Abstract
The Pt(IV) complex c,c,t-[Pt(NH3)2Cl2(OH)2] is an important intermediate in the synthesis of Pt(IV) anticancer prodrugs and has been investigated as an anticancer agent in its own right. An analysis of the vibrational spectroscopy of this molecule was previously reported (Faggiani et al., Can. J. Chem. 60:529, 1982), in which crystallographic determination of the structure of the complex permitted a site group approach. The space group, however, was incorrectly assigned. In the present study we have redetermined at high resolution crystal structures of c,c,t-[Pt(NH3)2Cl2(OH)2] and c,c,t-[Pt(NH3)2Cl2(OH)2]·H2O2, which makes possible discussion of the effect of hydrogen bonding on the N–H and O–H vibrational bands. The correct crystallographic site symmetry of the platinum complex in the c,c,t-[Pt(NH3)2Cl2(OH)2] structure is used to conduct a new vibrational analysis using both group-theoretical and modern density functional theory methods. This analysis reveals the nature and symmetry of the “missing band” described in the original publication and suggests a possible explanation for its disappearance.
Similar content being viewed by others
References
Hall MD, Mellor HR, Callaghan R, Hambley TW (2007) J Med Chem 50:3403–3411
Giandomenico CM, Abrams MJ, Murrer BA, Vollano JF, Rheinheimer MI, Wyer SB, Bossard GE, Higgins JD III (1995) Inorg Chem 34:1015–1021
Barnes KR, Kutikov A, Lippard SJ (2004) Chem Biol 11:557–564
Reithofer M, Galanski M, Roller A, Keppler BK (2006) Eur J Inorg Chem 2006:2612–2617
Olszewski U, Ach F, Ulsperger E, Baumgartner G, Zeillinger R, Bednarski P, Hamilton G (2009) Met Based Drugs 2009:1–11
Hall MD, Hambley TW (2002) Coord Chem Rev 232:49–67
Battle AR, Choi R, Hibbs DE, Hambley TW (2006) Inorg Chem 45:6317–6322
Zhang JZ, Wexselblatt E, Hambley TW, Gibson D (2012) Chem Commun 48:847–849
Singin AS, Mas’ko AS, Moldavanova LK, Lobanova EA, Serebryakov NG (1985) Pharm Chem J 19:589–593
Carr JL, Tingle MD, McKeage MJ (2002) Cancer Chemother Pharmacol 50:9–15
Gray HB, Banci L, Luchinat C, Turano P (2012) Nat Struct Mol Biol 19:868–869
Sabatini A, Bertini I (1965) Inorg Chem 4:959–961
Sabatini A, Bertini I (1966) Inorg Chem 5:204–206
Sabatini A, Bertini I (1965) Inorg Chem 4:1665–1667
Bertini I, Sabatini A (1966) Inorg Chem 5:1025–1028
Beattie IR (1975) Chem Soc Rev 4:107–153
Dyer RB, Woodruff WH (2011) In: Encyclopedia of inorganic and bioinorganic chemistry. Wiley, New York. doi:10.1002/9781119951438.eibc0304
Faggiani R, Howard-Lock HE, Lock CJL, Lippert B, Rosenberg B (1982) Can J Chem 60:529–534
Kuroda R, Neidle S, Ismail IM, Sadler PJ (1983) Inorg Chem 22:3620–3624
Marsh RE (1984) Inorg Chem 23:2363
Tschugájeff L, Chlopin W, Fritzmann E (1926) Z Anorg Allg Chem 151:253–268
Vollano JF, Blatter EE, Dabrowiak JC (1984) J Am Chem Soc 106:2732–2733
Bruker AXS (2008) APEX2. Bruker AXS, Madison
Bruker (2007) SAINT. Bruker AXS Inc., Madison, Wisconsin
Sheldrick GM (2008) SADABS. University of Göttingen, Göttingen
Bruker AXS (2008) XPREP. Bruker AXS, Madison
Sheldrick GM (2000) SHELXTL-97. University of Göttingen, Göttingen
Sheldrick GM (2008) Acta Crystallogr Sect A 64:112–122
Müller P (2009) Crystallogr Rev 15:57–83
Spek AL (2008) PLATON. Utrecht University, Utrecht
Roisnel T, Rodriguez-Carvajal J (2001) Mater Sci Forum 378–381:118–123
Cotton FA (1990) Chemical applications of group theory. Wiley, New York
Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Montgomery JA Jr, Vreven T, Kudin KN, Burant JC, Millam JM, Iyengar SS, Tomasi J, Barone V, Mennucci B, Cossi M, Scalmani G, Rega N, Petersson GA, Nakatsuji H, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Klene M, Li X, Knox JE, Hratchian HP, Cross JB, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Ayala PY, Morokuma K, Voth GA, Salvador P, Dannenberg JJ, Zakrzewski VG, Dapprich S, Daniels AD, Strain MC, Farkas O, Malick DK, Rabuck AD, Raghavachari K, Foresman JB, Ortiz JV, Cui Q, Baboul AG, Clifford S, Cioslowski J, Stefanov BB, Liu G, Liashenko A, Piskorz P, Komaromi I, Martin RL, Fox DJ, Keith T, Al-Laham MA, Peng CY, Nanayakkara A, Challacombe M, Gill PMW, Johnson B, Chen W, Wong MW, Gonzalez C, Pople JA (2003) Gaussian 03. Gaussian, Pittsburgh
Adamo C, Barone V (1999) J Chem Phys 110:6158–6170
Hay PJ, Wadt WR (1985) J Chem Phys 82:299–310
Dunham SO, Larsen RD, Abbott EH (1993) Inorg Chem 32:2049–2055
Acknowledgments
This work was supported by grant CA034992 (to S.J.L.) from the National Cancer Institute. Markrete Krikorian is thanked for her assistance in acquiring the X-ray powder diffraction data.
Author information
Authors and Affiliations
Corresponding author
Additional information
Dedicated to the memory of Ivano Bertini (1940–2012).
Responsible editors: Lucia Banci and Claudio Luchinat.
Electronic supplementary material
Below is the link to the electronic supplementary material.
Rights and permissions
About this article
Cite this article
Johnstone, T.C., Lippard, S.J. Reinterpretation of the vibrational spectroscopy of the medicinal bioinorganic synthon c,c,t-[Pt(NH3)2Cl2(OH)2]. J Biol Inorg Chem 19, 667–674 (2014). https://doi.org/10.1007/s00775-014-1109-6
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00775-014-1109-6