Biologicznie aktywne bisfosfoniany : struktura, synteza, właściwości i działanie

• Autorzy: Bałczewska E. , Bałczewski P.

Warianty tytułu

EN

Biologically active bisphosphonates : structure, synthesis, properties and action

• Języki publikacji: PL

Abstrakty

EN

The increasing interest in design and application of biologically active bisphosphonates and the lack of the relevant treatment of this subject in Polish language with emphasis of its chemical aspects, induced us, to review the literature up to April 2000 using Medline and Beilstein Cross Fire databases. Bisphosphonates are chemically and enzymatically stable analogs of physiological pyrophosphates which constitute natural inhibitors of mineralisation. Although first bisphosphonates were synthesized in the middle of XIX century, the concept of their use as inhibitors of bone resorption appeared in 1968. One group of biologically active bisphosphonates, which included the earliest bisphosphonates, constituted methylenebisphosphonates bearing simple 1-alkyl; 1,1-dihalo, 1-thiophenyl and/or 1-hydroxy substituents at the P-C-P grouping with a specific affinity to the bone tissue (etidronate, clodronate, tiludronate). The ability of bisphosphonates to bind to crystals of hydroxyapatites and to prevent both crystal growth and dissolution was enhanced when 1-chlorine atom (as in clodronate) was replaced by 1-hydroxyl group (as in etidronate). Newer bisphosphonates having a basic primary nitrogen atom in an alkyl chain (as in pamidronate and alendronate) and the recent ones containing a tertiary nitrogen (as in ibandronate and olpadronate) or a nitrogen atom within the heterocyclic ring (as in risedronate and zoledronate) are much more potent anti-resorptive compounds. The potency to inhibit bone resorption in rats increases from 1 to 10 000 in the sequence etidronate< clodronate, tiludronate< pamidronate, neridronate< alendronate, olpadronate< ibandronate, risendronate< zoledronate. Very small effective antiresorptive doses of the newest bisphosphonates clearly show that these bisphosphonates inhibit bone resorption by direct cellular effects on osteoclasts or by indirect effect through stimulation of osteoblasts to produce an osteoclast - inhibitory protein factor. In this review historically first syntheses of bisphosphonates described by Menschutkin (1865) and von Bayer-Hofmann (1898) as well as representative syntheses of clodronate, tiludronate, pamidronate, alendronate and risedronate are presented.

Słowa kluczowe

PL

bisfosfoniany; aktywność biologiczna

• Wydawca: Polskie Towarzystwo Chemiczne
• Czasopismo: Wiadomości Chemiczne
• Rocznik: 2000
• Tom: [Z] 54, 11-12
• Strony: 1075--1088
• Opis fizyczny: wykr., bibliogr. 19 poz.

Twórcy

autor

Bałczewska E.

• Zakład Chorób Błony Śluzowej, Jamy Ustnej i Przyzębia, Instytut Stomatologii AM ul. Pomorska 251, 92-213 Łódź

autor

Bałczewski P.

• Zakład Chorób Błony Śluzowej, Jamy Ustnej i Przyzębia, Instytut Stomatologii AM ul. Pomorska 251, 92-213 Łódź

• Zakład Chorób Błony Śluzowej, Jamy Ustnej i Przyzębia, Instytut Stomatologii AM ul. Pomorska 251, 92-213 Łódź

Bibliografia

• [1] H. Fleisch, [w:] Bisphosphonates in Bone Disease: From the Laboratory to the Patient, 3rd ed., The Parthenon Publishing Group, New York, London 1997 i literatura tam cytowana.
• [2] K. Galus, Z. Jaworski, K. Włodarski, [w:] Choroby metaboliczne kości, Med. Tour Press International, Wyd. Medyczne, Warszawa 1994 i literatura tam cytowana.
• [3] J. E. Badurski, A. Sawicki, S. Boczoń, [w:] J. E. Badurski (red.), Osteoporoza, Osteo-print, Białystok 1994.
• [4] Proceedings of the XIVth International Conference (XIVth ICPC) on Phosphorus Chemistry, Cincinnati, Ohio, USA; Phosphorus, Sulfur and Silicon, 1999, 144-146, 5-16, 321-328, 793-820 i literatura tam cytowana.
• [5] XIIIth International Conference on Phosphorus Chemistry - ICPC. Abstracts, Jerusalem, Israel, July 16-21, 1995, 48-50.
• [6] T. Książek, PoL Arch. Med. Wew., 1981, 65, 159-168, 169-175.
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• [10] H. Fleisch, R. G. G. Russell, M. D. Francis, Science, 1969, 165, 1262.
• [11] N. Menschutkin, Liebigs Ann. Chem., 1865, 133, 317.
• [12] H. von Bayer, K. A. Hofmann, Ber. Dtsch. Chem. Ges., 1898, 30, 1973.
• [13] D. A. Nicholson, H. Yaughn, J. Org. Chem., 1971, 36, 3843.
• [14] A. N. Pudovik, E. S. Batyeva, J. I. Girfanova, A. A. Karelov, Zh. Obshch. Khim., 1977, 48, 1420.
• [15] W. P. Kuhar, E. J. Sagina, Zh. Obshch. Khim., 1979, 49, 1470.
• [16] M. Mikołajczyk, P. Bałczewski, S. Grzejszczak, Synthesis, 1980, 127 i wyniki niepublikowane.
• [17] U. Schulke, Phosphorus, Sulfur, Silicon, 1990, 51/52, 153.
• [18] Y. Leroux, D. E. L. Manouni, A. Safsas, A. Neuman, H. Gillier, Phosphorus, Sulfur, Silicon, 1991, 63, 181.
• [19] J. J. Benedict, C. M. Perkins, European Patent, No 186405 (1986) i ref. [4].

Uwagi

PL

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