Anticancer Properties of Thio-diglycollic Acid

Sahasrabudhe, M. B.; Narurkar, M. V.; Kotnis, L. B.; Tilak, B. D.; Shah, L C; Ven, Gogte

doi:10.1038/191388a0

Cited by 4 publications

(2 citation statements)

References 4 publications

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“…2-Hexenoic acid lactone, and its dimeric form, as well as methylprotoanemonin also had no effect on tumour growth. Thiodiglycollic acid is not a member of the lactone series, but has been reported (Sahasrabudhe et al, 1961) to inhibit tumour growth, and was included for this reason. No significant inhibition of the growth of this sarcoma was obtained with daily injections of 5 mg. and 10 mg. of thiodiglycollic acid in our experiments (Table III). SUMMARY logically malignanit sarcomas, and many of them were successfully transplanted into other rats.…”

Section: Resultsmentioning

confidence: 99%

Further Studies on the Carcinogenic and Growth-Inhibitory Activity of Lactones and Related Substances

Dickens¹,

Jones²

1963

Br J Cancer

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IT was shown (Dickens and Jones, 1961;Dickens, 1962) that a number of lactones and related substances were slow-acting carcinogens in the rat when administered repeatedly by subcutaneous injection. The compounds tested which produced malignant tumours at the injection site included the 4-membered lactones f8-propiolactone, a-carboxy-,8-phenyl-fl-propiolactone, aa-diphenyl-flpropiolactone; and also sodium benzyl penicillin (penicillin G), which possesses a 4-membered lactam ring. That carcinogenic activity was not limited to 4-membered lactones was shown by the carcinogenicity of the following compounds which contained a 5-membered y-lactone ring: patulin, penicillic acid, methyl protoanemonin, 2-hexenoic lactone and 4-hexenoic lactone.The arachis oil used as solvent for these lactones did not itself produce any local tumours, and the freshly prepared aqueous solutions of /J-propiolactone were also carcinogenic. Tumours were not obtained with either 3-hexenoic lactone, aangelica lactone (3-pentenoic-y-lactone), or with the saturated compound ybutyrolactone.The tumours were nearly all fibroblastic with varying amounts of collagen and were classified as spindle cell sarcomas, fibrosarcomas or myxosarcomas.Before this study only f8-propiolactone in this series of compounds had been shown by Walpole et al. (1954) to possess carcinogenic properties: this compound is also capable of inducing skin tumours, including some carcinomas, in mice (Roe and Glendenning, 1956). As a result of our experiments we concluded that the high chemical reactivity associated with the highly strained ring of fl-propiolactone, e.g. the nucleophilic type of attack resulting in the alkylation of the SH group of cysteine which we demonstrated for f8-propiolactone (Dickens and Jones, 1961), was also a marked feature of the other carcinogenic lactones, which were also found to be capable of reacting with cysteine in neutral solution causing loss of the free SH group. Penicillin, because of its 4-membered,lactam ring, was already known to react similarly on incubation with cysteine, which abolishes its antibiotic properties. In this series of 5-membered lactone rings, such reactivity and carcinogenicity appears to be associated with either acfl-unsaturation or the presence of an external double-bond at the 4-position of the y-lactone ring, or preferably with both of these. If there was no double-bond, or if it was in the 3-position, carcinogenic activity was not demonstrable.In the present paper we report the results obtained with a further series of compounds of similar chemical type. These were the 4-membered ring of f,ldimethyltrimethylene oxide (I); the 5-membered ring of maleic anhydride (II);

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Section: Resultsmentioning

confidence: 99%

Further Studies on the Carcinogenic and Growth-Inhibitory Activity of Lactones and Related Substances

Dickens¹,

Jones²

1963

Br J Cancer

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“…The exposure in vitro of ascites cells and of tumor fragments to solutions of extreme pH diminishes their transplantability; earlier work on this (Sugiura et al, 1921 ;Sugiura and Benedict, 1927 ;Sugiura, 1928;Downes, 1929;Krontowski and Magath, 1929;Simoes Raposo, 1933) was summarized in part and extended by Collier (1934), as noted recently by Sugiura (1953). Mlost recently, the anti-tumor activities of over a hundred mono-and di-carboxylic acids have been measured by exposing tumor cells to them in vitro at various pH's for a few minutes before inoculation (Hodes et al, 1960;Morgan et al, 1960;Townsend et al, 1960;Sahasrabudhe et al, 1961 T'olnai and Morgan, 1961and Morgan, , 1962aand Morgan, , 1962bTownsend et al, 1961). The present work shows how a large percentage of young ascites tumors can be destroyed in vivo without killing the hosts.…”

Section: Discussionmentioning

confidence: 99%

Inhibition of an Ehrlich Ascites Tumor In Vivo by Partially Neutralized Solutions of Sodium Lactate

Stevens¹,

Atchley²,

Herzog³

et al. 1963

Br J Cancer

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Effect of 2:5-dicarbethoxy-3:4-dihydroxy-thiophene (dicetol) on glucose metabolism of homo- and heterofermentative bacteria

Nadkarni¹

1964

Biochemical Pharmacology

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Anticancer Properties of Thio-diglycollic Acid

Cited by 4 publications

References 4 publications

Further Studies on the Carcinogenic and Growth-Inhibitory Activity of Lactones and Related Substances

Further Studies on the Carcinogenic and Growth-Inhibitory Activity of Lactones and Related Substances

Inhibition of an Ehrlich Ascites Tumor In Vivo by Partially Neutralized Solutions of Sodium Lactate

Effect of 2:5-dicarbethoxy-3:4-dihydroxy-thiophene (dicetol) on glucose metabolism of homo- and heterofermentative bacteria

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