# Contryphan

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> Markdown URL: https://mediated.wiki/source/Contryphan.md
> Source: https://en.wikipedia.org/wiki/Contryphan
> Source revision: 1308748690
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{{Pfam_box
| Symbol = Contryphan_CS
| Name = Contryphan
| image = 1NXN.png
| width = 
| caption = [NMR](/source/NMR) structure of Contryphan-Vn.  The peptide backbone is depicted by a curved tube while the amino acid side-chains are represented by capped sticks.  Carbon atoms are colored grey, nitrogen atoms blue, oxygen atoms red, and sulfur atoms yellow.<ref name="pmid15150794">{{PDB|1NXN}}; {{cite journal | vauthors = Eliseo T, Cicero DO, Romeo C, Schininà ME, Massilia GR, Polticelli F, Ascenzi P, Paci M | title = Solution structure of the cyclic peptide contryphan-Vn, a Ca<sup>2+</sup>-dependent K<sup>+</sup> channel modulator | journal = Biopolymers | volume = 74 | issue = 3 | pages = 189–98 | date = June 2004 | pmid = 15150794 | doi = 10.1002/bip.20025 | s2cid = 24487744 }}</ref><br/>.
| Pfam = PF02950
| InterPro = IPR011062
| SMART =
| PROSITE = PS60027
| SCOP = 2cco
| TCDB =
| OPM family =
| OPM protein =
| PDB = {{PDB2|1dfy }}, {{PDB2|1dfz}} , {{PDB2|1dg0}} , {{PDB2|1nxn}} , {{PDB2|1qfb}}
}}

The '''contryphan'''s ('''con'''us + '''try'''pto'''phan''') are a family of [peptide](/source/peptide)s that are active constituents of the potent [venom](/source/venom) produced by [cone snail](/source/cone_snail) (genus ''[Conus](/source/Conus)'').  The two amino acid [cysteine](/source/cysteine) residues in contryphans are linked by a [disulfide bond](/source/disulfide_bond).  In addition, contryphans undergo an unusual degree of [post-translational modification](/source/post-translational_modification) including 
[epimerization](/source/epimerization) of [leucine](/source/leucine) and [tryptophan](/source/tryptophan), tryptophan [bromination](/source/bromination), [amidation](/source/amidation) of the [C-terminus](/source/C-terminus), and [proline hydroxylation](/source/hydroxyproline).<ref name="pmid15155730">{{cite journal | vauthors = Hansson K, Ma X, Eliasson L, Czerwiec E, Furie B, Furie BC, Rorsman P, Stenflo J | title = The first gamma-carboxyglutamic acid-containing contryphan. A selective L-type calcium ion channel blocker isolated from the venom of Conus marmoreus | journal = The Journal of Biological Chemistry | volume = 279 | issue = 31 | pages = 32453–63 | date = July 2004 | pmid = 15155730 | doi = 10.1074/jbc.M313825200 | doi-access = free }}</ref> In the broader scheme of genetic [conotoxin](/source/conotoxin) classification, contryphans are members of "Conotoxin Superfamily O2."<ref>{{cite journal | vauthors = Robinson SD, Norton RS | title = Conotoxin gene superfamilies | journal = Marine Drugs | volume = 12 | issue = 12 | pages = 6058–101 | date = December 2014 | pmid = 25522317 | pmc = 4278219 | doi = 10.3390/md12126058 | doi-access = free }}</ref>

==Family members==
[[Image:Textile cone.JPG|thumb|right|238px|''[Conus textile](/source/Conus_textile)'', which produces '''contryphans''']]

Contryphan family members include:
{| class="wikitable"
|-
! Peptide
! Sequence
! Species
! Reference
|-
| Des(Gly1)contryphan-R
| COwEPWC-NH2
| ''C. radiatus''
| <ref name="pmid8910408">{{cite journal | vauthors = Jimenéz EC, Olivera BM, Gray WR, Cruz LJ | title = Contryphan is a D-tryptophan-containing Conus peptide | journal = The Journal of Biological Chemistry | volume = 271 | issue = 45 | pages = 28002–5 | date = November 1996 | pmid = 8910408 | doi = 10.1074/jbc.271.45.28002 | doi-access = free }}</ref>
|-
| Contryphan-R
| GCOwEPWC-NH2
| ''[Conus radiatus](/source/Conus_radiatus)''
| <ref name="pmid8910408" />
|-
| Bromocontyphan-R
| GCOwEPXC-NH2
| ''C. radiatus''
| <ref name="pmid9033387">{{cite journal | vauthors = Jimenez EC, Craig AG, Watkins M, Hillyard DR, Gray WR, Gulyas J, Rivier JE, Cruz LJ, Olivera BM | title = Bromocontryphan: post-translational bromination of tryptophan | journal = Biochemistry | volume = 36 | issue = 5 | pages = 989–94 | date = February 1997 | pmid = 9033387 | doi = 10.1021/bi962840p }}</ref>
|-
| Contryphan-Sm
| GCOwQPWC-NH2
| ''[Conus stercusmuscarum](/source/Conus_stercusmuscarum)''
| <ref name="pmid9531419">{{cite journal | vauthors = Jacobsen R, Jimenez EC, Grilley M, Watkins M, Hillyard D, Cruz LJ, Olivera BM | title = The contryphans, a D-tryptophan-containing family of Conus peptides: interconversion between conformers | journal = The Journal of Peptide Research | volume = 51 | issue = 3 | pages = 173–9 | date = March 1998 | pmid = 9531419 | doi = 10.1111/j.1399-3011.1998.tb01213.x }}</ref>
|-
| Contryphan-P
| GCOwDPWC-NH<sub>2</sub>
| ''C. purpurascens''
| <ref name="pmid9531419" />
|-
| Contryphan-R/Tx
| GCOwEPWC-NH2
| ''[Conus textile](/source/Conus_textile)''
| <ref name="pmid9531419" />
|-
| Contryphan-Tx
| GCOWQPYC-NH2
| ''[Conus textile](/source/Conus_textile)''
| <ref name="pmid9531419" />
|-
| Contryphan-Vn
| GDCPwKPWC-NH<sub>2</sub>
| ''[Conus ventricosus](/source/Conus_ventricosus)''
| <ref name="pmid11688995">{{cite journal | vauthors = Massilia GR, Schininà ME, Ascenzi P, Polticelli F | title = Contryphan-Vn: a novel peptide from the venom of the Mediterranean snail Conus ventricosus | journal = Biochemical and Biophysical Research Communications | volume = 288 | issue = 4 | pages = 908–13 | date = November 2001 | pmid = 11688995 | doi = 10.1006/bbrc.2001.5833 | bibcode = 2001BBRC..288..908M }}</ref>
|-
| Leu-contryphan-P
| GCVlLPWC-OH
| ''[Conus purpurascens](/source/Conus_purpurascens)''
| <ref name="pmid10461743">{{cite journal | vauthors = Jacobsen RB, Jimenez EC, De la Cruz RG, Gray WR, Cruz LJ, Olivera BM | title = A novel D-leucine-containing Conus peptide: diverse conformational dynamics in the contryphan family | journal = The Journal of Peptide Research | volume = 54 | issue = 2 | pages = 93–9 | date = August 1999 | pmid = 10461743 | doi = 10.1034/j.1399-3011.1999.00093.x }}</ref>
|-
| Leu-contryphan-Tx
| CVlYPWC-NH<sub>2</sub>
| ''[Conus textile](/source/Conus_textile)''
| <ref name="pmid9531419" />
|-
| Glaconryphan-M
| NγSγCPWHPWC-NH<sub>2</sub>
| ''[Conus marmoreus](/source/Conus_marmoreus)''
| <ref name="pmid15155730" />
|}
 
where the [sequence](/source/peptide_sequence) abbreviations stand for:
* O = 4-trans-[hydroxyproline](/source/hydroxyproline),
* l = D-leucine, L = [L-leucine](/source/L-leucine),
* w = D-tryptophan, W = [L-tryptophan](/source/L-tryptophan),
* γ = [gamma-carboxyglutamic acid](/source/gamma-carboxyglutamic_acid),
* NH<sub>2</sub> = C-terminal amidation
and the remainder of the letters refer to the standard [one letter abbreviations](/source/amino_acid) for amino acids.

==Mechanism of toxicity==

The venom of cone snails cause [paralysis](/source/paralysis) of their fish prey.  The molecular target has not been determined for all contryphan peptides, however it is known that contryphan-Vn is a [Ca<sup>2+</sup>-dependent K<sup>+</sup> channel](/source/calcium-activated_potassium_channel) modulator,<ref name="pmid11688995" /> while glacontryphan-M is a [L-type calcium channel](/source/L-type_calcium_channel) blocker.<ref name="pmid15155730" />

== References ==
{{Reflist|2}}

== External links ==
* {{MeshName|Contryphan}}

Category:Neurotoxins
Category:Ion channel toxins
Category:Snail toxins

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Adapted from the Wikipedia article [Contryphan](https://en.wikipedia.org/wiki/Contryphan) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Contryphan?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.