PROFILPELAJAR.COM

Cisplatin

Cisplatin, historically called Peyrone's salt,[1] is a drug used in chemotherapy to treat many types of cancer.[2]

Chemistry

Cisplatin is a coordination complex of platinum with amine and chloride ligands. It has the chemical name cis-diamminodichloridoplatinum(II) and chemical formula Pt(NH3)2Cl2. It is specifically the cis isomer of this compound: the trans isomer, transplatin, does not have any effect on cancer. There is also a polymeric isomer called Magnus's green salt.

Preparation

Since its discovery in 1845,[3] cisplatin has been made from potassium tetrachloroplatinate. Three different routes have been used since the 20th century.[4] The first modern preparation was published by George B. Kauffman, and reacted potassium tetrachloroplatinate directly with aqueous ammonia:[1]

K2PtCl4 + 2 NH3 → KCl2 + P2(NH3)2Cl2

A more advanced preparation uses ammonium acetate instead:[5][better source needed]

K2PtCl4 + 2 NH4CO2CH3 → Pt(NH3)2Cl2 + 2 CH3COOH + 2 KCl

These methods also make Magnus's green salt as an impurity. To avoid this impurity, a more complicated synthesis developed by S.C. Dhara first makes potassium tetraiodoplatinate in situ:[5][better source needed]

K2PtCl4 + 4 KI → K2PtI4 + 4 KCl
K2PtI4 + 2 NH3 → Pt(NH3)2I2 + 2 KCl

The stronger cis effect of the iodide ligand means that the iodide relative of Magnus's green salt is not made. To change the iodido complex back to cisplatin, aqueous silver nitrate is used to precipitate silver iodide, making the cationic complex [Pt(NH3)2(H2O)2]2+:[6]

Pt(NH3)2I2 + 2 AgNO3 + 2 H2O → [Pt(NH3)2(H2O)2](NO3)2 + 2 AgI

This complex is then treated with a chloride source to make cisplatin.

[Pt(NH3)2(H2O)2]2+ + 2 Cl− → Pt(NH3)2Cl2 + 2 H2O

The Dhara process is the main route used to make cisplatin today.[4]

References

  1. ↑ 1.0 1.1 Kauffman, George B.; Cowan, Dwaine O.; Slusarczuk, George; Kirschner, Stanley (1963). "cis - and trans -Dichlorodiammineplatinum(II)". Inorganic Syntheses. Vol. 7. pp. 239–245. doi:10.1002/9780470132388.ch63.
  2. ↑ Ghosh, Sumit (2019). "Cisplatin: The first metal based anticancer drug". Bioorganic Chemistry. 88 102925. doi:10.1016/j.bioorg.2019.102925. PMID 31003078.
  3. ↑ Kauffman, George B.; Pentimalli, Raffaele; Doldi (1908–2001), Sandro; Hall, Matthew D. (2010). "Michele Peyrone (1813–1883), Discoverer of Cisplatin". Platinum Metals Review. 54 (4): 250–256. doi:10.1595/147106710X534326.{{cite journal}}: CS1 maint: numeric names: authors list (link)
  4. ↑ 4.0 4.1 Petruzzella, Emanuele; Chirosca, Cristian V.; Heidenga, Cameron S.; Hoeschele, James D. (2015). "Microwave-assisted synthesis of the anticancer drug cisplatin, cis-[Pt(NH3)2Cl2]". Dalton Transactions. 44 (7): 3384–3392. doi:10.1039/C4DT03617D. PMID 25600831.
  5. ↑ 5.0 5.1 Kukushikin, Vadim Yu.; Oskarsson, Åke; Elding, Lars I.; Farrell, Nicholas; Dunham, Stephen; Lippard, Stephen J. (1998). "Facile Synthesis of Isomerically Pure cis -Dichlorodiammineplatinum(II), Cisplatin". Inorganic Syntheses. Vol. 32. pp. 141–144. doi:10.1002/9780470132630.ch23. ISBN 978-0-471-24921-4.
  6. ↑ Wilson, Justin J.; Lippard, Stephen J. (2014). "Synthetic Methods for the Preparation of Platinum Anticancer Complexes". Chemical Reviews. 114 (8): 4470–4495. doi:10.1021/cr4004314. PMC 3999256. PMID 24283498.

Content Disclaimer

Informasi ini disarikan dari Wikipedia dan disajikan kembali untuk tujuan edukasi. Konten tersedia di bawah lisensi CC BY-SA 3.0. Kami tidak bertanggung jawab atas ketidakakuratan data yang bersumber dari kontribusi publik tersebut.

  1. The information displayed on this website is sourced in part or in whole from Wikipedia and has been adapted for the purpose of restating it. We strive to provide accurate and relevant information, however:
  2. There is no guarantee of absolute accuracy. Wikipedia is an open, collaborative project that can be edited by anyone, so information is subject to change.
  3. It is not intended to constitute professional advice. The content displayed is for informational and educational purposes only. For important decisions (e.g., medical, legal, or financial), please consult a professional.
  4. Content copyright. Wikipedia is licensed under the Creative Commons Attribution-ShareAlike License (CC BY-SA). This means that content may be reused with appropriate attribution and shared under a similar license.
  5. Responsible use. Any risk arising from the use of information from this website is entirely the responsibility of the user.