Can Satraplatin be hydrated before the reduction process occurs? The DFT computational study
Jazyk angličtina Země Německo Médium print-electronic
Typ dokumentu časopisecké články, práce podpořená grantem
- MeSH
- chemické modely MeSH
- kinetika MeSH
- kvantová teorie MeSH
- ligandy MeSH
- molekulární modely MeSH
- organoplatinové sloučeniny chemie MeSH
- oxidace-redukce MeSH
- protinádorové látky chemie MeSH
- termodynamika MeSH
- voda chemie MeSH
- Publikační typ
- časopisecké články MeSH
- práce podpořená grantem MeSH
- Názvy látek
- amminedichloro(cyclohexylamine)platinum(II) MeSH Prohlížeč
- JM 335 MeSH Prohlížeč
- ligandy MeSH
- organoplatinové sloučeniny MeSH
- protinádorové látky MeSH
- satraplatin MeSH Prohlížeč
- voda MeSH
Hydration reactions of two anticancer Pt(IV) complexes JM149 and JM216 (Satraplatin) were studied computationally together with the hydration of the Pt(II) complex JM118, which is a product of the Satraplatin reduction. Thermodynamic and kinetic parameters of the reactions were determined at the B3LYP/6-311++G(2df.2pd)//B3LYP/6-31 + G(d)) level of theory. The water solution was modeled using the COSMO implicit solvation model, with cavities constructed using Klamt's atomic radii. It was found that hydration of the Pt(IV) complexes is an endergonic/endothermic reaction. It follows the (pseudo)associative mechanism is substantially slower (k ≈ 10(-11) s(-1)) than the corresponding reaction of Pt(II) analogues ((k ≈ 10(-5) s(-1)). Such a low value of the reaction constant signifies that the hydration of JM149 and Satraplatin is with high probability a kinetically forbidden reaction. Similarly to JM149 and Satraplatin, the hydration of JM118 is an endothermic/endoergic reaction. On the other hand, the kinetic parameters are similar to those of cisplatin Zimmermann et al. (J Mol Model 17:2385-2393, 2011), allowing the hydration reaction to occur at physiological conditions. These results suggest that in order to become active Satraplatin has to be first reduced to JM118, which may be subsequently hydrated to yield the active species.
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J Chem Phys. 2011 Jan 14;134(2):024520 PubMed
J Chem Phys. 2008 Apr 28;128(16):165103 PubMed
Cancer Res. 1992 Sep 15;52(18):5065-72 PubMed
J Comput Chem. 2008 Nov 15;29(14):2370-81 PubMed
Biochem Pharmacol. 2004 Sep 1;68(5):857-66 PubMed
Biochemistry. 2003 Jan 28;42(3):792-800 PubMed
J Inorg Biochem. 2006 Oct;100(10):1594-605 PubMed
J Inorg Biochem. 1999 Oct;77(1-2):111-5 PubMed
J Phys Chem B. 2005 Jun 2;109(21):11006-15 PubMed
J Mol Model. 2011 Sep;17(9):2385-93 PubMed
Biochemistry. 2003 May 27;42(20):6321-32 PubMed
Dalton Trans. 2010 Feb 7;39(5):1295-301 PubMed
J Am Chem Soc. 2006 Feb 8;128(5):1654-63 PubMed
J Inorg Biochem. 2005 Nov;99(11):2184-96 PubMed
J Phys Chem B. 2005 Jun 23;109(24):12195-205 PubMed
J Biol Inorg Chem. 2000 Apr;5(2):178-88 PubMed
Cancer Chemother Pharmacol. 1996;38(2):155-62 PubMed
J Pharm Biomed Anal. 1995 Nov;13(12):1493-8 PubMed
J Phys Chem B. 2006 Jun 22;110(24):12047-54 PubMed
J Comput Chem. 2005 Jul 15;26(9):907-14 PubMed
Dalton Trans. 2010 Sep 21;39(35):8113-27 PubMed
Cancer Res. 1993 Jun 1;53(11):2581-6 PubMed
Biochem Pharmacol. 2002 Jun 1;63(11):1989-96 PubMed
Anticancer Res. 1996 Jan-Feb;16(1):33-8 PubMed
Inorg Chem. 2003 Nov 3;42(22):7162-72 PubMed
Med Oncol. 2002;19(4):261-5 PubMed
J Chem Phys. 2009 Oct 7;131(13):135101 PubMed
J Inorg Biochem. 2005 Feb;99(2):575-83 PubMed
J Chem Theory Comput. 2006 Jan;2(1):103-6 PubMed
