imported>Graeme Bartlett: removed Category:Invertebrate toxins; added Category:Snail toxins using HotCat

2021-10-23T19:24:24Z

removed Category:Invertebrate toxins; added Category:Snail toxins using HotCat

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{{Pfam_box
| Symbol = Contryphan_CS
| Name = Contryphan
| image = 1NXN.png
| width =
| caption = [[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 Ca2+-dependent K+ channel modulator | journal = Biopolymers | volume = 74 | issue = 3 | pages = 189–98 | date = June 2004 | pmid = 15150794 | doi = 10.1002/bip.20025 | s2cid = 24487744 }}</ref> .
| 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]]s that are active constituents of the potent [[venom]] produced by [[cone snail]] (genus ''[[Conus]]''). The two amino acid [[cysteine]] residues in contryphans are linked by a [[disulfide bond]]. In addition, contryphans undergo an unusual degree of [[post-translational modification]] including
[[epimerization]] of [[leucine]] and [[tryptophan]], tryptophan [[bromination]], [[amidation]] of the [[C-terminus]], and [[hydroxyproline|proline hydroxylation]].<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]] 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]]'', 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]]''
| <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]]''
| <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-NH2
| ''C. purpurascens''
| <ref name="pmid9531419" />
|-
| Contryphan-R/Tx
| GCOwEPWC-NH2
| ''[[Conus textile]]''
| <ref name="pmid9531419" />
|-
| Contryphan-Tx
| GCOWQPYC-NH2
| ''[[Conus textile]]''
| <ref name="pmid9531419" />
|-
| Contryphan-Vn
| GDCPwKPWC-NH2
| ''[[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 }}</ref>
|-
| Leu-contryphan-P
| GCVlLPWC-OH
| ''[[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-NH2
| ''[[Conus textile]]''
| <ref name="pmid9531419" />
|-
| Glaconryphan-M
| NγSγCPWHPWC-NH2
| ''[[Conus marmoreus]]''
| <ref name="pmid15155730" />
|}

where the [[peptide sequence|sequence]] abbreviations stand for:
* O = 4-trans-[[hydroxyproline]],
* l = D-leucine, L = [[L-leucine]],
* w = D-tryptophan, W = [[L-tryptophan]],
* γ = [[gamma-carboxyglutamic acid]],
* NH2 = C-terminal amidation
and the remainder of the letters refer to the standard [[amino acid#Table of standard amino acid abbreviations and properties|one letter abbreviations]] for amino acids.

==Mechanism of toxicity==

The venom of cone snails cause [[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 [[calcium-activated potassium channel|Ca2+-dependent K+ channel]] modulator,<ref name="pmid11688995" /> while glacontryphan-M is a [[L-type calcium channel]] blocker.<ref name="pmid15155730" />

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

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

[[Category:Neurotoxins]]
[[Category:Ion channel toxins]]
[[Category:Snail toxins]]

Contryphan - Revision history

imported>Graeme Bartlett: removed Category:Invertebrate toxins; added Category:Snail toxins using HotCat