Oxyntomodulin

Last updated
Oxyntomodulin
Names
IUPAC name
L-histidyl-L-seryl-L-glutaminylglycyl-L-threonyl-L-phenylalanyl-L-threonyl-L-seryl-L-α-aspartyl-L-tyrosyl-L-seryl-L-lysyl-L-tyrosyl-L-leucyl-L-α-aspartyl-L-seryl-L-arginyl-L-arginyl-L-alanyl-L-glutaminyl-L-α-aspartyl-L-phenylalanyl-L-valyl-L-glutaminyl-L-tryptophyl-L-leucyl-L-methionyl-L-α-aspartyl-L-threonyl-L-lysyl-L-arginyl-L-asparaginyl-L-lysyl-L-asparaginyl-L-asparaginyl-L-isoleucyl-L-alanine
Other names
OXM
Identifiers
3D model (JSmol)
  • InChI=1S/C192H294N58O61S/c1-15-93(8)150(185(306)217-95(10)189(310)311)248-178(299)129(77-143(202)265)236-172(293)128(76-142(201)264)235-161(282)110(39-24-27-60-193)221-171(292)127(75-141(200)263)234-162(283)115(44-32-65-212-192(207)208)220-158(279)112(41-26-29-62-195)226-187(308)152(97(12)256)250-179(300)133(81-148(273)274)238-165(286)119(59-66-312-14)225-166(287)120(67-90(2)3)229-170(291)126(73-103-82-213-109-38-23-22-37-107(103)109)233-164(285)118(55-58-140(199)262)227-184(305)149(92(6)7)247-176(297)124(69-99-33-18-16-19-34-99)232-173(294)130(78-145(267)268)237-163(284)117(54-57-139(198)261)218-154(275)94(9)216-157(278)113(42-30-63-210-190(203)204)219-159(280)114(43-31-64-211-191(205)206)223-182(303)136(87-253)244-175(296)132(80-147(271)272)239-167(288)121(68-91(4)5)228-168(289)122(71-101-45-49-105(258)50-46-101)230-160(281)111(40-25-28-61-194)222-181(302)135(86-252)243-169(290)123(72-102-47-51-106(259)52-48-102)231-174(295)131(79-146(269)270)240-183(304)137(88-254)245-188(309)153(98(13)257)249-177(298)125(70-100-35-20-17-21-36-100)241-186(307)151(96(11)255)246-144(266)84-214-156(277)116(53-56-138(197)260)224-180(301)134(85-251)242-155(276)108(196)74-104-83-209-89-215-104/h16-23,33-38,45-52,82-83,89-98,108,110-137,149-153,213,251-259H,15,24-32,39-44,53-81,84-88,193-196H2,1-14H3,(H2,197,260)(H2,198,261)(H2,199,262)(H2,200,263)(H2,201,264)(H2,202,265)(H,209,215)(H,214,277)(H,216,278)(H,217,306)(H,218,275)(H,219,280)(H,220,279)(H,221,292)(H,222,302)(H,223,303)(H,224,301)(H,225,287)(H,226,308)(H,227,305)(H,228,289)(H,229,291)(H,230,281)(H,231,295)(H,232,294)(H,233,285)(H,234,283)(H,235,282)(H,236,293)(H,237,284)(H,238,286)(H,239,288)(H,240,304)(H,241,307)(H,242,276)(H,243,290)(H,244,296)(H,245,309)(H,246,266)(H,247,297)(H,248,299)(H,249,298)(H,250,300)(H,267,268)(H,269,270)(H,271,272)(H,273,274)(H,310,311)(H4,203,204,210)(H4,205,206,211)(H4,207,208,212)/t93-,94-,95-,96+,97+,98+,108-,110-,111-,112-,113-,114-,115-,116-,117-,118-,119-,120-,121-,122-,123-,124-,125-,126-,127-,128-,129-,130-,131-,132-,133-,134-,135-,136-,137-,149-,150-,151-,152-,153-/m0/s1
    Key: BGXWJAWHUWPRAD-DPNMSELWSA-N
  • N[C@@]([H])(CC1=CN=C-N1)C(=O)N[C@@]([H])(CO)C(=O)N[C@@]([H])(CCC(=O)N)C(=O)NCC(=O)N[C@@]([H])([C@]([H])(O)C)C(=O)N[C@@]([H])(Cc1ccccc1)C(=O)N[C@@]([H])([C@]([H])(O)C)C(=O)N[C@@]([H])(CO)C(=O)N[C@@]([H])(CC(=O)O)C(=O)N[C@@]([H])(Cc1ccc(O)cc1)C(=O)N[C@@]([H])(CO)C(=O)N[C@@]([H])(CCCCN)C(=O)N[C@@]([H])(Cc1ccc(O)cc1)C(=O)N[C@@]([H])(CC(C)C)C(=O)N[C@@]([H])(CC(=O)O)C(=O)N[C@@]([H])(CO)C(=O)N[C@@]([H])(CCCNC(=N)N)C(=O)N[C@@]([H])(CCCNC(=N)N)C(=O)N[C@@]([H])(C)C(=O)N[C@@]([H])(CCC(=O)N)C(=O)N[C@@]([H])(CC(=O)O)C(=O)N[C@@]([H])(Cc1ccccc1)C(=O)N[C@@]([H])(C(C)C)C(=O)N[C@@]([H])(CCC(=O)N)C(=O)N[C@@]([H])(CC(=CN2)C1=C2C=CC=C1)C(=O)N[C@@]([H])(CC(C)C)C(=O)N[C@@]([H])(CCSC)C(=O)N[C@@]([H])(CC(=O)O)C(=O)N[C@@]([H])([C@]([H])(O)C)C(=O)N[C@@]([H])(CCCCN)C(=O)N[C@@]([H])(CCCNC(=N)N)C(=O)N[C@@]([H])(CC(=O)N)C(=O)N[C@@]([H])(CCCCN)C(=O)N[C@@]([H])(CC(=O)N)C(=O)N[C@@]([H])(CC(=O)N)C(=O)N[C@@]([H])([C@]([H])(CC)C)C(=O)N[C@@]([H])(C)C(=O)O
Properties
C192H294N58O61S
Molar mass 4422.87 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Oxyntomodulin (often abbreviated OXM) is a naturally occurring 37-amino acid peptide hormone found in the colon, produced by the oxyntic (fundic) cells of the oxyntic (fundic) mucosa. It has been found to suppress appetite.

Contents

The mechanism of action of oxyntomodulin is not well understood. It is known to bind both the GLP-1 receptor and the glucagon receptor, but it is not known whether the effects of the hormone are mediated through these receptors or through an unidentified receptor.

Oxyntomodulin has been linked to entrainment of the liver's circadian clock. [1]

Oxyntomodulin has been investigated as a blood-glucose regulation agent in connection with diabetes. [2]

Research

Oxyntomodulin could be a potential candidate for treating obesity because of its ability to suppress appetite. [3] In a 4 week study, healthy overweight and obese volunteers were given either saline or oxyntomodulin injections. Their body weight, energy intake, and the levels of adipose hormones were taken prior to the treatment. The volunteers maintained their usual diets and daily activities and self-administered the injections three times daily, 30 minutes before their meals. In the course of 4 weeks, volunteers treated with oxyntomodulin injections had an average weight loss of 2.3±0.4 kg compared to those treated with saline who had an average of 0.5±0.5 kg, indicating oxyntomodulin was successful in weight loss. [4]

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References

  1. "Oxyntomodulin regulates resetting of the liver circadian clock by food". www.uni-luebeck.de. University of Lübeck. 30 April 2015. Retrieved 22 September 2018.
  2. Hsu, Charlotte (27 January 2016). "Scientists pursue a diabetes drug that also fights obesity". phys.org. Retrieved 22 September 2018.
  3. Shankar, Sudha S.; Shankar, R. Ravi; Mixson, Lori A.; Miller, Deborah L.; Pramanik, Barnali; O'Dowd, Amy K.; Williams, Donna M.; Frederick, Clay B.; Beals, Chan R.; Stoch, S. Aubrey; Steinberg, Helmut O. (June 2018). "Native Oxyntomodulin Has Significant Glucoregulatory Effects Independent of Weight Loss in Obese Humans With and Without Type 2 Diabetes". Diabetes. 67 (6): 1105–1112. doi: 10.2337/db17-1331 . ISSN   1939-327X. PMID   29545266.
  4. Wynne, Katie; Park, Adrian J.; Small, Caroline J.; Patterson, Michael; Ellis, Sandra M.; Murphy, Kevin G.; Wren, Alison M.; Frost, Gary S.; Meeran, Karim; Ghatei, Mohammad A.; Bloom, Stephen R. (2005-08-01). "Subcutaneous Oxyntomodulin Reduces Body Weight in Overweight and Obese Subjects: A Double-Blind, Randomized, Controlled Trial". Diabetes. 54 (8): 2390–2395. doi: 10.2337/diabetes.54.8.2390 . ISSN   0012-1797. PMID   16046306.