Transplatin

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trans-Dichlorodiammineplatinum(II)
Names
IUPAC name
(SP-4-1)-diamminedichloridoplatinum(II)
Other names
Reiset's second chloride, transplatin
Identifiers
3D model (JSmol)
ECHA InfoCard 100.035.422 Edit this at Wikidata
UNII
  • InChI=1S/2ClH.2H3N.Pt/h2*1H;2*1H3;/q;;;;+2/p-2
    Key: LXZZYRPGZAFOLE-UHFFFAOYSA-L
  • ionic form: N.N.Cl[Pt]Cl
  • coordination form: Cl[Pt](Cl)([NH3])[NH3]
Properties
Cl2H6N2Pt
Molar mass 300.05 g·mol−1
Appearance yellow solid
low
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

trans-Dichlorodiammineplatinum(II) is the trans isomer of the coordination complex with the formula trans-PtCl2(NH3)2, sometimes called transplatin.[1] It is a yellow solid with low solubility in water but good solubility in DMF. The existence of two isomers of PtCl2(NH3)2 led Alfred Werner to propose square planar molecular geometry.[2] It belongs to the molecular symmetry point group D2h.

Preparation and reactions

The complex is prepared by treating [Pt(NH3)4]Cl2 with hydrochloric acid.[2]

Many of the reactions of this complex can be explained by the trans effect. It slowly hydrolyzes in aqueous solution to give the mixed aquo complex trans-[PtCl(H2O)(NH3)2]Cl. Similarly it reacts with thiourea (tu) to give colorless trans-[Pt(tu)2(NH3)2]Cl2. In contrast, the cis isomer gives [Pt(tu)4]Cl2. Oxidative addition of chlorine gives trans-PtCl4(NH3)2.

Medicinal chemistry

trans-Dichlorodiammineplatinum(II) has had far less impact on medicinal chemistry compared to its cis isomer, cisplatin, which is a major anticancer drug. Nonetheless, replacement of the ammonia with other ligands has led to highly active drugs that have attracted much attention.[3]

References

  1. ^ Nakata, B; Yamagata, S; Kanehara, I; Shirasaka, T; Hirakawa, K (25 June 2006). "Transplatin, a cisplatin trans-isomer, may enhance the anticancer effect of 5-fluorouracil". Journal of Experimental & Clinical Cancer Research. 25 (2): 195–200. PMID 16918130.
  2. ^ a b Kauffman, George B; Cowan, Dwaine O; Slusarczuk, George; Kirschner, Stanley (1963). "cis - and trans -Dichlorodiammineplatinum(II)". Inorganic Syntheses. Vol. VII. pp. 239–245. doi:10.1002/9780470132388.ch63. ISBN 978-0-470-13238-8.
  3. ^ Aris, S. M; Farrell, N. P (2009). "Towards Antitumor Active trans-Platinum Compounds". European Journal of Inorganic Chemistry. 2009 (10): 1293–1302. doi:10.1002/ejic.200801118. PMC 2821104. PMID 20161688.
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