Distamycin is a

polyamide A polyamide is a polymer with repeating units linked by amide bonds. Polyamides occur both naturally and artificially. Examples of naturally occurring polyamides are proteins, such as wool and silk. Artificially made polyamides can be made through ...

antibiotic An antibiotic is a type of antimicrobial substance active against bacteria. It is the most important type of antibacterial agent for fighting bacterial infections, and antibiotic medications are widely used in the treatment and prevention of ...

, which acts as a minor groove binder, binding to the small furrow of the

double helix A double is a look-alike or doppelgänger; one person or being that resembles another. Double, The Double or Dubble may also refer to: Film and television * Double (filmmaking), someone who substitutes for the credited actor of a character * ...

Properties

Distamycin is a

pyrrole Pyrrole is a heterocyclic aromatic organic compound, a five-membered ring with the formula C4 H4 NH. It is a colorless volatile liquid that darkens readily upon exposure to air. Substituted derivatives are also called pyrroles, e.g., ''N''-meth ...

amidine Amidines are organic compounds with the functional group RC(NR)NR2, where the R groups can be the same or different. They are the imine derivatives of amides (RC(O)NR2). The simplest amidine is formamidine, HC(=NH)NH2. Examples of amidines includ ...

antibiotic and analogous to

netropsin Netropsin (also termed congocidine or sinanomycin) is a polyamide with antibiotic and antiviral activity. Netropsin was discovered by Finlay ''et al.'', and first isolated from the actinobacterium ''Streptomyces netropsis''. It belongs to the class ...

and the class of

lexitropsin Lexitropsins are members of a family of semi-synthetic DNA-binding ligands. They are structural analogs of the natural antibiotics netropsin and distamycin. Antibiotics of this group can bind in the minor groove of DNA with different sequence-sele ...

s. As opposed to netropsin, distamycin contains three N-methyl-pyrrole units. It is harvested from ''

Streptomyces netropsis ''Streptomyces netropsis'' is a bacterium species from the genus of ''Streptomyces''. ''Streptomyces netropsis'' produces the antibiotics netropsin and distamycin A and the antifungal polyene mycoheptin. Further reading * * * * * * * ...

'' that also produces netropsin. Distamycin prefers AT-rich DNA-sequences and tetrades of GGGGTsub>4. Distamycin inhibits the

transcription Transcription refers to the process of converting sounds (voice, music etc.) into letters or musical notes, or producing a copy of something in another medium, including: Genetics * Transcription (biology), the copying of DNA into RNA, the fir ...

and increases the activity of the

topoisomerase II Type II topoisomerases are topoisomerases that cut both strands of the DNA helix simultaneously in order to manage DNA tangles and supercoils. They use the hydrolysis of ATP, unlike Type I topoisomerase. In this process, these enzymes change th ...

. Derivates from distamycin are used as

alkylating antineoplastic agent An alkylating antineoplastic agent is an alkylating agent used in cancer treatment that attaches an alkyl group (CnH2n+1) to DNA. The alkyl group is attached to the guanine base of DNA, at the number 7 nitrogen atom of the purine ring. Since ...

s to combat tumours. Derivates with

fluorophore A fluorophore (or fluorochrome, similarly to a chromophore) is a fluorescent chemical compound that can re-emit light upon light excitation. Fluorophores typically contain several combined aromatic groups, or planar or cyclic molecules with se ...

s are used as

fluorescent tag In molecular biology and biotechnology, a fluorescent tag, also known as a fluorescent label or fluorescent probe, is a molecule that is attached chemically to aid in the detection of a biomolecule such as a protein, antibody, or amino acid. Gener ...

s for double-stranded DNA. The compound is

hygroscopic Hygroscopy is the phenomenon of attracting and holding water molecules via either absorption or adsorption from the surrounding environment, which is usually at normal or room temperature. If water molecules become suspended among the substance ...

, and sensible to light, freeze and

hydrolysis Hydrolysis (; ) is any chemical reaction in which a molecule of water breaks one or more chemical bonds. The term is used broadly for substitution reaction, substitution, elimination reaction, elimination, and solvation reactions in which water ...

. Its

molar attenuation coefficient In chemistry, the molar absorption coefficient or molar attenuation coefficient is a measurement of how strongly a chemical species absorbs, and thereby attenuates, light at a given wavelength. It is an intrinsic property of the species. The Inter ...

is 37,000 M⁻¹ cm⁻¹ at a wavelength of 303 nm.

References

{{Reflist Peptides Antibiotics DNA-binding substances Imidazoles Pyrroles Amines

Properties

See also

References