Pierre Castera

An answer to the spiro versus ansa dilemma in cyclophosphazenes: Part XI. The first macro-SPIRO and macro-ANSA species from dioxodiamines☆

Abstract Aminolysis of N3P3Cl6 by dioxodiamines in suitable conditions leads to two kinds of cyclophosphazenic macro-ANSA and macro-SPIRO species which will be used for further applications as macrocyclic ligands.

An answer to the spiro versus ANSA dilemma in cyclophosphazenes: Part IX. The first genuine ANSA derivatives from N3P3Cl6 itself☆

Abstract The reaction of the simplest Lehns ligand, H 2 N(CH 2 ) 2 O(CH 2 ) 2 NH 2 , on N 3 P 3 Cl 6 in suitable stoichiometric conditions leads quite neatly to the first genuine MONOANSA and DIANSA derivatives.

An answer to the SPIRO versus ANSA dilemma in cyclophosphazenes. Part VII. Neither SPIRO nor ANSA: the BINOdicyclotriphosphazenes, N3P3Cl5 [HN(CH2)nNH] Cl5P3N3

Abstract Reactions of N 3 P 3 Cl 6 with cadaverine, H 2 N(CH 2 ) 5 NH 2 , and higher cousins lead to unique final products in which two N 3 P 3 Cl 5 moieties are bridged through a [HN(CH 2 ) n NH] entity in a two-ring assembly structure. This new type of configuration for the diamino-ligand, called BINO, is made conspicuous by concerted use of mass spectrometry and 31 P, 13 C and 1 H high resolution NMR.

Covalent binding of non-effective diaziridinocyclotriphosphazenes to natural polyamines as tumor finders makes potential anticancer agents

Covalent binding of diaziridinocyclotriphosphazenes, reputed as non-effective antitumor agents, to natural polyamines as tumor finders gives vectorized diaziridinocyclotriphosphazenes which display a significant effectiveness on murine tumors in vivo.

Singly, doubly and triply bridged polyazaheterophanes derived from hexachlorocyclotriphosphazene, N3P3Cl6

Abstract Singly, doubly and triply bridged polyazaheterophanes (1,2,3) have been synthesized from hexachlorocyclotriphosphazene, N3P3Cl6. 31P NMR spectra indicate that the molecules 2 exist in a single conformation when there are three differently populated conformations A, B and C, in molecules 3 at ambient temperature, A and (B + C) being separated by a high interconversion barrier (about 22 Kcal mole−1) whereas the barrier between B and C is much lower (about 4 Kcal mol−1).

An answer to the spiro versus ansa dilemma in cyclophosphazenes: Part X. The serendipitous chemistry of the genuine cyclophosphazenic monoANSA derivative N3P3Cl4[HNCH2)2OCH2)2NH]

Abstract Aminolysis of the genuine monoANSA derivative, N 3 P 3 Cl 4 [HN(CH 2 ) 2 O(CH 2 ) 2 NH], leads to neat new B.A.S.I.C. structures in which the chlorine atoms trans to the ANSA arch are never involved. This is the first time to our knowledge that non-reactive chlorine atoms of a phosphonitrilic chloride trimer are made conspicuous.

Anticancer and Immuno-Modulating Properties of Cyclophosphazenes

Abstract Clinical uses of aziridinocyclophosphazenes (“nude” drugs) as anticancer immuno-modulating drugs are severely limited by hematological toxicity. Benefits from vectorization through covalent linkage to biogenic polyamines as tumor finders are evidenced and further improvements through monoclonal antibodies are envisaged.

Attempts at the production of more selective antitumourals. Part III. Aziridinocyclophosphazenes linked to the polyamines 1,5-diaminopentane (cadaverine) and higher cousins

Abstract In an attempt to design antitumour cyclophosphazenes of improved specificity by linking them to biogenic polyamines as tumour finders, we studied the binding of N 3 P 3 Az 5 Cl to cadaverine and its cousins. Synthesis, NMR and mass spectrometry of the bino vectorized drugs (in which two N 3 P 3 Az 5 active principles are linked to the diamine in a bino configuration) are described. Unfortunately, these vectorized drugs display such poor water solubility (less than 4 g 1 −1 ) that studies of their biological activities could not be performed. In other words, vectorization of aziridinocyclotriphosphazenes through natural polyamines as tumour finders in a bino configuration is not suitable for industrial purposes, in contrast with what was previously demonstrated when vectorization occurs in spiro and dispiro-bino configuration.