The Malaria Pigment Haemozoin—A Focal Point of Action for Antimalarial Drugs

Senge, Ma­thias O.; Hatscher, Sabine S.

doi:10.1002/1439-7633(20001117)1:4<247::aid-cbic247>3.0.co;2-o

Cited by 9 publications

(2 citation statements)

References 36 publications

(6 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Other cyclic tetrapyrroles were synthesized in the following. Methyl protobacteriopheophorbide-d (1). According to reported procedures (23), Zn-4 was transformed to 1 as follows.…”

Section: Methodsmentioning

confidence: 99%

“…Two self-aggregates of porphyrinoids (cyclic tetrapyrroles) without any assistance of peptide scaffolds are naturally observed: (I) selfaggregates of Fe(III)-protoporphyrin-IX in malaria haemozoin (1) and (II) self-aggregates of bacteriochlorophyll(BChl)s-c/d/e in extramembranous light-harvesting antenna of photosynthetic green bacteria (2)(3)(4)(5)(6). The latter systems are called ''chlorosomes'' because of their green colored, submicrometer-sized apparatus (green þ body 5 chloro þ some).…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Self-aggregation of Synthetic Protobacteriochlorophyll-d Derivatives¶

Tamiaki¹,

Kitamoto²,

Watanabe³

et al. 2005

Photochem Photobiol

View full text Add to dashboard Cite

3(1)-Racemically pure zinc 3(1)-hydroxy-13(1)-oxo-porphyrins (zinc methyl 17,18-dehydro-bacteriopheophorbides-d) as well as their 3(1)-demethyl form were prepared by modifying chlorophyll-a through oxidation by 2,3-dichloro-5,6-dicyano-benzoquinone. From visible, circular dichroism and infrared spectral analyses, these synthetic pigments self-aggregated in 1%(vol/vol) tetrahydrofuran and cyclohexane to give large oligomers by an intermolecular bonding of 13-C=O...H-O(3(1))...Zn(central) and pi-pi interaction of the porphyrin chromophores. The supramolecular structures are similar to those of the corresponding chlorins and a core part of extramembranous light-harvesting antennas of photosynthetic green bacteria. The 17,18-dehydrogenation of a chlorin to porphyrin moiety did not disturb its self-aggregation and the synthetic zinc porphyrins are good models for naturally occurring self-aggregative bacteriochlorophylls.

show abstract

“…Other cyclic tetrapyrroles were synthesized in the following. Methyl protobacteriopheophorbide-d (1). According to reported procedures (23), Zn-4 was transformed to 1 as follows.…”

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Self-aggregation of Synthetic Protobacteriochlorophyll-d Derivatives¶

Tamiaki¹,

Kitamoto²,

Watanabe³

et al. 2005

Photochem Photobiol

View full text Add to dashboard Cite

show abstract

Molekulares Engineering freier Porphyrinbasen als Liganden – das N‐H⋅⋅⋅X‐Bindungsmotiv in Tetrapyrrolen

Kielmann¹,

Senge²

2018

Angewandte Chemie

View full text Add to dashboard Cite

Die N‐H‐Einheiten im Kern planarer Porphyrine sind oft nicht zugänglich, um Wasserstoffbrückenkomplexe mit Akzeptormolekülen zu bilden. Dies liegt daran, dass die funktionellen Aminogruppen durch das makrozyklische System abgeschirmt sind, was die Bildung intermolekularer H‐Brücken hemmt. Jedoch gibt es Methoden, um die Tetrapyrrolkonformationen so zu modulieren, dass der Vektor der N‐H‐Orientierung nach außen gerichtet wird, um so die Verfügbarkeit und Reaktivität der Pyrrolgruppen zu erhöhen. Mögliche Strategien dafür sind die Verwendung von Porpho(di)methenen und Phlorinen (Calixphyrinen) sowie sattelförmiger Porphyrine. Erstere bilden Hohlräume durch Unterbrechung des aromatischen Systems. Letztere sind hoch basische Systeme und können Anionen und neutrale Moleküle durch N‐H⋅⋅⋅X‐artige H‐Brücken binden. Dieser Aufsatz beschreibt die Rolle von Porphyrin(oid)liganden in verschiedenen komplexartigen Verbindungen und diskutiert Ansätze, mittels Wasserstoffbrücken auf den Porphyrinkern zuzugreifen, das Konzept konformativer Kontrolle und davon abgeleitete neue Anwendungen, etwa in der Organokatalyse und Sensorik.

show abstract

Molecular Engineering of Free‐Base Porphyrins as Ligands—The N−H⋅⋅⋅X Binding Motif in Tetrapyrroles

Kielmann

Senge

2018

Angew Chem Int Ed

View full text Add to dashboard Cite

The core N-H units of planar porphyrins are often inaccessible to forming hydrogen-bonding complexes with acceptor molecules. This is due to the fact that the amine moieties are "shielded" by the macrocyclic system, impeding the formation of intermolecular H-bonds. However, methods exist to modulate the tetrapyrrole conformations and to reshape the vector of N-H orientation outwards, thus increasing their availability and reactivity. Strategies include the use of porpho(di)methenes and phlorins (calixphyrins), as well as saddle-distorted porphyrins. The former form cavities due to interruption of the aromatic system. The latter are highly basic systems and capable of binding anions and neutral molecules via N-H⋅⋅⋅X-type H-bonds. This Review discusses the role of porphyrin(oid) ligands in various coordination-type complexes, means to access the core for hydrogen bonding, the concept of conformational control, and emerging applications, such as organocatalysis and sensors.

show abstract

The Malaria Pigment Haemozoin—A Focal Point of Action for Antimalarial Drugs

Cited by 9 publications

References 36 publications

Self-aggregation of Synthetic Protobacteriochlorophyll-d Derivatives¶

Self-aggregation of Synthetic Protobacteriochlorophyll-d Derivatives¶

Molekulares Engineering freier Porphyrinbasen als Liganden – das N‐H⋅⋅⋅X‐Bindungsmotiv in Tetrapyrrolen

Molecular Engineering of Free‐Base Porphyrins as Ligands—The N−H⋅⋅⋅X Binding Motif in Tetrapyrroles

Contact Info

Product

Resources

About