Actinomycine, XX. Antibiotica aus Actinomyceten, XLI. Chloractinomycine

Brockmann, Hans; Gröne, Heinz; Pampus, Gottfried

doi:10.1002/cber.19580910920

Chem. Ber.

1958

DOI: 10.1002/cber.19580910920

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Actinomycine, XX. Antibiotica aus Actinomyceten, XLI. Chloractinomycine

Hans Brockmann

Heinz Gröne

Gottfried Pampus

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1959

1977

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Cited by 18 publications

(1 citation statement)

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“…chromophore has been replaced by OH (2), Cl (3), or monoor disubstituted amines (NRH or NR2) have been nearly or completely inactive biologically. [12][13][14][15][16] It has been assumed therefore that the 2-amino group is required for DNA binding and biological activity.11 However, the 2-deamino analogue 4 has not been prepared and studied.…”

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confidence: 99%

2-Deaminoactinomycin D, synthesis and interaction with deoxyribonucleic acid

Mosher¹,

Kuhlmann²,

Kleid³

et al. 1977

J. Med. Chem.

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2-Deaminoactinomycin D has been synthesized and characterized. It binds to DNA by intercalation according to NMR, CD, thermal denaturation, and unwinding studies on the drug-DNA complex. Loss of the 2-amino group does not seriously affect binding parameters relative to actinomycin D; affinity for calf thymus DNA may even be increased, according to deltaTm measurements. The unwinding of circular DNA caused by this compound is at least as large as that effected by actinomycin D and ethidium bromide. Nevertheless, 2-deaminoactinomycin D is less effective than actinomycin D in inhibiting nucleic acid syntheses in L1210 cell culture and in in vivo antitumor activity against P388 leukemia.

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mentioning

confidence: 99%

2-Deaminoactinomycin D, synthesis and interaction with deoxyribonucleic acid

Mosher¹,

Kuhlmann²,

Kleid³

et al. 1977

J. Med. Chem.

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Die Actinomycine

Brockmann

1960

Angewandte Chemie

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Teniperatnr ca. 11 aiif 130 "C, evakuiert kurz zur Entfernunp der in dnr Sclimelze noch vorlianclenen Gasblaschen und ruhrt 20 p Butandiol-(1.4) ein. Nunmehr girlit man die hornogene Srhnielzc in vorhereitete Formen und fiihrt die Polyadditiori hei t o 0 'C' zil Elide. Rereits naeh 2 bis 3 niin t r i t t eine Viwositiitsrr-I~o h n n~ vin, die z u eincni Gelieren der Schmelze f u h r t . Nach etwa 20 miti knnnen dic eiit,standeiien Gielilinge entfornit c~r d e n .Ilurcli 24-st,iiiiili::cs Nac:lihcizPri hei 1 1 N i "C erhalten sie ilirc ?ndrultigeu Eigrnscliaftcn. 2ugfesti:keit 300 kp/r.m2Bruchdehnuiig 650 0;Rleihrnde Dehnung 15 n' ,

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Die Raumstruktur der Actinomycine

Lackner¹

1975

Angewandte Chemie

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Für Actinomycine, rote Chromopeptid‐Antibiotica mit ausgeprägter antineoplastischer Wirkung, lassen sich aufgrund ihrer einzigartigen Konstitution zahlreiche komplizierte Raumstrukturen formulieren. Da diese die spezifische Aktivität der Actinomycinmoleküle in der Wirtszelle weitgehend bestimmen, ist die Kenntnis der natürlichen, in Lösung vorliegenden Strukturformen eine entscheidende Voraussetzung für die Gewinnung detaillierter Vorstellungen über die biologische Wirkungsweise der Actionmycine. Untersuchungen nach mehreren Methoden ergaben, daß alle Actinomycine trotz unterschiedlicher Primärstruktur dem gleichen, sehr charakteristischen, pseudo‐C2‐symmetrischen und bemerkenswert stabilen Raumstrukturtyp angehören.

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Actinomycine, XX. Antibiotica aus Actinomyceten, XLI. Chloractinomycine

Cited by 18 publications

References 4 publications

2-Deaminoactinomycin D, synthesis and interaction with deoxyribonucleic acid

2-Deaminoactinomycin D, synthesis and interaction with deoxyribonucleic acid

Die Actinomycine

Die Raumstruktur der Actinomycine

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