Antitumour Potential of Boron Containing Organotin Carboxylates

A number of carboranyl-based organotin compounds have been screened for anti-cancer activity.80 82

Table 22.5 Typical ID50 values (ng/ml) of two selected fluorine-substituted di-w-butyltin carboxylates of types 1 and 2

Cell line

Table 22.5 Typical ID50 values (ng/ml) of two selected fluorine-substituted di-w-butyltin carboxylates of types 1 and 2

Cell line

Compound

MCF-7

EVSA-T

WIDr

IGROV

M19 MEL

A498

1, R = Bu,

55

43

275

60

114

105

R'COO =

C6F5CH2COO

2, R = Bu,

10

19

145

20

36

50

R'COO =

c6f5ch2coo

CPT

699

422

967

169

558

2253

DOX

10

8

11

60

16

90

A carborane moiety, C2B10Hn, is of about the same size as a phenyl ring but is spherical instead of planar. The replacement of an aromatic phenyl ring of an organic molecule by a hyper-aromatic carboranyl moiety is routinely used in the field of boron-based metallotherapeutic agents. In some of the compounds synthesized, the tin atom was linked directly to one of the boron or carbon atoms of the carboranyl moiety. In other compounds, the carboranyl moieties were bound to a CO2 or to a CH2CO2 group that served as a linker to tin atoms of a distannoxane structure (type 1). Their cytotoxicities are comparable to those of organotin carboxylates without the carborane moiety (Table 22.6).

An attempt to synthesize a carborane-based organotin compound with a polyoxaalkyl chain linked to the carboranyl moiety, in order to increase the water solubility (discussed later), produced a triphenylstannate83 instead of a derivative of type 3, which was expected to be formed (Figure 22.4).

The water solubility of this triphenylstannate is increased dramatically by the presence of the polyoxa substituent and probably primarily by the fact that the compound is a salt. Like other organotin salts, it exhibits a cytotoxicity similar to those obtained for carboranyltin compounds of type 3.

Table 22.6 Typical ID50 values (ng/ml) of two selected carborane-based organotin compounds of type 1: {[Bu2(R'COO)Sn]2O}2

Cell line

Compound

MCF-7

EVSA-T

WIDR

IGROV

M19 MEL

A498

H226

2-Ph-m-C2B10H11-1-COOH

56527

45168

42426

58292

>60000

55032

11747

1, R = Bu, R'COO

138

164

514

169

220

301

388

= 2-Ph-m-C2Bl0H„-l-COO

2, R'COO

146

142

439

139

174

195

291

= l,2-C2Bi0H h -9-COO

CPT

699

422

967

169

558

2253

3269

DOX

10

8

11

60

16

90

199

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