenterol Motil 20:1251
Rodella L, Lamon BD, Rezzani R, Sangras B, Goodman AI, Falck JR, Abraham NG (2006) Free Radical Biol Med 40:2198
Bani-Hani MG, Greenstein D, Mann BE, Green CJ, Motterlini R (2006) Pharmacol Rep 58(Suppl):132
Vannacci A, Marzocca C, Giannini L, Mazzetti L, Franchi-Micheli S, Failli P, Masini E, Motterlini R, Mannaioni PF (2006) Inflamm Res 55:S5
Bani-Hani MG, Greenstein D, Mann BE, Green CJ, Motterlini R (2006) J Pharmacol Exp Ther 318:1315
Xi Q, Umstot E, Zhao G, Narayanan D, Leffler CW, Jaggar JH (2010) Am J Physiol 298:H562
Ferrandiz ML, Maicas N, Garcia-Arnandis I, Terencio MC, Motterlini R, Devesa I, Joosten LAB, van den Berg WB, Alcaraz MJ (2008) Ann Rheum Dis 67:1211
Tayem Y, Johnson TR, Mann BE, Green CJ, Motterlini R (2006) Am J Physiol Renal Physiol 290:F789
Sandouka A, Fuller BJ, Mann BE, Green CJ, Foresti R, Motterlini R (2006) Kidney Int 69:239
Stec DE, Bishop C, Rimoldi JM, Poreddy SR, Vera T, Salahudeen AK (2007) Ren Fail 29:543
Ren Y, D’Ambrosio MA, Wang H, Liu R, Garvin JL, Carretero OA (2008) Am J Physiol Ren Physiol 295:F1207
Bagul A, Hosgood SA, Kaushik M, Nicholson ML (2008) Transplantation 85:576
Hosgood SA, Bagul A, Kaushik M, Rimoldi J, Gadepalli RS, Nicholson ML (2008) Br J Surg 95:1060
Pizarro MD, Rodriguez JV, Mamprin ME, Fuller BJ, Mann BE, Motterlini R, Guibert EE (2009) Cryobiology 58:248
Dong D-L, Zhang Y, Lin D-H, Chen J, Patschan S, Goligorsky MS, Nasjletti A, Yang B-F, Wang W-H (2007) Hypertension 50:643
Althaus M, Fronius M, Buchaeckert Y, Vadasz I, Clauss WG, Seeger W, Motterlini R, Morty RE (2009) Am J Respir Cell Mol Biol 41:639
Urquhart P, Rosignoli G, Cooper D, Motterlini R, Perretti M (2007) J Pharmacol Exp Ther 321:656
Mizuguchi S, Stephen J, Bihari R, Markovic N, Suehiro S, Capretta A, Potter Richard F, Cepinskas G (2009) Am J Physiol 297:H920
Aziz MTA, El-Asmar MF, Mostafa T, Atta H, Fouad HH, Roshdy NK, Rashed LA, Obaia EA, Sabry DA, Aziz ATA, Drummond G, Olszanecki R (2008) J Sex Med 5:336
Barbagallo I, Tibullo D, Di Rosa M, Giallongo C, Palumbo GA, Raciti G, Campisi A, Vanella A, Green CJ, Motterlini R (2008) J Neurosci Res 86:1927
Masini E, Vannacci A, Failli P, Mastroianni R, Giannini L, Vinci MC, Uliva C, Motterlini R, Mannaioni PF (2008) FASEB J 22:3380
Vannacci A, Giannini L, Fabrizi F, Uliva C, Mastroianni R, Masini E, Motterlini R, Mannaioni PF (2007) Inflamm Res 56:S13
Stagni E, Privitera MG, Bucolo C, Leggio GM, Motterlini R, Drago F (2009) Br J Ophthalmol 93:254
Hascalovici JR, Song W, Vaya J, Khatib S, Fuhrman B, Aviram M, Schipper HM (2009) J Neurochem 108:72
Lancel S, Hassoun SM, Favory R, Decoster B, Motterlini R, Neviere R (2009) J Pharmacol Exp Ther 329:641
Romão CC, Rodrigues SS, Seixas JD, Pina ARM, Roya B, Fernandes AC, Goncalves I, Haas W (2007) Method using CO-releasing molybdenum carbonyl complexes for the treatment of inflammatory diseases. Patent WO 2007/073226
Desmard M, Davidge KS, Bouvet O, Morin D, Roux D, Foresti R, Ricard JD, Denamur E, Poole RK, Montravers P, Motterlini R, Boczkowski J (2009) FASEB J 23:1023
Herrmann F, List H (1995) Transdermal therapeutic system comprosong active substances representing carbon monoxide sources. Patent WO 95/35105
Winslow RM (2006) Composition and methods for delivering carbon monoxide (CO) and nitric oxide (NO) to tissue using heme proteins as carriers. Patent WO 2006/096774
Vandegriff KD, Young MA, Lohman J, Bellelli A, Samaja M, Malavalli A, Winslow RM (2008) Br J Pharmacol 154:1649
Motterlini RA, Mann BE, Johnson TR, Scapens DA, Aqil R (2007) Therapeutic delivery of carbon monoxide via organometallic complexes. Patent WO 2007/085806
Scapens D, Adams H, Johnson TR, Mann BE, Sawle P, Aqil R, Perrior T, Motterlini R (2007) Dalton Trans 43:4962
Fairlamb IJS, Lynam JM, Moulton BE, Taylor IE, Duhme-Klair AK, Sawle P, Motterlini R (2007) Dalton Trans 3603
Fairlamb IJS, Duhme-Klair AK, Lynam JM, Moulton BE, O’Brien CT, Sawle P, Hammad J, Motterlini R (2006) Bioorg Med Chem Lett 16:995
Sawle P, Hammad J, Fairlamb IJS, Moulton B, O’Brien CT, Lynam JM, Duhme-Klair AK, Foresti R, Motterlini R (2006) J Pharmacol Exp Ther 318:403
Zhang W-Q, Atkin AJ, Thatcher RJ, Whitwood AC, Fairlamb IJS, Lynam JM (2009) Dalton Trans 4351
Fiumana E, Parfenova H, Jaggar JH, Leffler CW (2003) Am J Physiol Heart Circul Physiol 284:H1073
Barkoudah E, Jaggar JH, Leffler CW (2004) Am J Physiol Heart Circul Physiol 287:H1459
Koneru P, Leffler CW (2004) Am J Physiol Heart Circ Physiol 286:H304
Xi Q, Tcheranova D, Parfenova H, Horowitz B, Leffler CW, Jaggar JH (2004) Am J Physiol Heart Circ Physiol 286:H610
Arregui B, Lopez B, Salom MG, Valero F, Navarro C, Fenoy FJ (2004) Kidney Int 65:564
Motterlini RA, Mann BE, Scapens DA (2008) Therapeutic delivery of carbon monoxide. Patent WO 2008/003953
Niesel J, Pinto A, N’Dongo HWP, Merz K, Ott I, Gustb R, Schatzschneider U (2008) Chem Comm 1798
Pfeiffer H, Rojas A, Niesel J, Schatzschneider U (2009) J Chem Soc, Dalton Trans 4292
Kunz PC, Huber W, Rojas A, Schatzschneider U, Spingler B (2009) Eur J Inorg Chem 5358
Haas W, Romão CC, Rodrigues SS, Seixas JD, Pina ARM (2007) Molybdenum carbonyl complexes for treating rheumatoid arthritis and other inflammatory diseases. Patent WO 2007/073225
Rodrigues SS, Seixas JD, Guerreiro B, Pereira NMP, Romao CC, Haas WE, Goncalves IMDS (2009) Prevention of gastric ulcers by carbon monoxide. Patent 2008-IB1945; WO 2009/013612
Rimmer RD, Richter H, Ford PC (2010) Inorg Chem 49:1180
Atkin AJ, Williams S, Sawle P, Motterlini R, Lynam JM, Fairlamb IJS (2009) Dalton Trans 3653
Malone LJ Jr, Parry RW (1967) Inorg Chem 6:817
Alberto RA (2001) Carbon monoxide source for preparation of transition metal carbonyl complexes. Patent WO 2001/025243
Motterlini RA, Alberto RA (2005) Use of boranocarbonates for the therapeutic delivery of carbon monoxide. Patent WO 2005/013691
Motterlini R, Sawle P, Bains S, Hammad J, Alberto R, Foresti R, Green CJ (2004) FASEB J 19:284
Kelsen S, Patel BJ, Parker LB, Vera T, Rimoldi JM, Gadepalli RSV, Drummond HA, Stec DE (2008) Am J Physiol Ren Physiol 295:F1158
Stec DE, Vera T, McLemore GR Jr, Kelsen S, Rimoldi JM, Gadepalli RSV, Ryan MJ (2008) Am J Hypertens 21:189
Wegiel B, Gallo DJ, Raman KG, Karlsson JM, Ozanich B, Chin BY, Tzeng E, Ahmad S, Ahmed A, Baty CJ, Otterbein LE (2010) Circulation 121:537
Ryan MJ, Jernigan NL, Drummond HA, McLemore GR, Rimoldi JM, Poreddy SR, Gadepalli RSV, Stec DE (2006) Pharmacol Res 54:24
Zimmermann A, Leffler CW, Tcheranova D, Fedinec AL, Parfenova H (2007) Am J Physiol 293:H2501
Basuroy S, Bhattacharya S, Tcheranova D, Qu Y, Regan RF, Leffler CW, Parfenova H (2006) Am J Physiol 291:C897
Parfenova H, Basuroy S, Bhattacharya S, Tcheranova D, Qu Y, Regan RF, Leffler CW (2006) Am J Physiol Cell Physiol 290:C1399
Basuroy S, Bhattacharya S, Leffler CW, Parfenova H (2009) Am J Physiol 296:C422
Wu L, Wang R, Ndisang JF (2006) Chronic hemin treatment of vascular diseases. Patent CA 2005/2504643
Buelow R, Woo J (2002) Carbon monoxide-generating compounds for treatment of vascular, inflammatory and immune disorders. Patent WO 2002/078684
Buelow R, Woo J, Iyer S (2004) Carbon monoxide generating compounds for treatment of vascular inflammatory and immune disorders. Patent US 2004/0143025
De Matos MN, Romão CC (2007) Methods for treating inflammatory disease by administering aldehydes and derivatives thereof. Patent US 2007/219120
De Matos MN, Romão CC (2008) Methods for treating inflammatory disease by administering aldehydes and derivatives thereof. Patent US 2008/026984
Battino R (1990) Carbon monoxide, vol 43, Solubility data series. Pergamon, Headington Hill Hall, p 2
Peng C (1990) Chromatographia 29:347
Giner JD (1986) Gas sensor and method of using same. Patent US 4729824
Motterlini RA (2005) Electrode calibration. Patent WO 2005/114161
Bowen WJ (1949) J Biol Chem 179:235
Pathak B, Majumdar D, Leszczynski J (2009) Int J Quantum Chem 109:2263
Acute Exposure Levels Guidelines http://www.epa.gov/oppt/aegl/pubs/chemlist.htm. Accessed: 10 Jan 2009
Ren Y, D’Ambrosio MA, Wang H, Liu RS, Garvin JL, Carretero OA (2008) Am J Physiol Renal Physiol 295:F1207
Motterlini R (2007) Biochem Soc Trans 35:1142
Haas W, Romão C, Royo B, Fernandes AC, Goncalves I (2003) Method for treating a mammal by administration of a compound having the ability to release CO, compounds having the ability to release CO and pharmaceutical compositions thereof. Patent WO 2003/066067
Motterlini RA, Mann BE (2004) Therapeutic delivery of carbon monoxide using metal carbonyl complexes. Patent WO 2004/045598
Motterlini RA, Mann BE (2004) Combination of a metal carbonyl compound and a guanylate cyclase stimulant or stabilizer for the therapeutic delivery of carbon monoxide. Patent WO 2004/045599
Matos MRPN, Romão CC, Lage Pereira CC, Rodrigues SS, Mora M, Silva MJP, Alves PM, Reis CA (2005) Compositions comprising organometallic molybdenum compounds for treating cancer. Patent WO 2005/087783
Haas WE, Romão CC, Rodrigues SS, Seixas JD, Pina ARM, Royo B, Fernandes AC, Goncalves I (2007) Method for treating a mammal by administration of a compound having the ability to release CO. Patent US 2007/207217
DiSorbo DM, Reeves R (1994) Compositions including heme-containing proteis and methods relating thereto. Patent WO 94/22482
Tsuchida H, Sakai H, Intaliertta M (2007) Intravenous fluids containing heme with carbon monooxide or nitrogen monooxide. Patent JP 2007/269665
Takagi T, Naito Y, Okuda T, Suzuki T, Mizushima K, Tsuboi H, Kajikawa H, Okayama T, Omatsu T, Hirata I, Ichikawa H, Handa O, Furukura S, Yoshida N, Yoshikawa T, Ueda H (2008) Drugs for local intestinal administration, and method for administration of drugs. Patent JP 2008/179569
Capelli CC, Dennis AP (2008) Devices such as soft tissue implants and methods for inhibiting fibrosis comprising non-gaseous CO with anti-fibrotic activity. Patent WO 2008/080128
Hoenig M (2007) A method of treatment and prophylaxis of events, conditions and diseases of the systemic vasculature and immune function to decrease cardiovascular risk and pathogenic infection. Patent WO 2007/140525 (A1)
Chung HT, Pae HO, Choi BM (2006) Composition for treating autoimmune disease comprising heme oxygenase-1 inducer or CO donor capable of inhibiting proliferation of CD4+ T-cell causing autoimmune disease. Patent KR 2006/034061
Cheesman MR, Watmough NJ, Pires CA, Turner R, Brittain T, Gennis RB, Greenwood C, Thomson AJ (1993) Biochem J 289:709
Davidge KS, Sanguinetti G, Yee CH, Mann BE, Motterlini R, Poole RK (2009) J Biol Chem 284:4516
Zuckerbraun BS (2008) Expert Opin Ther Pat 18:1321
Acknowledgments
I wish to thank Dr R. Motterlini for reading the manuscript and providing valuable modifications. I also wish to thank Hemocorm (now Alfama) for financial support and declare a financial interest in the company.
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Mann, B.E. (2010). Carbon Monoxide: An Essential Signalling Molecule. In: Jaouen, G., Metzler-Nolte, N. (eds) Medicinal Organometallic Chemistry. Topics in Organometallic Chemistry, vol 32. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-13185-1_10
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