Citation: Jun-Die ZHANG, Xiu-Juan JIANG, Zhi-Yin XIAO, Li-Mei CHEN, Xue-Mei WANG, Xiao-Ming LIU. Preventing CO-Releasing Systems from Forming Precipitates and Tuning CO-Releasing Rate via Ligand Exchange Reaction[J]. Chinese Journal of Inorganic Chemistry, ;2022, 38(8): 1593-1600. doi: 10.11862/CJIC.2022.151 shu

Preventing CO-Releasing Systems from Forming Precipitates and Tuning CO-Releasing Rate via Ligand Exchange Reaction

College of Biological, Chemical Sciences and Engineering, Jiaxing University, Jiaxing, Zhejiang 314001, China

Corresponding author: Xiu-Juan JIANG, jiangxj@mail.zjxu.edu.cn Xiao-Ming LIU, xiaoming.liu@mail.zjxu.edu.cn
Received Date: 9 January 2022
Revised Date: 18 April 2022

Figures(6)

In this work, three water-soluble compounds (tiopronin, cysteamine, and mercaptoglycerol) which contain a thiol group have been used to initiate CO - release from a diiron hexacarbonyl complex [Fe₂(μ-SCH₂CH(OH)CH₂ (OH))₂(CO)₆] (1). To overcome forming precipitates during the CO-releasing process, we investigated using ethylene- diaminetetraacetic acid (EDTA) as the agent to solubilize products derived from the decomposition. Our results sug- gest that EDTA not only successfully prevents the CO-releasing system from forming precipitates, but also synergis- tically facilitates the CO-release from complex 1. Despite the fact that the chosen ligands possess a thiol functional group, their behaviors in promoting the CO-release from complex 1 are rather different, which can be exploited to tune the CO-releasing rate in potential applications.
- CO-releasing molecules,
- diiron carbonyl complex,
- ligand exchange reaction,
- precipitation prevention,
- CO-release tuning
1. [1]
  Marks G S, Brien J F, Nakatsu K, McLaughlin B E. Does Carbon Monoxide Have a Physiological Function?[J]. Trends Pharmacol. Sci., 1991,12:185-188. doi: 10.1016/0165-6147(91)90544-3
2. [2]
  Mann B E, Motterlini R. CO and NO in Medicine[J]. Chem. Commun., 2007:4197-4208.
3. [3]
  Mann B E. Carbon Monoxide: An Essential Signalling Molecule[J]. Top. Organomet. Chem., 2010,32:247-285.
4. [4]
  Johnson T R, Mann B E, Clark J E, Foresti R, Green C J, Motterlini R. Metal Carbonyls: A New Class of Pharmaceuticals?[J]. Angew. Chem. Int. Ed., 2003,42(32):3722-3729. doi: 10.1002/anie.200301634
5. [5]
  Gonzales M A, Mascharak P K. Photoactive Metal Carbonyl Complexes as Potential Agents for Targeted CO Delivery[J]. J. Inorg. Biochem., 2014,133:127-135. doi: 10.1016/j.jinorgbio.2013.10.015
6. [6]
  Motterlini R. Heme Oxygenase-1-Derived Carbon Monoxide Contributes to the Suppression of Acute Hypertensive Responses In Vivo[J]. Circ. Res., 1998,83(5):568-577. doi: 10.1161/01.RES.83.5.568
7. [7]
  Kohmoto J, Nakao A, Kaizu T, Tsung A, Ikeda A, Tomiyama K, Bilhar T R, Choi A M K, Murase N, McCurry K R. Low-Dose Carbon Monoxide Inhalation Prevents Ischemia/Reperfusion Injury of Transplanted Rat Lung Grafts[J]. Surgery., 2006,140(2):179-185. doi: 10.1016/j.surg.2006.03.004
8. [8]
  Li Volti G, Rodella L F, Di Giacomo C, Rezzani R, Bianchi R, Borsani E, Gazzolo D, Motterlini R. Role of Carbon Monoxide and Biliverdin in Renal Ischemia/Reperfusion Injury[J]. Nephron Exp. Nephrol., 2006,104(4):E135-E139. doi: 10.1159/000094964
9. [9]
  Motterlini R, Clark J E, Foresti R, Sarathchandra P, Mann B E, Green C J. Carbon Monoxide-Releasing Mole Cules-Characterization of Biochemical and Vascular Activities[J]. Circ. Res., 2002,90(2):E17-E24.
10. [10]
  Motterlini R, Otterbein L E. The Therapeutic Potential of Carbon Monoxide[J]. Nat. Rev. Drug Discov., 2010,9(9):728-743. doi: 10.1038/nrd3228
11. [11]
  Romao C C, Blaettler W A, Seixas J D, Bernardes G J L. Developing Drug Molecules for Therapy with Carbon Monoxide[J]. Chem. Soc. Rev., 2012,41(9):3571-3583. doi: 10.1039/c2cs15317c
12. [12]
  Schatzschneider U. Novel Lead Structures and Activation Mechanisms for CO-Releasing Molecules (CORMs)[J]. Brit. J. Pharmacol., 2015,172(6):1638-1650. doi: 10.1111/bph.12688
13. [13]
  Fairlamb I J S, Lynam J M. Advances in Bioorganometallic Chemistry. Amsterdam: Elsevier, 2019: 137-154
14. [14]
  LI Y, WANG X, XIE X L, ZHANG J, TANG B. Progress in Organic Fluorescent Probes and Photocontrolled Releasers for Carbon Monoxide[J]. Acta Chim. Sinica, 2021,79(1):36-44.
15. [15]
  Faizan M, Muhammad N, Niazi K U K, Hu Y X, Wang Y Y, Wu Y, Sun H M, Liu R X, Dong W S, Zhang W Q, Gao Z W. CO-Releasing Materials: An Emphasis on Therapeutic Implications, as Release and Subsequent Cytotoxicity are the Part of Therapy[J]. Materials, 2019,12(10)1643. doi: 10.3390/ma12101643
16. [16]
  Ferrandiz M L, Maicas N, Garcia-Arnandis I, Terencio Mx C, Motterlini R, Devesa I, Joosten L A, van den Berg W B, Alcaraz M J. Treatment with a CO-Releasing Molecule (CORM-3) Reduces Joint Inflammation and Erosion in Murine Collagen-Induced Arthritis[J]. Ann. Rheum. Dis., 2008,67(9):1211-1217.
17. [17]
  Zhang W Q, Atkin A J, Thatcher R J, Whitwood A C, Fairlamb I J, Lynam J M. Diversity and Design of Metal-Based Carbon MonoxideReleasing Molecules (CO -RMs) in Aqueous Systems: Revealing the Essential Trends[J]. Dalton Trans., 2009,14(22):4351-4358.
18. [18]
  Kretschmer R, Gessner G, Gorls H, Heinemann S H, Westerhausen M. Dicarbonyl-bis(cysteamine)iron(Ⅱ): A Light Induced Carbon Monoxide Releasing Molecule Based on Iron (CORM-S1)[J]. J. Inorg. Biochem., 2011,105(1):6-9. doi: 10.1016/j.jinorgbio.2010.10.006
19. [19]
  Crook S H, Mann B E, Meijer A J H M, Adams H, Sawle P, Scapens D, Motterlini R. [Mn(CO)₄{S₂CNMe(CH₂CO₂H)}], A New Water-Soluble CO-Releasing Molecule[J]. Dalton Trans., 2011,40(16):4230-235. doi: 10.1039/c1dt10125k
20. [20]
  Gullotta F, Di Masi A, Ascenzi P. Carbon Monoxide: An Unusual Drug[J]. Iubmb Life, 2012,64(5):378-386. doi: 10.1002/iub.1015
21. [21]
  Nobre L S, Seixas J D, Romao C C, Saraiva L M. Antimicrobial Action of Carbon Monoxide-Releasing Compounds.Antimicrob[J]. Agents Chemother., 2007,51(12):4303-4307. doi: 10.1128/AAC.00802-07
22. [22]
  Bannenberg G L, Vieira H L A. Therapeutic Applications of the Gaseous Mediators Carbon Monoxide and Hydrogen Sulfide[J]. Expert Opin. Ther. Pat., 2009,19(5):663-682. doi: 10.1517/13543770902858824
23. [23]
  Zobi F, Blacque O, Jacobs R A, Schaub M C, Bogdanova A Y. 17 e^- Rhenium Dicarbonyl CO-Releasing Molecules on a Cobalamin Scaffold for Biological Application[J]. Dalton Trans., 2011,41(2):370-378.
24. [24]
  Sitnikov N S, Malysheva Y B, Fedorov A Y, Schmalz H G. Design and Synthesis of New Protease-Triggered CO-Releasing Peptide-Metal-Complex Conjugates[J]. Eur. J. Org. Chem., 2019(40):6830-6837.
25. [25]
  Kunz P C, Meyer H, Barthel J, Sollazzo S, Schmidt A M, Janiak C. Metal Carbonyls Supported on Iron Oxide Nanoparticles to Trigger the CO-Gasotransmitter Release by Magnetic Heating[J]. Chem. Commun., 2013,49(43):4896-4898. doi: 10.1039/c3cc41411f
26. [26]
  Heinemann S H, Hoshi T, Westerhausen M, Schiller A. Carbon Monoxide-Physiology, Detection and Controlled Release[J]. Chem. Commun., 2014,50(28):3644-3660. doi: 10.1039/C3CC49196J
27. [27]
  Ling K, Men F, Wang W C, Zhou Y Q, Zhang H W, Ye D W. Carbon Monoxide and Its Controlled Release: Therapeutic Application, Detection, and Development of Carbon Monoxide Releasing Molecules (CORMs)[J]. J. Med. Chem., 2018,61(7):2611-2635. doi: 10.1021/acs.jmedchem.6b01153
28. [28]
  Hasegawa U, Van der Vlies A J, Simeoni E, Wandrey C, Hubbell J A. Carbon Monoxide-Releasing Micelles for Immunotherapy[J]. J. Am. Chem. Soc., 2010,132(51):18273-18280. doi: 10.1021/ja1075025
29. [29]
  Long L, Jiang X J, Wang X, Xiao Z Y, Liu X M. Water -Soluble Diiron Hexacarbonyl Complex as a CO-RM: Controllable CO-Releasing, Releasing Mechanism and Biocompatibility[J]. Dalton Trans., 2013,42:15663-15669. doi: 10.1039/c3dt51281a
30. [30]
  Chen L M, Jiang X U, Wang X L, Long L, Zhang J Y, Liu X M. A Kinetic Analysis of CO Release from a Diiron Hexacarbonyl Complex Promoted by Amino Acids[J]. New J. Chem., 2014,38(12):5957-5963. doi: 10.1039/C4NJ00661E
31. [31]
  Jiang X J, Long L, Wang H L, Chen L M, Liu X M. Diiron Hexacarbonyl Complexes as Potential CO-RMs: CO -Releasing Initiated by a Substitution Reaction with Cysteamine and Structural Correlation to the Bridging Linkage[J]. Dalton Trans., 2014,43(26):9968-9975. doi: 10.1039/C3DT53620C
32. [32]
  Jiang X J, Chen L M, Wang X, Long L, Xiao Z Y, Liu X M. Photoinduced Carbon Monoxide Release from Half-Sandwich Iron(Ⅱ) Carbonyl Complexes by Visible Irradiation: Kinetic Analysis and Mechanistic Investigation[J]. Chem. Eur. J., 2015,21(37):13065-13072. doi: 10.1002/chem.201501348
33. [33]
  Guo Z M, Jin J, Xiao Z Y, Chen N W, Jiang X J, Liu X M, Wu L F, He Y, Zhang S H. Four Iron Carbonyl Complexes Containing both Pyridyl and Halide Ligands: Their Synthesis, Characterization, Stability, and Anticancer Activity[J]. Appl. Organomet. Chem., 2021,35(1)e6045.
34. [34]
  Yang X Q, Jin J, Guo Z M, Xiao Z Y, Chen N W, Jiang X J, He Y, Liu X M. The Monoiron Anion fac -Fe(CO)₃I₃^- and Its Organic Aminium Salts: Their Preparation, CO-Release, and Cytotoxicity[J]. New J. Chem., 2020,44(25):10300-10308. doi: 10.1039/D0NJ01182G
35. [35]
  Xiao Z Y, Jiang R, Jin J, Yang X Q, Xu B Y, Liu X M, He Y B, He Y. Diiron(Ⅱ) Pentacarbonyl Complexes as CO-Releasing Molecules: Their Synthesis, Characterization, CO-Releasing Behaviour and Biocompatibility[J]. Dalton Trans., 2019,48(2):468-477. doi: 10.1039/C8DT03982H
36. [36]
  Pierri A E, Huang P J, Garcia J V, Stanfill J G, Chui M, Wu G, Zheng N, Ford P C. A PhotoCORM Nanocarrier for CO Release Using NIR Light[J]. Chem. Commun., 2015,51(11):2072-2075.
37. [37]
  Ou J, Zheng W H, Xiao Z Y, Yan Y P, Jiang X J, Dou Y, Jiang R, Liu X M. Core-Shell Materials Bearing Iron(Ⅱ) Carbonyl Units and Their CO-Release via an Upconversion Process[J]. J. Mater. Chem. B, 2017,5(41):8161-8168. doi: 10.1039/C7TB01434A
38. [38]
  Scapens D, Adams H, Johnson T R, Mann B E, Sawle P, Aqil R, Perrior T, Motterlini R. [(η-C₅H ₄R)Fe(CO) ₂X], X=Cl, Br, I, NO₃, CO₂Me and[(η-C₅ H ₄R)Fe(CO) ₃]⁺, R= (CH₂)_nCO₂Me (n=0-2), and CO₂CH ₂CH₂OH: A New Group of CO-Releasing Molecules[J]. Dalton Trans., 2007,43:4962-4973.
39. [39]
  Holleman A F, Wiberg E. Inorganic Chemistry. San Diego: Academic Press, 2001: 136-140
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