The Active Groups in the Structure of Thiamine Tetrahydrofurfuryldisulfide in its Anti-Potassium, Anti-Quinidine, and Anti-Acetylcholine Effects on Guinea-Pig Atria

• Published in: Journal of vitaminology 1972/12/10, Vol.18(4), pp.225-234
• Main Authors: MORITA, MASAO, SUGIMOTO, JIRO, NAGATA, MITSUHIRO, KINUGAWA, IWAO
• Format: Article
• Language: English
• Subjects: Acetylcholine - antagonists & inhibitors; Animals; Disulfides - pharmacology; Electric Stimulation; Furans - pharmacology; Guinea Pigs; Heart Atria - drug effects; In Vitro Techniques; Male; Potassium - antagonists & inhibitors; Pyrimidines - pharmacology; Quinidine - antagonists & inhibitors; Sinoatrial Node - drug effects; Structure-Activity Relationship; Sulfides - pharmacology
• ISSN: 0022-5398
• DOI: 10.5925/jnsv1954.18.225

Anti-potassium, anti-quinidine, and anti-acetylcholine effects of thiamine tetrahydrofurfuryldisulfide (TTFD) on isolated guinea-pig atria were compared with those of thialium, dimethialium, dimethiamine propyldisulfide (DMPD), oxythiamine, and oxythiamine propyldisulfide (OTPD). From the different effects of these thiamine derivatives having different chemical structures, the following findings were obtained in relation to their possible active atom groups in above effects. 1) TTFD and DMPD showed an anti-potassium effect on the spontaneous contractions; this action may be caused by atom groups common to their chemical structures, that is, the presence of an S-S bond and presumedly also of a pair of nitrogen atoms, one of which is in a 4-amino group in a pyrimidine ring and the other of which is in an open thiazole ring at a distance of about 4 ångström from the first. 2) TTFD and DMPD showed an anti-quinidine effect on the atrial contractions. 3) In its high concentrations, DMPD depressed the sino-atrial node activity. 4) The anti-acetylcholine effect of thiamine related compounds tested may be due to the fact that they have neither an S-S bond nor an amino group in their pyrimidine rings. 5) The anti-potassium, anti-quinidine effects of thiamine were weak, while those of the thiamine derivatives such as TTFD and DMPD were remarkable because of the presence of an S-S bond which may promote an affinity of the thiamine molecule for atria.