One-flask synthesis of meso-substituted dipyrromethanes and their application in the synthesis of trans-substituted porphyrin building blocks

Lee, Changhee; Lindsey, Jonathan S.

doi:10.1016/s0040-4020(01)89282-6

Cited by 544 publications

(349 citation statements)

References 45 publications

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“…This compound was previously prepared by a less efficient method (45). Following a standard procedure (40), 4-bromobenzaldehyde (5.55 g, 30.0 mmol) was dissolved in dry pyrrole (208 mL, 3.00 mol), and the solution was flushed with argon for 10 min.…”

Section: -(4-bromophenyl)dipyrromethane (7b)mentioning

confidence: 99%

Bioconjugatable Porphyrins Bearing a Compact Swallowtail Motif for Water Solubility

et al. 2006

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A broad range of applications requires access to water-soluble, bioconjugatable porphyrins. Branched alkyl groups attached at the branching site to the porphyrin meso position are known to impart high organic solubility. Such "swallowtail" motifs bearing a polar group (hydroxy, dihydroxyphosphoryl, dihydroxyphosphoryloxy) at the terminus of each branch have now been incorporated at a meso site in trans-AB-porphyrins. The incorporation of the swallowtail motif relies on rational synthetic methods whereby a 1,9-bis(N-propylimino)dipyrromethane (bearing a bioconjugatable tether at the 5-position) is condensed with a dipyrromethane (bearing a protected 1,5-dihydroxypent-3-yl unit at the 5-position). The two hydroxy groups in the swallowtail motif of each of the resulting zinc porphyrins can be transformed to the corresponding diphosphate or diphosphonate product. A 4-(carboxymethyloxy)phenyl group provides the bioconjugatable tether. The six such porphyrins reported here are highly water-soluble (≥20 mM at room temperature in water at pH 7) as determined by visual inspection, UV-vis absorption spectroscopy, or 1 H NMR spectroscopy. Covalent attachment was carried out in aqueous solution with the unprotected porphyrin diphosphonate and a monoclonal antibody against the T-cell receptor CD3ε. The resulting conjugate performed comparably to a commercially available fluorescein isothiocyanatelabeled antibody with Jurkat cells in flow cytometry and fluorescence microscopy assays. Taken together, this work enables preparation of useful quantities of water-soluble, bioconjugatable porphyrins in a compact architecture for applications in the life sciences.

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Section: -(4-bromophenyl)dipyrromethane (7b)mentioning

confidence: 99%

Bioconjugatable Porphyrins Bearing a Compact Swallowtail Motif for Water Solubility

et al. 2006

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“…according to the procedure of Lee and Lindsey. 15,16 After purification, the product was isolated in 15-23% yield. While this purified tripyrrane proved stable when stored in the freezer for over two weeks, it darkened rapidly, turning from pink to dark brown, when dissolved in common organic solvents and left to stand on the bench top unprotected from air or light.…”

Section: Synthesismentioning

confidence: 99%

New polyethyleneglycol-functionalized texaphyrins: synthesis and in vitro biological studies

et al. 2006

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The synthesis of four new analogues of motexafin gadolinium (MGd), a gadolinium(III) texaphyrin complex in clinical trials for its anticancer properties, is described. These new derivatives contain either 1,2-diaminobenzene or 2,3-diaminonaphthalene subunits as the source of the imine nitrogens and bear multiple 2-[2-(2-methoxyethoxy)ethoxy]ethoxy (PEG) groups, on either meso aryl or beta-pyrrolic substituents, to increase their water solubility. All four analogues were found to be more active in vitro than the parent system MGd as judged from cell proliferation assays using the PC3 and A549 cell lines.

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“…[1][2][3][4] Recently, its applications have been extended for synthesis of gold nanoparticles. 5 The condensation of aldehydes with excess of pyrrole in the presence of acid such as trifluoroacetic acid, 6 BF3etherate, 7,8 ptoluenesulfonic acid, 9 acetic acid, 10,11 indium chloride, 12 or metal triflates 13 in organic solvents or in the absence of solvent has been reported as general methods for synthesis of mesosubstituted dipyrromethanes along with oligomeric byproducts. 14,15 The major disadvantages of these methods include the requirement of large amounts of pyrrole, corrosive acidic catalyst and the use of chlorinated solvents.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of dipyrromethanes in aqueous media using boric acid

Singhal¹,

Singh²,

Chauhan³

2017

Arkivoc

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Boric acid acts as an efficient and green catalyst for the condensation reaction of pyrrole and aldehydes in aqueous medium to produce parallel library of dipyrromethanes including new compound analogue, meso-acetyldipyrromethane in moderate to good yield. The use of boric acid as catalyst and selective reactivity of aldehydes over ketones in its presence, and water as reaction medium are important attributes in the present protocol.

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One-flask synthesis of meso-substituted dipyrromethanes and their application in the synthesis of trans-substituted porphyrin building blocks

Cited by 544 publications

References 45 publications

Bioconjugatable Porphyrins Bearing a Compact Swallowtail Motif for Water Solubility

Bioconjugatable Porphyrins Bearing a Compact Swallowtail Motif for Water Solubility

New polyethyleneglycol-functionalized texaphyrins: synthesis and in vitro biological studies

Synthesis of dipyrromethanes in aqueous media using boric acid

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