{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,4,3]],"date-time":"2026-04-03T15:36:36Z","timestamp":1775230596013,"version":"3.50.1"},"reference-count":23,"publisher":"Wiley","issue":"2","license":[{"start":{"date-parts":[[2005,3,3]],"date-time":"2005-03-03T00:00:00Z","timestamp":1109808000000},"content-version":"vor","delay-in-days":6027,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["European Journal of Biochemistry"],"published-print":{"date-parts":[[1988,9]]},"abstract":"<jats:p>A series of mono\u2010and geminal difluorinated analogues of spermidine (4\u2010azaoctane\u20101, 8\u2010diamine) have been tested as potential substrates of partially purified rat hepatoma (HTC) cell or pure bovine spleen spermine synthase (EC 2.5.1.22).<\/jats:p><jats:p>Substitution of the hydrogen atoms of the methylene group at position 7 by one or two fluorine atoms decreases 8\u2010fold and 160\u2010fold the apparent <jats:italic>K<\/jats:italic><jats:sub>m<\/jats:sub> values for the HTC cell enzyme respectively. Similarly, the <jats:italic>K<\/jats:italic><jats:sub>m<\/jats:sub> values of 7\u2010monofluoro and 7, 7\u2010difluorospermidine for the pure bovine enzyme are reduced 8\u2010fold and 100\u2010fold respectively, incomparison with spermidine. Di\u2010, but not monofluoro substitution, in the 6\u2010position causes a 5\u2010fold reduction in the affinity for the HTC cell enzyme. Gem\u2010fluorine substitution in the 2\u2010position a abolishes substrate capability.<\/jats:p><jats:p>In addition to their high affinity for spermine synthase, 7\u2010monoflurospermidine and 7, 7\u2010difluorospermidine cause substrate inhibition. This phenomenom, which is more pronounced in the case of the difluorinated analogues is pH\u2010dependent.<\/jats:p><jats:p>These enzymatic findings are discussed with regard to the protonation sites of the spermidine analogues, determined by potentiometric titration, which vary as a function of the number and position of the fluorine substituents relative to the basic amino groups.<\/jats:p>","DOI":"10.1111\/j.1432-1033.1988.tb14274.x","type":"journal-article","created":{"date-parts":[[2005,3,4]],"date-time":"2005-03-04T02:31:05Z","timestamp":1109903465000},"page":"237-242","source":"Crossref","is-referenced-by-count":21,"title":["Fluorinated analogues of spermidine as substrates of spermine synthase"],"prefix":"10.1111","volume":"176","author":[{"given":"Jean G.","family":"BAILLON","sequence":"first","affiliation":[]},{"given":"Pierre S.","family":"MAMONT","sequence":"additional","affiliation":[]},{"given":"Joseph","family":"WAGNER","sequence":"additional","affiliation":[]},{"given":"Fritz","family":"GERHART","sequence":"additional","affiliation":[]},{"given":"Philippe","family":"LUX","sequence":"additional","affiliation":[]}],"member":"311","published-online":{"date-parts":[[2005,3,3]]},"reference":[{"key":"e_1_2_3_2_2","first-page":"245","volume-title":"Advances in polyamine research","author":"Raina A.","year":"1983"},{"key":"e_1_2_3_3_2","doi-asserted-by":"publisher","DOI":"10.1111\/j.1432-1033.1979.tb19756.x"},{"key":"e_1_2_3_4_2","doi-asserted-by":"publisher","DOI":"10.1042\/bj2150669"},{"key":"e_1_2_3_5_2","doi-asserted-by":"publisher","DOI":"10.1042\/bj1970315"},{"key":"e_1_2_3_6_2","doi-asserted-by":"publisher","DOI":"10.1021\/jm00347a014"},{"key":"e_1_2_3_7_2","doi-asserted-by":"publisher","DOI":"10.1016\/0003-9861(64)90161-4"},{"key":"e_1_2_3_8_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0378-4347(00)80389-8"},{"key":"e_1_2_3_9_2","doi-asserted-by":"publisher","DOI":"10.1016\/0014-4827(78)90292-6"},{"key":"e_1_2_3_10_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0076-6879(83)94048-X"},{"key":"e_1_2_3_11_2","doi-asserted-by":"publisher","DOI":"10.1016\/0020-711X(78)90135-0"},{"key":"e_1_2_3_12_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0378-4347(00)84307-8"},{"key":"e_1_2_3_13_2","doi-asserted-by":"crossref","first-page":"12324","DOI":"10.1016\/S0021-9258(18)67242-4","volume":"261","author":"Della Ragione F.","year":"1986","journal-title":"J. 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