Abstract
The synthesis and X-ray structure (as the tetrahydrate) of the platinum(IV) complex trans, trans, trans[Pt(N-3)(2)(OH)(2)(NH3)(2)] 3 are described and its photochemistry and photobiology are compared with those of the cis isomer cis,trans,cis-[Pt(N-3)(2)(OH)(2)(NH3)(2)] 4. Complexes 4 and 3 are potential precursors of the anticancer drug cisplatin and its inactive trans isomer transplatin, respectively. The trans complex 3 is octahedral, contains almost linear azide ligands, and adopts a layer structure with extensive inter-molecular hydrogen bonding. The intense azide-to-platinum(iv) charge-transfer band of complex 3 (285 nm; epsilon = 19 500 m(-1) cm(-1)) is more intense and bathochromically shifted relative to that of the cis isomer 4. In contrast to transplatin, complex 3 rapidly formed a platinum(n) bis(5'-guanosine monophosphate) (5'-GMP) adduct when irradiated with UVA light, and did not react in the dark. Complexes 3 and 4 were non-toxic to human skin cells (keratinocytes) in the dark, but were as cytotoxic as cisplatin on irradiation for a short time (50 min). Damage to the DNA of these cells was detected by using the "comet" assay. Both trans- and cis-diammine platinum(iv) diazide complexes therefore have potential as photochemotherapeutic agents.
| Original language | English |
|---|---|
| Pages (from-to) | 3155-3161 |
| Number of pages | 7 |
| Journal | Chemistry: a European Journal |
| Volume | 12 |
| Issue number | 11 |
| DOIs | |
| Publication status | Published - 2006 |
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Mackay, F. S., Woods, J. A., Moseley, H., Ferguson, J., Dawson, A., Parsons, S., & Sadler, P. J. (2006). A photoactivated trans-diammine platinum complex as cytotoxic as cisplatin. Chemistry: a European Journal, 12(11), 3155-3161. https://doi.org/10.1002/chem.200501601
Mackay, Fiona S. ; Woods, Julie A. ; Moseley, Harry et al. / A photoactivated trans-diammine platinum complex as cytotoxic as cisplatin. In: Chemistry: a European Journal. 2006 ; Vol. 12, No. 11. pp. 3155-3161.
@article{77590d3a02b34a39b7f3d6ffd38146fd,
title = "A photoactivated trans-diammine platinum complex as cytotoxic as cisplatin",
abstract = "The synthesis and X-ray structure (as the tetrahydrate) of the platinum(IV) complex trans, trans, trans[Pt(N-3)(2)(OH)(2)(NH3)(2)] 3 are described and its photochemistry and photobiology are compared with those of the cis isomer cis,trans,cis-[Pt(N-3)(2)(OH)(2)(NH3)(2)] 4. Complexes 4 and 3 are potential precursors of the anticancer drug cisplatin and its inactive trans isomer transplatin, respectively. The trans complex 3 is octahedral, contains almost linear azide ligands, and adopts a layer structure with extensive inter-molecular hydrogen bonding. The intense azide-to-platinum(iv) charge-transfer band of complex 3 (285 nm; epsilon = 19 500 m(-1) cm(-1)) is more intense and bathochromically shifted relative to that of the cis isomer 4. In contrast to transplatin, complex 3 rapidly formed a platinum(n) bis(5'-guanosine monophosphate) (5'-GMP) adduct when irradiated with UVA light, and did not react in the dark. Complexes 3 and 4 were non-toxic to human skin cells (keratinocytes) in the dark, but were as cytotoxic as cisplatin on irradiation for a short time (50 min). Damage to the DNA of these cells was detected by using the {"}comet{"} assay. Both trans- and cis-diammine platinum(iv) diazide complexes therefore have potential as photochemotherapeutic agents.",
author = "Mackay, {Fiona S.} and Woods, {Julie A.} and Harry Moseley and James Ferguson and Alice Dawson and Simon Parsons and Sadler, {Peter J.}",
year = "2006",
doi = "10.1002/chem.200501601",
language = "English",
volume = "12",
pages = "3155--3161",
journal = "Chemistry: a European Journal",
issn = "0947-6539",
publisher = "Wiley",
number = "11",
}
Mackay, FS, Woods, JA, Moseley, H, Ferguson, J, Dawson, A, Parsons, S & Sadler, PJ 2006, 'A photoactivated trans-diammine platinum complex as cytotoxic as cisplatin', Chemistry: a European Journal, vol. 12, no. 11, pp. 3155-3161. https://doi.org/10.1002/chem.200501601
A photoactivated trans-diammine platinum complex as cytotoxic as cisplatin. / Mackay, Fiona S.; Woods, Julie A.; Moseley, Harry et al.
In: Chemistry: a European Journal, Vol. 12, No. 11, 2006, p. 3155-3161.
Research output: Contribution to journal › Article › peer-review
TY - JOUR
T1 - A photoactivated trans-diammine platinum complex as cytotoxic as cisplatin
AU - Mackay, Fiona S.
AU - Woods, Julie A.
AU - Moseley, Harry
AU - Ferguson, James
AU - Dawson, Alice
AU - Parsons, Simon
AU - Sadler, Peter J.
PY - 2006
Y1 - 2006
N2 - The synthesis and X-ray structure (as the tetrahydrate) of the platinum(IV) complex trans, trans, trans[Pt(N-3)(2)(OH)(2)(NH3)(2)] 3 are described and its photochemistry and photobiology are compared with those of the cis isomer cis,trans,cis-[Pt(N-3)(2)(OH)(2)(NH3)(2)] 4. Complexes 4 and 3 are potential precursors of the anticancer drug cisplatin and its inactive trans isomer transplatin, respectively. The trans complex 3 is octahedral, contains almost linear azide ligands, and adopts a layer structure with extensive inter-molecular hydrogen bonding. The intense azide-to-platinum(iv) charge-transfer band of complex 3 (285 nm; epsilon = 19 500 m(-1) cm(-1)) is more intense and bathochromically shifted relative to that of the cis isomer 4. In contrast to transplatin, complex 3 rapidly formed a platinum(n) bis(5'-guanosine monophosphate) (5'-GMP) adduct when irradiated with UVA light, and did not react in the dark. Complexes 3 and 4 were non-toxic to human skin cells (keratinocytes) in the dark, but were as cytotoxic as cisplatin on irradiation for a short time (50 min). Damage to the DNA of these cells was detected by using the "comet" assay. Both trans- and cis-diammine platinum(iv) diazide complexes therefore have potential as photochemotherapeutic agents.
AB - The synthesis and X-ray structure (as the tetrahydrate) of the platinum(IV) complex trans, trans, trans[Pt(N-3)(2)(OH)(2)(NH3)(2)] 3 are described and its photochemistry and photobiology are compared with those of the cis isomer cis,trans,cis-[Pt(N-3)(2)(OH)(2)(NH3)(2)] 4. Complexes 4 and 3 are potential precursors of the anticancer drug cisplatin and its inactive trans isomer transplatin, respectively. The trans complex 3 is octahedral, contains almost linear azide ligands, and adopts a layer structure with extensive inter-molecular hydrogen bonding. The intense azide-to-platinum(iv) charge-transfer band of complex 3 (285 nm; epsilon = 19 500 m(-1) cm(-1)) is more intense and bathochromically shifted relative to that of the cis isomer 4. In contrast to transplatin, complex 3 rapidly formed a platinum(n) bis(5'-guanosine monophosphate) (5'-GMP) adduct when irradiated with UVA light, and did not react in the dark. Complexes 3 and 4 were non-toxic to human skin cells (keratinocytes) in the dark, but were as cytotoxic as cisplatin on irradiation for a short time (50 min). Damage to the DNA of these cells was detected by using the "comet" assay. Both trans- and cis-diammine platinum(iv) diazide complexes therefore have potential as photochemotherapeutic agents.
U2 - 10.1002/chem.200501601
DO - 10.1002/chem.200501601
M3 - Article
C2 - 16470886
SN - 0947-6539
VL - 12
SP - 3155
EP - 3161
JO - Chemistry: a European Journal
JF - Chemistry: a European Journal
IS - 11
ER -
Mackay FS, Woods JA, Moseley H, Ferguson J, Dawson A, Parsons S et al. A photoactivated trans-diammine platinum complex as cytotoxic as cisplatin. Chemistry: a European Journal. 2006;12(11):3155-3161. doi: 10.1002/chem.200501601
